The Marvelettes was an American girl group that achieved popularity in the early- to mid-1960s. They consisted of schoolmates Gladys Horton, Katherine Anderson (now Schaffner), Georgeanna Tillman (later Gordon), Juanita Cowart (now Cowart Motley), and Georgia Dobbins, who was replaced by Wanda Young (now Rogers) prior to the group signing their first deal. They were the first major successful act of Motown Records after the Miracles and its first significantly successful girl group after the release of the 1961 number-one single, “Please Mr. Postman“, one of the first number-one singles recorded by an all-female vocal group and the first by a Motown recording act.
Founded in 1960 while the group’s founding members performed together at their glee club at Inkster High School in Inkster, Michigan, they eventually were signed to Motown’s Tamla label in 1961. Some of the group’s early hits were written by band members and some of Motown’s rising singer-songwriters such as Smokey Robinson and Marvin Gaye, who played drums on a majority of their early recordings. Despite their early successes, the group was eclipsed in popularity by groups like The Supremes, with whom they shared an intense rivalry.
Nevertheless, they managed a major comeback in 1966 with “Don’t Mess with Bill“, along with several other smaller hits. They struggled with issues of poor promotion from Motown, illnesses, and mental breakdowns, with Cowart the first to leave in 1963, followed by Georgeanna Tillman two years later, and Gladys Horton two after that. The group ceased performing together in 1969 and, following the release of The Return of the Marvelettes in 1970, featuring only Wanda Rogers, disbanded for good, with both Rogers and Katherine Anderson leaving the music business.
The group has received several honors including induction into the Vocal Group Hall of Fame, as well as receiving the Pioneer Award from the Rhythm and Blues Foundation. In 2005, two of the group’s most successful recordings, “Please Mr. Postman” and “Don’t Mess with Bill” earned million-selling Gold singles from the RIAA. On August 17, 2013, in Cleveland, Ohio, at Cleveland State University, the Marvelettes were inducted into the 1st class of the Official Rhythm & Blues Music Hall of Fame.
The group that would become the Marvelettes formed at Inkster High School in Inkster, Michigan, a suburb located west of Detroit, Michigan by fifteen-year-old glee club member Gladys Horton in the fall of 1960. Horton enlisted older glee club members Katherine Anderson, Georgeanna Tillman, Juanita Cowart, and Georgia Dobbins (already a high school graduate) to join her. The members struggled to come up with a name for their new act until one of the members jokingly took a stab at their own singing abilities, saying “we can’t sing yet.” Horton altered the saying to “The Casinyets”.
In 1961, the quintet, now called the Marvels, entered a talent show contest on the behest of their teacher and ended up finishing in fourth place. Though only the first three winners were offered a trip to audition for the fledgling Motown label, two of the girls’ schoolteachers advised that they be allowed to audition too. Upon auditioning for Motown executives including Brian Holland and Robert Bateman, they had a second audition with bigger staff including Smokey Robinson and the label president and founder, Berry Gordy, who while impressed with their vocal styles advised them to come back with their own composition. Returning to Inkster, Georgia Dobbins contacted a local musician named William Garrett, who had an unfinished blues composition titled “Please Mr. Postman“; Garrett allowed Dobbins to use it as long as he received songwriting credit if the song became a hit. Despite having no previous songwriting experience, Dobbins took the song home and reshaped it overnight to reflect the teenage sound of doo-wop.
Prior to returning to Motown, Dobbins left the group due to her growing family and her father, who advised her not to continue her career in show business. Dobbins’ departure left Horton in full charge of the group. To replace her, Horton asked another Inkster graduate, Wanda Young, to replace Dobbins. When the group returned and performed their composition, Gordy agreed to work with the group but under the advice that they change their name. Gordy renamed them The Marvelettes and signed the act to Motown’s Tamla division in July 1961. The following month, the group recorded “Please Mr. Postman”, which was polished by Brian Holland, Robert Bateman and Freddie Gorman, another songwriting partner of Holland (before Holland became part of the Holland–Dozier–Holland team), who moonlighted as a mailman, as well as the song “So Long Baby”, sung by Wanda. Tamla issued “Please Mr. Postman” the following September. The song then climbed to the top of the singles chart, reaching #1 that December. making them the first Motown act to have a #1 hit on the Hot 100.
To follow up on this success, Motown had the group record “Twistin’ Postman” to take advantage of the twist dance craze and the re-release of Chubby Checker‘s “The Twist“. The song eventually peaked at #34 on the pop chart in early 1962. Before the end of 1961, Tamla issued the first Marvelettes album, also named Please Mr. Postman, but it failed to chart. The group’s next single, “Playboy“, marked the second time one of their singles was written by a band member, this time by Gladys Horton. Like “Postman”, the song was retooled by other writers and upon its release in early 1962, reached #7. A fourth hit, “Beechwood 4-5789“, co-written by Marvin Gaye, reached #17. During 1962, two more albums would be issued by the band including The Marvelettes Sing and Playboy. Following the success of “Beechwood”, R&B radio stations also frequently played the single’s flip side, “Someday, Someway”, which paid off sending the song to #8 on the R&B chart—their first double-sided hit.
Due to their success, the group had to leave school in order to perform and despite the promise of tutors to help with their schooling, they were never granted any. Due to their young ages and Horton being an orphaned ward of the courts, they eventually were taken in by Esther Gordy Edwards, who bused them to Motortown Revue shows. After several successful Top 40 recordings, the group released the modest success, “Strange I Know”, which peaked at #49. In early 1963, the group was shortened to a quartet when Juanita Cowart opted to leave the band citing a mental breakdown—caused by stress from performing on the road and a mistake she made in describing the group’s background during an appearance on American Bandstand. Carrying on as a quartet, the group issued one of Holland–Dozier–Holland‘s early compositions, “Locking Up My Heart“, which peaked at #44. It was one of the first singles to feature Horton and Young in co-leads. The success of “Locking” was probably tested due to strong airplay by the song’s B-side, the Young-led ballad “Forever”, which also received a pop charting, peaking at #78. Then Berry Gordy composed and produced the single, “My Daddy Knows Best”, but it was their lowest charting at the time, #67.
The departure of Georgeanna Tillman and renewed success
By 1964, the majority of American vocal groups especially all female bands such as the Shirelles and the Ronettes started struggling with finding a hit after the arrival of British pop and rock acts. In the meantime, other Motown girl groups such as Martha and the Vandellas and the Supremes were starting to get promoted by Motown staff with the Vandellas becoming the top girl group of 1963. The following year, the Supremes took their place as the label’s top primary female group after a succession of hit recordings that year, culminating in the release of their second album, Where Did Our Love Go, which Motown was able to promote successfully. Regarding the aforementioned ‘Where Did Our Love Go’, page 97 of the book The Original Marvelettes: Motown’s Mystery Girl Group by Marc Taylor makes it clear that the Marvelettes did turn it down. Gladys recalls “When they played ‘Where Did Our Love Go’ they played ‘Too Many Fish In The Sea’. We picked ‘Too Many Fish In The Sea’ because it had all the music and all the bongos. We were all together and said at the same time we didn’t want ‘Where Did Our Love Go’.”
That year, the Marvelettes reached the top forty with the Norman Whitfield production, “Too Many Fish in the Sea“, reaching #25 with the recording. By now, Motown had begun its charm school hiring choreographer Cholly Atkins and Maxine Powell to refine the label’s acts. Atkins began polishing the Marvelettes’ dance moves while Powell taught the group to be more graceful. telling them and every other Motown act that they would “perform in front of kings and queens”. Meanwhile, two of the Marvelettes got married: Georgeanna Tillman married longtime boyfriend Billy Gordon of the Contours and Wanda Young married her longtime boyfriend Bobby Rogers of the Miracles changing her name to Wanda Rogers. By the end of 1964, Georgeanna Tillman, a longtime sufferer of sickle cell anemia was diagnosed with lupus. By early 1965, struggling to keep up with their stringent recording sessions and touring schedules and her illnesses, a doctor of Tillman’s advised her to leave performing for good. The rest of the Marvelettes carried on as a trio from then on.
In mid-1965, Wanda Rogers took over as lead vocalist, as Motown producers felt Rogers’ voice was more suitable for this role than Horton’s. With Rogers as lead, the group had a hit with “I’ll Keep Holding On“, which reached #34 while “Danger! Heartbreak Dead Ahead” settled for a #61 showing but was #11 on the R&B chart. Later in 1965, the group released the Smokey Robinson composition, “Don’t Mess with Bill“, which brought the group back to the top ten reaching #7 and becoming their second single to sell over a million copies. From then on, with Robinson mainly in charge, most of the Marvelettes singles would feature Rogers on lead. In 1966, they had a modest success with “You’re the One” and by the end of that year, they reached the top 20 with the “The Hunter Gets Captured by the Game“, which Smokey had to fight to get released. In 1967, the group recorded the Van McCoy composition, “When You’re Young and in Love“, which had been originally recorded by Ruby & the Romantics. The song reached #23 in the U.S. and peaked at #13 in the UK, becoming their only hit there.
By 1967, Gladys Horton had reconsidered her involvement with the Marvelettes. After her first child, Sammie, was born with cerebral palsy, Horton decided to leave the group entirely, doing so before the release of the hit “My Baby Must Be a Magician“. The song peaked at #17 and was noted for featuring the Temptations‘ Melvin Franklin providing the opening line. With Horton out, Harvey Fuqua introduced the group to Ann Bogan who became Horton’s replacement. However, by the time Bogan joined the group in 1968, most of the musicians of Motown’s early years had left, mainly due to financial disputes with the label. The group struggled with recordings after the release of “Magician”, with Motown offering little to no promotion. The 1968 singles “Here I Am Baby” and “Destination: Anywhere” were only modestly successful, peaking at #44 and #63 respectively. The release of their 1969 album, In Full Bloom, failed as did its only single, the remake of Justine Washington‘s “That’s How Heartaches Are Made”.
Wanda Rogers, who had suffered from a number of personal problems for some time, became unreliable and difficult to work with. Concert scheduling was difficult as she sometimes failed to turn up for performances. In 1970, Rogers recorded songs for a solo album, produced by Smokey Robinson and including covers of earlier Motown recordings, which Motown decided to market as The Return of The Marvelettes. As this album featured no other Marvelettes, original member Katherine Anderson refused to participate in appearing on the cover of the album due to what she felt was Motown’s disrespect towards her and the group. The album was only a modest hit, reaching #50 on the R&B album charts and featured no charted hit singles. Following this, the group disbanded with Katherine Anderson settling briefly as a staff writer for Motown. After Motown moved to Los Angeles in 1972, Anderson and Rogers left the business altogether returning to Michigan with Anderson settling in her hometown of Inkster while Rogers moved to Southfield, Michigan. Meanwhile, Gladys Horton had moved to Los Angeles where she raised her three sons.
In January 1980, former Marvelette and original member Georgeanna Tillman died from complications of lupus, in her mother’s house in Inkster, at the age of 36. Shortly afterwards, several of the former members filed suit against Motown, complaining of not receiving any royalties from their work. In 1989, Gladys Horton tried to reunite the original Marvelettes after being offered a contract with Motorcity Records. Wanda Young was the only other Marvelette to agree to sing on the recording. Following this, Horton continued to perform, sometimes as “Gladys Horton of the Marvelettes”. Due to a legal disagreement with Larry Marshak, who bought the Marvelettes’ name from Motown after the label lost rights to the name, Horton would fight for years to retain ownership of the name. Marshak had several groups billing themselves as “The Marvelettes”, but the women who portrayed themselves as the Marvelettes were much younger than the original lineup, and had not recorded on any of the Marvelettes’ original Motown hits.
By 2006, thanks to the efforts of former Supremes singer Mary Wilson, legislation had been launched in 33 states via The Truth In Music Act to prevent performers from using the name of a group that didn’t have at least one original member, causing the groups who Marshak had hired as Marvelettes to bill themselves as “Tribute to the Marvelettes”. Both Horton and Katherine Anderson began fighting to get back ownership of the name and were in their final stages of having the name returned to them when Horton died from a stroke at a California nursing home in January 2011. Following their exits from the Marvelettes, both Georgia Dobbins and Juanita Cowart remained in Inkster and settled into life outside the entertainment industry, with Cowart being active in her Inkster church choir. Wanda Rogers now lives with her daughter in Westland, Michigan while Katherine Anderson resides in Inkster and mentors several Detroit-area vocal groups. Ann Bogan, the latter-day member of the group, now lives in Cleveland, Ohio and became a part of the New Birth and their subgroup, Love, Peace & Happiness, before retiring to raise her children. All the surviving members of the group were recently interviewed for an episode of their lives on the TV-One show, Unsung.
In 2005, the group was awarded with two gold plaques for their biggest hits, “Please Mr. Postman” and “Don’t Mess with Bill” after the RIAA had certified the singles as million-sellers. The following year, Horton appeared on the PBS concert special, My Music Salute to Early Motown, along with other Motown stars from the label’s early years. Some of the group’s recordings were later sampled for songs by rap musicians, most notably Jay-Z‘s song, “Poppin’ Tags”, sampled the group’s 1970 cover of Smokey Robinson‘s composition, “After All“, from his 2002 album, The Blueprint 2: The Gift & The Curse.
In 1995, they were honored with the “Pioneer Award” at the Rhythm & Blues Foundation. In 2004, the group was inducted to the Vocal Group Hall of Fame. In 2006, Marc Taylor issued the biography, The Original Marvelettes: Motown’s Mystery Girl Group. The group’s story had been documented several years before in Goldmine magazine from a 1984 article.
In 2009, as part of Motown’s 50th Anniversary celebrations, a new limited-edition triple-CD set on the group entitled The Marvelettes: Forever – The Complete Motown Albums Vol. 1 was released. This featured the group’s first six albums, some of which had never been released on CD. The Marvelettes: Forever More – The Complete Motown Albums Vol. 2, which included their later albums and bonus material, was released in 2011.Their much-covered 1961 million-selling # 1 hit tune “Please Mr Postman” was inducted into the Grammy Hall of Fame in 2011.
The Marvelettes were nominated for 2013 induction into the Rock and Roll Hall of Fame. They became eligible for induction in 1987. Although they did not garner enough votes for induction, they made the ballot a second time for induction in the year 2015.
“Keep grinding. No matter how much it hurts, no matter how hard it gets, you got to keep grinding. And that’s how we’re gonna win. And we’re gonna win. We’re gonna save Cass, we’re gonna ice the Devil, and we’re gonna shank the Darkness. And anyone that gets in our way, well, God help them.”
Both Dean and Sam were raised in the hunting life by their father, after the demon Azazel killed their mother. Dean’s main role in the series is being the self-appointed guardian of Sam and often going to extreme lengths to protect him regardless of personal cost. Often in these occurrences Dean finds himself the center of a much larger picture.
Dean Winchester was born on January 24, 1979 in Lawrence, Kansas. He was the eldest child of John and Mary Winchester.
Dean lived in relative peace for the first four years of his life. When his parents had an argument when he was about three, Dean comforted his mother, promising her that John still loved her. Dean was soon joined by a brother, Sam. Six months later, Azazel visited the house to feed Sam demon blood. Mary tried to stop him, leading Azazel to set the nursery on fire with Mary pinned to the ceiling.
John came rushing in and took Sam from his crib and handed him to Dean. He then instructed his son to get out of the house as fast as he could. Dean ran out and watched as the flames destroyed his home, his childhood, and his mother. John left Lawrence with Dean and Sam before Dean’s fifth birthday.
When Dean was 6 or 7, John took Dean out shooting for the first time, using bottles as target practice. According to Dean, he bulls-eyed every one of them. Dean has cited this story as one of his fonder memories of his father.
On an occasion when John was hunting a Shtriga in Wisconsin and left Sam and Dean alone in a hotel room, Dean got bored and went out. When he came back, he found the Shtriga feeding on Sam. John returned in time to scare the Shtriga off. For a long time Dean was haunted by his failure to defend his brother. In 1991, when Dean was in sixth grade, he made his first sawed-off shotgun.
Once when 12 year-old Dean was left to babysit Sam (8 years old) while John was on a hunt, Sam began to interrogate Dean about what it was that their dad actually did. Dean responded with “You know that. He sells stuff.” When Sam moved on to ask about their mother, Dean got angry and stormed out after yelling, “Shut up! Don’t you ever talk about mom! Ever!” Upon his return, Sam revealed to Dean that he had found and read their dad’s journal, and demanded to know if monsters are real. Dean finally resigned himself to telling Sam the truth.
Dean: “I swear, if you ever tell dad I told you any of this, I will end you.” Sam: “Promise.” Dean: “First thing you have to know is…we have the coolest dad in the world. He’s a superhero.” Sam: “He is?” Dean: “Yeah. Monsters are real. Dad fights em. He’s fighting them right now.”
Dean continually excused his father’s flaws while the tension between Sam and John was clearly starting to take root. Disappointed with John’s lying and absence, Sam gave Dean a Christmas present intended for his father: an amulet. Dean wears the amulet from this time on.
In 1995, Dean lost all of his and Sam’s food money in a poker game and was caught stealing food. As a result, he was sent to a reform school run by a man named Sonny who is an ex-con that turned his life around and eventually got the charges against Dean dropped. While living at the home, Dean flourished.
He became a high school wrestling champion, made friends and was doing well in school. Dean met a girl named Robin who was Dean’s first love interest. She shared Dean’s desire not to go into the “family business”. Dean’s dreams at the time was to become a rockstar or a mechanic and he was supposed to go to a dance with Robin, but his father returned the night of the dance to pick him up and refused to delay even for one night. Sonny offered Dean the chance to stay permanently, but Dean reluctantly left because he couldn’t leave Sam..In New York, Dean, Sam and John were working on a haunting in Long Island when Dean and Sam asked John to let them go out into the city and enjoy the sights. After convincing John, they all go out, see the sights, ride on the subway, eat a lot of pizza, etc. Then one night at midnight, when Sam and John are tuckered out and sleeping, Dean snuck away from them and went to CBGB where he gets completely drunk for the first time, despite being “way underage at the time“, according to Sam. Dean snuck in to the bar, and he describes it as “nuts.” He saw people drinking, smoking, etc. Dean says he saw a “500-pound guy on stage with a mohawk just screamin’.” Dean’s mind was blown and was not sure of what to do. Then a woman walks to Dean and asks him to join her and her friends at a table, which Dean immediately agreed to. Though they get him drunk, Dean says it wasn’t “fun drunk.” He wasn’t sure what was in the drink, but after drinking, he saw that the room started spinning and he even felt like he was gonna throw-up, forever. But at that same moment, John then shows up, and when he says “Dean Winchester”, everyone around Dean is suddenly afraid of him, nobody was even looking at him. Dean was freaked out because John was just standing there not saying anything. Even a boy with a safety pin through his nose and a “Kill Everything” tattoo says to John, “Sorry, Sir”. So after getting him out of there, Dean yelled at him for embarrassing him and tells John he hates him. But John stopped, turn to Dean, and responds, “Son, you don’t like me? That’s fine. It’s not my job to be liked. It’s my job to raise you right.”
Sometime later in 1995, Dean goes on a hunt with his father and burns the monster they were hunting in the nearby woods. As it burns, Dean thinks to himself he’s only sixteen and he’s seeing things normal teenagers would never even know of. From that point, Dean chooses to forget being regular and embraces the hunting life. 
Sammy’s waiting in the car and me and my dad take the thing into the woods, burn it to a crisp. I’m sitting there and looking into the fire and thinking to myself, ‘I’m sixteen-years old. Most kids my age are worried about pimples, prom dates. I’m seeing things they’ll never even know. Never even dream of’.
— Dean on when he embraced the hunting life
During the summer of 1997 John, Dean, and Sam were hunting a werewolf. In November 1997, John “parked” the kids in a small town in Indiana where they attended Truman High School. While Sam was having trouble with a bully named Dirk, Dean got a girlfriend, Amanda. He became uncomfortable when she asked him to meet her parents. When she caught Dean cheating on her with another girl, she challenged him, charging that his “cool”, persona was just a cover for his pathetically sad loneliness.
Amanda: “I thought maybe … under your whole “I could give a crap”, bad boy thing that there was something more going on. Like the way you are with you brother. But I was wrong. You spent so much time trying to convince people that you’re cool, but it’s just an act. We both know that you’re just a sad, lonely little kid and I feel sorry for you, Dean.” Dean: “You feel sorry for me, huh? Don’t feel sorry for me. You don’t know anything about me. I save lives. I’m a hero. A hero!”
Dean never graduated high school, but did manage to get his GED.  Around 1998, Dean and John left Sam alone to go hunt a Kitsune. At this time, Dean also gave Sam advice over the phone on how to talk to girls.
In 1998 or 1999, Dean went on a road trip that was supposed to be “5 states, 5 days” while Sam was “in Orlando with dad, wrapping up that banshee thing”. However, he spent most of his time in Lisa Braeden‘s loft.
Sometime between 2001-2005, Sam left for Stanford. While there, he became estranged from Dean and his father and didn’t speak to them for at least a couple of years. During this time, Dean met Cassie Robinson while he and John were in Athens, Ohio, for a hunt. She and Dean dated for a couple of weeks. Before Dean left, he told Cassie the ‘big family secret’ about hunting. It was then that Cassie promptly called him ‘nuts’ and dumped him. Dean hunted a Vetala by himself during this period.
On June 21, 2003 in Nyac, New York, Dean hunted Edward Trenton, a man who had become an unknown species of monster that ate livers. Dean never encountered Edward’s race of monster before or since but was able to kill him by slitting Edward’s throat with a silver-coated steel knife. After killing Edward, Dean was found by his 13 year old son Cole who believed Dean had murdered his father.
When Dean was four years old, his mother Mary was killed in his younger brother Sam’s bedroom. Twenty-two years later, the demon responsible for their mother’s death kills Sam’s girlfriend, Jessica Moore. Together, Dean and Sam go on a road trip to fend off supernatural creatures and search for their father, John, who occasionally leaves new missions for them to complete.
Early in the season (Skin), Dean and Sam battle a shapeshifter responsible for a string of brutal murders in the St. Louis, MO area. During the course of the episode, the shape-shifter assumes Dean’s form, causing police to believe that Dean is responsible for the murders. The shapeshifter also gains insight on Dean’s inner conflict, partially revealing his secret self-loathing and resentment of his father being gone and Sam leaving them to go off to college. However, Dean kills the shape-shifter while it is still in his form, and the authorities officially declare him dead.
He’s sure got issues with you. You got to go to college. He had to stay home. I mean, I had to stay home. With Dad. You don’t think I had dreams of my own? But Dad needed me. Where the hell where you? […] See, deep down, I’m just jealous. You got friends. You could have a life. Me? I know I’m a freak. And sooner or later, everybody’s gonna leave me.
— Shapeshifter channeling Dean’s hidden insecurities and frustration
In Home, Dean first becomes aware of Sam’s psychic abilities when Sam has a vision of trouble at their old home in Lawrence, Kansas. In Asylum, while influenced by the spirit of Doctor Ellicott, Sam tries to shoot Dean in a spirit-induced rage over Dean’s insistence in obeying John’s orders rather than going to California to find their father. In the following episode, Sam actually does leave Dean, insisting he and John are both selfish because all they care about is revenge. Later, Dean tells Sam he was always proud of how he pursued what he wanted. Sam eventually goes looking for Dean when he can’t reach his brother on his cell phone.
In Faith, Dean acquires a fatal heart condition when he is electrocuted during a hunt. Later, he is saved by a faith healer, Roy Le Grange, whose wife is controlling a Reaper. When Dean asks why he was saved, Roy Le Grange says he looked into Dean’s heart and saw “A young man with an important purpose. A job to do. And it isn’t finished.”
In Shadow, as they prepare to battle Meg, Sam confesses to Dean that he will return to Stanford after they kill Azazel, the demon who killed their mother and Sam’s girlfriend, Jessica Moore. Dean becomes upset with Sam and insists that they keep fighting together.
Don’t say just in case something happens to you, I don’t want to hear that freaking speech, man. Nobody’s dying tonight, not us, not that family, nobody. Except that demon. That evil son of a bitch ain’t getting any older than tonight, understand me?
In the last episode of Season One, Azazel possesses Dean’s father in an attempt to get The Colt for his own. After Dean realizes this, The Yellow-Eyed Demon pins him and Sam to a wall and reveals that John favors Sam over Dean. The demon also tells Dean that he was responsible for sending the demon’s children back to Hell. After Dean makes a sarcastic remark about the situation, the demon tortures him and Dean pleads for his father’s help before losing consciousness.
The season finale concludes with Sam, Dean, and John escaping from a clash with The Yellow-Eyed Demon in Salvation, Iowa. While Sam is driving to the hospital after Dean and John were injured, a demon-possessed driver drives his truck into the Impala, causing massive damage to the car and the Winchesters inside.
Back at the hospital, I made a full recovery. It was miracle. Five minutes later Dad’s dead and The Colt’s gone. You can’t tell me there’s not a connection there. I don’t know how the demon was involved, I don’t know how it went down exactly, but Dad’s dead because of me and that much I do know.[…] You and Dad … you’re the most important people in my life. And now … I never should’ve came back. I was dead. And I should’ve stayed dead.
— Dean’s spiraling depression
in Children Shouldn’t Play With Dead Things
All three of the Winchesters survived the wreck, although Dean was more severely injured than his father or brother. In the first episode of Season 2, In My Time of Dying, Dean is in a coma and a reaper, Tessa, tries to convince him to cross over. In an effort to save Dean, John makes a deal with Azazel, trading his life for Dean’s. Before John dies, he tells Dean that someday Dean may have to kill Sam.
Over the course of the second season, Dean struggles with the death of his father and the resulting guilt that he should have died instead. This, however, Dean’s hides under hunting and at first brushing off every attempt Sam did to make him talk about his feelings. Dean became more reckless and harsh, particularly in hunting until Sam finally made him get more of a handle on it.
You’re lucky this turned out to be a real case. Because if it wasn’t, you would’ve just found something else to kill.[…] You’re on edge, you’re erratic. Except when you’re hunting because then you’re downright scary. You’re tailspinning, man. And you refuse to talk about it and you won’t let me help you.
— Sam describing Dean’s reckless behavior
in Children Shouldn’t Play With Dead Things
During an investigation in Baltimore, MD, (The Usual Suspects), Dean is arrested in connection with another series of murders. It is revealed that Dean has a rather impressive police record with charges including credit card fraud, breaking and entering, and grave desecration. Although Sam and Dean are able to prove that the murders were actually committed by one of the detectives on the case, it is unclear whether or not the charges against Dean were ever officially dropped. However, the problem still remains that the authorities have realized that Dean is not dead as they had previously believed.
Shortly afterward, while doing a case revolving around deals with the crossroads demon and trying to save a man named Evan, Dean learns from the demon John went to Hell when he exchanged his soul for Dean’s life. Dean’s self-loathing and guilt increases, believing John should’ve went out fighting against the yellow-eyed demon, not bargaining and getting tortured for his sake. While Sam believes it’s enough to save people and keep up his memory, Dean remains unconvinced.
Dean becomes more and more pressured under John’s final order– to kill Sam if he couldn’t “save” him—after knowledge of Sam’s destiny to turn evil and side with the Yellow-eyed demon in coming war. He continues to draw in on himself, tormented between obeying his father and his love for Sam. Dean begins to consider quitting hunting, chalking the “job” as nothing more than a catalyst for all the bad luck they ever had.
During this time, after hunting cases and misunderstandings in Baltimore and Milwaukee, Sam and Dean gain attention from the cops. Dean, in particular, is described as a wanted criminal and charged for “murder” and several different crimes. Both brothers are tailed by the relentless Special Agent Henriksen and forced to cover their tracks more persistently. Sam and Dean allow themselves to be arrested once while doing a case for an old friend of John’s, but soon break out of prison.
Later, Dean is caught by a djinn and cast in an alternate reality where their mother never died and he and Sam never became hunters. He has a girlfriend and a normal life. John is still dead and the brothers were no longer close since they never hunted together, though in real life Dean is slowly dying from the monster. Dean is happier in this life, but suffers the guilt of realizing every one they saved died. Ultimately Dean was forced to sacrifice his happiness for his life and the lives of everyone he saved, but the experience left him more disillusioned and tired of the hunting life.
All of them. Everyone you saved, every one Sammy and I saved. They’re all dead. […] It’s like my old life is coming after me or something. Like it doesn’t want me to be happy. […] Why? Why is it my job to save these people? Why do I have to be some kind of hero? What about us, huh? Mom’s not allowed to live her life, Sammy’s not allowed to get married. Why do we have to sacrifice everything, Dad?!
— Dean talking to John’s gravestone in an alternate reality
in What Is And What Should Never Be
After Sam suddenly disappears, whisked away with other “special children” by Azazel to an old ghost town, Dean is desperate to find him. He learns from Ash something major is happening and visits, only to find the Roadhouse burned down and Ash dead. Andy manages to transmission an image in his head of their whereabouts and both him and Bobby immediately leave. Just as Dean arrives to rescue his younger brother, however, Sam is suddenly stabbed by Jake Talley and collapses in Dean’s arms. Amidst his brother’s pleas to stay with him, Sam dies, leaving Dean alone as the last living Winchester.
Look at me, Sam. It’s not even that bad. It’s not even that bad, alright? Sammy? Sam! Listen to me. We’re going to patch you up, okay? You’ll be as good as new. I’m gonna take care of you, okay? I’m going to take care of you. I’ve got you, because that’s my job, right? Watching after my pain in the ass little brother? (realizes Sam is already dead) Sam? Sam? Sam?! Sammy?! No. No, no, no, no. Oh no come on. Oh God. (pulls Sam’s body against his and yells) SAM!
— Dean while Sam dies
in All Hell Breaks Loose – Part 1
Inconsolable, Dean lapses into anger and self-loathing. He brushes off the incoming threat and outright refuses when Bobby Singer suggests they burn Sam’s body, prompting Bobby to leave the cabin. After his monologue with Sam, during which he confesses his failure as an older brother, Dean storms out of the cabin in a furious rage. At his wits end, he travels to a crossroads to recklessly make a deal with a “crossroads demon” for Sam’s life in exchange for his soul. In the end, Dean is allowed one year to live and Sam is resurrected.
You know, when we were little, you couldn’t have been more than five, you’d just started asking questions. How come we didn’t have a mom; Why do we always have to move around; Where’d Dad go.. when he’d take off for days at a time. I remember I begged you, quit askin’ Sammy. Man, you don’t wanna know. I just wanted you to be a kid. Just for a little while longer. I always tried to protect you, keep you safe. Dad didn’t even have to tell me. This was always my responsibility, you know. It’s like, I had one job. I had one job. And I screwed it up. I blew it. And for that I’m sorry. I guess, that’s what I do. I let down the people I love. I let Dad down, and now I guess I’m supposed to let you down too. How can I? Am I supposed to live with that? What am I supposed to do? Sammy… God.. What am I supposed to do? WHAT AM I SUPPOSED TO DO?!
Sam quickly comes to life, but with no memory of anything past Jake stabbing him. Dean is overjoyed to see his brother alive, but hides the fact he died and that he made a deal. Bobby is the only one to figure it out immediately and furiously yells at Dean for his impulsiveness and sending himself to Hell. Dean explains everything to him, even admitting he felt like this deal made his life mean something again, and pleads for him to not tell Sam as he knows it will upset him.
Soon after, along with Sam, Bobby, and Ellen, Dean arrives at a Devil’s Gate that had been sealed off from other demons thanks a huge devil’s trap made by Samuel Colt. Jake, however, manages to open it with the Colt, releasing hundreds of demons from Hell. Dean is visibly disturbed when he sees Sam brutally kill Jake without hesitation afterwards, nursed further nursed when the Yellow-eyed Demon mocks if he truly believes what he brought back was “pure Sam”. John’s spirit, which escaped from Hell, suddenly appeared and distracted Azazel just long enough for Dean to kill him with the Colt’s last bullet, avenging his parents’ death. John makes peace with both of them, then flickers out.
Sam soon figures out Dean’s deal, realizing he only has one year, and is angry and hurt over his decision. Dean pleads that his job was to protect him and he couldn’t let him die like that. Sam vows to find a way to get him out of the deal and the two brothers set out to exterminate the freed demons.
I’ve got nothing to lose now, right? […] Dad brought me back, Bobby. I’m not even supposed to be here. At least this way, something good can come of it, y’know? It’s like my life can mean something. […] I couldn’t let him die, Bobby. I couldn’t. He’s my brother.
— Dean to Bobby on his deal
in All Hell Breaks Loose – Part 2
Yeah, you’re right. It was selfish. But I’m okay with that. […] After everything I’ve done for this family, I think I’m entitled. Truth is, I’m tired, Sam. I don’t know, it’s like there’s a light at the end of the tunnel […] You’re alive. I feel good, for the first time in a long time. I got a year to live, Sam. I’d like to make the most of it. So what do you say we kill some evil sons of bitches and raise a little hell, huh?
Dean decides to make the best of his final year, indulging in various acts of hedonism while Sam tries desperately to find a loophole in the crossroads demon’s deal. Dean accepts his deal to Hell with unnerving calm, telling Sam there was no way out of this without Sam himself dying again and that he should give up on saving him. Dean seems to have lost will for life and just wants to save as many people as he can before he goes. Against his brother’s wishes, Sam continues to look for loopholes anyway.
While doing a case, Dean drops by an old girlfriend Lisa Braeden that hasn’t seen in almost nine years. She has a son named Ben that’s just turned eight and bears striking resemblance to Dean. Dean believes him to be his son. After saving them from changelings, Lisa insists Ben isn’t his and she did a blood test long ago just to be sure. Dean is disappointed, admitting that since he was going to Hell he was starting to wonder what he would leave behind.
After hearing the female demon Ruby’s proposition to Sam, Dean is angry at his brother’s lenience with her and believes Ruby to be lying about getting him out of Hell. He refuses to trust her, though Sam wants to use her. Dean learns from a surprisingly amicable demon named Casey the chaos surrounding the demon word with Sam’s refusal to lead them and how many are after his brother. After Sam kills two demons–including Casey who wanted to spare Dean– with the remade Colt thanks to Ruby and Bobby, Dean is shocked at his brother’s ruthlessness and starts worrying Sam truly came back “different”.
Early in the season, the brothers meet up with another beautiful woman, Bela Talbot. Bela acquires magical objects and sells them for a large profit, is unscrupulous and seemingly amoral. Meanwhile, Dean continues to bar Sam’s attempts to break his deal of going to Hell, not still not to wanting Sam to risk dying. Dean tries to tell him he’ll be fine with him and he’s sorry for the pressure he put on him, but Sam only grows angrier and insists he care more about the fact he’s dying, not how he feels.
After being pitted against Gordon Walker once again, Dean is show to be increasingly more reckless in his hunting, knowing he was going to die soon anyways. Sam is furious over this and calls out Dean’s cavalier behavior on going to Hell being only a front to hide how scared he truly was. Dean denies this, but nonetheless decides to hold back on his recklessness in hunting for Sam’s sake. He still seems resigned to his death, teaching Sam a “thing or two” on working on his Impala and even celebrating Christmas since it’s his “last year”.
Dean finally comes face to face to Ruby during a witch case, who warns them to stay away considering the powerful demon they’re worshipping. Dean immediately points the Colt at her, accusing her of manipulating Sam. The two argue and Dean shoots at her, only for Sam to make him miss. He is angry at his brother defending Ruby and demands they kill her before she betrays them, but Sam is adamant on using her. Dean also confronts Sam on his growing ruthless and learns Sam is trying to “change” for this war to be “more like Dean”, worrying him.
After Dean is about to die from the powerful demon’s spell, Ruby suddenly swoops in and saves him with witchcraft. Dean begins to soften towards her, particularly after she fought against the head demon of the witches, but realizes she lied about being able to break his deal. The brothers also learn from her that all demons used to be human but had their humanity burned away in the fires of Hell. Dean realizes this will eventually happen to him when he goes to Hell and begins to show real fear of dying for the first time.
Ruby shares with them a knife that can kill demons. Dean begins to train Sam to fight demons alone for after Dean’s contract is up.
In Dream a Little Dream of Me, when Bobby falls into a coma, Sam and Dean investigate the murder of a scientist. While viewing Dean’s dreams it becomes clear that Dean believes Sam was their father’s favorite but only thought of Dean as a tool. It confirms that Dean is so resigned to death out of self-loathing and his belief that he is worthless. Dean also encounters a future, demonic version of himself in a nightmare, which shocks him into starting to fight for his life. After waking up, Dean admits to Sam that he doesn’t want to die. Meanwhile, Bela steals the Colt, meaning they won’t have it when the hellhounds come for Dean.
My father was an obsessed bastard! All that crap he put on me about protecting Sam, that was his crap. He was the one who couldn’t protect his family. He’s the one who let Mom die! He wasn’t there for Sam, I always was! He wasn’t fair! I didn’t deserve what he put on me! And I don’t deserve to go to Hell!
— Dean to himself
in Dream A Little Dream Of Me
In Mystery Spot, Sam is forced to relive the same day, a Tuesday, over and over again. On each new day, Dean dies a different way despite Sam’s frantic efforts to save him. Sam later discovers that the culprit is the Trickster, a villain from Season 2. It finally becomes Wednesday, but this time, Dean dies and doesn’t come back. Sam spends months trying to hunt down the Trickster, who reveals that he has been trying to get Sam to understand that he and Dean can’t keep making sacrifices for each other, and that Dean is going to die no matter what Sam does. The Trickster then sends Sam back to Wednesday, despite Sam failing to learn the Trickster’s lesson. Sam is warned by Ruby that Dean might not make it back from hell.
In Jus In Bello, the FBI and Agent Henriksen capture Sam and Dean, thanks to a tip from Bela. While Sam and Dean are in jail, a host of demons come to kill them. Ruby comes to help them, but is furious to learn that they have lost the Colt. She says that she knows of a spell that will destroy all the demons nearby, including herself, and that she is willing to die in order to help Sam. However, they will need the heart of a virgin. Sam and the virgin, Nancy, agree to the plan, but Dean refuses to let her die. Dean’s plan to exorcise the demons works, but one demon manages to escape and tells Lilith who, taking the form of a little girl, blows the police station up, killing everyone inside.
Lilith, it turns out, wants to kill Sam, as she sees him as a rival. According to Azazel’s plan, Sam was supposed to lead the demon army, and Ruby was ready to follow Sam. Now, Lilith has become their main enemy.
Dean and Sam do a case of people committing suicide because of phone calls from their dead loved ones’. Dean gets a call from John, who tells him the demon is holding his contract is in town and there’s an exorcism that can kill it. Despite the suspicious timing, Dean obeys the phone calls unquestionably in hopes he could be saved. In actuality, the calls were a Crocotta. Lured to a house, Dean nearly kills a man until he realizes it was a human and not a demon. After killing the monster, Dean apologizes to Sam and admits he just wanted to believe there was a chance he could’ve been saved.
I wanted to believe so badly there was a way outta this. I mean, I’m staring down the barrel at this thing. Y’know, Hell, for real, forever and I just …[…] I’m scared Sam. I really, really scared. I guess I was willing to believe anything.[…] Hope doesn’t get you jack squat. I can’t expect Dad to show up with some miracle at the last minute. I can’t expect anyone to, y’know? I mean, the only person that can get me out of this thing is me.
— Dean to Sam
in Long-Distance Call
Dean continues to search for a means to save himself from his fate, though knows there is likely no way out of it. Shortly before Dean’s contract comes due, he learns from Bela that Lilith, the demon pursuing Sam, holds his contract; Bela had also made a deal with a demon. Bela pleads with Dean that she needs help and explains everything. Dean is unsympathetic, telling they might’ve helped her if she told them sooner and leaves Bela to die by Hellhounds and dragged to Hell.
As the brothers search for Lilith with Bobby’s help, Dean begins suffering nightmares and hallucinations of his hellish fate. When Lilith is located, the three head to New Harmony, Indiana, and Dean discovers that he now has the ability to see the faces of demons underneath their human hosts.
If this is my last day on earth, I don’t want it to be socially awkward.
Dean, with 30 hours left, still desperately tries to free himself. However, Dean outright refuses to summon Ruby when Sam suggests to and reiterates he still sees her as nothing more than a liar and a manipulator. Knowing Sam would summon her anyway, Dean challenges her and uses the opportunity to steal her demon-killing knife. With help from Bobby, he discovers Lilith is in Indiana. While the trio head to Indiana, Dean discovers he can see who is possessed and can see demons, such as hellhounds. After a quick struggle with Ruby, the four manage to escape a mob of demons using holy water. Now inside the house where Lilith was hiding, the three quickly manage to locate her.
However, Dean discovers that Lilith has switched bodies as Sam is about to kill the little girl. As the clock strikes midnight, Dean smiles and tells Sam to be brave and to continue what he’s doing. The brothers and Ruby run from the hellhounds and place a salt barrier to protect themselves. However, Dean realizes Lilith is in Ruby.
Sam: “I’m not gonna let you go to Hell, Dean!” Dean: “YES, YOU ARE! Yes, you are … I’m sorry. I mean, this is all my fault. I know that. But what you’re doing, it’s not gonna save me. It’s only gonna kill you. […] Keep fighting. Take care of my wheels. Sam, remember what Dad taught you … okay? And remember what I taught you.”
Too late. The demon uses her powers to subdue the two, opening the door for the hellhounds. Sam watches as his brother is mauled to death by the hellhounds, pleading that Lilith stop. As Lilith leaves an unconscious Ruby, Sam holds the dying Dean in his hands, frantically yelling out to him.
Now in Hell, Dean is desperately yelling for help, calling out for Sam.
Dean was in Hell for a total of four months, which he later tells Sam “felt like 40 years”, as in Hell, time is different from the mortal world. He was tortured by Alastair every day, and was even offered the option to torture other souls instead. Dean refused his offer for thirty years until finally giving in, triggering the first seal to Lucifer’s Cage. Dean spent his last 10 years in Hell torturing other souls until Castiel pulls him out and declares that Dean is the only one who can stop Lilith from freeing Lucifer from Hell.
Do you even know how far off the reservation you’ve gone? How far from normal? From human?[…] Slippery slope, brother. Just wait and see. Because it’s gonna get darker and darker and God knows where it ends.[..] It’s already gone too far, Sam. If I didn’t know you … I would want to hunt you.
— Dean to Sam
The fourth season premiere, Lazarus Rising, begins four months after the third season finale. Dean awakes to find himself in a coffin and manages to dig himself out. He then breaks into a nearby gas station where he gets some water, food and cash. Before leaving the store, Dean sees the television and radio flicker on and a powerful whine that shatters the gas station’s windows. Dean calls Sam but learns that Sam’s number has been disconnected. He calls Bobby who hangs up on him. As a last resort, he hot-wires a parked car and goes to Bobby’s house. A fight ensues until Dean is able to prove to Bobby that it is really him. Dean and Bobby then find Sam in a town right near where Dean was buried—he’s in a hotel with a girl, but claims he is in town searching for a demon.
The Winchesters soon attempt to track down the force that ripped Dean from Hell. Dean is functional, albeit dazed, from his experience in Hell. He claims he has no memory of it, but it’s clear it’s a lie as he continues to get flashes of the torture. At first Dean believes Sam made a deal to save him and is furious, but Sam insists while he tried, it wasn’t him. By the end of the episode, it is revealed that an angel named Castiel pulled Dean from Hell on God’s command; Castiel tells Dean that God has work for him. The girl in Sam’s room, it turns out, is Ruby in a new vessel, and it becomes clear that Sam lied to Dean when he told him he didn’t know where Ruby was. T
In Are You There God? It’s Me, Dean Winchester, Dean is unwilling to believe angels exist and is unnerved that God ordered himself ordered him to be brought back. He becomes further disillusioned, showing contempt for God allowing all these horrible things to happen to people and not absolutely anything to stop it. During this time, the brothers are haunted by the spirits of Meg Masters, Henriksen and Ronald Reznick who want to kill them for not saving them. Bobby figures out they’re witnesses and the appearance of them is meant to be the first sign of the apocalypse. Dean, with guidance from Bobby, ultimately lays their souls to rest.
See, this is why I can’t get behind God. […] If he doesn’t exist, fine. Bad things happen to good people. That’s how it is. There’s no rhyme or reason. Just random, horrible evil. I get it, okay? I can roll with that. But if he is out there, what’s wrong with him? Where the hell is he while all these decent people are getting torn to shreds? How does he live with himself? You know, why doesn’t he help?
— Dean’s disgust with God
in Are You There God? It’s Me, Dean Winchester
Bobby’s suspicions are later confirmed by Castiel, who visits Dean in the middle of the night. He reveals the angels are trying to stop Lilith breaking the 66 Seals for if she does, Lucifer will be freed from his cage and walk the Earth. Dean believes that Lucifer is a fairy tale told in “Demon Sunday School,” but Castiel is serious and confirms Lucifer is all too real.
In In The Beginning, it takes us to 1973 where Dean learns about the Winchester history. He meets his parents, John Winchester and Mary Campbell, before he is born. Although tempted to stop Azazel from killing his mother, he realizes that he and Sam will no longer be hunters and all the people they saved will die. Dean learns that his mother was a hunter from a long line of hunters. Teaming up with his future mother and grandfather, they plan to take out Azazel with a borrowed Colt. Azazel, however, is one step ahead and possesses Samuel, Dean’s grandfather. Dean fails to stop him and the possessed elder finds John about to propose to Mary. Samuel kills John. A heartbroken Mary confirms a deal with Azazel, allowing him “permission” in 10 years. Dean arrives home shortly and realizes he can’t change destiny. Castiel warns Dean of Sam’s dark actions behind his back and they must stop before the angels have to kill him.
Your brother is headed down a dangerous road, Dean. And we don’t know where it leads. So stop it… or we will.
in Metamorphosis, Dean catches Sam exorcising a demon with his mind and discovers Ruby is still working with him. He is furious with Sam for lying and using his demon-given powers, but Sam explains he’s using it to help people. Dean is unconvinced, knowing it was only going to get darker from here. The brothers argue, but after a case of a rugaru, Dean acknowledges he was too judgmental, though stands by his uneasiness over his psychic ability. Sam suddenly tells him he was right and that he wasn’t going to use his powers anymore.
Dean continues hunting with Sam, but still suffers from flashes of his torment in Hell. It’s revealed time flows differently in Hell and he was there for “forty years” rather than four months. Despite this, he still hides this from his brother. Dean also begins to feel the weight of the angels’ special interest in him and feels more responsible for people’s lives. in Monster Movie, Dean admits while he recently resented the cost of hunting, ever since he came back from Hell he sees it as more as a “mission from God”.
In It’s the Great Pumpkin, Sam Winchester, Dean and Sam work to stop the rise of a powerful demon called Samhain, who’s presence would break one of the 66 seals. Uriel and Castiel are prepared to wipe out an entire town to stop it from happening, but both brothers refuse. The angels back down under Dean’s orders, who forces them to give them more time to stop it. Unfortunately they fail and the seal breaks, letting Samhain roam free. Sam manages to use his psychic ability to exorcise the demon, which Dean witnesses in secret.
So I failed your test, huh? I get it. But y’know what? If you waved that time-travelling magic wand of yours and we had to do it all over again, I’d make the same call. ‘Cause see, I don’t know what’s gonna happen when these seals are broken. Hell, I don’t even know what’s gonna happen tomorrow. But what I do know is that this, here? These kids, the swings, the trees … all of it is still here because of my brother and me.
— Dean to Castiel
in It’s the Great Pumpkin, Sam Winchester
In the aftermath, Castiel visits Dean and the two talk. Castiel reveals he’s not as black-and-white as the other angels and their “true” orders is to follow whatever Dean says. The choice with the town had been a test. Castiel informs Dean that a seal is still broken nonetheless and he doesn’t envy his importance in the upcoming battles.
Dean starts to become overwhelmed by all his memories of Hell, using alcohol and work as a crutch. Sam, who was told by Uriel he remembers Hell, is suspicious of his excessive drinking and tries to get Dean to tell him the truth. Eventually, Dean at last admits he remembers Hell, but refuses to open up about it, telling Sam there’s nothing he could say to make him feel better.
In I Know What You Did Last Summer, Dean and Sam hearing a young woman in a mental ward named Anna Milton who hears angels and has suspiciously accurate knowledge about the apocalypse. Sam and Dean warily protect her, knowing she didn’t seem like a bad person. However, they’re attacked by a powerful demon named Alastair, Hell’s grand torturer who Dean has a history with “downstairs”. Sam and Dean are badly wounded, but manage to get Anna to safety and escape. During this time, Dean finally learns what Sam did during the four months he was in Hell and why he suddenly trusts Ruby so much. Dean still doesn’t trust Ruby fully, but is grateful she was there for Sam. Just then, Castiel and Uriel demand for Anna to kill her.
In Heaven and Hell, both brothers refuse to hand Anna over. Anna then activates a angel banishing sigil with her blood, though doesn’t know how she knew. Sam and Dean take her to psychic Pamela Barnes to retrieve her memory and it’s revealed Anna was once an angel who “fell” for becoming too human (catching human emotions). The group tracks down Anna’s grace which will turn her into an angel again and grant protection, but the time they arrive at the location it’s already gone. During this time, Dean develops a soft spot for Anna, intrigued that she’d rather be human than an angel and relates to her unease of taking orders from an absent father.
Sam, Dean, and Ruby continue to protect Anna, but the angels raise the stakes and demand her or they’ll send Dean back to Hell. Still they refuse. Anna and Dean have a moment and have sex in the backseat of The Impala, but Uriel invades Dean’s dreams and now threaten to kill Sam. Dean reluctantly gives up their location, but demons appear too and a battle between both sides take place. With them distracted, Anna takes her grace and becomes an angel again, disappearing in a white light.
In the aftermath Dean, finally reveals to Sam what happened to him in Hell: Time flows differently there, so four months on Earth was forty years in Hell. During that time, he was “cut, carved, and torn” until there was nothing left of him, only to be made whole again just so the demons could start over. Dean reveals that at the end of every day the demon Alastair would offer to take him “off the rack” if Dean would put souls on and torture them. Dean resisted for thirty years (three months), but eventually gave in and spent ten years torturing people in Hell to escape being tortured himself. In Family Remains, Dean confesses to Sam that he enjoyed torturing souls, as he finally had the chance to dish out the same pain that he’d endured for the past thirty years.
It wasn’t four months, you know. It was four months up here, but down there…I don’t know. Time’s different. It was more like 40 years. […] They, uh…sliced and carved and tore at me in ways that you…Until there was nothing left. And then, suddenly…I would be whole again…like magic…just so they could start in all over. And Alastair…at the end of every day…every one…he would come over. And he would make me an offer to take me off the rack…if I put souls on…If I started the torturing. And every day, I told him to stick it where the sun shines. For 30 years, I told him. But then I couldn’t do it anymore, Sammy. I couldn’t. And I got off the rack. God help me, I got right off it, and I started ripping them apart. I lost count of how many souls. The — the things that I did to them. […] How I feel…this…inside me…I wish I couldn’t feel anything, Sammy. I wish I couldn’t feel a damn thing.
— Dean on his experience in Hell
in Heaven and Hell
In Death Takes a Holiday, Dean meets up again with the reaper, Tessa, who wakens his memories of their previous encounter with a kiss; Dean confesses that there has been a “hole” in him since that time and realizes that it is related to her. Soon after, Tessa is taken by Alastair in his quest to break another of the 66 seals; breaking the current seal involves killing reapers. The boys ask their psychic friend Pamela Barnes to help them astral project so that they may find the kidnapped reapers. Once they have, they are captured, but Sam is able to break them out and Tessa is able to continue reaping souls. However, before Dean is able to return to his body, Alastair corners him only to be captured by the angels; Castiel then appears and informs Dean that they have won this seal. As Dean awakes in his body, Pamela is dying from the injuries she obtained during a fight with a demon, while the boys were “out.” Dean and Sam sit beside her as she dies, but Pamela secretly whispers to Sam she “sensed” his powers and his intentions are far from pure.
Since he was Alastair’s “student” in Hell, Dean is pressed into service by Castiel and Uriel, who need him to torture Alastair for information on who is killing angels in On the Head of a Pin. Dean refuses at first, not wanting to stir his old self who tortured in Hell, but eventually agrees. Dean brutally tortures him and even seems to enjoy it, but is distracted when Alastair succeeds in getting Alastair to reveal that Dean himself was the first seal to break by virtue of giving in and torturing souls in Hell. (“The first seal shall be broken when a righteous man sheds blood in Hell. As he breaks, so shall it break.”) It was also revealed John was originally meant to break it, but even after a hundred years of torture, he still didn’t break. As a result, Dean is plagued with further guilt and self-loathing as well as the realization he still couldn’t live up to his father.
Alasdair manages to free himself, the Devil’s Trap set up by Castiel having been eroded by a leaking pipe. Alastair nearly kills Dean and then comes close to sending Castiel back to Heaven when Sam, having grown stronger in his demonic abilities, arrives and uses his powers to torture Alastair in to revealing he does not know who is killing the angels; Sam kills Alastair shortly thereafter. Later, as Dean recovers in the hospital, Castiel informs him about Uriel’s betrayal; Uriel had been killing angels who did not join his cause to free Lucifer from Hell. Castiel also confirms Alastair’s claim that Dean was the first seal, but adds that because of this, Dean is the only man capable of averting the Apocalypse. However, Dean does not believe he is able to do it and tells Castiel to find someone else as tears run down his face.
Castiel: “It’s not blame that falls on you, Dean. It’s fate. The righteous man who started it is the only one who can finish it. You have to stop it. […] I know our fate rests with you.” Dean: “Well, then you guys are screwed. I can’t do it, Cass. It’s too big. Alasdair was right. I’m not all here. I’m not-I’m not strong enough. Well, I guess I’m not the man either of our dads wanted me to be. Find someone else. It’s not me.
In It’s a Terrible Life, in an effort to put Dean back on the “right path,” Zachariah, Castiel’s superior, re-writes Dean and Sam’s memories to remove their knowledge of supernatural creatures, making them believe they are average people working regular jobs, and drops them in a haunted building. Ironically, Dean, unlike Sam, is the one who most rebels against life hunting monsters, but eventually realizes he wasn’t meant for his normal job. After the brothers proceed to defeat the ghost behind the hauntings, Zachariah (who posed as Dean’s boss) restores Dean’s memories to show him that hunting is in his blood. This only renews Dean’s resolve.
In the episode The Monster at the End of This Book, Dean and Sam discover their lives were turned into a book series called “Supernatural” by a prophet named Chuck Shurley and that he had a vision of Lilith coming to town and about to sleep with Sam. While Sam wants to use it as a plan to kill Lilith, Dean refuses and knows they’re not ready to kill her. Dean admits he doesn’t trust Sam, that he knows that he killed Alastair, but not how and is afraid he’ll turn evil. He enlists Castiel for help and the angel suggests he uses Chuck as bait. Dean brings Chuck to the motel room where Lilith is. Her presence near Chuck summons an archangel. Lilith is thus forced to flee. Sam tells Dean the vision was Lilith making a deal with him–the deal was they both die and she doesn’t break any more seals (it’s written she doesn’t survive the apocalypse)–but he refused it on the grounds of not trusting her. Dean doubts his sincerity, knowing demons rarely break contracts, and fears Sam might now value revenge more than self-sacrifice.
In The Rapture, Castiel contacts Dean in his dreams to warn him about something, but is expelled from his vessel Jimmy Novak and sent back to Heaven for his near-rebellion. Dean later witnesses Sam drink the blood of a demon in the midst of battle and then promptly exorcise a demon possessing Amelia Novak, discovering the source of his power. Meanwhile, Castiel, now restored in his true vessel, dismisses his warning to Dean and that his allegiance lies only with Heaven. Later in the Impala, Sam receives a request to go to Bobby’s house. Once there, they trick Sam and lock him in Bobby’s panic room to detox him from the demon blood.
While Sam is going through painful withdrawal symptoms from the demon blood, Dean asks Castiel for help. He takes an oath to serve God and the angels if it would mean that Sam wouldn’t have to kill Lilith. Sam escapes the panic room after Castiel releases him, and Dean tracks him down to a hotel, despite Sam’s efforts to shake him. They argue over whether or not Ruby is corrupting Sam, if Dean is supposed to stop the Apocalypse, and if Sam is turning into a monster. The argument leads to a fight that Sam wins. On the floor and in pain, Dean calls to Sam, “If you walk out that door, don’t you ever come back” — the same ultimatum John gave Sam when he left for college years before — after which Sam leaves the room.
She’s poison, Sam! Look what she did to you. I mean, she up and vanishes weeks at a time, leaving you cracking for another hit. […] That is French for manipulating your ass ten ways from Sunday! […] You don’t know what you’re doing, Sam. […] Because it’s not something you’re doing, it’s what you are! It means … it means you’re a monster.
— Dean’a anguish at Sam’s choices
in When the Levee Breaks
Dean swears his alliance to serve Christ and is then held captive by Zachariah. Dean realizes the angels never wanted to stop the Apocalypse and that they want to free Lucifer to destroy him. Dean does have a “destiny”, but only to stop Lucifer. A paradise will exist once Lucifer is destroyed, but at the cost of thousands of lives. Sam as well plays a part. Dean horrified at their lack of concern for the lives of innocent people and is desperate to get free. Castiel, after much resisting, admits Lilith is the final seal and rebels to give Dean a chance to escape. Dean goes after Sam, but arrives too late. Ruby, who had been manipulating Sam all along for this moment, is later killed by Dean. Sam, ashamed and broken beyond description, apologizes. The season ends with Sam and Dean watching as Lucifer rises and the Apocalypse begins.
Destiny? Don’t give me that destiny crap. It’s all a bunch of lies, you poor, stupid, son of a bitch! It’s just a way for your bosses to keep me and keep you in line. You know what’s real? People. Families. That’s real. And you’re gonna watch them all burn? […] You can take your peace and shove it up your lily-white ass. ‘Cause I’ll take the pain and the guilt. I’ll even take Sam as is. It’s a lot better than being some Stepford bitch in paradise!
Dean: “It’s my job. Somebody has to save people’s asses’, yours included. […] I mean, it’s a damn biblical Apocalypse, and if I don’t stop it and save everyone, then no one will and we all die.” Dr.Carthwright: “That’s horrible. […] I mean, apocalypse or no apocalypse, monsters or no monsters … that’s a crushing weight to have on your shoulders. To feel like six billion lives depend on you … God. How do you get up in the morning?” Dean: ” … That’s a good question.”
The fifth season picks up right where season 4 ends when the portal to Hell opens. As Lucifer escapes, the brothers are teleported into an airplane by an unknown force (later revealed to be God). Bobby gets possessed by a demon and instead of killing Dean he kills the demon inside himself, using Ruby’s knife, in turn paralyzing himself from the waist down. Dean is told by Zachariah that he is the “Sword of Michael”, which means the Archangel Michael will use his body as a vessel to lead the forces of heaven, but Dean must consent to this. Dean refuses and Castiel saves him when Zachariah tries to force Dean to agree by harming him and Sam. Castiel brands them with an Enochian Sigil, hiding them from all demons and angels, Lucifer included. Dean’s relationship with Sam is severely damaged by Sam starting to Apocalypse and eventually he admits to him he doesn’t think he can trust him the way he did ever again.
Dean and Sam fight the HorsemanWar in a town where the people think that their neighbors are demons. In this town are Ellen, Jo, and Rufus all trying to hunt the demons, who turn out to be normal people War has altered to make look like demons. Once the brothers cut the ring finger off of war, sending the town back to normal, Dean worries that Sam cannot control his urge to drink demon blood. The brothers then agree to go their separate ways because Sam is a liability with his demon blood lust. Later, Castiel finds Dean and they capture the ArchangelRaphael to ask the location of God. Dean also grows closer to Castiel, admitting he had more fun with him in 24 hours than he had with Sam in years.
In The End, Dean is transported five years in the future by Zachariah to the year 2014. He meets his future self, a hardened and cynical leader leading a ragtag group of Croatoan Virus survivors in a post-apocalyptic world. Present Dean realizes Sam said “yes” to Lucifer and that Future Dean’s biggest regret was never agreeing to Michael to stop all this from happening. Dean is shocked at his future self’s ruthless, both in torture and willingness to sacrifice his friends to defeat the devil, but Future Dean recklessly goes ahead with his plan to use The Colt on Lucifer, only to die at his hands. Lucifer tells present Dean nothing will change this outcome before he is brought back to present. Despite Zachariah and Future Dean’s protests, Dean still refuses to become Michael’s vessel. Nonetheless shaken by his grim future, Dean calls Sam and decides they should stay together to “keep each other human”.
In the episode Changing Channels, the brothers are thrown in an alternate universe where they’re in TV shows and have to “play their roles”. It’s revealed this had been another “lesson” to “accept” their roles as Michael and Lucifer and that the Trickster they know had actually been the archangel Gabriel all along. Dean and Sam learn that their relationship (Dean, the older brother loyal to an absent father, and Sam the younger brother, rebellious to the father’s plan) mirrored the relationship between Lucifer and Michael and that was only further proof there was no stopping their “destiny”. Sam and Dean still refuse, though began to doubt how they’ll be able to stop the “inevitable”.
No, we’re not. ‘Cause we don’t screw with people the way you do. And for the record, this isn’t about some prized fight between your brothers or some destiny that can’t be stopped. This is about you being too afraid to stand up to your family! Don’t say I never did anything for you.
— Dean to Gabriel
in Changing Channels
Sam and Dean learn from the Becky the Colt is in possession of a demon named Crowley, who gives the Winchesters the gun to kill Lucifer and end the Apocalypse. Sam and Dean spent their “last night on Earth” with Jo, Ellen, Castiel and Bobby before setting out to find and kill Lucifer the next day. While looking for Lucifer in Carthage, Missouri, Castiel sees reapers all over the town and is later captured by Lucifer while investigating. The hunters run into Meg, who sicks a pack of hellhounds on the group. Jo is severely injured by one of the hellhounds during their escape while saving Dean.
The group finds shelter in a hardware store where they make bombs out of rock salt and iron nails to kill the hellhounds. Jo plans on setting off the bomb since she is going to die anyways, but Ellen insists on staying with Jo and both die in the blast. Sam and Dean find Lucifer performing his ritual. Dean manages to shoot Lucifer point-blank with the Colt, only to find it has no affect. The Winchesters find out Lucifer is one of the five things in the world the Colt cannot kill. The brothers return home and both grieve with Bobby for Ellen and Jo. Having failed to kill Lucifer and lost two allies and friends, Dean becomes more disillusioned and hopeless.
Sam and Dean check themselves in a mental institution to hunt a monster for their old friend Martin. Dean admits he feels personally responsible for the lives of everyone, not just a few. It’s indicted in the hallucinations the wraith conjures for him that this mostly driven out of his own self-loathing enhanced by Jo and Ellen’s death along with his failure to kill Lucifer, believing that he can never save anyone and always fails. The brother manage to kill the wraith and break out of the institution.
When Anna travels back in the year 1978 to kill John and Mary, resolving to prevent the Winchesters’ birth to stop the Apocalypse and Lucifer, Sam and Dean follow her with help of Castiel. The brothers work with their younger parents, but Anna enlists the help of a past Uriel and soon catches up with them. Dean struggles against Uriel. Ultimately, Anna succeeds in landing a fatal blow on Sam, but Michael at last appears (in John’s body) and burns her alive. Dean and Michael then talk. Dean discovers that his whole bloodline are possible vessels dating back to Cain and Abel (their ancestors), but he is Michael’s true vessel. Michael appeals to Dean that he can relate to him for his love to his little brother, but he still has to kill Lucifer for his father. Dean doesn’t like the idea but Michael counters saying everything happened due to destiny, and that free will is an illusion. Michael resurrects Sam and sends the brothers back to the future.
Under pressure of his “destiny” combined with his responsibility for the Apocalypse and repeated losses, Dean is gradually driven into depression. After the Horseman Famine plagues a town and affects everyone with insatiable hunger (money, sex, food, etc.), Dean is the only one unaffected. It’s indicated by Famine that Dean is so broken and defeated, he’s too “dead inside” to want anything. Sam manages to defeat Famine with his psychic powers after feeding on demons due to his effect, but is quickly locked away by Dean and Castiel in Bobby’s panic room again. This triggers Dean to break down and pray to God for help.
That is one deep, dark nothing you got there, Dean. Can’t fill it, can’t you? Not with food or drink. Not even with sex. […] I can see inside you, Dean. I can see how broken you are, how defeated. You can’t win, and you know it. But you just keep fighting. Keep … going through the motions. You’re not hungry, Dean. Because inside … you’re already dead.
— Famine to Dean
in My Bloody Valentine
In Dark Side of the Moon, Dean and Sam are shot by hunters and sent to Heaven. They discover Heaven is just a collection of the person’s best memories and that they’ve both been there before (the angels having removed their memories). Dean is upset by Sam’s “heaven” being of memories away from him while Dean’s is the exact opposite. Sam and Dean meet Joshua—an angel that ‘talks’ to God— who tells them God’s message is to stop looking for him. He could do something to stop the apocalypse, but he won’t. Dean is deeply upset, as God had been his last hope.
Sam and Dean return to Earth in their bodies, this time with memories of their experience in Heaven. Dean, losing faith knowing God doesn’t see the battle with Lucifer to be ‘his’ problem, throws out the amulet Sam gave him and starts to see no way out of his destiny as Michael’s vessel.
During Point of No Return, Dean prepares for his possession by Michael before he’s found by Sam and Castiel who return him to Bobby’s house. Dean justifies he can’t bear the guilt of the whole world burning if he didn’t agree and later admits to Sam he doesn’t trust him enough to say no to Lucifer forever. If anyone will stop him, it would have to be him. They convince Dean to allow them some more time in order to research another method of stopping Lucifer; however, the resurrection of their brother Adam Milligan (who agreed to be Michael’s vessel) forces Sam, Bobby and Castiel to keep both Adam and Dean from Zachariah. When Dean escapes and tries to lure the angels, both Castiel and Sam leave to find him, allowing Adam to be removed by angels.
Despite Bobby and Castiel’s insistence on keeping Dean from Zachariah, Sam allows him to try to rescue Adam. Castiel dispatches the angelic guards and the brothers attempt to rescue Adam, but Sam’s ambush on Zachariah fails and Zachariah causes internal damage to both Adam and Sam to coerce Dean to consent to Michael. Ultimately, he relents, but after Zachariah summons Michael, Dean taunts him into sacrificing himself in order to allow Michael in. Zachariah angrily refuses, and Dean stabs him and ushers his brothers out of the room. Unfortunately Adam does not escape in time and is locked in the room with the approaching Michael. As they leave, Dean admits that he would have accepted Michael, but because of Sam’s faith he decides that he will “take the fight to them”.
I don’t know if it’s being a big brother or what, but to me, you’ve always been this snot-nosed kid that I’ve had to keep on the straight and narrow. I think we both know that’s not you anymore. I mean, hell, if you’re grown up enough to find faith in me, the least I can do is return the favor. So screw destiny right in the face. I say we take the fight to them and do it our way.
— Dean changing his mind about being Michael‘s vessel
in Point of No Return
In Hammer of the Gods, when Dean and Sam are forced to help several other deities against Lucifer, they team up with Gabriel, who finally decided to support their side. They manage to lure Lucifer to their location, but Gabriel is the one that faces him and ultimately dies in the process. Despite, Gabriel gives them the first real key to defeating Lucifer: find the four “keys” to Lucifer’s Cage before luring him there and sealing him back in his cage. The four “keys” are revealed as the four rings of the Horsemen. The brothers already have two from War and Famine so set up to find the last two.
Dean and Sam, with help of the Crowley and a now human Castiel, face off against the Horsemen Pestilence and manage to get his ring. However, trouble brews in Chicago from an epidemic of the Croatoan Virus. Dean locates the last Horsemen, Death, who gives his ring to Dean in hopes of locking Lucifer back in his cage. He’s “chained” to Lucifer and wants to be free of him. Sam proposes he say yes, somehow takes control of Lucifer, and throw himself in the cage—sacrificing himself to stop the Apocalypse. Dean opposes it, finding it risky and unwilling to sacrifice his brother, but Sam still believes his choice is right. Bobby talks to Dean, telling him to have faith in his brother whatever happens.
I’m not gonna lie to you though. It goes against every fiber I got. I mean, truth is …You know, watching out for you … it’s been kinda my job, you know? But more than that … it’s kinda who I am. You’re not a kid anymore, Sam, and I can’t keep treating you like one. Maybe I gotta grow up a little too. I don’t know if we got a snowball’s chance. But … but I do know, that if anybody can do it .. it’s you.
— Dean agreeing with Sam’s plan for Lucifer
in Swan Song
It is reluctantly decided that the plan to throw Lucifer back in the cage requires Sam to become Lucifer’s vessel. Dean knows he will lose his brother, but tries have faith in him and respects his choice. Once Sam says “yes” to Lucifer, the archangel takes Sam over and closes the portal with ease. He leaves Dean alive as he leaves to go fight his older brother, Michael, who is now in Adam’s body.
Just as Lucifer and Michael are about to begin, Dean shows up in the Impala to witness the fight as if to try and stop the inevitable one last time. Having had enough of Dean’s attempts to save Sam, Lucifer goes on a rampage and begins to beat Dean to a bloody pulp. Lucifer kills Castiel and Bobby as he continues to beat Dean until Sam is able to regain control long enough to open the portal to Lucifer’s cage. Sam grabs hold of Michael and falls into the cage. The portal is then sealed, leaving nothing behind but the key. Castiel, now a seraph returns from the dead, having been resurrected by God, heals Dean and resurrects Bobby. Dean is heartbroken at having lost Sam and resentful towards God for letting all of this happen. Since Michael is no longer in Heaven, Castiel disappears to restore order.
Dean: “He brought you back. But what about Sam? What about me, huh? Where’s my grand prize? All I got is my brother in a hole!” Castiel: “You got what you asked for, Dean. No paradise. No hell. Just more of the same. I mean it, Dean. What would you rather have? Peace? Or freedom?
Dean gives a goodbye to Castiel and Bobby, but cuts contact off them for a very long time. In the end, Dean keeps the promise Sam wanted for him: to not resurrect him, quit hunting, and go to live with Lisa and Ben. Unknown to him, Sam watches outside in the last scene, having been released from the cage.
Dean didn’t want Cass to save him. Every part of him, every fiber he’s got wants to die or find a way to bring Sam back. But he’s not gonna do either. Because he made a promise.
Do you have any idea what walking away meant for me? […] I showed up at their doorstep half out of my head with grief. God know why they even let me in. I drank too much. I had nightmares. I looked everywhere. I collected hundreds of books, trying to find anything to bust you out. […] A damn year?! You couldn’t put me out of my misery?!
in Exile on Main Street
One year later, Dean is living a normal life with Lisa and Ben, having a normal job and having the Impala covered up with his weapons locked away in the garage. He seems somewhat happy, though still struggles with his grief over losing Sam. Despite retiring, he retains his old hunting habits such as keeping guns handy, hiding a Devil’s Trap under Lisa’s rug, and sleeping with salt and holy water under his bed. Dean’s “apple pie” life is halted when he notices supernatural occurrences around his neighborhood. As he prepares to fight, he has an impossible encounter with Azazel, but it turns out to be a hallucination created by Djinns and he is snapped out of it by none other than his brother, Sam. Dean is happy to see Sam alive but is soon enraged when he learns that Sam has been out of Lucifer’s cage and back on earth for over a year and didn’t tell him. Dean’s “normal life” was far from happy, ranging from having frequent nightmares to excessively drinking. It’s revealed he tried finding ways for Sam to get out his Cage despite Sam telling him not to. Soon, he is reunited with his resurrected grandfather Samuel Campbell and other members of the Campbell Family. Dean is distrustful of Sam and Samuel both being brought back and by extension greatly distrusts the Campbells.
Dean takes Lisa and Ben to
Bobby’s for safety, and discovers that Bobby knew Sam was back as well and didn’t tell him. Dean and Sam use themselves as bait to lure the djinns in but Dean becomes affected again with hallucinations of Azazel killing Lisa and feeding Ben demon blood. Sam is able to snap Dean out of it as the Djinn are captured. Sam leaves after Dean decides to stay with Lisa and Ben.Dean relocates Lisa and Ben to a different home and starts acting like his father, getting on edge and limiting their movements to ‘protect them’. He is called back to hunting when Sam finds an abandoned baby from a crime scene, and needs help taking care of it. They take the baby to Samuel, where Dean is distrustful of the Campbells. Samuel wants to raise the baby as a hunter which infuriates Dean, but before they can discuss it any further, the Alpha Shifter arrives and kills one of the cousins, also taking down the rest of the Campbells. Then the Alpha defeats Sam and Dean and takes the baby. Dean returns to Lisa and Ben but is conflicted with staying or hunting with Sam. Despite the previous pressure of his hunting life, Dean is still too much of a hunter at his core and can’t so easily mesh into a “normal life”. Lisa forces him to accept this and suggests a compromise: he can go hunting and come back whenever he can. He agrees and gets the Impala out of the garage.
Lisa: “Maybe we’re safer with you here, maybe gone. I don’t know. The one thing I do know is you’re not a construction worker. You’re a hunter. And now you know your brother’s out here, things are different. You don’t want to be here, Dean.” Dean: “Yes, I do.” Lisa: “Okay, but you also want to be there. I get it. You’re white-knuckling, living like this. Like what you are is some bad, awful thing. But you’re not. But I’m not going to have this discussion every time you leave. And this is just going to keep happening so I need you to go. […] Me and Ben will be here and you come when you can. Just come in one piece, okay?”
Dean is called to a case by Sam to investigate the mysterious deaths of several cops. Dean suggests they call Castiel, but Sam doesn’t believe he’ll come. To his surprise, Castiel responds to Dean’s call and tells them that the staff of Moses is responsible for the deaths. He also informs them that heaven is embroiled in a civil war as Raphael is trying to take over and resume the Apocalypse that Sam and Dean prevented.
They find the child responsible for the deaths and discover that he sold his soul to an angel for the staff. Castiel soul probes the child against Dean’s wishes but with Sam’s consent. The angel Balthazar is responsible for the transaction
and Castiel tracks him down, with Dean and Sam staying behind and fighting Raphael’s angel henchmen who have been hunting Cass. They help Castiel trap Balthazar after Raphael is defeated and force him to relinquish the child’s soul. Afterwards, Sam joins Dean in the Impala again as his own car was destroyed, and Dean questions Sam’s strange behavior and his time in hell, but Sam doesn’t want to talk about it at all.In Weekend At Bobby’s, Dean calls Bobby for help with a Lamia. Dean continues to grow more unsettled over Sam’s strange behavior and calls Bobby to talk to him about it. Bobby yells at Dean for being selfish and oblivious to Bobby’s own problems. Abashed, Dean flies to Scotland with Sam in an effort to help get Bobby’s soul back from Crowley. Crowley is forced to give him back his soul and the brothers fly back to America.
Sam and Dean investigate what appears to be a vampire attack, and Dean becomes entangled with the vampire Boris. Sam walks by as Boris attacks Dean, but merely watches as Boris turns Dean into a vampire. Dean notices Sam isn’t freaked out about his vampirism, as he can hear Sam’s steady heartbeat. Sam tries to reason with Dean, assuring him that Samuel will know what to do. Dean then decides to sneak out to visit Lisa in order to say one last goodbye. While visiting, Dean struggles with his bloodlust for Lisa. He comes close to biting her, but retreats into the hallway. As he is leaving Ben approaches Dean despite Dean’s warnings, and Dean shoves Ben into the wall in an effort to put some distance between them. He then leaves and returns to the motel.
Upon Samuel’s arrival, Dean demands that he kill him, but Samuel refuses and informs him that there is a cure for vampirism. As long as Dean hasn’t fed, then the cure can turn him back. The cure requires blood from the vampire who turned you, so Dean infiltrates the nest, and encounters Boris, who explains to him the vampires’ aim. When Boris smells the dead man’s blood drop from Dean’s syringe, he attacks. Before the vampire can make his move, all the vampires in the nest collapse, including Dean. He has a vision of the Alpha Vampire.
When he awakens, Boris is rallying the coven of the vampire to attack Dean. Dean, however, has the upper hand and takes out the entire nest single-handedly, including Boris. Back at the motel, Dean drinks the cure, and goes through a painful process of turning back. His short time as a vampire flashes before him, highlighting Sam’s hesitation to save him from Boris. Dean now has lost trust in his brother completely.
Dean becomes so uncomfortable around Sam, beginning making excuses to stay away from him. He informs Bobby of the situation, and digs up information on whatever could possibly be Sam’s diagnosis. He then asks aloud for the truth, and is infected with a truth curse from the goddess Veritas where people tell truths to him against their will. Sam, however, proves to be immune to this, as the curse doesn’t affect him and lies to him. Dean believes Sam and feels guilty for suspecting his brother. During this time, Dean’s relationship with Lisa ends permanently, as she is unable to deal with his issues stemming from his hunting life and his co-dependence on Sam. In a confrontation with Veritas, Dean admits to her truth spell he did want a family, but now sees himself self-deprecatingly as only being good at hunting and could never be normal. During this, Dean also learns Sam is immune to her truth affect and calls him not human. He loses complete trust in him and puts a knife on his brother. This time, Sam comes clean, fessing up to allowing him to become a vampire to get closer to the alpha and his chilling inability to feel anything ever since he got out of the cage, including the safety of his brother. Dean, emotional, processes the truth about Sam, and responds with beating Sam unconscious.
It’s the gig. You’re covered in blood until you’re covered in your own blood. Half the time, you’re about to die. Like right now. I told myself I wanted out … that I wanted a family. […] But what I’m good at … is slicing throats. I ain’t a father. I’m a killer. And there’s no changing that. I know that now.
— Dean’s self-deprecation
in You Can’t Handle The Truth
Dean takes matters into his own hands, and calls Castiel for assistance with diagnosing Sam. Castiel confirms that Sam has no soul, and that it is still in the cage with Michael and Lucifer. Dean intends on holding Sam in the motel room, but when Sam unties the bonds he’s in and refuses, Dean states he’ll be watching every move he makes, which Sam agrees to. The two brothers then chase the only lead they have towards Sam’s soullessness: Samuel. Samuel has a lead on the Alpha vampire, and Dean volunteers himself and Sam to join the hunt. Samuel reluctantly lets Dean join the hunt.
Dean is left with Gwen to stand guard while Sam joins the other Campbells on the hunt. Dean sneaks away
and catches Sam helping Samuel and a few other Campbells loading the Alpha vampire into the van. He later confronts Sam about it, and Sam admits that keeping this from Dean was his own idea because they needed to interrogate creatures, and apparently Dean ‘messes it up’. Dean is furious about Sam’s lack of instinct, and gives him two options: to work with him, or to go off with Samuel and see how that goes. Dean is shocked when Sam comes back, admitting he gave it a 60/40 prediction of whether his brother would come back.
Sam and Dean follow Samuel via his cell phone’s GPS to a warehouse where they are holding the Alpha vampire. When Samuel leaves the room, the brothers take the opportunity to question the creature themselves. The Alpha remembers Dean even by name, referring to him as ‘his child for a time’. When the brothers ask the Alpha what Samuel wants from him, the vampire reveals that it is Purgatory Samuel is looking for and that Samuel is merely working for someone else. Dean confronts Samuel about it, but is interrupted by the escape of the Alpha. Christian, revealed as a demon, and a few other demons recapture the Alpha and take it away.
Crowley appears on the scene, and reveals that he’s Samuel’s boss, and is the one who’s looking for Purgatory. He is also responsible from raising both Samuel and Sam, and is in possession of Sam’s soul. If they cooperate, Sam gets his soul back. If they don’t, Crowley shoves Sam back in Lucifer’s cage.
Dean is reluctant to work for Crowley, but Sam convinces him it’s the only way they’ll find a way to get his soul back. Dean is still not convinced that Sam is his brother, and later admits that he doesn’t know what he is. When Sam states that he thinks it might be best to go back to being the old Sam, Dean accepts his offer, and says it’s ‘time to get his brother back.’
Dean and Sam are more on the same page now, but Dean still seems to struggle with Sam’s behavior and then starts to act as his ‘Jiminy Cricket’ to Sam’s ‘Pinocchio’. They investigate a case of crop circle abductions, leading people to believe it is a UFO sighting. Dean decides to check out the crop circles for himself, but gets abducted.
He returns a while later, and walks in on Sam having sex with a hippie chick. Dean expresses irritation at this, and states that he ‘had a close encounter, and won it’. However, it’s proven that he didn’t exactly ‘win’ anything, as he starts seeing things that no one else can see. There’s one moment when Dean’s alone, and the door to the motel bursts open and a “little, glowing, hot, naked lady” flies in and starts hitting him. He traps her in the microwave and cooks her, but when he tries to show Sam her remains, Sam can’t see them. Sam then draws the conclusion that the UFO encounters are because of Fairies.
Dean and Sam go to visit Marion, a woman they interviewed earlier who had said that fairies were behind the disappearances. She tells them all about fairies, including that they like cream and that they must count every grain of salt or sugar that is spilled in front of them. After they leave, they see Mr. Brennan loading boxes of cream into his car. Dean breaks into his shop and sees elves working on watches for him. Afterwards, Dean is being stalked by a fairy, a Red Cap in particular, and he mistakenly tackles a midget and is arrested for a hate crime. While in jail, Dean was being beaten by the Red Cap in his jail cell, but is saved by Sam in time and is released from jail the next morning. The midget, who was also the district attorney for Tipton county, dropped the charges against him. Dean learns that the leprechaun struck terms of making a deal with Sam, to lift his soul from the cage (and make him a ‘real boy’). He questions Sam’s way of thinking, and wonders if Sam is having second thoughts.
Dean quickly becomes tired of working for Crowley, as he sees that it’s not getting them anywhere. He tries to reason with Sam that Crowley may not keep his end, but Sam has left the room. When Dean slowly walks the motel room looking for Sam, he gets knocked out by demons, led by none other than Meg. Dean responds emotionally, saying he’s been dying to see her again to get back at her for being responsible of Ellen and Jo’s deaths. Meg seemingly approves of this, but not before demanding where their “boss” is. While neither of the brothers answer, she puts a knife to Dean’s neck, getting impatient. Sam, however, merely laughs at her, and reassures Dean that she can’t kill them because she needs them to get her to Crowley so she could kill him. Dean says he hopes they both lose. Sam suggests that she works with them and makes a deal with her, which Dean is not in favor of.
When the demons leave, he confronts Sam about it. He is unsure whether working with a demon again will go anywhere good, and their tendencies to double-cross work against them. Sam assures Dean that they will get the jump on the demons first because he’ll be bringing Castiel along for the ride. Dean expresses surprise when Sam actually succeeds in calling the angel.
When Castiel performs a ritual to find Crowley’s location and can’t find him, Dean suggests they search Samuel’s office for a map or any hint on Crowley’s base. They are interrupted by Samuel. Dean first suggests that Samuel tells them where Crowley is, which he refuses to do. When all his attempts to obtain the information lead to nothing, Dean consents to ask Samuel what Crowley is holding over him. Samuel takes a picture out of his desk drawer, and hands it to Dean: it’s a picture of their mother, Mary. Dean expresses a somber opposition towards working with Crowley to bring Mary back, and tries to convince Samuel to learn from the brothers’ mistakes. When Samuel’s had enough of his protests, he asks them to leave. Samuel later knocks on their door to give them the location, despite his wishing for them not to go there.
Before they leave for the prison, Castiel talks to Dean about how he doesn’t think retrieving Sam’s soul is wise. He believes that Sam will be broken beyond repair if they force his “mutilated” soul back in. Dean doesn’t want to believe this, and reassures Castiel that they’ll deal with whatever complications come up.
Upon arriving and infiltrating the prison, Dean expresses apprehension on how easy it was getting in, which then comes to fruition when the guards are let out and come after the group. When Meg decides to stay behind to hold off the hounds, Dean, Sam, and Castiel head further in the prison in search for Crowley. Castiel is banished by Samuel, much to Dean’s surprise, and the brothers are locked in separate cells by demons. When Samuel later tries to make Dean understand, the two express different ways of seeing the betrayal: Samuel saw it as Dean choosing Sam over Mary, while Dean saw it as Samuel choosing Crowley over his own grandsons. He also challenges Samuel that he’s going to escape from the prison and the next time he meets Samuel, he’ll kill him. Demons then let him out his cell to be taken to a bigger cell to be eaten alive by Ghouls. Dean fights back, but to no avail. Sam later busts in and kills the ghouls.
Dean then finds where Christian has Meg, kills Christian, and then sets off the fire alarm to get Crowley’s attention. When the King of Hell enters the room, the brothers confront him and demand he return Sam’s soul. Crowley says he can’t, and that he was lucky enough to get his body out of the cage. Crowley breaks from the devil’s trap, and flings Sam and Dean pinned to the wall. Castiel soon arrives on the scene and rescues them.
Later, outside the prison, Dean thanks Castiel for his help. Castiel tells Dean about the civil war in Heaven, and Dean is genuinely concerned, and asks if there’s anything they can do to help. When the angel says there’s nothing they can do and apologizes, Dean reassures him that there’s no need to apologize, that they understand and are his friends. Dean tries to reason with Sam, who now has second thoughts on all this trouble for his soul, saying that he doesn’t know how wrong, how messed up he is without a soul. Sam disagrees and walks away without a word.
Dean, now more desperate than ever for Sam’s soul, seeks out Death to ask for his help. Dean requests not only for Sam’s soul, but for their half-brother Adam as well (Death however forces Dean to pick one, in which he chooses Sam). Death hints he has the power to jailbreak Lucifer’s cage, and makes a wager with Dean: he will restore Sam’s soul if Dean agrees to be Death for a day. He also says he will be able to put a mental wall inside Sam’s mind to hold back the memories of the cage, as he also confirms that the results of those memories (or of the wall collapsing) would be fatal. Before the horseman can explain why he wants this from Dean, he is resurrected by Dr. Robert.
Dean informs Sam and Bobby on his deal with Death. Sam is very adamant about keeping his soul out of his body, but later backs down and gives Dean false hope not to mess up. Dean, still very suspicious of his soulless brother, tells Bobby to watch him while he’s gone.
Dean slips on Death’s ring, giving him some of Death’s powers and effectively taking his place for 24 hours. The reaper Tessa is assigned to keep an eye on Dean to make sure he has the “minimum screw-up”, despite her dislike for Dean’s habits of throwing a wrench in everything. Dean does a fair job and kills a few people with a simple touch, following Tessa’s list of people, but becomes hesitant when he is supposed to kill a 12-year-old girl. He refuses to kill her, but this sets up a chain of events. The girl survives, but innocent people die in her place as she is disrupting the natural order being alive. Dean tries to save one of these innocent people, going as far as taking off Death’s ring. Realizing the mistake he’s made, he reluctantly accepts defeat, and finally decides to kill the girl.
Meanwhile, Sam has tied Bobby up and intends to kill him. Dean manages to arrive in time and knocks Sam out and chains him to the cot in the panic room. Dean expresses deep sadness at how he’s failed to fulfill his lifelong promise of saving his brother: this replicant of Sam could not stay alive; he’s dangerous, he’s cold, and he’s capable of anything.
Dean leaves the basement to let his defeat sink in, and finds Death eating. Dean gives back the horseman’s ring, and claims his loss of their wager. Dean then informs him that his wager was rigged right from the start, as he thinks Death would’ve known he wouldn’t last a day. Death denies this, and declares their business is finished, but he offers a bonus: he will still go to Hell to raise Sam’s soul. He then encourages Dean to keep digging in what he’s learning regarding the souls.
Dean quickly heads to the panic room, as they witness Sam struggling to stay away from Death, who has returned with Sam’s soul. Despite Sam’s protests, Death restores Sam’s soul to his body, with a conflicted Dean watching as his brother screams in pain. A week passes and Sam has still not woken up. During this time, Dean calls Castiel to check on Sam and asks if Cass thinks Sam will ever wake up. Castiel tells Dean that he doesn’t think so, leaving Dean alone. Dean heads up stairs and Bobby offers him a drink and a case. Then, to Dean’s joy, Sam wakes up and gives Dean a hug, as well as Bobby. Sam later reveals to Dean that he doesn’t remember anything other than jumping into the cage. Dean is surprised but relieved to hear this, despite Bobby’s suspicion. Dean and Sam go to work on a case involving dragons, during which Dean is overjoyed to have his brother back.
When Bobby finds a sword that could kill the dragons, he sends Dean goes to visit Dr. Visyak. When Dean tries to pull the sword from the stone he only falls off, and has to resort to blowing up the stone instead. He returns to Sam and the two go after the dragons. They fight off the dragons and save the girls they had held captive. Later on as Dean is happily going through the pile of gold they found at the dragon lair, Sam confronts him about being soulless and apologizes to Dean. Dean is shocked that Sam knows and asks who told Sam (who then answers that it was Castiel). Dean tells Sam about the wall inside his head, and that what Sam became wasn’t really him.
Then Sam gets a mysterious text message about a case, which gets Dean worried. As they investigate, Dean finds out that Sam has been in this town before, and wants to leave. Sam doesn’t want to, which makes Dean angry and he begins to quote John’s rules. But they stick around, and Sam begins remembering what happened, much to Dean’s displeasure. They do figure out its an Arachne with a grudge against Sam, and defeat it. Afterwards, Sam and Dean have a talk about what happened and Dean tries to make Sam feel better. Then Sam collapses, and Dean rushes to Sam calling his name.
Minutes pass by as a worried Dean tries to wake Sam up. Sam does wake up and Dean helps him up. Dean and Sam talk about what just happened and Dean tells Sam not to scratch the wall again. With that they head out on a case with a mannequin killing people, but Dean gets called away by an “emergency” call from Ben. When Dean arrives, he finds Lisa going out on a date. He and Lisa have a talk, which later results in him leaving permanently. When he comes back, he helps Sam finish the case.
Then things take a turn for the weird when Balthazar shows up with someone on his tail. He gives Dean a “key” and sends the two into the world of “Jared” and “Jensen”, where their lives are a television show. After a great deal of effort and in end derailing the entire TV show by “quitting” and telling off Bob Singer, they manage to get back to their own world. Castiel informs them he has Balthazar’s weapons now.
You heard my brother. That’s right, I said “brother”. ‘Cause you know what, Bob? We’re not actors. We’re hunters. We’re the Winchesters. Always have been and always will be. And where we’re from, people don’t know who we are. But you know what? We mattered in that world. In fact, we even saved the son of bitch once or twice. And yeah, okay, here maybe there’s some—some fans that give a crap about this nonsense. But Bob Singer – if that even is your name – tell me this. What does it all mean?
— Dean telling off Robert Singer in an alternate universe
in The French Mistake
Later on, Dean runs into Samuel again, and it takes Sam and Bobby to hold him back from fulfilling his promise of killing Samuel. In the hall, Gwen goes out to talk to him, and Dean shoots her. It turns out, Dean was possessed by Eve‘s latest invention. Unsure who its possessing, the group rid themselves of their weapons. In a turn of events, its Bobby who is possessed by the Khan worm, and Dean questions and kills it. Bobby does survive.
Things again become strange when Balthazar alters history and saves the Titanic. With history changed, Dean finally wins rock, paper, sissors when trying to see whos going to cheer Bobby up and now drives a mustang. He and Sam investigate a string of strange murders, and make the connect to the Titanic. They summon Balthazar who tells them why he did and leaves. When almost killed by Fate, Castiel saves them. He tells them, it’s Fate, and she is trying to kill them. The only way to survive is to kill her. So Dean and Sam draw out Fate, and Castiel rights the past. Only Sam and Dean remember the past.
Dean, Sam and Bobby research how to kill the mother of all, and they find that the ashes of the phoenix can kill her. Dean finds the diary of Samuel Colt, which en-tales how he killed on. So they enlist the help of Castiel to send them back that time to find the ashes. Dean is beside himself with excitement to go back to the wild west. So they head back, and find out the Phoenix is killing people. So Dean tries to set up posse, but it backfires and he ends up as sheriff. So Dean and Finch end up having a showdown, and Dean wins. As Dean rushes for the ashes, Castiel transports them back. Lucky for them, Samuel Colt got the ashes and mailed it to them.
So Sam, Dean, Castiel and Bobby, begin to hunt for Eve. Thanks to Lenore‘s information, they find out that Eve is in Organ Pass, and they head there. There, they discover Eve’s experiments, and Dean even names one of her experiments when Bobby gives him naming rights. So Dean names a cross-breed between a wrath and vampire, Jefferson Starship. Then the police show up (Dean hides), but they too are Jefferson Starships. They eventually find Eve in a diner working as a waitress, and she tries to makes a deal with them. She even turns into Mary Winchester to get them to work with her, but Dean refuses nether less, and tells her to bite him. Which she does, only to find out that Dean had swallowed some phoenix ashes earlier. The bite could’ve possibly turned Dean into a Jefferson Starship, but Castiel cured the infection before it could spread.
After their encounter with Eve, everyone begins to question Castiel. Everyone but Dean who still believes in Castiel. When Castiel comes to save them, he accidentally gives himself away, and Dean catches this. helps them trap Castiel, and questions him. Dean is the most hurt and furious by Castiel’s actions but nonetheless still wants him to stop before Castiel goes to far. Castiel still disagrees. When demons come, Dean and the others are forced to flee. Castiel is now free, and later visits Dean to explain himself. Dean does not approve of his actions and chastises him harshly, but admits that Castiel is like a brother to him and that’s why he’s asking him to stop or else he’ll have to “do what he has to.” Castiel doesn’t budge and disappears, breaking their friendship.
Castiel: “I did it to protect you. I did it to protect all of you! […] Raphael will kill us all. He’ll turn the world into a graveyard. I had no choice.” Dean: “No, you had a choice. You just made the wrong one.” Castiel: “You don’t understand. It’s complicated.” Dean: “No, actually it’s not and you know that. Why else would you keep this whole thing a secret, huh? Unless you knew it was wrong. When crap like this comes around, we deal with it! Like we always have. What we don’t do is we don’t go out and make another deal with the Devil! Castiel: “It sounds so simple when you say it like that. Where were you when I needed to hear it?” Dean: “I was there. Where were you?”
After Castiel’s visit, Bobby reveals that Castiel also stole a diary from Bobby’s house. As they read Bobby’s photocopies, Dean gets a call from Ben. Ben tells Dean that men are in the house and killed Lisa’s boyfriend. Dean tries to help from the phone, but Ben too is captured. Crowley, now on the other line, tells Dean to back off or he will kill Lisa and Ben. Dean refuses to back down, and begins to hunt down Lisa and Ben. He even begins to torture demons for their location. Sam tries to help him, but Dean tells Sam to back off. Then Dean accidentally breaks the Devil’s Trap, and the demon attack. Castiel comes in and saves Dean. Dean doesn’t want anything to do with Castiel though. Later, its Balthazar who gives Dean Lisa and Ben’s location.
So Balthazar transports them there, and they storm the building. Dean finds Ben and Lisa after taking out some of Crowley’s goons. He unties them, only to find out that Lisa is possessed by a demon, and she hold Ben hostage. Dean manages to free Ben by splashing holy water at “Lisa”. Then he manages to free the knife from “Lisa’s” hand and begins to exorcise her. He continues to exorcise her after the demon stabbed Lisa’s body. Once the demon is out, Dean moves quickly to save Lisa’s life, and carries her out to the car, and rushes her to the hospital. Dean stays by Lisa’s bedside, and then Castiel arrives and heals her. Dean asks Castiel for favor to erase Lisa and Ben’s memory of him. Dean approaches them after this and apologizes to them. In the car, Sam tries to help Dean, but Dean tells Sam not to mention Lisa or Ben to him ever again, or he will break Sam’s nose.
A week later, Bobby, Dean and Sam go looking for Dr. Visyak, and they find her in an alley. She is bleeding and tells them how to open the door to Purgatory. Then Castiel appears, and Dean tells Castiel to leave. Castiel tells him he is done playing nice, and promises to put Sam back.
This confuses Dean, until Castiel touches Sam, and breaks down the wall inside his head, sending Sam into a comatose state. Dean stays by Sam’s bedside, while Sam is comatose. After Balthazar giving them Castiel’s location, Bobby manages to convince Dean to go with him after Castiel. Before Dean leaves, he leaves Sam their location. So Dean and Bobby head out. When they arrive they scope out the place, which is full of angels. Then a demon cloud comes, and Dean and Bobby run back to the Impala. The demon smash into the impala, flipping it over.When Dean wakes up, he checks on Bobby, who is okay. The two then sneak into the place, and walk in as Crowley and Raphael are doing the ritual. Dean throws an angel blade at Raphael, who catches it and flings Dean and Bobby away. Soon after, Castiel shows up, and shows everyone his new power. With it he kills Raphael while Crowley runs away. Dean tries to talk Castiel into powering down, and even reminds Castiel that he used to be family. But Castiel doesn’t want to power down and after Sam stabs him, he is proven to no longer be an angel. Dean is very shocked when Castiel proclaims himself God.
Dean: “Listen. I know there’s a lot of bad water under the bridge, but we were family once. I’d have died for you. Almost did a few times. So if that means anything to you … please. I’ve lost Lisa. I’ve lost Ben. And now I’ve lost Sam. Don’t make me lose you too. You don’t need this juice anymore, Cass! Get rid of it before it kills us all!” Castiel: “You’re just saying that because I won. Because you’re afraid. You’re not my family, Dean. I have no family.”
This is stupid. Our quality of life is crap. We got Purgatory’s least wanted everywhere, and we’re on our third ‘The World’s Screwed’ issue in what, three years? We’ve steered the bus away from the cliff twice already. […] I think if we didn’t take it’s belt and all it’s pens away each year, that the whole enchilada would’ve offed itself already!
— Dean losing faith in saving people
in How To Win Friends And Influence Monsters
When Castiel leaves, Dean and the others head back to Bobby’s, and Dean begins to fix the Impala, since there is nothing else he can do. Dean is concerned for Sam’s mental health since the wall is gone. Dean admits to Bobby that he can’t take anymore hits, and will believe that Sam is “fine”. Then they manage to summon and bind Death.
Dean tries to appease Death, and then Castiel shows up and Dean orders Death to kill him. Castiel frees Death and leaves. Death tells Dean the only way to stop Castiel is for Castiel to let the souls back into Purgatory. Dean doesn’t think Castiel will do this, until Castiel comes asking for help. In turn, Dean helps Castiel and the souls are released back into Purgatory, but the Leviathans remain. Dean watches them destroy Castiel and spread throughout the water, leaving only his trench-coat behind.
He also deals with Sam seeing Lucifer while looking into a Leviathan killing. When he returns, he finds Sam gone. Dean eventually finds Sam and convinces him that his reality is real. He and Sam return to Bobby’s, but find it burned down. Dean calls Bobby, but gets Bobby’s voice mail, and finally tells Bobby how he is really doing. He and Sam are soon attacked by Edgar, and Dean’s leg gets broken. On the way to the hospital, Dean begs them not to take them to Sioux Falls General, but is ignored.
He wakes up with his leg in a cast, and Bobby comes in and saves Dean from the hospital. Dean spends 3 weeks in a cast until Sam takes off, and Dean saws the cast off. Dean soon catches up with Sam, and punches Sam for taking the Impala. Sam explains the situation to Dean about the kitsune Amy and her decision to stop killing with her son no longer sick, but Dean sees her as only a monster that will kill again. Dean seem to eventually agree with Sam, but actually goes behind Sam’s back and kills her. Dean finds Jacob, Amy’s son, but spares him even against the kid’s threats and tells him to “look him up in a few years”.
I know, I know. But people … they are who they are. No matter how hard you try, you are what you are. You will kill again. […] Maybe in a year, maybe ten. But eventually the other shoe will drop. It always does. I’m sorry.
— Dean as he kills Amy
in The Girl Next Door
Dean feels guilty about the incident with Amy, plus feeling guilty lying to Sam about it and begins drinking more than normal. This guilt is what Osiris hones onto and puts Dean on trial. On trial he encounters Jo’s spirit as a witness and so is Sam. It’s revealed by Osiris Dean feels Jo died because of him since he let her do her first official hunt with them and blames himself for everything Sam went through since he left Stanford. Before Osiris can call the third witness, Amy, Dean accepts the charges. Jo’s spirit is controlled by Osiris to kill him, though Dean apologizes for dragging her and Sam into hunting, admitting he just didn’t want to be alone. Dean is saved when Sam stabs Osiris and Jo flickers out.
Dean: “You were a kid. You and Sam. I just – you know, hunters are never kids. I never was. I didn’t even stop to think about it. […] But I didn’t want to do it alone. Who does? No, the right thing would’ve been to send your ass back home to your mom.” Jo: “Like to have seen you try. He was right about one thing. […] You carry all kinds of crap you don’t have to, Dean. Kind of gets clearer when you’re dead.” Dean: “Well, in that case you should be able to see I’m 90% … crap. Take away that, and what’s left?”
Dean still has nightmares about Castiel dying and killing Amy along with Sam’s mental instability, leading to drink more heavily. Nonetheless, Dean continues working. He and Sam find a case where witches are wreaking havoc in Prosperity, Indiana. When they fail to stop the witches, Sam and Dean manage to get Maggie and Don to calm down. Sam approaches Dean about what’s bothering him, but Dean brushes him off.
When Dean is cloned by a Leviathan, Dean is forced to lock the Impala up and it not too happy about it. Although, before he can cut the off his clone, the clone tells Sam that Dean killed Amy. This causes Sam to leave Dean. A week later Dean runs into Sam in Lily Dale. Sam is still angry with Dean, but the two do a case together involving ghosts and psychics. After finishing the case and given some advice from the other side, Dean apologizes to Sam, but says he doesn’t feel bad for what he did to Amy and believes all his drinking to be because he didn’t like lying to him. Sam and him reconcile.
I went with my gut. And that felt right. I didn’t trust her, Sam. Of course, ever since Cass, I’m having a hard time trusting anybody. And as far as I’ve been acting … I don’t know. Maybe it’s cause I don’t like lying to you. You know, it doesn’t feel right. You got me there. I been climbing the walls.
— Dean explaining his behavior
in The Mentalists
Dean and Sam are forced to lay low, still having to hide from cops and the Leviathans tracking them who they still don’t know how to kill. In combined factors of losing Castiel, Sam’s broken wall, and their failure to keep Leviathans out (causing yet another apocalypse), Dean’s cynicism and frustration skyrockets. In How To Win Friends And Influence Monsters, even goes as far to say the world seems to want to end and he feels like nothing they do seems good enough. Bobby, however, chastises Dean and tells him to find a motivation to keep doing his job, whatever it is, or he’ll wind up dead. Sam, Dean, and Bobby get in a confrontation with the leader of the Leviathans—Dick Roman, who secured himself as powerful businessman for further reach. They narrowly escape, though Bobby is fatally shot in the head as they make their escape.
Bobby: “‘The world’s a suicide case, we save it, it just steals more pills? […] I’ve seen a lot of hunters live and die. You’re starting to talk like one of the dead ones, Dean.” Dean: “No, I’m talking the way a person talks when they had it. When they can’t figure out why they used to think all this mattered.” Bobby: “You’re not a person. […] You tried to hang it up and be a person with Lisa and Ben. And now here you are with a mean old coot and a van full of guns. That ain’t person behavior, son. You’re a hunter, meaning you’re whatever the job you’re doing today. Now, you get a case of the Anne Sextons, something’s gonna come up behind you and rip your fool head off. Now you find your reasons to get back in the game. I don’t care if it’s love or spite or a ten-dollar bet. I’ve been to enough funerals. I mean it. You die before me, and I’ll kill you.”
In Death’s Door, Sam and Dean rush Bobby to the ER where he falls into a coma. Both brothers are stressed over Bobby’s critical condition. Sam brings up the possibility that Bobby might not make it, but Dean refuses to consider it. Ultimately Bobby dies, but manages to wake up a moment to write down coordinates he discovered during their last encounter with Dick Roman.
Weeks pass after Bobby’s death. Sam and Dean are devastated, though Dean takes his loss the worst. He becomes obsessed with vengeance against Dick Roman and pays Frank Devereaux to help him track the meaning of the numbers Bobby left them with no luck. Eventually, with help from Frank in Adventures in Babysitting, Dean tracks down a new subsidiary of Dick’s and manages to tap into its surveillance. Dean’s apathy towards hunting heightens considerably after yet another loss, but wants revenge on Dick and couldn’t bear to leave Sam hunting alone. After advice from Frank, Dean tries to cover up his private misery and continues doing jobs.
In The Slice Girls, it’s revealed Dean keeps Bobby’s old flask as a memento and frequently uses it. Sam grows frustrated with Dean’s drinking and lack of interest in cases that don’t revolve around Dick Roman. During this time, Dean unknowingly sleeps with and has a daughter, named Emma, with an Amazon. The Amazons age and grow in a very short period of time until they reach adulthood, and so the baby is birthed in mere hours, and reaches adolescence in a few days. Amazon teens must go through a rite of passage in which they must kill their fathers – the event that Dean and Sam were investigating in the first place. Meanwhile, a clue is given to them by a strange “breeze” in the room. Dean believes it may be Bobby’s spirit, but Sam doesn’t think so and gets mad at him for the suggestion.
When Dean’s daughter comes to Dean, she lies and tells him she needs his help to escape the other Amazons. A wary Dean eventually sees through her scheme and they end up drawing their weapons and stand ready to face one another. Sam, recently enlightened to his brother’s situation, upon entering the room decides that Dean cannot bring himself to kill his own daughter, and so, after a short confrontation, he kills her. Sam then reminds Dean that he had to do it, just like Dean “had” to kill Amy.
When Sam’s hallucinations eventually worsen and he suffers a complete psychotic break he’s admitted to a psychiatric ward in The Born-Again Identity, Dean is determined to find a healer for his brother’s mind. He stumbles upon a “faith healer” named Emmanuel, but is revealed to actually be an amnesiac Castiel. Dean is shocked to see him alive and is stricken with mixed feelings, still blaming Castiel for his mistakes to Sam’s mind and the world.
I just know that … this whole thing couldn’t be messier. You know, I used to be able to shake this stuff off, whatever it was. It might take some time, but … I always could. What Cass did … I just can’t. I don’t know why.
— Dean to amnesiac Castiel
in The Born-Again Identity
Him and Meg take Emmanuel to Sam where Castiel slowly regains his memories. Castiel is almost too ashamed to help Sam, but Dean nonetheless convinces him he still can fix it. Thanks to Dean, Castiel shifts Sam’s hallucinations to his own mind and saves his brother, though at the cost of Castiel’s own sanity. In the aftermath, Dean made an agreement with Meg to keep an eye on Castiel – who was now insane in psychiatric ward – but hadn’t completely forgiven him.
Dean continues to work cases with Sam and tries to stop Leviathans, but the strange activity around them continues. Eventually, the brothers discover in Of Grave Importance, Bobby is a ghost and is tied to his old flask that Dean carries around. He had been helping them in small ways with their hunting for a while. Dean is particularly unsettled, glad to be around Bobby but upset that he chose to stay to help them when he could’ve found peace. Bobby, however, justified his choice. Unsure what to do next with the situation, the brothers at the moment let it rest.
Soon after, in The Girl With The Dungeons and Dragons Tattoo, Sam and Dean receive an automatic email from Frank, who had been recently killed by Leviathans. The message informs them a hacker of Dick’s at Roman Enterprises is hacking into Frank’s information about them. The hacker turned out to be Charlie Bradbury, who discovered the truth about Dick Roman and Leviathans after hacking it. It’s discovered that the Leviathan’s ultimate plan is to turn people into “perfect cattle” for their meals. Sam and Dean rush to location by GPS tracker on Frank’s hard drive, managing to get a reluctant Charlie to sneak in Dick Roman’s office and get his private information. Bobby, however, set on vengeance follows them despite Sam and Dean’s warnings.
Charlie manages to get Dick Roman’s information and give the brothers a chance to steal a private package being transported to Dick, but is injured accidentally by Bobby who lost control seeing Dick. Sam and Dean narrowly escape, discovering the package to be an tablet. Charlie survives with a broken arm and departs, leaving the brothers with an unknown tablet and concerns of Bobby turning into a vengeful spirit.
Sam and Dean crack open the tablet in Reading Is Fundamental, unknowingly calling forth Kevin Tran as the next prophet. Simultaneously Castiel awakens in the mental ward. The brothers rush over to him, who manages to decipher it an angel tablet called the Word of God. Dean tries to seek answers from Castiel and is still angry over his actions, but Castiel is clearly insane and has given up fighting even to help them. Meanwhile, Kevin tries to steal the tablet and they discover he’s a prophet.
After Kevin is stabilized, he fully deciphers the tablet before leaving and they figure out how to kill Leviathans: “a bone of a righteous mortal dipped three bloods of the fallen”. Sam and Dean have the first type of blood—Castiel’s, a fallen angel—and set out for the other two.
Dick Roman’s power grows. Dean and Sam are resorted to eating organic food on a daily basis as all other foods are infected by Leviathans, something Dean is not happy about. The brothers discover the other blood types are from an alpha and Crowley. Crowley refuses to give his blood right away so Sam and Dean go after the Alpha Vampire. After discovering the Leviathans plan to exterminate not just humans but monsters, the alpha grudgingly gives them his blood. Sam and Dean’s plan is successful until they go to the motel to find Bobby gone and the place ransacked. Dean is upset at Bobby’s violent and reckless impatience to get Dick, unwilling to admit he was close to being a vengeful spirit.
In Survival of the Fittest, Sam and Dean get a bone of nun and try to summon Crowley but he doesn’t show. This makes the brothers doubt his word, though sure enough Crowley appears later with a vial of his blood. He explains the deal Dick tried to make with him to bring them another demon’s blood, but this was the real deal. Neither Dean or Sam trust them, but know they don’t have another option. Meanwhile, Castiel and Meg rally with them. Crowley indicates Castiel can help against the Leviathans, but he still refuses to actively involve himself in the matter. Dean grows frustrated with this.
We can’t leave it. You let these friggin’ things in. So you don’t get to make a sandwich. You don’t get a damned cat. Nobody cares that you’re broken, Cass! Clean up your mess!
— Dean to Castiel
in Survival of the Fittest
Afterwards, Bobby reappears after nearly killing a maid and Sam in his obsession with vengeance against Dick. Bobby realizes he’s dangerous and wants his flask burned before he loses himself entirely as a vengeful spirit. Both Sam and Dean are sad at losing their surrogate father yet again, but do the right thing and burn it, putting him to res. The day before they infiltrate Dick’s base of operations, Castiel transports Dean to his Impala which had been on lockdown all year since Slash Fiction. Castiel shares his reluctance to fight because he fears he’s only bad luck. Dean disregards this and tells him he’s the only one left who can help. Dean finally forgives Castiel for his actions and motivates him to fight. Slowly more like his old self and as the only one who could identify the real Dick Roman among to copiers at the base of operations, Castiel agrees.
Castiel: “I’m not good luck, Dean.” Dean: “Yeah, but you know what? Bottom of the ninth and you’re the only one left on the bench. Sorry, but I’d rather have you. And anyway, nut up, alright? We’re all cursed. Do I seem like good luck to you?”
The next day, Dean, Sam and Castiel infiltrate SucroCorp. Meg stays out in the open to distract the Leviathans, Sam goes to get Kevin, and Dean and Castiel go after Dick. Castiel is able to locate him and they confront the leader. Dean stabs Dick with the bone, but it has no affect. Castiel holds him place from behind while Dean pulls out the real bone, tricking him into lowering his guard. Dean kills Dick by stabbing him through the neck, causing him to convulse and pulse strangely. Sam appears and watches as Dick suddenly explodes in black goo, Dean and Castiel disappearing with him.
Dean wakes up in shadowed plane with Castiel, now trapped in Purgatory as a side-effect of the weapon. Dean wants to get out, but Castiel grimly tells they’re more likely to get ripped to shreds than escape. Castiel suddenly disappears, leaving Dean alone as monsters come up to attack.
It was bloody. Messy. Thirty-one flavors of bottom-dwelling nasties. Hell, most days felt like 360-degree combat. But there was something about being there. It felt pure.
— Dean describing his experience in Purgatory
in We Need To Talk About Kevin
Following Castiel’s mysterious disappearance, Dean survives his brush with gorilla-wolves after arriving and sets out to find his friend. Some time passes and already Dean is changed by paranoia and survival instinct. He was constantly targeted by monsters, never had sleep, and was completely on his own. At some point early on, Dean forged a personal weapon from the environment in Purgatory and used it on nearly every monster he came across. It’s a implied a part of Dean even enjoyed Purgatory for it’s simplicity and the “pureness” of relying on his darker, survival instincts. Dean later states “I always did like this place” while hallucinating Purgatory, showing further his enjoyment of his time there.
Dean finds a lone vampire and interrogates him on information for Castiel’s whereabouts, but gets nothing out of him. He kills the vampire with ruthless primal ease, only to be attacked by another. A vampire named Benny saves him. Dean is hostile, but Benny approaches him with the possibility of escape. There was a spell out of Purgatory only a human could do, but he would only give him the details if he gets him out of there too. Dean naturally distrusts him, but agrees to work with Benny if he helps him find Castiel. 
Eventually, after interrogating more monsters, Dean and Benny locate Castiel on the far side of Purgatory. Dean is happy to see Castiel alive until Benny reminds him of the angel’s sudden disappearance. Dean believes he was just attacked, but Castiel admits he ran away. He explains he left because the Leviathans in Purgatory want him destroyed more than anyone so he wanted them after him to protect Dean. Castiel requests to stay and Benny admits he doesn’t know if the spell works on angels, but Dean refuses to leave without him. 
We’ll figure it out, Cass. Buddy, I need you. […] And if the Leviathans want to take a shot at us, let ’em. We ganked those bitches once before. We can do it again. […] I’m not leaving here without you.
— Dean to Castiel
in What’s Up, Tiger Mommy?
Dean, Castiel, and Benny trek throughout Purgatory. Dean still shows distrust towards Benny for being a vampire despite working with him. He also clashes with him over Castiel, who was attracting more monsters coming with them. Castiel agrees that he’s only cause trouble going with them, not knowing if he can even make it through the portal, but Dean doesn’t care. Eventually, Castiel attracts Leviathans. As they’re fighting, Castiel is about to be killed. Dean looks in in horror, but Benny saves the angel. This made Dean begin to trust Benny.
Eventually, Dean, Castiel, and Benny make it towards the portal Dean can activate. Using a spell, Dean successfully transports Benny’s soul in his arm and is ready to leave with Castiel. As they make their escape, Dean and Castiel are attacked by Leviathans. Going through them, the portal opens for Dean. Castiel lets go of Dean just as they’re about to make it. Dean is sucked up by the portal and returned to Earth. 
I can’t believe what I’m hearing. Sam, we have an opportunity to wipe the slate clean. We take Kevin to the tablet, he tells us the spell, we send every demon back to hell – forever. Every single bastard that destroyed our lives, killed our mother, killed Jess, and you’re not sure?
— Dean’s determination to close the gates
in We Need To Talk About Kevin
After spending a year in Purgatory (it is unknown how time differs in Purgatory, so it’s possible Dean was there for a significantly longer period of time), Dean uses a spell to return to Earth with help of Benny. Dean carries Benny’s soul out of Purgatory and resurrects him on Earth. Dean bids goodbye to Benny and they go their separate ways. Dean travels to the safehouse in Whitefish, Montana and reunites with Sam.
Sam and Dean catch up, though Dean refuses to disclose the fate of Castiel. Dean is disapproving that Sam retired from hunting and even more upset Sam made no attempt to look for him. He checks Sam’s old mobiles (which he had ditched) where he played voicemails of Kevin over the course of months that had escaped Crowley and was in hiding. Dean is angry Sam left Kevin alone. It becomes clear Dean’s perspective on hunting changed significantly since Purgatory and he now holds tighter responsibility on saving lives than ever. Sam and Dean find him and discover Crowley wanted him to read another Word of God which detailed different ways to defeat demons, including a spell to shut the gates of Hell. Dean is motivated to close the gates of Hell forever through Kevin’s help, though Sam is less sure and needs to be convinced. Crowley appears for Kevin, but they escape.
After escaping, Dean gets a call from Benny. Dean tells his friend not to call him for a while, hiding their friendship from Sam. Despite being out of Purgatory, Dean is still continually on edge and seems more guarded than he ever has been before. 
In What’s Up, Tiger Mommy?, Sam and Dean go to Kevin’s mother’s house under Kevin’s request to see if she was safe. After rescuing Ms. Tran from demons, she decides to go with the group to help protect her son. When they discover the tablet was stolen from the place Kevin was hiding it, they track it down ultimately to an auction house. The group ends up in a bidding war when Crowley shows up, and Kevin ends up being auctioned off along with the tablet. Ms. Tran offers up her own soul in order to save her son. When that offer is accepted Crowley possesses Ms. Tran’s body to steal the tablet. Dean fights against Crowley and nearly killed him despite being inside Ms. Tran’s body, highlighting Dean’s more ruthless nature since Purgatory. Crowley, however exits out of her body just in time and manages to escape with the tablet. After asking for a moment alone with his mother, Sam and Dean find Kevin and his mother gone and note from Kevin saying he didn’t want to end up killed being useless to them like Crowley warned.
Dean continues to hop on every hunting case he can find with remarkable enthusiasm. Sam tags along reluctantly, missing his year of normal and only interested in finding Kevin. This creates strain between the brothers. Eventually Dean’s suddenly intense sense of purpose alienates Sam so much he admits after closing the gates of Hell, he wants to quit and live normally. Dean doesn’t believe he means it, but Sam insists.
All right, man. Look, I get it. You took a year off to do yoga and play the lute. Whatever. But I’m back. Okay, we’re back, which means that we walk and kill monsters at the same time. We’ll find Kevin. But in the meantime, do we ignore stuff like this? Or are innocent people supposed to die so that you can shop for produce?
— Dean’s newfound purpose
After another failed attempt to locate Kevin in Blood Brother, Dean receives a call from Benny who needs help taking down the vampires that turned him. Dean leaves without telling Sam about where he’s going and finds the vampires’ nest. Eventually, Dean gives into Sam’s calling and tells him he’s with his friend and needs help taking down the nest. Sam shows up after they take down the nest and officially meets Benny, but quickly realizes he’s a vampire.
Sam is angry with Dean trusting a vampire in Southern Comfort, but Dean insists he’s good. Sam still doesn’t trust it. While doing a case with Garth, Dean gets possessed by a specter that forces you to kill the people you have a grudge against. Dean goes after Sam, revealing he still holds resentment for Sam not trying to find him in Purgatory and all his other past mistakes. Dean also highlights his disappointment in both Sam and Castiel, who he feels both betrayed him so trusts Benny because he’s the only that hasn’t.
Mistakes? Well, let’s go through some of Sammy’s greatest hits. Drinking demon blood? Check. Being in cahoots with Ruby. Not telling me that you lost your soul. Or how about running around with Samuel for a whole year, letting me think that you were dead while you were doing all kinds of crazy. Those aren’t mistakes, Sam. Those are choices! […] Yeah, I might’ve lied, but I never once betrayed you. I never once left you to die. And for what a girl? You left me to die for a girl?!
— Dean’s hidden resentment towards Sam
in Southern Comfort
When specter is defeated, Dean tries to brush off what happened between him and Sam. Sam, however, knows he had meant everything he said. Sam stands up to him and tells him he needs to get over it before he drives him away.
In A Little Slice of Kevin, Castiel mysteriously returns to Earth with no memory how while Sam and Dean are examining a case of strange kidnappings. Dean is shocked to see Castiel back, but is wary of his sudden return. They discover Crowley is kidnapping future prophets after losing Kevin in hopes they can analyze the tablet. Soon Crowley kidnaps Kevin and the brothers get a call from Mrs. Tran asking for help. Castiel, Sam, and Dean inflitate Crowley’s hideout. With Castiel’s help, they manage to secure Kevin tough the tablet breaks in half and half is missing. It’s revealed Dean blames himself for not bringing back Castiel, but Castiel tells him he always planned to be trapped in Purgatory for punishment and chose to stay. Dean didn’t fail.
You can’t save everyone, my friend … though you try.
— Castiel to Dean
in A Little Slice of Kevin
In Citizen Fang, Sam confronts Dean on a trail of a bodies leading towards Benny in Louisiana that Martin Creaser tracked. Dean doesn’t believe Benny did it, but is willing to do what he has to only if Sam and Martin give him time to get Benny’s side. Benny explains he didn’t do it, but another vampire from his past did and he’s trying to clean up his mess. Dean trusts Benny and tries to convince Sam and Martin of the same. Martin knocks him out and they go after Benny themselves. Desperate, Dean uses the fake number of Amelia’s he swapped on Sam’s phone with one of his phones and sends a fake S.O.S protect Benny. Dean tries to help Benny escape, but ultimately Benny is forced to kill Martin in self-defense. Sam, who had left the scene and rush to the rescue as Dean guessed, figures out it the truth later. Sam is angry with his brother, but Dean believes he did the right thing.
In Torn and Frayed, Sam and Dean argue about Benny and the fake text on Amelia. The brothers take a break, but are brought back together to help Castiel rescue the angel Samandriel who was kidnapped by Crowley. Dean and Sam are suspicious over Castiel’s strange behavior after seeing Samandriel suddenly dead beside him. They also sort out their issues. Dean admits he could never separate himself from hunting for normal the way Sam could and, tired of arguing with him, gives him his blessing to be with Amelia if it makes him happy.
I’m just tired of all the fighting. […] And y’know, maybe I’m a little bit jealous. I could never separate myself from the job the way you could. Hell, maybe it’s time for at least one of us to be happy.
— Dean gives Sam his blessing to be with Amelia
in Torn and Frayed
Ultimately, Sam realizes there are too many important things he has to take care of and choses to stay with Dean. Dean, out of loyalty to Sam, is forced to end direct contact with Benny.
In As Time Goes By, Dean and Sam meet their grandfather, Henry Winchester, who travelled in time on the run from the Knight of HellAbbadon protecting a vital key. The brothers also discover the Winchester bloodline were composed of the Men of Letters—chroniclers with vast knowledge of the unexplained and supernatural which they passed on to hunters that they deemed worthy. Dean at first resents Henry for leaving John to grow up alone, as he had disappeared doing Men Of Letters duties, but ultimately comes to respect him. They help Henry capture Abbadon and manage to protect the key, but at the cost of Henry’s life. Henry dies in 2013 and the brothers bury him with his fallen Men of Letters comrades.
The key left behind by Henry leads Sam and Dean to the Men of Letters headquarters in Everybody Hates Hitler, which is remarkably well-preserved despite being abandoned. After doing a case about the Judah Initiative, Sam and Dean adopt the place as their home and base of operations, becoming official Men of Letters.
In Trial and Error, Dean receives a call from Kevin who deciphered part of the tablet that would close the Gates of Hell forever: three trials completed by somewhere worthy and the first was killing a hellhound. Dean is enthusiastic about this and automatically elects himself to do it. Sam and Dean track down ten-year contracts to find a hellhound and are lead to a farm where Crowley made multiple deals. Dean recklessly sets out to kill the hellhound. Dean expresses his jaded picture of his future and knows these trials will have a fatal consequence, but wants Sam safe and to have a family. Dean is determined to do the trials because he feels he has nothing left to lose.
I’m a grunt, Sam. You’re not. […] And you told me yourself you see a way out. You see a light at the end of this ugly-ass tunnel. I don’t. But I’ll tell you what I do know. It’s that I’m gonna die with a gun in my hand. ‘Cause that’s what I have waiting for me. That’s all I have waiting for me. I want you to get out. I want you to have a life- become a Man of Letters, whatever. You with a wife and kids and grandkids, livin’ ’til you’re fat and bald and chugging Viagra. That is my perfect ending and that’s the only one I’m gonna get. So I’m gonna do these trials. I’m gonna do them alone. End of story.
— Dean’ s resolve to do the trials
in Trial and Error
Dean finds the hellhound and is nearly killed until Sam comes to his rescue, killing it and becoming the person for the trial. Dean refuses to let Sam do this, but Sam expresses his faith in both of them. Dean reluctantly lets Sam carry out the rest of the trials.
In Man’s Best Friend With Benefits, Dean is still concerned over the trials and continues to try to convince Sam he can do them instead. Sam, frustrated, admits he believes Dean can’t trust anyone but himself. Dean and Sam are infected fight a witch named Spencer Wallis who infected them with some of their worst memories. Dean is affected by remembering everything they went through and decides to stand by Sam’s choices to do the trials.
In Goodbye Stranger, Dean spots a bloody tissue of Sam’s and realizes he’s been hiding the toll the trials have on his health. Castiel returns, telling them Crowley has been searching for Lucifer’s crypts. He lies and says he’s looking for parchment to decipher the tablet, but Sam and Dean later find out he’s searching for an angel tablet. The brother’s distrust over Castiel heightens, but they nonetheless work with him and find Meg who knows about the location of the crypts.
When finding the tablet, Dean wants to give it to Kevin, but Castiel wants to take it to Heaven. Dean refuses. Castiel, under control of Naomi, proceeds to beat him brutally. Dean knows Castiel isn’t himself and desperately tries to snap him out of it. Just as Castiel is about to kill him, Castiel stops and heals Dean. Castiel apologizes, but leaves with the tablet to protect it from Naomi – and them. Outside, Crowley is there for the tablet. He kills Meg, but the brothers escape. Soon after, Dean confronts Sam about lying and that he’s there for him. Dean, still shaken about Castiel, doesn’t want to be lied to anymore.
In Taxi Driver, Kevin translates the second trial which is to “rescue a soul from Hell.” The brothers contact a rogue reaper and find out Bobby’s soul is in Hell. Dean wants to help him save Bobby, but Sam tells him it’s his trial and convinces Dean to stay. As Sam rescues Bobby, Dean visits Kevin, who hears Crowley in his thoughts and is convinced he knows where he is. In a panic, Kevin hides the tablet and Dean is visited by Naomi who tries to convince him she’s trustworthy.
Kevin: “Just tell me when this all ends ’cause that’s the only thing I want to hear.” Dean: “No. Like I told you before, this isn’t going to end. Look, man. Other guys, they got it easy, y’know? It’s all backyard barbeques … and bowling teams, but you and me? We got to carry a little extra weight.” Kevin: “I can’t take it.” Dean: “Yes, you can. Hey, look at me. Now, this whole thing sucks. I know. But you suck it up and push through because that’s what we do. And when you get on board with that, the ride is a lot smoother.”
When finding out Sam is in Purgatory, Dean contacts Benny and asks him if he can help get him out to get them both out. Dean is guilty, but has to save his brother. Benny agrees, admitting he didn’t like being on Earth and Dean reluctantly kills him. Benny rescues Sam and Bobby’s soul is sent to Heaven, completing the second trial. Dean is upset Benny didn’t come with even though according Sam he chose to stay and decides not to burn his bones, in hopes that one day he’ll be able to bring him back. The brothers visit Kevin, only to find him missing.
In The Great Escapist, Dean continues to take care of Sam who’s health is rapidly declining from the trials. The brothers receive an automatic message from Kevin, who assumes he’s dead and sends them notes from his deciphering of the tablet. This leads Sam and Dean to meet Metatron, the scribe of God. With come convincing needed, he saves Kevin from Crowley. Kevin has the other half of the tablet and has figured out the third trial: to cure a demon.
In Clip Show, Sam and Dean watch a serious of old exorcism videos on the Men of Letters files, proving a curing a demon is possible. The brothers dig up Abaddon’s body and intend to cure her, but are distracted when Crowley calls detailing his plans to kill everyone they ever saved if they didn’t surrender the tablet. Abbadon escapes and with no demon to cure, Sam and Dean go after Crowley. Crowley massacre is lead to Sarah Blake Sam’s old fling. Sam and Dean do everything in their power to save her, but are too late. Sam considers surrendering, but Dean is determined and convinces him to push on.
In Sacrifice, Dean and Sam seem to give in to Crowley’s demands after nearly killing Jody Mills. However, when the deal is made, Dean handcuffs Crowley which has a devil’s trap on it, steals the angel’s tablet, and traps him to use for him to the third trial. Dean is called away by Castiel and gives Kevin the tablet to translate as Sam cures Crowley. Ultimately, it’s revealed Castiel’s deal with Metatron was a trick and Sam will die if he completes the trials. Dean rushes to the scene just as Sam is about to completely cure Crowley. Sam wants to carry out the trials even if he dies, admitting he feels like all does is let Dean down and it hurts him to watch his brother to trust Castiel or Benny more than him. Dean tells him none of that is true and there’s no one else in the world he cares about more than Sam. Dean convinces Sam to stop and they agree to save people their own way.
However, Sam is still affected by trials and falls to the ground in pain. Dean calls out for Castiel, but he’s nowhere. The brothers watch as angels fall from the sky, Metatron’s plan to self-destruct Heaven completed.
Listen, man. I know we’ve had our disagreements, okay? Hell, I know I’ve said some junk that sets you back on your heels. But Sammy … come on. I killed Benny to save you. I’m willing to let this bastard and all those sons of bitches that killed Mom walk because of you. Don’t you there think that there is anything past or present that I would ever put in front of you! It has never been like that! Ever! I need you to see that. I’m begging you.
This is nuts. I mean, you’re Sam, but you’re not Sam, and normally he’s the one I’m talking to about all this stuff. I’m trusting you, Zeke. I just gotta hope that you’re one of the good guys.
— Dean’s uneasy alliance with “Ezekiel”
in Devil May Care
When Sam falls into a coma in I Think I’m Gonna Like It Here, he takes him to a local hospital and finds out that Sam is going to die. Dean then goes to a church and prays to all the angels for help. As a consequence, Dean is attacked by several angels looking for Castiel and is forced to banish them all save for one named “Ezekiel“. Ezekiel tells him Sam’s condition is too severe to be healed and he must possess him to heal both Sam and himself fully. Dean at first refuses, knowing Sam would never agree, but desperate to save his brother, gives in. Ezekiel casts an image of Dean in Sam’s head to get him to say yes and it works. Dean guiltily keeps his possession by Ezekiel a secret from his brother.
In Devil May Care, Dean and Sam work together to use Crowley for information to kill all the demons loose on Earth. Meanwhile, they discover Abaddon is still alive and kidnapping hunters for them to give up Crowley. The brothers team up with Irv and Tracy Bell where Dean gets in a violent confrontation one-on-one with Abaddon. She flees from Ezekiel, who took control of Sam to save them from demons. Dean is uncomfortable with the situation and admits he also feels guilty about not closing the gates of Hell after seeing the damage the demons are causing, but Ezekiel reassures him. He is still skeptical about the angel’s motives, who only asks him to trust him. Dean also stops Kevin from leaving them, and calls him family.
Dean: “This is on me. I was the one that talked Sam out of boarding up Hell. Okay? So every demon deal, every kill that they make … well, you’re looking at the person that let it happen.” Zeke: “You were protecting your brother. I am in Sam’s head. Everything he knows, I know. And I know what you did, you did out of love.”
In I’m No Angel, Dean is alerted by Ezekiel the faction that is after Castiel and fears for his safety. He makes an excuse to Sam about his knowledge and together they search for their friend, leading them to a rogue reaper. She kills Castiel, but Ezekiel takes over Sam and brings him back to life. Sam questions again Dean’s knowledge about angels and Castiel on how he survived, but he lies to both of them. They take Castiel back to their bunker, only for Ezekiel to possess Sam and warn that Castiel can’t be here without drawing attention to himself. Dean initially refuses, but when Ezekiel warns he’ll be forced to leave Sam’s body if he stays, he reconsiders. Dean reluctantly forces Castiel to leave without explanation.
In Slumber Party, Sam and Dean fight to stop The Wicked Witch from entering Oz. They meet up again with Charlie. After she gets killed by the Witch, Dean begs “Ezekiel” to save her, which he reluctantly does. Later, Dean and Sam get possessed from the Witch and are turned into minions of hers. They then hunt down Charlie and Dorothy to try and kill them. They aren’t turned back until Charlies saves them by killing the Witch.
In Dog Dean Afternoon, Sam and Dean solve two bizarre cases in which a dog is the sole witness. Dean uses a spell that gives him the ability to talk to animals. He gets along quite well with their witness The Colonel, despite the fact that he doesn’t really like dogs.
In Heaven Can’t Wait, Dean works with Sam and Kevin to research ways to undo Metratron’s spell on the angels and return them to Heaven. Dean is called away by Castiel for a case where he greets his friend working a mediocre job at a place called Gas-n-Sip. Dean at first believes it’s beneath him and encourages him to get back on track, but after facing off against a dangerous angel type Zit Rein, he encourages Castiel to live normal. Dean finds out by Sam through Crowley’s there’s no reversal for the angels who got expelled for Heaven, but doesn’t tell Castiel this and tells him to just leave it to them.
In Rock and a Hard Place, he and Sam catch up again with Sheriff Mills. Dean and Sam also renews their virginity and join a chastity group to get closer to the source of mysterious kidnappings. Dean has sex with an ex-porn star chastity counselor after the meeting. This causes them to get abducted by Vesta, a goddess after virgins that broke their vows. Sam and Jody arrive as Dean tries to free himself and the other victims. Jody kills Vesta and they say their goodbyes. Dean feels increasingly guilty after Sam admits he thinks there’s something wrong with him—that he’ll never be normal—and is close to telling him about Ezekiel, but the angel stops him and warns the consequences if Sam ejects him. Dean lies to his brother yet again.
In Holy Terror, Dean is still unsure of the idea to not tell Sam about “Ezekiel”, but is convinced by the angel to still use the trials as an excuse. Sam and Dean work a case with Castiel, where it becomes apparent Dean didn’t tell Sam why Castiel left. Dean finds out from Castiel–now an angel again by stealing another one’s grace—that “Ezekiel” died during the fall and the one possessing Sam isn’t him. Determined to expel the unknown angel, Dean works with Kevin to perform a ritual weakening the angel for Sam to expel him. Dean performs the ritual and explains to Sam quickly, including his motivations for lying and that he was trying to save him. Sam, actually still possessed and nearly acting, punches Dean and kills Kevin under request of Metatron.
Dean wakes just in time to see Kevin die. It’s revealed the ritual had been altered by the angel, making it useless. Dean tries to attack “Ezekiel”, but the angel overpowers him and leaves with full possession over Sam. Dean is left alone, having lose both Kevin and Sam.
In Road Trip, Dean is devastated by grief and guilt. He gives Kevin a hunter’s funeral and is determined to kill the angel possessing Sam in revenge. Castiel appears and they reluctantly work with Crowley for him to help them expel the angel from Sam. They discover the angel is Gadreel, the angel that first let Lucifer out of his cage and into the “garden”. After torturing Gadreel to bring out Sam doesn’t work, Crowley temporarily possesses Sam to connect to his mind and expel the angel in exchange for his freedom. Sam expels the angel and Castiel heals the rest of his damage from the trials.
Sam is furious with Dean for tricking him by letting Gadreel possess him, but Dean stands by his reason to save him. Dean brokenly leaves to hunt Gadreel on his own, convincing himself all he does is hurt the people around him. Sam doesn’t try to stop him.
Kevin’s blood is on my hands, and that ain’t ever getting clean. I’ll burn for that. I will. But I’ll find Gadreel and I’ll end that son of a bitch. But I’ll do it alone. […] I’m poison, Sam. People get close to me, they get killed. Or worse. You know, I tell myself I-I help more people than I hurt, and I tell myself I’m doing it for the right reasons, and I-I believe that. But I can’t. I won’t … drag anyone through the muck with me. Not anymore.
— Dean’s decision
in Road Trip
In First Born, alone in a bar, Dean is approached by Crowley for help with finding the First Blade, the only weapon that can kill Abaddon. Dean reluctantly allies himself with the demon and begins the search by looking for information on a hunt his father did where he captured, interrogated and exorcised a demon who claimed to know about the Blade. The information they find leads them to a hunter named Tara and eventually to the biblical Cain who is now a very powerful demon. Dean asks for Cain’s help in locating the Blade, telling him they need to kill a Knight of Hell. Dean is pissed at Crowley when Cain reveals that he created the Knights which Crowley knew, but is surprised to learn that Cain was the one that killed them all. When Cain refuses to help, Dean sneaks back with Crowley to search for the Blade only to be caught by Cain. When four demons show up, Dean is left to fight three of them single-handedly. He wins and Cain tells him how he slaughtered the Knights after they kidnapped his wife who was killed by Abaddon. Cain still refuses to help and is unimpressed by Dean’s threats. Cain leaves as a demon army arrives, but returns willing to help and explains that the Blade is useless without the Mark of Cain which he can transfer to someone worthy, such as another killer. He’d let Dean fight alone to see if he was worthy and offers him the Mark, trying to warn him that it comes with a terrible price. Dean takes the Mark anyway without learning what the price is and after telling them that the Blade is at the bottom of the ocean, Cain teleports Dean and Crowley to safety while he takes on the demon army, asking for Dean to return after he kills Abaddon to kill him too. Dean is pissed at Crowley as he realizes Crowley used him to get access to the Blade. Crowley confirms this, but while Dean threatens to kill him when everything is over, he recognizes he still needs Crowley and sends him after the Blade.
Sam and Dean run into each other in Sharp Teeth after working on the same case involving Garth (now a werewolf) and a werewolf cult. They work together reluctantly, Sam still furious and Dean still guilty. After the case, Dean again apologizes to Sam and tries to suggest they work together again in hopes they can patch it up. Sam agrees to work with him, but insists to keep it professional because he doesn’t think he can’t trust Dean. Dean resignedly agrees to his terms.
In The Purge, after another tense case, Dean finally erupts and insists he did the “right thing” saving him. Sam disagrees and believes Dean simply didn’t want to let him go if it meant he was alone. Dean challenges Sam that he would’ve done the same thing if the roles had been reversed. Sam says he wouldn’t, shocking Dean.
Dean: “You know, Sam. I saved your hide back there. And I saved your hide at that church … and the hospital. I may not always think things all the way through, okay? But what I do, I do because it’s the right thing. I’d do it again.” Sam “And that is the problem. You think you’re my savior. My brother, the hero. You swoop in, and even when you mess up, you think what you’re doing is worth it ’cause you’re convinced you’re doing more good than bad … but you’re not.[…] Please tell me, what is the upside of me being alive?” Dean: “Are you kidding me? You and me. Fighting the good fight together.” Sam: “Just once, be honest with me. You didn’t save me for me. You did it for you. […] I was ready to die. I should’ve died, but you … you didn’t want to be alone. And that’s what this all boils down to. You can’t stand the thought of being alone. […] I’ll give you this much. You are certainly willing to do the sacrificing. As long as you’re not the one getting hurt.”
In Captives, it’s revealed Kevin’s spirit is haunting the bunker due to an after-affect of Metatron’s spell. Dean is still stricken with guilt over his death and apologizes to him, though Kevin doesn’t blame him. By Kevin’s last request, Sam and Dean search for Kevin’s mother and find her still kidnapped by Crowley. The boys rescue her and Linda reunites tearfully with her son, deciding to take him with her until Kevin can move on. The brothers make peace with him and vow to find a way to send Kevin to Heaven.
In Blade Runners, Sam and Dean work with Crowley to track down the First Blade. Their search leads them to a rogue member of the Man of Letters named Cuthbert Sinclair a.k.a. “Magnus” who tries to keep Dean as a “collectible” upon discovering he has the Mark of Cain. Dean uses the First Blade to kill Magnus, uncharacteristically beheading him as he’s pulled by the dark power of the Blade. Sam snaps Dean out of his aggression. The brothers decide to kill Crowley now they have the blade, but Crowley steals it and will only give it back when it’s time to kill Abbadon.
In Mother’s Little Helper, Dean grapples with the after-effects of holding the First Blade. He struggles between wanting it’s power or just using it to kill Abaddon. Dean becomes uneasy over taking up the First Blade again even it means killing Abaddon, afraid of what it’ll turn him into. Crowley pushes Dean to accept his role and eventually he reluctantly decides he’ll have to do what he’ll have to.
I want to kill Abaddon. That’s what I want. So whatever happens with the Blade, I can’t worry about that. […] What I want, what I fear, none of that means squat. Because this is the one chance we have to kill Abaddon. So I’m all in, no matter what the consequences.
— Dean taking on the burden of The Blade
in Mother’s Little Helper
In King of the Damned, in the presence of the First Blade, the Mark grants Dean immunity to Abaddon’s powers at first with great concentration and then no effort. He also displays telekinesis and strength great enough to lift Abaddon off her feet effortlessly. However, the Mark and Blade’s effects cause him to go overboard and repeatedly stab the dead Abaddon after he kills her. Sam confronts Dean about this and Dean explains he knew from the start he had to kill Abaddon alone and whatever else he had to kill it with. Worried about what it’s doing to him, Sam tries to tell Dean to stash the Blade away, but Dean refuses.
In Stairway to Heaven, the brothers investigate a case of angels blowing themselves up along with innocent people supposedly in the name of Castiel. Under influence of the mark, Dean is quick to blame Castiel for the crimes and is shown aggressive in his dealings with the angels and Tessa. Despite telling Sam he hadn’t, Dean brings the First Blade with him and accidentally kills Tessa, wanting to be free of hearing the lost souls. Castiel is forced to give up his army after refusing to kill Dean under their orders. It’s revealed the martyring angels were Metatron’s double-agents and used for this very reason. Dean slips in deeper control of the mark and tries to kill Gadreel who arrives to join their side, having to be held back by Sam and Castiel.
The Blade’s the only thing that can kill Metatron, and I am the only one who can use it. So from here on out, I’m calling the shots. […] Until I jam that blade through that douchebag’s heart, we are not a team. This is a dictatorship. Now you don’t have to like it, but that’s how it’s gonna be.
— Dean to Sam
in Stairway to Heaven
In Do You Believe In Miracles?, Dean is shown to be over-aggressive and has no control over his desire to kill Metatron. His need for the First Blade is also very detrimental to his health. He even works with Crowley to hunt down Metatron. When he does find Metatron, he tries to kill him but fails. Metatron then stabs Dean in the heart, killing him. Crowley approaches Dean and tells him that Dean is a lot like Cain who also died because he wasn’t willing to kill innocents but Cain’s very sacrifice is what made him become a demon. Crowley then tells Dean to open his eyes. Dean does so, but returns as a demon (more specifically a knight of hell).
It’s better this way. The Mark. It’s turning me into something I don’t wanna be. […] I’m proud of us.
— Dean’s last words to Sam as he dies
in Do You Believe In Miracles?
Crowley: “What are you doing?” Dean: “Oh, whatever I want.” Crowley: “Really? Because I think you don’t know what you want. Tell me, Dean. What are you? A demon? If so, why isn’t Lester’s wife dead? Did you feel sorry for her? So maybe you’re human. Except you have those pretty black peepers and you’re working alongside me. Why don’t you do us all a great big favor and PICK A BLOODY SIDE?!” Dean: “Or what? Make a move. See how that ends. I ain’t your friggin’ bestie and I ain’t taking orders from you. When I need to kill, I’ll call. Until then, stay out of my way.”
In Black, six weeks have passed since Dean became a demon. He left Sam a note telling him not to look for him and formed somewhat of a partnership with Crowley. Dean lives in excess—drinking, doing drunk karaoke, sex, and brawl fights—and resists Crowley attempts to monitor him. Dean receives a call from Cole Trenton, a man who devoted his entire life to revenge on Dean for killing a father during a hunt two years before the pilot. Cole has Sam tied up and threatens to kill him if he doesn’t come. Dean callously tells him Sam isn’t his responsibility anymore, but nonetheless promises to kill Cole next time he sees him.
In Reichenbach, Dean continues his carefree and aggressive activities. Crowley grows concerned the mark on Dean will act up if he doesn’t kill soon and gives Dean a job to kill a woman her husband sold his soul to be killed for. Dean reluctantly goes to her house, but after seeing Lester outside to “watch the hit” Dean instead kills him. Crowley is appalled Dean ruined his deal (he could no longer get the soul now that Lester was killed without his wife dead) and challenges Dean for not knowing whether he’s good or bad. Dean humiliates Crowley and ends their partnership.
Shortly after, Crowley betrays Dean by telling Sam where he is. Dean rejects Sam’s attempts to bring him back to cure him and is finally found by Cole, who followed Sam. Dean shows no apparent remorse for Cole’s dead father and mercilessly beats him. Sam traps Dean with Devil Trap handcuffs while Crowley takes the First Blade and hides it far away. Sam questions Dean’s decision not to kill Cole and believes he showed mercy. Dean replies letting him live with the knowledge he could never get his revenge was the worst thing he could’ve done to him.
In Soul Survivor, Dean is tied inside a Devil’s Trap as Sam starts the curing ritual. Dean expresses his condescension towards hunting monsters (“the natural order”) and is completely jaded over any point it ever had. He also calls out Sam for being responsible for Lester’s deal and believes him to be just as bad as himself if not worse. As the ritual continues, Dean starts to be in pain, causing Sam to fear if it was killing him. As a demon Dean shows true resentment towards Sam and their family, telling Sam he was the reason their mother died and their father wasted their entire lives hunting for nothing.
You notice I try to get as far away from you as possible? Away from your whining, your complaining. I chose the King of Hell over you! Maybe I was just … tired of babysitting you. Or always having to yank your lame ass out of the fire since … forever. Or maybe … maybe it was the fact that my mother would still be alive if it wasn’t for you. That your very existence sucked the life out of my life! […] You never had a brother! Just an excuse for not manning up. But guess what. I quit.
— Demon Dean taunting Sam
in Soul Survivor
Eventually, Dean is less demon enough to escape the Devils’ Trap and tries to kill Sam with a hammer, still not wanting to be human again. Castiel saves Sam and restrains Dean, letting them continue the rest of the ritual. When Sam is upset that a barely demon Dean still didn’t want to be human, Castiel comments it was because it was easier for Dean to stay that way in favor of feeling human pain. The ritual is a success and Dean is human again, but with a heavy conscience over everything he did as a demon.
In Paper Moon, Sam and Dean are taking a break from hunting. They relax by a lake, but Dean is quickly motivated by a case. Sam is concerned it’s too soon for Dean to get back to work, but Dean insists. The attacks turn out to be werewolf and they run into Kate whose now werewolf sister Tasha is killing people. Meanwhile, Dean tries to get Sam to open up about killing Lester while Sam tries to get him to open up about his actions as demon, but neither succeed. After Tasha is dead, Dean admits to Sam he’s not alright and it’s too soon for him to hunt, but he has to because he wants to do the right thing.
In Girls, Girls, Girls, Sam and Dean run into a dangerous witch named Rowena who is trying to train other girls to be to be witches. Dean corners her, but is trapped by Cole, allowing her to escape. Cole quickly realizes he’s no longer a demon. Dean tries to apologize for their last meeting and explain he’s no longer the same, but Cole attacks. Dean wins the fight, telling Cole his father had been a monster and he had killed him working a case. Dean gives Cole the choice whether to shoot him or spare him, describing himself already as a “lost cause”. Cole hesitates, but believes Dean and lets him live.
I get it. That was your story. Look, man, I’ve got one of those too. But those stories we tell to keep us going? Sometimes they blind us. They take us to dark places. The kind of place where I’d beat the crap out of a good man just for the fun of it. […] Cole, once you touch that darkness … it never goes away. Now, the truth is … I’m past saving. I know how my story’s gonna end. It’s the edge of a blade or the barrel of a gun. So the question is, is that gonna be today? That gonna be that gun?
— Dean’s speech to Cole
in Girls, Girls, Girls
In The Things We Left Behind, Dean is having nightmares of killing people from the mark. He and Sam help Castiel connect with Jimmy’s long-lost daughter Claire who’s been taken in by a man named Randy to makes her steal to help him pay off his debts. In a conversation with Castiel, Dean makes him promise to kill him if the mark gains too much control, not wanting to be what he was before. Randy betrays Claire after being found out by thugs and they come to her rescue. Castiel and Sam take Claire to safety, but the mark on Dean acts up. Dean’s nightmares becomes reality when he mercilessly slaughters all the thugs, causing all three to realize things have finally gotten worse.
In The Hunter Games, Dean is now desperate to have the mark removed. Castiel takes Metatron briefly out of prison to be used for information, only getting that they need the First Blade. Dean is reluctant to take back the Blade, but goes along with it as long as the Blade is kept directly away from him. They enlist Crowley, who takes the Blade out of hiding but refuses to give it back until needed. Dean goes to Metatron for information, but is provoked and nearly kills him. Sam and Castiel stop Dean while Metratron is returned to prison. Dean is upset at how easily he lost control and only has one hint from Metatron (“the river ends at the source”). Sam encourages Dean to fight the mark harder.
In There’s No Place Like Home, Dean is trying a series of methods to keep the mark under control. Sam and Dean discover Charlie returned from Oz and was split between her good and bad selves. Dark Charlie gets revenge on the man that killed her parents and tries to stop Good Charlie from conjoining them again. Dean loses control while fighting Dark Charlie, seriously wounding her and causing harm to Good Charlie in the process. Charlie becomes herself again and forgives Dean, but Dean doesn’t forgive himself.
In Halt & Catch Fire, Sam and Dean find a case revolving around college students getting killed by a vengeful spirit through the internet. The brothers save the last of the four students and get rid of the ghost. While Sam is still hopeful for getting rid of the Mark of Cain, Dean gives up on the search and decides that he’ll just keep fighting the mark until he can’t anymore. Sam protests, but Dean can’t invest in anymore “false hope”.
My peace is helping people. Working cases. That’s all I want to do. […] I’m done looking for a cure, Sammy. […] I appreciate the effort, okay? I do. But the answer is not out there. It’s with me. I need to be the one calling the shots here, okay? I can’t keep waking up every morning with false hope. […] So I’m gonna fight it until I can’t fight it anymore. And when all is said and done … I’m gonna go down swinging.
— Dean giving up on removing the mark
in Halt & Catch Fire
When Cain starts killing off his descendents to “purify” the world of a bloodline made mostly of killers in The Executioner’s Song, Dean takes responsibility for this and reluctantly decides he needs to kill Cain with the First Blade. Dean tricks Crowley into giving him the Blade and with Sam and Castiel, follows Cain’s trail to a 12-year-old boy who they manage to save. Dean is scared of fighting Cain, fearing losing control again, but is adamant on going alone. Dean stands off against Cain while Sam, Crowley, and Castiel wait. Cain declares Dean is living his story in reverse and that eventually he’ll kill Crowley, Castiel, and Sam himself before becoming a complete monster.
Cain nearly kills Dean, but Dean manages to immobilizes him. He pleads if there was any chance Cain could stop killing, wanting hope for himself, but Cain knows he won’t stop. Dean kills Cain and gives the Blade to Castiel to hide, but is devastated by the bleak future that awaits him.
Dean’s fear of becoming a demon and killing again steadily heightens. He’s having terrible nightmares in the middle of the night, but tries unsuccessfully to hide this from Sam. After Sam goes out on his own in Inside Man, unbeknownst to Dean to try to find out a way to remove his mark. Dean gets in a confrontation with Rowena. She uses the Attack Dog Spell on college students. Dean stops himself from killing them just in time for Rowena to try to kill him in a flash of light, but it doesn’t work. It’s revealed bearing the Mark of Cain gives Dean limited immunity to certain types of attacks. Dean wants to kill Rowena, but choses not to she can end her spell on the rabid college students.
In Book of the Damned, Charlie comes to the brothers on the run from the Styne family. She stole the Book of the Damned from them, a powerful dark magic book that might be able to remove the mark from him. Dean starts to think there’s hope for him, but when in the contact with the book he senses it’s darkness and the mark reacts to it. Sam and Charlie try to translate it, but Dean decides he doesn’t want to use it because of the consequences it might have. Sam protests, but Dean is firm and demands he burn it. They’re attacked by the Stynes, but make it out. Dean thinks Sam burned the book, but Sam actually burned another and is working with Rowena to translate it.
The book’s been calling to me ever since I laid eyes on it, okay? Calling out to the mark. I can hear it like it’s alive. It wants me to use it, but not for good. […] This is my cross to bear, Sam. Mine. And that book is not the answer. Now we got to destroy it before it falls into the wrong hands, and that includes me.
— Dean rejecting the Book of the Damned
in Book of the Damned
In The Werther Project, Dean takes down a nest of six vampires by himself. When Sam goes alone to an address, Dean follows him. Sam explains the backstory of the Werther Box and the Men of Letters without giving away why he came there (working with Rowena). Sam opens the box, which drives the people around them to suicide. Dean imagines himself in Purgatory with Benny who tries to get him to die and come here so he wouldn’t kill anymore. It’s also revealed Dean knows neither Sam or Castiel will do what they have to when he gets out of control. Dean refuses to kill himself because of the mark, but admits he would if he really had to. He breaks out to save Sam, who’s trying to shut down the Werther Box with his blood. Dean shuts down the box with some of his own and destroys it, but still doesn’t know Sam is lying to him.
In Dark Dynasty, Dean starts to become suspicious of Sam and senses he’s hiding something from him. The brothers find a case revolving around the Stynes and they manage to capture one, learning more about their history and abilities. Dean finds out the Book of the Damned can’t be destroyed and realizes Sam lied to him. Dean confronts his brother, but the Styne escapes. When Charlie is put in danger decrypting notes from the book, Dean is furious at Sam and they both rush to her rescue. Sam and Dean arrive, only to see Charlie dead.
In The Prisoner, Dean is devastated by Charlie’s death. He blames Sam for her dying and lying to him, separating from his brother to go hunting for the Stynes. His emotions fed by the mark, Dean attacks their headquarters and coldly kills every last member of the American Styne family – including Cyrus Styne, a non-violent teenager that didn’t want to follow in his family’s footsteps. Castiel and Sam are shocked at his uncharacteristic brutality, leading Castiel to confront him. Dean also blames Castiel for lying and intending to go forward with using the Book of the Damned despite the risks. Dean ends up attacking Castiel and nearly kills him, but stops at the last minute. Dean leaves Castiel, bloodied and beaten, telling him and Sam to stay away from him.
The massive dark cloud washes over the Impala, and Dean soon finds himself confronted by a woman wearing a dark dress inside it. She reveals herself to be The Darkness, whom Dean set free, and she informs Dean that they will always help each other. Dean then finds himself a few miles away from where he originally was. He and Sam soon regroup. They discover that the dark cloud has transformed various people into what they call “Rabid“. The brothers are forced inside a hospital, where Dean meets a baby girl named Amara, who later turns out to be The Darkness herself, but Dean is unable to do anything as Crowley eventually disappears with the child.
A couple of weeks after the incident, Dean and Sam drive to Quaker Valley, Oregon. Unable to figure out what monster they are up against, Dean calls Castiel and discusses the case with him. In the middle of their conversation, Dean is attacked by the town’s Sheriff, who turns out to be responsible for the murders Although Dean manages to defend himself, he fails to execute the Sheriff for he does not know the correct method. Upon providing Castiel with a photograph of the monster’s teeth, Castiel is able to give Dean the right information, revealing the monster to be a Nachzehrer. One night, though, Sam wakes up from a vision of their father, and while Sam is rather enthusiastic about believing it was God leaving a massage, Dean disagrees.
In Our Little World, Dean and Sam hunt down Amara at Crowley’s lair. Dean finds a teenage Amara, but is unable to attack her, for reasons he cannot understand. When Crowley threatens Dean’s life, it is Amara who demands Crowley to release Dean or else die. Crowley complies, and Dean regroups with Sam at the bunker, where they discover from Castiel that Amara is in fact God’s sister.
Dean and Sam handle a case involving possessed costumes, and work together to save the people the spirit is after. They are assisted by Sheriff Donna. During another case, Dean meets Sam’s childhood imaginary friend, Sully, who is in need of their help.
In O Brother, Where Art Thou? Sam manages to convince Dean to follow his visions and contact Lucifer. Although heavily against the idea, Dean relents so long as Sam is able to remain safe during the encounter. The brothers then contact Crowley and Rowena, who can use the Book of the Damned to find a means to summon Lucifer. While Sam watches over Rowena, Dean investigates a massacre in a church, which they correctly assume was caused by The Darkness. At a park, Dean senses The Darkness and is taken away by her to a countryside. This prevents Dean from meeting up with Sam, who goes to face Lucifer without him.
The Darkness tries to explain herself to Dean, though Dean remains steadfast in his conviction to fight against her, but an attempt to stab her with a knife proves fruitless. The Darkness makes a move to consume his soul, but doesn’t seem able to, instead she kisses Dean passionately. Their meeting is interrupted by the arrival of angels. Although The Darkness successfully kills all three, Heaven prepares to attack her with a powerful blast. For his safety, The Darkness teleports him back to the park.
In The Devil in the Details, Dean attempts to drive back to the location where The Darkness was, but the smiting caused by the angels poisoned the air. Dean falls out of his car and starts to throw up. Castiel arrives just in time to warn Dean not to proceed any further and that he will go himself. Dean returns to the Men of Letters’ bunker hoping to find Sam. There is no one present. He calls Crowley and finds out that Sam is trapped in Hell with Lucifer. Dean then makes his way towards Billie the Reaper, who provides him with the witchcatcher and a means to get into Hell and Limbo.
Together with Crowley, Dean traps Rowena in the witchcatcher and forces her to return Lucifer to his Cage. Castiel arrives shortly after bearing a message from The Darkness, promising her arrival. Dean then hears noises and rushes to go check on Sam along with Castiel. When the two of them arrive just outside the cage, Lucifer teleports them into it and a battle ensues. Lucifer proves to have the upper hand against all three, knocking them about and strangles Dean to convince Sam to say “yes”. Castiel pushes the archangel off of Dean, who then rushes over towards Sam. While sitting next to Sam, Dean watches as a bright light signals the archangel’s return to the Cage. Dean and Sam leave Hell at Crowley’s demand. Dean remarks that it was a rough day for all of them.
A few days later, Dean presents Sam with a new case for them to work on. When asked if Castiel is alright, Dean reassures him that Castiel “always is”. The brothers arrive at a retirement home and investigate the strange death of a patron there. They question one of the residents, Mildred Baker, when a second death occurs. Midred shows an interest in Dean. Mildred, a witness to the death of Arthur, explains the incident in enough detail that the brothers realize it was a banshee attack. Upon returning to the Bunker, Dean hears noises and prepares his handgun. To his surprise, he finds Castiel among a pile of books and sheets. Castiel tells him he is in search of a way to trap the Darkness. When Dean reveals his own failed attempts to kill Amara, Castiel prompts him to explain further, which he does. Dean reveals he has an irresistible attraction towards Amara and that it scares him, though Castiel comforts him, believing this to be a good thing.
When Sam comes up with a plan to use Mildred as bait against the banshee, Dean rejoins with him at the retirement home and stays with Mildred until the sun sets. Mildred tells him how to live happily, and that is by following “your heart”. Suddenly, Dean hears the banshee’s screams and it turns out that it’s targeting him. Sam and Eileen Leahy arrive and with Mildred’s assistance, they defeat the banshee before Dean cracks his skull on the wall. Case closed, Dean and Mildred walk out the building, arms linked. Mildred tells Dean that she can tell that he has his eyes on someone, and offers to be his woman if he ever wants. At the Bunker, Sam inquires as to why the banshee attacked him, since its victims are weak people. Dean is unable to give an answer.
In Don’t You Forget About Me, Sam and Dean get a call from Claire about a possible monster problem. They reunite with Jody and Alex who both claim Claire has not been hunting real monsters as she claims to be. When Claire reveals Alex’s intent to have sex with her boyfriend, Jody initiates a sex talk which leaves everyone – including Dean – uncomfortable. Claire’s concern for monsters lurking around proves true, when she, Jody and Alex get kidnapped by vampires intent on getting revenge on Alex. Sam and Dean arrive soon enough to stop one of them from hurting Claire. In the ensuing battle, both vampires are killed and the women are saved.
In Love Hurts, Dean hooks up with a woman in Kansas, who leaves a hickey on his neck, which Sam notices. The brothers then investigate the death of a babysitter, and afterwards, her lover. When the wife of the lover comes to them and reveals a spell she used, the brothers realize the deaths are caused by a curse. When a qareen comes for the wife, Dean kisses her to take on the curse. With Dean as its new target, the qareen shapeshifts into the form of Dean’s darkest desire, which is revealed to be Amara. “Amara” proceeds to attack Dean, intent on ripping his heart out, but Sam locates the qareen’s heart in time and stabs it, killing the monster. Back at their motel, Dean reveals his attraction to The Darkness to Sam, and he admits that he cannot help defeat her, for whenever they are near, he cannot control himself. Sam doesn’t blame him for this, since it is not Dean’s fault.
In The Vessel, Dean agrees to go back in time to retrieve a Hand of God, a weapon to use against Amara. Dean doesn’t allow Sam to join him in case “things go sideways”, adding that Dean can’t kill Amara anyhow. Dean calls Castiel to be taken onboard the USS Bluefin, but finds himself alone inside the submarine. Dean hides under the beds as some of the crewmen enter, and spots a warding on the wall near the door. After stealing the clothes of one of the crewmen, Dean goes after Delphine and introduces himself to her. He warns the captain of the submarine’s fate and the importance of his mission. Delphine eventually comes to trust Dean since they are both from the Men of Letters. She opens the box and shows Dean the Hand of God, which is a piece from the Ark of the Covenant. Delphine removes the wardings keeping Castiel from entering the submarine, but reveals that the last warding is carved into her chest. She convinces Dean to kill her to let his friend in, but before Dean can proceed, the submarine gets attacked by a German Destroyer.
Delphine uses the Hand of God to destroy the submarine and the Destroyer. Before her body erupts, she gives Dean back the weapon and Castiel arrives to take Dean away. Dean returns to the present. Sam, lying on the floor, yells at Dean, telling him that “Castiel” isn’t Cass. The angel responds by throwing Dean across the room and taking the weapon. Dean realizes then that it is in fact Lucifer. However, the Hand of God was depleted when used by Delphine. Furious at Dean over the loss of its power, Lucifer stalks towards Dean, who he has pinned to the wall, but before he can lay a hand on Dean, Sam banishes the archangel from the Bunker. Dean and Sam later make an agreement to hunt down Lucifer and rescue Castiel, though Sam warns Dean that Castiel might not want to be saved. Dean doesn’t listen.
A week later, Dean decides they need a break and takes a case that involves boxing. Dean is highly enthusiastic about meeting Gunner Lawless, whom he was a major fan of since childhood. The brothers get to watch a match while there. Dean and Sam later discover that Lawless is behind the death of one boxer and the disappearance of another. They track him down to his hideout and Dean finds out that Lawless is working with a crossroads demon. The demon Duke orders Lawless to attack Dean, however, Dean manages to convince the boxer to do the right thing. Lawless disobeys his master and kills Duke. To Dean’s misery, Lawless chooses to die for his sins, and lets the hellhound take him to Hell.
Two weeks after, Dean and Sam pick up a case Bobby once dealt with years before. They find out they are hunting a Soul Eater and through the Men of Letters’ archives they discover a way to kill it. Dean lets the Soul Eater take him to its nest so he can draw a sigil inside the nest while Sam draws one inside the house. Once the spell is completed, Dean catches a glimpse of Bobby from the past, before they are both transported out of the nest.
During a werewolf hunt, Sam gets shot and seemingly dies from the wound. Desperate, Dean chooses to overdose on drugs so he can “die” and speak with Billie, in order to have her revive Sam and let them trade places. He claims that Sam is the one who can defeat the Darkness, but when asked how, he is unable to provide an answer. Billie nonetheless rejects his offer and the people watching over his body revive him. Dean soon discovers that Sam wasn’t really dead, and is relieved by the fact.
Sometime later, Dean receives a call from Crowley to meet up with him at a secret location. Dean and Sam learn that Crowley has not only escaped imprisonment, but also possesses a Hand of God, but he plans to get their help in using it against Lucifer. The brothers decline since they want Lucifer out of Castiel first. When Rowena joins their side, Dean and Sam prepare a trap for Lucifer and Dean summons him through an incantation. Using the angel suppressing sigil, Dean attempts to talk to Castiel but he only manages a few seconds before Lucifer regains control, and proceeds to mock Dean over his demand for his friend.
Crowley opts to speak with Castiel directly by possessing the angel’s vessel. Dean waits for the demon’s return but much to his dismay, Crowley instead gets trapped inside and requires their assistance to get out. As Sam begins exorcising Crowley from Castiel’s vessel, Dean reluctantly sprays holy water, which does the trick. Lucifer, in retaliation, starts suffocating the brothers but he is soon interrupted by Amara. The two face off but Lucifer proves incapable of harming his aunt, even with a Hand of God. Before the pair leave, Dean shouts to Castiel one last time, much to the surprise of both Amara and Lucifer.
Dean is later shown at the bunker drinking heavily, but is nevertheless determined to get Castiel back. During a hunt involving a bisaan, Dean understands the task will not be easy, and that it’s best that the two of them do not ask for help, especially from other hunters. When a case possibly involving Amara catches their attention, Sam and Dean drive into a town soon attacked by a giant fog that turns people into a new version of the rabids. They try to escape and end up locked inside a police station with a few other survivors, but Sam becomes sick from the fog, and briefly falls under its influence.
Like a previous victim, the rabid-infected Sam accuses Dean of choosing Amara, which Dean denies. In the midst of their desperation, Dean spots something glowing in Sam’s jacket pocket, and finds his amulet inside. Suddenly, the fog disperses and Sam recovers completely. Realizing that it must be God, the brothers walk outside and discover other infected victims healed and the people dead now alive. Walking along the road, Dean and Sam spot the presumably deceased Chuck Shurley, whose presence causes the amulet to burn hot, as it would do in God’s presence, thus revealing to them who Chuck really is.
At first Dean is skeptical, until the man they knew as Chuck teleports them back to the Bunker and reveals Kevin Tran‘s ghost as having been in the Veil this entire time. Kevin greets them and requests that they trust God, before Chuck sends him up to Heaven where he belongs, thus sealing Dean and Sam’s trust. While Sam acts enthusiastic and almost happy about finally meeting God, Dean is less thrilled and sheds a tear over how abandoned God made him feel. God tells him not to compare him to his own father, and promises him that he did try to help, time and time again, until he chose to just allow his children to decide for themselves.However, God proves less interested in dealing with his sister than they do, going so far as to shower, sleep, wear Dean’s robe and watch porn from his laptop. Dean and Sam later find out why from Metatron, who calls them to show a “suicide note” God wrote. Frustrated, Dean confronts God at a park to tell him to change his mind, with success. Meanwhile, Sam and Dean encounter another prophet, Kevin’s successor, who is a survivor of a town engulfed and destroyed by Amara’s fog. With the assistance of both Donatello and Metatron, the brothers form a plan to rescue Lucifer while Dean distracts Amara.
Dean calls out to Amara, and meets up with her in a forest. Amara is overjoyed to see him again, but Dean brushes off her hopes of the two of them being together. Amara informs of him that some day, he will give up his humanity and be a part of her, and urges him to stop resisting. When Amara touches Dean, she realizes that she can no longer read his thoughts and it’s because Dean has been in contact with God. Feeling betrayed, Amara abandons Dean and goes after Lucifer’s rescue party. The plan succeeds regardless, thanks to God.
At the Bunker, Dean and Sam are forced to become counselors for Lucifer and God when Lucifer begins demanding an apology. The brothers fail in their task but God does manage to give what Lucifer wants. The four then plan an attack on Amara, and agree to use demons, witches and angels in the absence of the three other archangels. Dean is tasked with getting Crowley to join. During discussion, Dean believes it is best to just kill Amara, seeing it as a rational decision since it would mean Amara would not escape prison again. Lucifer points out that Dean just wants to get rid of Amara because of their attraction, so Sam points out that for once, they can finally leave the decision-making to God, and not worry about the decisions themselves. Dean finally relents.
The group arrive at a warehouse where they are joined by Crowley and Rowena. God then reveals the plan to give Sam the Mark since Dean was already tainted by it. Dean is enraged, and drags Sam away to talk to him privately. Again, Sam convinces Dean to accept the plan because it is God’s plan. Amara soon arrives outside their location, where witches, angels and demons each attack her in order to weaken her. Her vessel severely damaged, Amara still manages to stumble into the warehouse, and is stabbed by Lucifer. Dean attemps to approach, but Sam holds him back.
The two watch as God and Amara exchange words, and Dean holds onto Sam when the Mark begins to form on his arm. Unfortunately, Amara manages to lash out and attack God. Dean tries to stop her, but Amara simply flings him away and leaves God dying and unconscious on the floor, and promises the end of all of God’s creations, before leaving. Sam goes to check on God, while Dean carefully approaches Lucifer, who was flung away in his attempt to rescue God. Dean wakes what he presumes is still Lucifer, only to discover it’s Castiel, who explains that Lucifer was expelled.
Rowena returns from outside to tell them about the state of the sun. Because of God’s condition, the sun is slowly dying, which would mean the end of everything. This causes everyone including Dean to grow depressed and hopeless, and they start drinking. Sam tries vigorously to get everyone to figure something out. Castiel offers using souls to fight Amara. This sparks Rowena to suggest creating a soul bomb. Dean and Sam thus go to Waverly Hills Sanatorium to collect souls for the bomb. However, the souls prove insufficient. Luck comes in the form of Billie the Reaper, who saw the boys collect the souls and offers to help by raiding the Veil for more.
With the crystal packed, Rowena reveals to the group that she will turn Dean into the bomb itself, since he is the only person who can get close to Amara. Dean accepts, and eventually heads out to Amara’s location. At the park, Dean and Amara discuss about what Amara truly wants, because Amara is not happy about what is happening to the Earth as a result of what she did to her brother. Dean tells her that in truth, she does not wish to kill her brother despite how angry she is at him, because he is still family and she still cares about him.
Dean’s words dig deep and Amara decides to summon her brother to their location. The two manage to reconcile, and Amara heals God, thus restoring the sun. The two decide to depart, leaving Earth to the Winchesters. In thanks, Amara gives Dean a gift which Dean soon finds out is the resurrection of his mother Mary Winchester.
I gotta tell ya, every women in this place – they want to eat you up.
— Hooker to Dean Winchester
in Sin City
Dean has green eyes, light freckles on his face and short-cropped Ivy-league hair that is dark blonde. He is 6’1″–ironically making him shorter than his younger brother Sam–and muscular. Dean is noted to be “handsome” or even “pretty” by other characters constantly.
He usually wears a plaid shirt over a T-shirt, jeans, and boots, unless he has to wear a disguise in order to impersonate someone. Until Season 6, Dean often wore his father’sleather jacket. He also used to wear a watch and a silver ring. As of Season 4, Dean has a hand-shaped burn scar on his left shoulder from where Castiel pulled him out of Hell. This mark has since disappeared from his body.
For the first four seasons, Dean also wore an amulet around his neck that resembled the head of a bull made of brass, attached to a black cord. This amulet was given to him by Sam as a Christmas gift when they were children. Throughout the first half of Season 5, Castiel attempts to use this amulet to find God, as its claimed power is to burn hot in God’s presence. When Castiel is unsuccessful, he declares the amulet “useless,” and Dean throws it away.
Dean mentions to Haley Collins in season 1 that he doesn’t wear shorts. However, he is actually wearing shorts while cleaning The Impala in the episode Baby.
Dean recently received the Mark of Cain, manifesting just below his elbow. Since separating from Sam, his appearance has become more scruffy and unshaven. His hair had also grown out a bit. Dean later briefly possessed a pair of black eyes while he was a demon.
What’s the matter? You don’t think you deserve to be saved?
Dean Winchester, from the moment of his debut, was shown to be an understanding, funny, mischievous, and, in contrast to his younger brother, a little immature. Dean’s shown countless times to be good with kids and the ladies. At an early age, Dean was trained by his father, John Winchester, to hunt and kill creatures of the supernatural. However, unlike his brother Sam, he did not resent his father for having him “raised like a warrior”. He seemed to prefer hunting the supernatural over any normal “apple pie” life, though it was revealed that when he was sixteen, he did in fact desire (or at least hope for) a normal life: He just couldn’t leave Sam. This however did not last long, as later on while still sixteen, following a Werewolf hunt he realized just how unique his life was. However, by Season 7, following all that he has seen and done, Dean admits to Eliot Ness that he no longer wants to be a hunter and would give it up if he could.
Dean is an avid fan of classic rock music. Many of his aliases have included the names of famous rock musicians. He is known to use crude humor, use pop culture references, make sexual innuendos, and indulge in pornography (especially about Busty Asian Beauties). He has even stated once that he does enjoy anime and Japanese animated porn (Hentai).
Dean typically avoids emotional intimacy, preferring to engage with women only as sexual partners. However, he has had a few long term relationships over the years, with Cassie Robinson, pre-series, and Lisa Braeden, in season 6. After the tragic events that led Dean to ask Castiel to make it as if Lisa and her son Ben had never met him, Dean seemed to give up on ever having a family other than his brother. After his break up with Lisa, Dean was reluctant to get back into his old routine of “new town, new girl”. However, the one time he was shown to indulge in a one-night stand in The Slice Girls he ended up fathering an Amazon that tried to kill him. He was reluctant to defend himself against his Amazonian daughter and Sam ended up making the kill. After these events he became even more reluctant to get in a physical relationship let alone an emotional one.
Dean values his family’s safety over anything else, even going so far as to kill a demon and its human host in order to save Sam’s life, as well as sacrificing his very soul and suffering in hell to resuscitate his brother.
Even though Dean keeps himself in excellent physical shape, he is known to have very bad eating habits. He is often shown enjoying greasy, fattening or otherwise unhealthy food, especially cheeseburgers and pie, and dismisses salads as “rabbit food”.
Dean is terrified of flying and claims that is the reason why he drives everywhere.
Despite his working knowledge of the supernatural, Dean is skeptical with regard to the “good aspects of religion.” However, he becomes somewhat more open-minded after meeting the angel Castiel, yet the antagonistic behavior of most angels and God’s reluctant to openly participate in events prevents him from being a true believer, like Sam.
Dean has also shown on several occasions that he is a great fan of movies, particularly westerns, and was thrilled to be given a chance to go to the old west. He was also overjoyed when he met and was able to work with Eliot Ness, frequently referencing The Untouchables during the episode.
Dean is typically ruthless and aggressive when he is hunting, a task which he approaches enthusiastically, making him the more merciless of the Winchester siblings. But in spite of that, he is capable of acknowledging whenever he’s going too far, as seen with his interaction with Lenore and Gordon (Bloodlust). Whereas Sam is at least willing to sympathize with what they hunt, provided that their motives can be counted as morally gray, Dean mostly sees the world as black and white. He passionately despises what he hunts, especially demons, and is prepared to kill without question more often than not, unlike his brother. This has caused him to develop a bigotry against most supernatural creatures and beings.
He dislikes showing his emotions to monsters, and when facing beings like Abaddon or Azazel he acts threatening and determined. When facing the angels, even knowing what they could do to him, Dean is sarcastic, rude, and insulting. The only being he was openly afraid of was Death; on the rare occasions that they met, Dean was nervous and cautious, and when Dean was angry or frustrated enough to talk back, he became visibly scared and backed off the moment Death appeared annoyed.
Despite these traits, Dean is very laid-back and well-disposed when not on the hunt, and he values the safety of his family and innocent civilians above all else, even his own life. Though on occasion he can be somewhat impulsive as well as arrogant, Dean is both extremely intelligent and competent. He is more likely to exhibit irrational behavior when his family is threatened.
Despite being the better hunter, Dean admits he doesn’t see himself as anything other than a “grunt”. He is constantly called out for feeling this way by Bobby and Sam. But regardless his feelings always return. These feelings can be traced back to his relationship with his father John, who at times treated him as a tool rather than as a son and who held him to unrealistic or unfair standards.
Dean enjoys the uncomplicated things in life, such as good food and television. He almost constantly displays some level of humorous behavior, and frequently makes light of tense situations. He sometimes appears foolish due to this habit, but this seems to be merely his means of dealing with the stress of hunting.
Dean shows on multiple occasions a soft spot for children. He is very good with them, able to talk to them with ease, and he is always very sympathetic; this most likely stems from the fact he practically raised Sam when he was a child. Dean’s affection extends to nearly all children, particularly young ones, although he also cares about teenagers. Dean is more willing to put his life in danger for children than he is for nearly any others. Dean’s affection even extends to monster children, and despite his ruthless approach to hunting he’s usually unwilling to kill monster children unless he has a crucial need.
After his extraction from Hell by Castiel, Dean began exhibiting noticeable anxiety and experienced chronic, abominable nightmares of his experience there. He initially lied to Sam that he remembered nothing of his time in Hell, but eventually confessed and told him he remembered every detail. The fact that he tortured souls just to escape torture himself weighed heavily on Dean, leaving him visibly sad and guilt-ridden. Due to this, he believed he was unworthy of rescue. He also explained to his brother that he wished he couldn’t feel anything, as the sorrow he felt is so overwhelming. Dean later revealed in Family Remainsthat it was not just the fact he tortured souls, but the fact he enjoyed it.
Another side of Dean is his utter disgust at Sam for many of his dangerous or foolish actions, such as drinking demon blood, and having a sexual relationship with a demon. While this made him angry, Dean continues to love Sam since he knows their family isn’t perfect. His reluctance to completely leave his brother made it difficult for Dean to stay with the Braedens during season 6, and many a times Dean has chosen his brother over others.
Dean also drinks a lot of alcohol, especially during times of stress. This worsened during season 7 when life was becoming too difficult for him to bear. Dean also fell into a period of depression. Following Bobby’s death at the hands of Dick Roman, Dean developed a very strong, obsessive revenge streak in him and spent the entirety of the season hunting Dick down to kill him. As part of Bobby’s last wishes he tried to let go of his anger and vengeance, and while in the end he succeeded in killing Dick, it was as part of the job and not for vengeance.
The constant life-or-death situations Dean was forced into while in Purgatory created an extreme change in him. While he was stuck there, he became emotionless and paranoid of the fear of getting attacked. He killed monsters of Purgatory with ease and was always fighting for his survival. When returned to Earth, his new outlook on life was clear. He became hardened, emotionless, and at times ruthless; his humor and puns were nonexistent when hunting. That changed with Castiel’s return from Purgatory after which he started to show his light-hearted side again.
Having a now haunted sense of self-created in him during that year, he became firmer in his belief of hunting. He had personally seen all the monsters they hunted in Purgatory and in doing so, developed a strong sense of responsibility to the people they saved. Dean now believes that it is their duty to save people and quitting out of the hunting business is permanently out of the question. Despite becoming more ruthless, Dean has developed more faith in monsters managing to recover their humanity, as shown with him willing to let Kate go, presumably developed from his time with Benny.
Following Kevin’s death, and Gadreel taking complete control of Sam, Dean became desperate to save him. When Sam was freed, Dean’s self-loathing seems to have reached a new height: He claims he’s poison, and that anyone near him dies. Dean decided to obtain the Mark of Cain, and by doing so, his personality became darker, with extreme levels of aggression and wrath. He also became more distrusting and suspicious, and more hate-filled toward the supernatural.
As a demon, Dean’s soul became twisted and he no longer empathized with others. He cared only for himself and what he needed. His change was so drastic that he stalked Sam throughout the Bunker with the intent of killing him using a hammer, only to miss by a few inches. He carried out this task calmly, and coupled it with taunts, giving the impression that he was enjoying himself. This is furthered by the fact that instead of an axe, he decides to use a hammer to break through a door and kill Sam, despite both tasks requiring much more force with a hammer than with an axe. Demon!Dean apparently cared about the natural order, something old Dean despised. He even considered himself, as a demon, a part of the natural order, and that it was all set up in this certain way.
Dean did retain a few former traits, such as his love of drinking, playing pool, darts and foosball. He is still more brutal, happily beating people and demons beyond a reasonable point, with limited provocation. He is also colder, and while initially coming across down-to-earth and charismatic, he quickly turned cold and ruthless when others proved to be uncooperative, as shown by him outright shaming and humiliating Ann Marie for sleeping with him the moment she rejected his advances, not caring that he had left her near tears.
Dean’s concern for Sam, innocent people and the Impala disappeared while he was a demon. He told Cole that Sam’s well-being did not matter to him. He took innocent lives just to satisfy the Mark’s lust for blood. He referred to the Impala as “just a car” and didn’t bother to tend to its condition. Dean returns completely to normal once Sam cures him through the Demon Curing Ritual.
In Season 11, Dean suffers from the fact that he unleashed The Darkness upon the world. Although he has every intention of defeating The Darkness by whatever means necessary, he soon realizes he himself cannot harm her, and has developed an unwilling attraction towards her. This has caused a banshee to deem him vulnerable and a qareen to take the form of Amara, who has become Dean’s darkest desire. These facts leave Dean feeling noticeably sad and down, but he’s not yet ready to give up.
With the revelation that Castiel had said “yes” to Lucifer, Dean shows great determination in saving his friend, even going against Sam who believes this to be Castiel’s choice. Dean’s desperation drives him to use every method possible to free Castiel, and to put Castiel’s safety as among his top priorities.
In a bid to stop the Darkness, Dean was shown to be a good strategist, planning the rescue of Lucifer and talking the Darkness out of her anger. This led him to save the world, and regain his mother.
In Season 12, Dean struggles with the changes in his life. Mary is not the woman he remembers, nor is he the son she remembers, leading the two to part ways much to Dean’s distress. Dean tries to bury his initial discomfort with being abandoned by Mary, but an eventual reconciliation restores some of Dean’s happiness about her return. Another issue is Crowley and Castiel’s partnership, which Dean expresses disdain in. Conflicts with Lucifer and the British Men of Letters also become major concerns for Dean.
When a witch curses him to lose his memory, Dean gradually forgets important facts about himself, but a more childlike demeanor, coupled with a fascination in cartoons and a happy, normality-loving personality begins to surface, a likely indication of what kind of person Dean could have been had he not become a hunter. As noted throughout the season, Dean has become more open about his interests and preferences, switching within a day from hating vegetable juice to drinking it without another word. As of recent, Dean may be losing much of his bravado, the tough, sarcastic and careless personality he carried with him for most of his life is slowly slipping away to reveal the true Dean Winchester underneath, one that not even Sam recognizes.
Dean has been seen using a variety of weapons over the course of the series, and is very inventive while improvising weapons from his surroundings, but there are some particular armaments he seems to prefer. Dean tends to use a brushed stainless steel Colt 1911 with pearl grips, which John is seen using in a flashback, and also uses a Baikal sawed-off double barrel shotgun when he needs extra firepower. However lately he has used a lever action Winchester 1887 shotgun (given to him by Jo before she died) on a more regular basis than his usual shotgun.
He has also been seen with an G3 SG1 marksman rifle in “Simon Said” and “All Dogs Go To Heaven” and was proficient enough with the weapon to act as a sniper and kill several skinwalkers. Dean is shown to possess a large machete in “Dead Man’s Blood“, and among other regular hunting items. Also, both Dean and Sam have acquired angelic blades which Dean has successfully used. Dean uses one to kill Zachariah, becoming the first known non-angel to kill an angel in the series. After emerging from Purgatory, Dean started using a large, machete-like blade from the monster realm. The blade is crude in design, featuring a large bone hilt and a stone-like blade. The blade is powerful as Dean used it to behead a Leviathan and later a group of vampires.
The trunk of the Chevy Impala contains numerous weapons which are implied as having been needed in the past, notable examples sheath knives and an DefTech 37mm grenade launcher.
Since moving in to the Men of Letters Bunker, Dean has kept many of his weapons hanging up on his wall.
The First Blade is another one of Dean’s weapons that can kill any demon no matter their age or power. Because it draws its power from the mark, which has the power of The Darkness, it can kill any supernatural being. The First Blade can only be used if the user has the Mark of Cain which means only Dean could use it and make it powerful to kill anyone. The Mark of Cain gives him incredible strength, telekinesis (only in the presence of the blade) and immunity to all demonic powers, as seen in “King of the Damned“.
Dean was transformed into a Knight of Hell by the Mark of Cain and possessed powers that far surpass that of low and mid-tier demons. Since then he has been cured of both being a demon and the Mark.
Possession – Dean was resurrected as a demon in his own body, but it is likely that he has the ability to leave his own body, and possess the bodies of others, and take control of them.
Immunity – Dean, as a Knight of Hell and the bearer of the Mark of Cain is much more resilient than most demons. While vulnerable to holy water, he was shown to recover quickly from it. He also retains his demon mannerisms for a longer period of time while being cured than other demons. He also became immune to a Devil’s Trap briefly due to his humanity being restored.
Super senses/Astral Perception – As a demon, Dean’s senses were heightened and expanded. He was able to detect when other demons were nearby as shown when he was stalked by an Abaddon loyalist and instantly recognized him as a demon.
Super strength– As a Knight of Hell, Dean is significantly stronger than common demons: he was able to easily shove Crowley, the King of Hell, to the ground and toy with before quickly overpowering Cole during their fight. He was also easily able to overpower lower demons. However, Castiel was able to restrain him, albeit while Dean was being cured and was in the process of having his humanity restored.
Immortality – Unless he transfers the mark to someone else, and is killed by The First Blade, Dean will never die by neither natural or superficial means. It is highly implied that he cannot kill himself with the blade, as it had no effect on him when he slit open his hand.
Regeneration – After being reborn, Dean’s wounds, including the stab wound from an angel blade, were completely healed. Dean also healed near-instantly from a knife cut to the face, and a cut from the First Blade that he made in his hand healed within seconds.
Invulnerability – Knights of Hell are little affected by damage dealt to their hosts, even injuries as severe as being stabbed, gunshot wounds, decapitation, and dismemberment.
Super stamina – Demons do not require food, water, or sleep to maintain themselves. Dean, as a demon, can consume vast amounts of alcohol without dying and very little effect. He was also unaffected by tear gas.
Uncontrollable Bloodlust – While Dean had the Mark of Cain, even in human form, his bloodlust was very high as slaughtering people provided him with mental and emotional satisfaction.
Wielding the First Blade – As the bearer of the Mark of Cain, Dean was able to wield the First Blade against all types of enemies who would otherwise be invulnerable to harm such as other Knights of Hell.
Abilities with the title of Death
Dean gained the following abilities while wearing Death’s ring for a day:
Intangibility – While wearing Death’s ring, Dean could phase and walk through physical barriers.
Invisibility – While wearing Death’s ring, Dean could turn himself invisible.
Teleportation – While wearing Death’s ring, Dean could teleport from once place to another in the blink of an eye. He teleported from the street the man crashed his car to Bobby’s bunker.
Killing touch – While wearing Death’s ring, Dean could kill anything he touched.
Abilities with the Mark of Cain
Dean demonstrated the following abilities while wielding the Mark of Cain:
Super Strength – When under the influence of the Mark of Cain or using its powers, Dean displayed superhuman strength at times. He was able to overpower and kill the vampireConnor, while killing Abaddon, Dean lifted her off of her feet and into the air, while under the influence of the Mark’s rage he was able to beat a group of human criminals while outnumbered and he was able to break out of the Styne Family restraints and later beat the SeraphCastiel into submission with ease.
Telekinesis – On two occasions, Dean displayed a telekinetic control of the First Blade. After losing the First Blade during his fight with Abaddon, Dean was able to use telekinesis to summon the First Blade into his hand, albeit with great concentration. After being badly beaten by Metatron, Dean used telekinesis to pull the First Blade into his hand from across the room in a last-ditch effort to defeat Metatron.
Dean possessed all the typical abilities of a vampire after being transformed by Boris:
Super Strength – Vampires possess strength that is greater than humans. Young vampires experience a formidable increase in physical strength; able to lift heavy objects and overpower grown humans. Older vampires, however, can overpower their own makers and other creatures. As a vampire, Dean had much greater strength than he had as a human, but was still weaker than the over-600 year old Boris.
Fangs – Vampires possess a set of retractable fangs. Their teeth are superhumanly strong and can rip open a human’s neck and leave huge bite marks on the corpse of the victim it has fed on.
Super Agility – Vampires possess amazing agility. They can climb up walls and jump off buildings without hurting themselves. Vampires also have greater reflexes than humans. While a vampire, Dean was able to jump from a balcony to the floor below without harm and continue fighting.
Super Senses – Vampires have extremely keen senses that are superior to those of humans. They can see in the dark, hear a human’s heart beat, and possess enhanced sense of smell. A vampire can track a human’s blood over long distances. Dean was able to use this ability to locate the nest of vampires responsible for turning him.
Immortality – Vampires can potentially live forever. They can’t grow old and don’t acquire conventional diseases that affect humans.
Invulnerability – Vampires can not be killed by conventional methods, such as stab wounds or gunshots. Vampires have an extreme durability to pain.
Regeneration – As long as they have enough human blood, vampires can quickly heal any wound that does not include amputation.
Super Stamina – Despite their hunger, vampires don’t tire easily. Dean, although a new vampire who had yet to complete the transition, took on an entire nest of over twenty other vampires, in a fight to the death, and emerged almost unfazed.
Abilities granted by spells
Dean displayed the following powerful abilities while using magic:
Dream Walking – After taking African Dream Root, Dean gains the ability to enter the dreams of the person who’s hair is in the potion. However, unlike Sam and Jeremy Frost, Dean’s ability to manipulate the events of the dream he enters is limited to interacting the dreaming person and getting them to change things as demonstrated with Bobby Singer and Charlie Bradbury.
Invisibility – As a ghost through astral projection, Dean was naturally invisible.
Telekinesis – As a ghost through astral projection, Dean demonstrated a limited telekinetic ability, hampered by his inability to concentrate on an object well. However, despite this, he was able to drop a chandelier onto the floor by combining his telekinesis with Sam’s.
Super Strength – As a ghost through astral projection, Dean was able to knock demons around with ease while using his invisibility to his advantage.
Teleportation – As a ghost through astral projection, Dean could teleport as demonstrated when he teleported out of a funeral home after being set free by the ReaperTessa.
Warding – Over time, Dean has learned how to ward buildings against demons and angels. He has also displayed the ability to “power down” the wards of the Men of Letters bunker without removing them completely.
Binding – With the right spell, Dean has proven capable of binding beings to his will such as when he boundDeath using a spell provided by Crowley.
Spell Knowledge – Dean has displayed a knowledge and understanding of certain types of magic at times. When Lady Toni Bevell used the Chinese Mind-Control Technique to threaten his mother to get Dean to surrender, Dean possessed the knowledge to recognize the spell and the method to counter it, something Toni clearly didn’t expect him to know.
Expert Hunting Skills – Trained by his father from early childhood, Dean possesses excellent combat and hunting abilities; he is established throughout the series as an extremely dangerous individual, and he is more than capable of taking a stand against even the most formidable of opponents, such as demons, vampires and leviathans. By Trial and Error, Sam lists Dean as the best hunter he knows of beyond more experienced hunters such as Bobby Singer and their own father.
Expert Hand-to-Hand combat – Dean is adept with martial arts, and knife fighting as well; he has subdued several human assailants with ease in multiple episodes and bested physically more powerful creatures, often unarmed or equipped with only a blade. Dean has also beaten his younger brother Sam in a fight a few times. Due to his year-long stay in Purgatory and the realm’s animal-like survival of the fittest environment, Dean greatly honed his hunting skills and instincts. Even when up against three demons, Dean was able to take them down single-handedly using only his hand-to-hand experience and the demon killing knife, something which impressed the powerful demon, and his ancestor, Cain greatly.
Marksmanship – Dean is well-versed with multiple types of firearms and is an expert marksman, he seldom misses his intended target and can efficiently put down anything vulnerable to bullets. During an old-fashioned duel with Elias Finch, Dean won, killing Finch without being harmed in the process despite Finch getting a shot off. The same also happened in an impromptu duel with werewolfJoy.
Tactician – Dean is also a proficient tracker and possesses prudent tactical skills. Highly resourceful, he frequently utilizes improvised weapons and explosive devices; in Croatoan, he demonstrated in constructing Molotov cocktails and improvised explosive devices. When fighting Cain and on the verge of defeat, Dean was able to turn the tables through a move come up with in seconds by using Cain’s own knife to cut off his hand as he moved to kill Dean.
Intellect – Dean possesses extensive knowledge of supernatural mythology. He is well-versed in how police, fire departments and various government agencies (FBI, CDC) typically operate and conduct investigations. He also knows how to both impersonate and evade them effectively. Dean is a virtuoso of escape, evasion, silent movement, and when the situation requires, subtlety and stealth. Lastly, he is also alarmingly skillful in many areas frowned upon by the law: lock picking, breaking into security systems (not so much computers, which often falls on Sam), car jacking and gaining an ‘advantageous purchase’ comes naturally to him. Dean states that he believes himself to be a simple grunt but according to Sam, he’s a lot smarter than he gives himself credit for.
Leadership qualities – Dean has shown on several occasions to be a natural leader, when operating in groups, he commonly takes command, unless the group includes someone who he himself sees as a leader, such as his father or Bobby. Between him and Sam (and Castiel), he nearly always calls the shots, and acts as de facto leader. Dean also has a skill for motivation, and is a capable orator, being able to motivate others to remain strong and carry on, even in darkest moments, with mere words. This skill also allows him to inspire trust in others, something which comes in handy, when he has to explain the existence of the supernatural to non-believers.
Strategist – Dean is also shown to be quite a capable strategist, able to come up with many quite clever, and unorthodox methods of defeating his more powerful opponents, for example he defeated the mother of all, by swallowing Phoenix Ashes (her only weakness) and tricking her in to biting him, causing her to swallow the ashes. He also devised a way to trick Dick Roman so he, Sam and Castiel could not only sneak in, but so that he could catch Dick off-guard and kill him. This was quite a feat as Dick was a master strategist capable of developing very complex and long-term plans. Another show of his strategic abilities is when he manages to capture Crowley by luring him in with a deal and then slapping handcuffs on him when he least expects it painted with a Devil’s Trap. Crowley, who is shown to be a cunning strategist himself, is caught completely off-guard by this and doesn’t even realize what Dean has fully done until he tells him. However he will also rush into situations, particularly if he doesn’t believe there’s time to stop and plan.
Dean is also a capable survivalist, as he was able to survive a year in Purgatory with limited resources.
An accomplished mechanic, he maintains his Impala in tip-top condition (and once rebuilt the vehicle entirely from being severely disfigured) and has maintained an intimate knowledge of automobiles and engines since childhood. He is also very talented at making electronic devices, most notably his EMF meter which he made using an old Walkman and an electromagnet powerful to wipe out an entire room full of computers in “Ghostfacers“.
Torture – Due to his time spent in Hell as Alastair‘s “student”, Dean has an in-depth knowledge of torture, able to inflict the maximum amount of pain and agony on a victim while keeping them alive as long as possible. In On the Head of a Pin, the angels believed Dean’s skills to be good enough to break Alastair himself who held up under angelic torture.
Cooking – As shown in Trial and Error, Dean is an adept cook. He makes burgers and they are apparently (according to Sam) delicious. Death also showed a fon
Fairy Awareness – Having been abducted to Avalon, Dean can since perceive fairies that may appear invisible or just like normal humans on Earth.
Link to The Darkness – Due to being responsible for unleashing The Darkness, Dean developed the ability to sense her, but also the inability to kill her. The Darkness claims they are “bound” to each other. The Darkness also granted Dean immunity to her fog.
Exorcism – Over time, Dean has gotten somewhat proficient at performing exorcisms on demons. However, he is not as proficient as Sam and usually leaves exorcising demons up to his brother.
Despite all of this, he believes himself to be only a “grunt,” but according to Sam, Dean is actually the best at lore (Sam refers to him as a “genius”) and is a better hunter than anyone Sam has ever encountered including Sam himself and John Winchester.
As a male human, Dean possesses common weaknesses of human.
Teleportation– Whenever a being teleports Dean to a place, he feels a stomachache. When Castiel teleported him, he couldn’t poop for a week and when God apported Dean he felt a stomachache.
Higher Beings – Although gifted in combat, certain powerful individuals, such as Alastair and Lucifer, are able to beat Dean effortlessly.
Mortality – Since Dean is a human, he is vulnerable to diseases and any form of physical harm. Dean also has a limited lifespan.
Magic – Like most beings, Dean is susceptible to the influences of magic and witchcraft.
Devil’s Trap – Just like any other demon, Dean can be imprisoned in a Devil’s trap or Devil’s trap handcuffs. As he became more human while being cured, he became less susceptible and eventually could walk right out even though he still retained demon mannerisms and desires.
Holy water – Dean finds contact with holy water painful and it can be used to stun him. However he still takes it better than a regular demon, recovering from its effects quicker.
Purified blood – Dean is affected by purified blood like any demon but as a Knight, he apparently retains his demon mannerisms much longer than other demons. The blood apparently causes him a great deal more pain than it does for other demons, possibly due to the Mark of Cain.
Angels – A newly empowered Castiel was able to overpower and restrain Dean from behind. However, at this point he had been subjected to the demon curing ritual so it’s possible his physical strength had lessened significantly.
Angel Blades (possibly) – An angel blade may have been able to at least hurt Dean as the demon possessing Drew Neely and the other Abaddon loyalist armed themselves with one when attacking Dean. Castiel also armed himself with an angel blade while waiting to see if the demon curing ritual had worked.
Death – Death said that while he could not kill Dean while he bore the Mark of Cain, he could remove the mark, and then kill him.
The First Blade – The First Blade is the only thing able to kill somebody with the Mark of Cain.
In the Season 3 finale “No Rest for the Wicked“, Dean is viciously mauled by Lilith’s hellhounds and dragged down to Hell due to a deal with a crossroads demon to resurrect Sam.
In Season 5 episode 4, “The End“, Dean died in an alternate timeline, in the year 2014, when Lucifer snapped Future-Dean’s neck.
In the Season 5 episode “Dark Side of the Moon” Sam and Dean are once again killed, ambushed by two hunters who blame them for the Apocalypse. Its revealed that this is not the first time they’ve died as it’s mentioned that they’ve gone to Heaven before but never remembered it.
In the Season 11 episode Red Meat, Dean commits suicide with a drug overdose to speak to the ReaperBillie in hopes of getting her to save Sam’s life. Billie refuses and reveals that Sam is still alive. Before she can take him to the Empty, Doctor Kessler manages to revive Dean with adrenaline to the heart.
In the Season 12 episode First Blood, Dean makes a deal with the ReaperBillie in which she stops his and Sam’s hearts then resurrects them awhile later to give them a chance to escape Site 94. In exchange, they agree that a Winchester will die permanently at midnight. However, this part of the deal is broken when Castiel kills Billie instead.
Dean: “Why’s it always gotta be me that makes the call? Not that Cass lives in my ass, that dude’s busy.”
Castiel: *appears behind Dean*
Dean: “Cass, get out of my ass!”
Castiel: “I was never in your…?”
“You hold him down while we knife him, and then we’ll all go out for icecream and strippers.”
(pulls down pants and raises arms) “PUDDINNGGG!……. crazy works.”
“Well that’s great, because without your power, you’re basically just a baby in a trench coat.”
“Life as an angel condom. That´s real fun.”
“Seriously. Why? Why would anybody want to watch our lives?”
“What kind of douchebag names a character after himself?”
Victor: “I-I I shot the sheriff!”
Dean: “But you didn’t shoot the deputy!”
“You married fake Ruby?”
“Look at these male model sons of bitches. Nice ‘Blue Steel’, Sam.”
“Misha? Jensen? What’s up with the names around here?”
“I’m not wearing any makeup. Oh crap. I’m a painted whore.”
“So, what? We’ve got a bunch of killer dolls? Like Chucky?”
“My Spidey senses are tingling.”
“I’m going to go hit the poop deck.”
“What was I suppose to do? Let T-1000 walk around and hope that he doesn’t open fire?”
Sam: “What kind of thing likes virgins and gold?”
Dean: “P. Diddy?”
“Shawshank’s a great flick, but let’s skip the shower scene.”
“Karma’s a bitch, bitch.”
Christian: “Who you calling?”
Dean: “Your wife. Let her know I’m not gonna make it over tonight.”
“Let me get dressed, Robo-Cop.”
[to Samuel] “So what’s so important that you’re the King of Hell’s cabana boy? What did he offer you: girls, money, hair?”
“Gramps threw a barbeque and left us off the e-vite list?”
“You go with Efron. I’ve got Bieber.”
Dean: “Are you wearing glitter?”
Kid: “I only do it to get laid, man.”
Dean: “…Does it work?”
“Now I lay me down to sleep, I pray to Castiel to get his feathery ass down here.”
“What, did you lose the ability to send a text message?”
“We can either take on the Devil together, or you lame-ass bitches can eat me. Literally.”
“What are you, the Hamburglar?”
“Why does Heaven care if Harry meets Sally?”
“Team Free Will. One ex-blood junkie, one dropout with six bucks to his name, and Mr. Comatose over there. It’s awesome.”
“A bloody, violent monster… and you wanna be Facebook friends with him? Nice, Sammy.”
“Calm down? I am wearing sunglasses at night. You know who does that? No-talent douche bags. I hate this game. I hate that we’re in a procedural cop show. And you want to know why? Because I hate procedural cop shows. There’s like 300 of them on television, they’re all the freaking same.”
Castiel: “Archangel. The one who killed me.”
Dean: “Excuse me?”
Castiel: “His name is Raphael.”
Dean: “You were wasted by Teenage Mutant Ninja Angel?”
“Eat it, Twilight!”
“Well, how ’bout this, the suite life of Zach and Cass?”
“I’m sitting in a laundry-mat, reading about myself… sitting in a laundry-mat reading about myself. My head hurts.”
“Go have your Robin Williams ‘Oh Captain! my Captain!’ moment.”
Tessa: “You don’t remember me?”
Dean: “Honestly, if I had a nickel for every time I heard a girl say that…”
“Boy, three bedrooms, two baths, and one homicide. This place is going to sell like hotcakes.”
“I have been Re-Hymenated.”
“Dude, on my car, he showed up naked, covered in bees.”
“Come on, Sammy. Let’s have a beer, talk about it. I’m tired of playing.”
“So tell me which one of us is really the monster.”
“Do it. It’s all you.”
“Yes, an Archangel so badass that he was personally dumped into the cage by God himself.”
Dean and Sam are the only characters to appear in every single episode of Supernatural.
Dean’s leather jacket, that he inherited from John, is nearly identical to the one worn by the title character of the movie Taffin (Played by Pierce Brosnan).
Dean has time traveled more than any other character. Going back in time 5 times (To the 1800s, the 1940s and the 1970s twice) and going forward once (to an Alternate 2014). Counting return trips, Dean has time traveled twelve times.
Dean has both been aged both forward into an old man and aged back into a teenager on different occasions.
Dean seems to be rather clueless about Pop culture, evidenced by him not knowing what an Xbox is, and believing MySpace to be a porn site. However, he seems to have gotten better over time as he now has a phone with apps, something that shocked Sam.
Dean is a big movie buff. Sam stated that Dean knows all of Clint Eastwoods movies line for line, especially the “the monkey movies.” He is also a huge fan of Chuck Norris. He also claims “Untouchables” is one of his favorite movies.
Dean suffers from pteromerhanophobia (fear of flying).
Dean is very good at flirting, proven in notable episodes. He also coached a lesbian, i.e., Charlie Bradbury into flirting with a male security guard.
Dean has been to the most number of different realms out of all the characters: Heaven, Hell, Avalon and Purgatory.
Dean is descended from one of the biblical brothers Cain or Abel, the latter who is the first murder victim who died at the hand of his brother.
During his time in Purgatory, Dean seems to have adopted a new, slightly unstable personality. He’s ruthless, volatile at times, and seems to have developed an underlying blood-lust that bubbles to the surface occasionally. Not unlike his time in hell, he immersed himself the darker aspects of his being in Purgatory. Whereas in hell, Dean gave into his darker thoughts and enjoyed torturing, in Purgatory, he appears to have given into his darker instincts and embraced the warrior lifestyle that he’d basically been raised for his entire life.
When playing Rock, Paper, Scissors, Dean almost always loses because he picks scissors. However, he beat Sam twice, once in “My Heart Will Go On“, and again in “Love Hurts“.
Dean’s Impala was a gift from John, which is why he’s so protective of it.
He is allergic to cats as evidenced in the episode “Man’s Best Friend With Benefits“. He also strongly dislikes dogs for some unknown reason though he develops a bond with the Colonel due to the human/animal mind meld he underwent to talk to him. He also briefly had some dog-like mannerisms as a result of the ritual for about a day.
In “Changing Channels“, Dean reveals that he hates procedural cop shows because say how they are all the same. He also thinks that only “no talent douchebags” wear sunglasses at night. He later tells Sam that he thinks that only blind people and douchebags wear sunglasses inside.
Of all the supernatural beings and creatures that he has met and hunted, Death is the only being that Dean was afraid of.
Dean is considered an “honorary dog” by at least the Colonel. As a result, the Colonel tried to tell him what a dog’s true role is as its not man’s best friend. The spell he was using wore off before Dean could find out however.
So far, Dean, along with Cain and Lilith, is one of the three known characters to become a demon without going through hundreds of years of torture in Hell.
Dean’s favorite song is a tie between Led Zeppelin’s “Ramble On” and “Traveling Riverside Blues.”
Dean is one of only two people known to be cured of being a demon.
Through his behavior in the early episodes of Season 10, it is evident that Dean considers himself to be superior to Crowley, who is the King of Hell, and may thus have been the strongest demon.
Even though he has a stronger connection with angels throughout the series, he’s the Winchester to eventually becomes a demon, specifically a Knight of Hell.
Dean has proven to be a skilled vampire hunter whenever the Winchesters encounter the species, once killing five vampires single-handedly out of a nest of ten, three of the others having been killed before the hunt during Blood Brother. While briefly a vampire himself, Dean single-handedly slaughtered a massive nest, including a powerful vampire who had easily overpowered him only minutes before. When he was trying to “take the edge off” of the Mark of Cain, Dean single-handedly killed six vampires before Sam even arrived, something he regarded as a new personal best. While Sam has killed a number of vampires himself, he doesn’t seem to be as skilled at it as Dean.
After being turned into a teenager, Dean gained an appreciation for Taylor Swift despite it being far from his usual taste in music. To Sam’s surprise, this like of Taylor Swift seems to have stayed with him even after the spell was reversed.
Dean has been transformed into the most supernatural creatures on the show: a vampire, a Jefferson Starship (however the process was not complete) and a demon.
Dean has killed some of the strongest creatures of their species. So far, he has killed Azazel, Eve, Cain, and Dick Roman. He has also just recently killed one of the most powerful beings in existence, Death.
Before Dean killed Death, while he helped Sam defeat War, he never actually stopped a Horseman on his own unlike Sam and Castiel who stopped Famine and Pestilence respectively.
As Dean was born in 1979, he is physically 36 years old, but since time is different in Hell than it is on Earth, he is spiritually 76 years old.
Willerton began her modelling career at the age of 15, after being scouted by Kate Marshall of Room 3 model agency whilst out shopping with her sister. Appearing on catwalks around the world for brands such as Karen Millen and Guess and winning campaigns such as the face of Sure and the body of Slendertone.
In 2011, Willerton caused controversy at the Miss Asia Pacific World pageant, held in South Korea, while representing the United Kingdom. Willerton, as well as a number of other contestants demanded answers from organisers after discovering that some contestants had been offered automatic top-ranking placements in exchange for sex, by organisers. 
The events were filmed by Willerton and other contestants (which were later uploaded to YouTube under the title Confessions of a Beauty Queen and spread throughout the pageant industry). Subsequently, she and the representatives from Guyana and Costa Rica fled their hotel to the airport, where the pageant organisers had tried to keep them there against their will and had followed them to the airport to stop them escaping. Despite the organisers denying all accusations the pageant has continued to cause controversy with subsequent winners also fleeing the country and making similar claims of indecency.
On 8 June 2013, Willerton was crowned Miss Universe Great Britain in Birmingham and was quickly tipped as a potential winner of Miss Universe by international media and pageant forums. On 9 November 2013, Willerton participated at the Miss Universe contest in Moscow, Russia. Where she became the first woman competing as Miss Great Britain to place in the semifinals, eventually finishing in the Top 10. Previous British contestants have placed as 1st Runner-up at Miss Universe, competing as Miss England, Miss Scotland and Miss Wales respectively. Willerton is the first UK contestant in thirty years to reach the top ten at Miss Universe, the previous woman to achieve this being Karen Moore, who as Miss England, reached the top five in 1983.
Willerton’s charitable work has focussed on helping the disabled. She organised her first event, Bristol Rockstyle for the Variety Club children’s charity as a teenager. In 2014 she ran the London Marathon to raise money for The Chickenshed Theatre School. In 2016, she hosted an Oscars viewing party for the Children Uniting Nations charity.
Suranne Jones (born Sarah Anne Jones; 27 August 1978) is an English actress and producer. Her first prominent television role was the character Karen McDonald, introduced to the ITV1 soap opera Coronation Street in 2001. She left the series in 2004 and furthered her acting career in numerous television drama series, including Vincent (2005–06), Strictly Confidential (2006), Harley Street (2008), Five Days (2010) and Single Father (2010). Her turn as convicted murderer Ruth Slater in the mini-series Unforgiven (2009) was critically acclaimed and noted as a breakthrough role for Jones.
Jones was born Sarah Anne Jones in Chadderton, Oldham, on 27 August 1978, the daughter of Chris and Jenny Jones, an engineer and a secretary, respectively. She has a sibling, an older brother named Gary. Jones was brought up a Catholic; her priest suggested to her father she be christened Sarah Anne, instead of Suranne, her great-grandmother’s name, as Suranne was not “a proper name”.
Jones grew up in a house on Foxdenton Lane, surrounded by two farms and their fields and commented that one of her earliest memories is of “cows looking in the window as we ate our tea”. As a child she was talkative, and later recounted that her priest would say to her: “I’m praying you can concentrate just a bit more”. Jones suffers from carpophobia (fear of wrists), which she believes possibly developed from viewing imagery of Christ‘s crucifixion and stigmata as a child.
Jones began acting professionally aged 16. Andrew Billen of The Times, while acknowledging her professional career beginnings at 16, noted that “she took to the stage at 8”. Jones later recalled that her first role was at the age of 8, in Wait Until Dark as Gloria. Upon joining the trade union Equity, Jones took on the stage name ‘Suranne’, as her birth name was already taken, and union rules dictate that each union member must have a different name. Having secured herself an agent aged 15, she soon after began to act in the theatre. Jones’s television career began, however, in 1997, where she had a very small role in Coronation Street in April 1997 as Mandy Phillips, a girlfriend of Chris Collins (Matthew Marsden). She was then cast in a television advert for Maltesers, guest starred in episodes of series such as City Central and had a small role in My Wonderful Life. She auditioned for the role of Charity Dingle on the soap opera Emmerdale, becoming one of the final four actors considered for the part, though the role was eventually given to Emma Atkins. She also auditioned for the part of Geena Gregory on Coronation Street, though she felt she knew Jennifer James would win the role—which she did—upon seeing her at the auditions.
In 2000, some weeks after her unsuccessful audition for Geena Gregory, Jones was contacted by Coronation Street bosses, who offered her a part of a new character. Jones took on the role of Karen Phillips (no relation to Mandy), making her first appearance on 21 June. The character, after marrying Steve McDonald (Simon Gregson), took on his surname, and became Karen McDonald. Described as “a bulldog in hoop earrings” and a “Victoria Beckham wannabe”, the role garnered Jones public attention, with episodes involving feuds between her and rival Tracy Barlow (Kate Ford) receiving millions of viewers; the episode featuring Karen and Steve’s (second) wedding, ruined by Tracy Barlow’s revelation that her daughter Amy Barlow was Steve’s love child, received 16.3 million viewers. Jones also began modelling for men’s magazines such as FHM and Loaded, saying: “I was 21, and within three weeks of me joining Corrie I was in Barbados doing a bikini shoot […] I was quite impressionable and I’d just say yes to everything because I wanted to keep my job. The press officer is saying: ‘Do this and you’ll be the new young funky sexy girl.’ We were all doing it at that time, but I realised quite quickly that I needed to concentrate on what I was doing”.
In May 2004, it was announced that Jones was to leave Coronation Street after four years of playing Karen. She described working on a soap opera as “exhausting”, remarking, “I was living and breathing Karen McDonald”. She made her last appearance as Karen on Boxing Day 2004. Of her tenure as Karen McDonald on Coronation Street, Jones later remarked: “I just thought, while she’s brilliant and I’m enjoying her, I’ve got to get out”.
In January 2009, Jones appeared in Unforgiven, a three-part drama on ITV1, where she plays Ruth Slater, a woman released from prison after serving a 15-year prison sentence for the murder of two policemen. Naturally brown-haired, Jones dyed her hair “tobacco yellow” with “big roots”; Jones joked that whilst not filming she “really should have worn a wig”. Additionally, the character of Ruth wore no make-up throughout, with Jones stating she was left feeling “quite exposed”, but nonetheless saying “Ruth wouldn’t have worn any make-up, I don’t think”. Jones received favourable reviews for her portrayal, with Brian Viner of The Independent writing: “a stunning performance, the stuff of Bafta nominations if ever I saw it. Heck, on the back of it she might even get propelled into the movies, and bring a bit of North Country sense to the Golden Globes“. Viner summarised his review of Unforgiven by stating, “Five stars all round, and six for Jones”. Jones later stated, “I loved that role. They don’t come along that often. It was seen by the broadsheets as well as the tabloids. It gave me a little bit of credibility, I suppose”.
Later in the year, in November, she played the role of the Mona Lisa in the two-part episode “Mona Lisa’s Revenge” in The Sarah Jane Adventures. In December, Jones starred in the Manchester Royal Exchange’s production of Blithe Spirit, by Noël Coward, which ran until late January 2010. Jones was nominated for the Times Breakthrough Award at the 2010 South Bank Show Awards, the last ever ceremony, but lost to David Blandy. When discussing her nomination she said, “You do question ‘What am I breaking through?’ Am I breaking through the perception of people who just thought I was a screaming banshee in Coronation Street? Is it that I’ve worked hard and I’ve got better? Is it that now it’s alright to say that I’m alright? I don’t know what I was breaking through, but I knew that it was nice to feel included and patted on the back for a lot of hard work”. Jones was described by Andrew Billen of The Times as being in a category of “those brave, talented few who earn their wings on a soap and then fly gloriously beyond it”. In March 2010 Jones starred in Five Days, a non-connected sequel to the 2007 series of the same name, as the female lead DC Laurie Franklin. Later in the year, she starred as Sarah in Single Father on BBC1, a character who falls in love with a widower, Dave (David Tennant), who was married to her best friend before her death.
In May 2011, Jones played the central character of Idris in the Doctor Who episode “The Doctor’s Wife“. Jones was cast due to writer Neil Gaiman wanting an actress, in the words of Jones, who is “odd; beautiful but strange-looking, and quite funny” to play the role of Idris. Dan Martin, reviewer for The Guardian, noted that “Suranne Jones arguably sets the standard by which all guest stars must now be judged here […] Jones was electrifying throughout”. Later, Jones played DC Rachel Bailey in ITV’s detective series, Scott & Bailey, opposite Lesley Sharp, who plays DC Janet Scott. The series is based upon an original idea by Jones and Sally Lindsay, her former Coronation Street co-star.Scott & Bailey returned in 2012 for a second series. In July 2011, Jones starred as Marlene, a career-woman living in Thatcher‘s Britain, in the Minerva Theatre‘s production of Top Girls by Caryl Churchill in Chichester. Michael Billington, reviewer for The Guardian, remarked that “Suranne Jones captures excellently the hidden regrets of the go-getting Marlene”. The production was later transferred to the West End‘s Trafalgar Studios. In August 2011, it was announced that Jones would star alongside John Hannah in a spoof detective drama written by Charlie Brooker and Daniel Maier called A Touch of Cloth. The programme aired in August 2012 on Sky1. Jones plays DC Anne Oldman, the “plucky, no-nonsense sidekick” of DCI Jack Cloth (Hannah). In March 2012, Jones began filming The Secret of Crickley Hall, a BBC1 dramatisation of the 2006 best selling novel by James Herbert. She plays the lead role of Eve Caleigh, a woman who moves to Crickley Hall in an attempt to move on from the loss of her son, only to be haunted by supernatural occurrences. Jones described the series as a “classic haunted house spine-chiller with an emotional family story at its heart.”
Jones returned to the London stage in 2013 in a 20th anniversary revival of Jonathan Harvey‘s play, Beautiful Thing. The play is scheduled to run between 13 April and 25 May at the Arts Theatre, London followed by a short national tour. She is also due to appear in the second series of the television play anthology Playhouse Presents. Jones starred as herself in “Stage Door Johnnies”, a comedy mockumentary about obsessive theatre fans. In June, it was announced that Jones is to play a judge “battling to keep her head above water in the murky depths of the justice system in Lawless.Lawless, a pilot episode, was broadcast on Sky1 as part of its Drama Matters pilot season. In August, it was announced that Jones was cast opposite Hermione Norris and Oona Chaplin in The Crimson Field, a BBC drama set in a field hospital in France during the First World War. The drama, which began filming in August and was broadcast in April 2014, marks Jones’s first acting appearance in a period drama.
Jones lives in London with her husband, magazine editor Laurence Akers. It was reported in 2014 that Jones had become engaged to Akers after meeting him at a wedding earlier in the year. In August 2015, it was reported that the pair had married at a ceremony in Islington. However, Jones later clarified that the pair had in fact married the previous year. In January at the 2016 National Television Awards, Jones, visibly pregnant, announced she was expecting their first child. On 11 March at the Broadcasting Press Guild Awards, in a speech via video accepting an award, Jones alluded to having given birth. The following day a representative for the couple confirmed to the press that Jones had given birth to a baby boy the week prior.
Davidson, the youngest of six children, was born in Artesia, California to Charlotte (1922–2016), a homemaker, and Richard Davidson (1915–1981), an airplane parts manufacturer. She was raised Catholic. Davidson started her career as a model in Mexico City and California, eventually adding commercials and print work in Europe. Her roommate had recommended that she take acting classes and she trained at the Staircase Theater, after which she landed roles in two feature films: Goin’ all the Way and The House on Sorority Row.
Davidson originated the role of Ashley Abbott on The Young and the Restless in March 1982, beating out more than 100 candidates. The character of Ashley became a front-burner character, and Davidson became an integral part of the show. She quit the show in December 1988 and the producers took her recommendation of hiring a look-alike actress named Brenda Epperson Doumani, whom Davidson had discovered waiting tables at a charity function.
Davidson then appeared in primetime television, but her show, Broken Badges (1990–1991), was canceled. She returned to daytime when she assumed the role of Kelly Capwell on Santa Barbara from November 1991 until the soap’s cancellation in January 1993. She next appeared as Kristen Blake on Days of Our Lives beginning in May 1993. As originally conceived, Kristen was a heroine, who had an Achilles’ heel in that the show’s supervillain, Stefano, had raised her after the death of her parents. James E. Reilly, who assumed head writing reins in 1993, began to make Kristen more of a villainess. Reilly eventually developed an outrageous second role for Davidson, having her play Susan Banks, a Kristen look-alike. Reilly eventually penned three more roles for Davidson (Sister Mary Moira, Thomas, and Penelope). Her character, Kristen, intended to keep her other character, Susan, prisoner on an island, but Susan ultimately prevailed and Kristen remained on the island until she returned to Salem in 2012. All other related characters were last seen in May 1998. Davidson’s five roles earned her a Daytime Emmy nomination for Outstanding Lead Actress in 1998.
After a year-long vacation from acting, she returned to her role on The Young and the Restless in March 1999. After a successful return as Ashley Abbott, which included Davidson’s second Daytime Emmy nomination for Outstanding Lead Actress, Davidson was fired from the show. In December 2006, Davidson told TV Guide that she was fired from The Young and the Restless due to lack of storyline. Her last airdate as Ashley was January 11, 2007. According to co-star Melody Thomas Scott, the firing was protested behind the scenes of The Young and the Restless and was seen as unfair. Scott said: “That was so heartbreaking. We’re still upset about that. That was a blow. Terrible. Eileen Davidson was such a part of the core of the show and such a brilliant actress; beautiful and always prepared. It was crazy. I’m not the only one who feels that way.” In a surprise move a few months later, Davidson signed a three-year contract with The Young and the Restless’s sister soap The Bold and the Beautiful to once again play her The Young and the Restless character Ashley Abbott at the request of The Bold and the Beautiful executive producer Bradley Bell. She first aired on March 9, 2007.Ken Corday called Davidson about a week before she was fired from The Young and the Restless to get permission to use a picture of her on Days of Our Lives. The picture, which featured Davidson as Susan, was shown in December 2006.
Davidson co-wrote her first novel with author Robert J. Randisi, a mystery set in the soap opera world titled Death in Daytime, released in October 2008. She followed it up with three sequels: Dial Emmy for Murder (2009), Diva Las Vegas (2010), and Swinging in the Rain (2011).
In July 2008, Eileen was downgraded to recurring status at The Bold and the Beautiful. She returned to The Young and the Restless full-time as Ashley on September 26, 2008. In 2012, Nelson Branco announced that Sony Pictures Entertainment wanted Davidson on both The Young and the Restless and Days of Our Lives, but that Y&R would not share the actress, leading Sony to terminate her contract with them. Thus, it was announced that Davidson would reprise her role as Kristen Blake DiMera on Days of Our Lives.
Davidson made a brief appearance on The Young and the Restless in February 2013 for the soap’s 40th anniversary. In July 2013, it was announced that Davidson made the decision to leave Days of Our Lives after a year as Kristen. Davidson exited the role on-screen on November 13, 2013. In late November, it was confirmed that Davidson would return for an episode scheduled to air on December 3, 2013.
On January 28, 2014, it was announced that Davidson would return to the role of Kristen DiMera in the summer of 2014. On May 1, 2014, it was formally announced that Davidson was nominated for a Daytime Emmy Award in the category of Outstanding Lead Actress In A Drama Series for Days of Our Lives. It’s her third Daytime Emmy Award nomination, her second for Days. She won the award on June 22, 2014.
On June 17, 2014, it was announced that Davidson had signed a contract to return to The Young and the Restless. Subsequently, Davidson revealed that her Y&R contract was for two years and that it included a stipulation that she could continue doing Days of Our Lives in the future, as well as having the option of taking a break if work became too hectic. Davidson also joined the cast of the fifth season of Bravo reality television series, The Real Housewives of Beverly Hills. On November 17, 2014, it was announced that Davidson was back on-set of Days of Our Lives, with a stint set to air in spring 2015.
She is currently married to actor, former tennis professional, and World Poker Tour commentator Vincent Van Patten. They have 1 child together, a son. The pair met in 2000, when Van Patten briefly appeared as Christian, Ashley’s “boyfriend” during a cruise, on The Young and the Restless.
“So many fucking people… Fucking weak, fucking weakass fucking people. Crying. Scared. Doing every-fucking thing in their power to get themselves killed. Spineless fucks cowering in fear until there ripped to shreds. I was surrounded by them. Watching them all die… So many I lost fucking count. After a while… I just started seeing everyone like that. Hell, most everyone Is like that. Dwight, those pussies at the gate– fucking running in terror. I just lost all respect for the human race. Makes it really easy to bash a man’s brain in when you think might save all his friends… Especially when you think the only way his friends can be tricked into living is if they’re made into slaves. you stop seeing people as humans after a while…“
Negan is a casual, jolly, savage man who adores violence and mayhem. He is very intelligent and logical, possessing a knack for controlling and manipulating others. He has a strong affinity for profane language and offensive comments and a morbid, perverse sense of humor, seeming to enjoy the shock value. His charismatic persona and domineering presence allows him to easily intimidate friends and foes alike.
Perhaps stemming from his years as a school coach, he has a pedantic nature to him, reveling in helping others explore their thoughts, feelings, and ideas. He displays profound moments of wisdom when counseling people, keenly perceptive of abstractions that others may have missed.
In spite of his violent and savage nature, Negan can be very reasonable for the sake of practicality, like when he spared Carl’s life to keep relations steady with Rick, even though Carl slaughtered many of the Saviors.
Negan does possess a sense of sympathy underneath his cold exterior, and even a sense of honor that leads him to be repulsed by certain acts against the weak, such as rape. He believes that his horrific methods of keeping his people in line, which involve burning the faces of rule breakers and using fear to keep people subjected, are to justify a greater good, and he does stick by his own code of ethics.
He adamantly believes in a philosophy that the strong are to protect the defenseless. For instance, he murders a Savior after he tries to rape Holly, claiming that if his men are to commit rape, then their goal of rebuilding civilization can never be achieved.
He also yells at Dwight for daring to beat a “defenseless child” and is even seen losing his temper at another leader who allows rape to ensue within their ranks, declaring them less than human, apparently unaware of the hypocrisy. Despite his odd sense of sympathy, he admits he has trouble feeling emotions properly due to losing someone close to him in the past.
Negan’s imprisonment has caused a change in him that many of the other survivors find hard to see, or to believe. While he is still ruthless, and struggles to express emotions, he has begun to show a desire to make up for the things that he did in the past.
Negan was high school gym coach where he practiced a range of sports including billiards and ping-pong. He also worked as a used-car salesman, presumably as a part time occupation.
At some point, Negan married a woman named, Lucille where they presumably lived together as an average married couple. Negan was involved in at least one extra-marital affair. As a school faculty member, Negan constantly strived to gain the admiration of his peers. He occasionally invited several of his fellow students to play ping-pong against him inside his own personal garage, however he frequently belittled and humiliated his pupils through the use of his expressive and aggressive language which resulted in him receiving several complaints from the students’ parents.
At some point after the outbreak, Negan established “The Saviors” and fiercely ruled over his men. Negan, along with his team (which includes at least 50 or more other men), had made a deal with the Hilltop Colony; they would use the weaponry that the other group was lacking to kill all zombies wandering near their premises, and in return, they would obtain half of Hilltop’s supplies; such as livestock and crops. To get his point across, if a potential problem would arise, Negan and his men would resort to cruel and manic measures.
If they sense they are being tracked or if they feel they aren’t getting a sufficient enough amount of supplies, they beat or kill the people from Hilltop. The group also sends “messages” to the community, which are usually very deadly, such as Gregory being stabbed by Ethan.
Later, Negan, along with fifty other Saviors, snuck up on Rick’s group and subdued Rick by surprise. They lined up all of the survivors from the van (Rick Grimes, Carl Grimes, Glenn, Maggie Greene, Sophia, Michonne, and Heath), telling them that he wanted revenge for the Saviors that were killed.
Without an agreement from Rick, Negan made a deal; everything that belonged to the Alexandria Safe-Zone, now belonged to the Saviors. He introduced his weapon of choice: Lucille, a baseball bat covered in barbed wire.
After a long talk about the new world order and whom he should beat to death using Lucille. He finally chose his victim at random: Glenn. Maggie panicked, as Glenn attempted talking Negan out of it. Negan ignored him and smashed Glenn’s skull in by slamming Lucille down hard on Glenn’s head. Negan laughed and when Glenn attempted to get to his feet, the former remarked that “he’s taking it like a champ” before swinging Lucille at Glenn, dislocating his jaw and beating Glenn to death.
Negan told the group that the Saviors would be back in one week to collect half of everything they have, or there would be more killings. Rick vowed that he would avenge Glenn and kill Negan. He laughed at this, beating Rick with his bare hands in response, before leaving with his Saviors.
Negan and The Saviors later arrived at the Alexandria Safe-Zone for their first offering. Spencer Monroe arrived at the gate, questioning Negan’s identity, to which Negan laughs.
Amused that not everyone knew his name, Negan remarks that he “had to make a pretty fucking strong first impression” and asks him to get Rick. Negan and the Saviors then begin killing the roamers surrounding the area. While the Saviors scavenge each of the houses for supplies, Negan makes several rude comments about his beating of Glenn, about Olivia being overweight, and towards Carl.
He forces Rick to hold “Lucille” while he explores the area himself. When Denise threatens a Savior for taking important medical supplies, Rick attempts to reason with him, and in response he says the group that their big walls are the only medicine they need. Before departing, he retrieves Lucille from Rick and whispers, “I just slid my dick down your throat and you thanked me for it.”
He and his men depart from the Safe-Zone with supplies, but unbeknownst to him, Carl is hiding in the truck with an assault rifle. Once he and his men get back to their base, he is amazed to see that Dwight was still alive. “There is always next time, I suppose” he says, much to Dwight’s disgust.
A Savior finds Carl, who kills six Saviors with the assault rifle. They surround the boy and he demands to speak with Negan. When he arrives, Carl fires at them until he loses control of his gun. Dwight is about to kill him when Negan stops him, asking if that’s any way of treating their guest.
Instead of taking immediate action against the boy, Negan shows quite a bit of interest in getting to know him, leading him through the Saviors facility, revealing that he is the leader of a cult-like domain of selfless followers who bow to his every word and command. Many followers of his ranks are living on a point system in order to sustain their lives, though many give into his graces for a better living, most notably the women he considers his “wives.”
It is brought to his attention that one of his many wives, Amber, has committed adultery against him with her former lover. As he goes to handle the situation, he brings Carl along to see his wives and how he handles his affairs before degrading the terrified Amber in front of them all.
Afterwards, he and Carl share a private moment in his quarters where he reveals that he’d like to get know to Carl a little better, but gets distracted by Carl’s bandaged face. He orders Carl to remove the bandages, showing interest in seeing the injury to his eye. Carl allows him to see it only after being threatened; removing the bandages to reveal the disturbing effects that being shot had left him with.
Negan, in a state of disbelief and awe, jokingly mocks the deformity and goes as far as to ask Carl if he can touch the part of his skull showing through his exposed eye-socket, which causes Carl to finally break and cry. This prompts Negan to take back the gesture and apologize, seeing that he has finally found a weakness in the child he finds so dangerous.
They are interrupted by one of his followers who returns Lucille to him. Negan reverts to coldness as he orders Carl to sing a song for him while he swings the bat dangerously close by. After this intense encounter between the two, they are interrupted once again and Negan is told that the iron is ready. Negan has Carl hold the bat while following him to witness the event.
In ritualistic fashion, complete with chanting from the followers answering to Negan’s words, he shows that whoever falls onto his bad graces are dealt with by having their faces burned by a searing iron. Tied to the end of a pole, the tool once used to straighten clothes is held over a fire before being handed to Negan, who presses it against the victims face as punishment for their betrayal.
In this case, it was the face of Amber’s former lover Mark, who is left deformed in the same manner as Dwight with a portion of his face permanently scarred and leaving an exposed eyeball.
After the ritual, Negan dismisses his congregation before turning to Carl who hands back Lucille and leads him away, contemplating what to do with him.
Negan runs into Rick while the latter was on his way to find Carl. Negan then tells Rick how eager he is to show him “what he has done to his son”. He is then attacked by Rick in a fit of rage before revealing that Carl is fine and he meant that he is eager to show Rick “that he has done nothing to his son”.
Several days later, Negan arrives at the Alexandria Safe-Zone a few days ahead of schedule; he’s informed that the community is practically out of supplies and that Rick went out looking for more.
He decides that he will stay in Alexandria until Rick returns from the supply run. He makes an offhand comment about Olivia’s weight, who overhears it and starts to cry. He tries to apologize, but, she merely slaps him. Despite several Saviors offering to kill her, Negan dismisses them.
He is later approached by Spencer and asks for a little background on the Safe-Zone. After awhile, Negan gets impatient with him and wants to know why he came to him. Spencer then tells Negan that Rick is not a suitable leader for the community and asks that once Negan kills him, Spencer be given control over the Safe-Zone.
Negan feels insulted that Spencer would wait until Rick is gone to tell him this. He responds by telling Spencer that Rick may hate him, but he has guts, unlike Spencer who acted like a coward. He then slashes Spencer’s stomach, killing him almost instantly, remarking that he had guts after all. He then orders Seth of his men to clean the mess up before a kid sees it.
Rick returns and confronts Negan, who casually blows him off. Rick demands to know what happened or he won’t leave Alexandria alive. After picking up Lucille and praying to give him strength, Negan drops the excessive profanity he normally uses and tells Rick that he feels like he’s bent over backwards to show how reasonable I can be in regards how he brought Carl back to the safe-zone safely and hints about how Spencer wanted to have him kill Rick.
After seeing the supplies gathered by Rick, Negan initially demands all of it, but, then decides to take nothing as payment for killing Spencer. Rick insists that they take their share and Negan has no objections.
As they are driving back to the foundry, Negan notices Rick and a few others were following them. An instant later, the driver is shot and killed. Confused and angry, Negan takes Lucille and sees Rick pointing a gun at his head.
A gunshot is heard and Rick’s gun is destroyed as well as the other’s who came out with him. Negan remarks on how stupid Rick and the others are by using bullets on the roamers instead of saving them for the much more dangerous thinkers.
Negan reveals that before every pickup, he has a back-up team armed with guns surround the area while he and the others go in and salvage for supplies.
With a crazed smile on his face, Negan leans in to Rick and says that him and the safe-zone residents are fucking fucked, smiling, saying that in a stand-off situation, snipers tend to give away their position after several shots.
He clarifies that Rick’s “sniper bitch” is as good as dead, causing Rick to try and strike him. As Negan holds him off, Carl shoots off a portion of Lucille, causing the Saviors to open fire at the safe-zone walls.
Negan orders them to stop and is shocked and angry about the damage to Lucille. Rick tackles him from behind, but Negan subdues him once more. He calls Carl a one-eyed asshole and shouts for Carl to be thrown over the wall, saying he wants him to pay for what he’s done. Rick tries to object, but Negan beats him again and issues an ultimatum: “Give me the boy or I’ll bash in all four skulls of the people out here!”
Negan admits that he liked Carl at first, saying he never had a kid of his own, but if he did, he wanted them to be like Carl. Rick says that if Carl dies, their agreement is over, but, Negan states that it already is over. He orders his men to line up Rick, Heath, Nicholas, and Holly, and begins to decide which one to kill first. He notices a figure falling from the bell tower and smugly repeats that he knew Rick’s sniper was good as dead, not realizing that it’s not her, but Connor.
He taunts Rick about Andrea’s supposed demise and Nicholas interrupts him, pleading for his life. Negan berates Nicholas for doing this and accuses him of being a coward, he asks Rick, Heath or Holly to ask him to kill Nicholas and that if they do so, he will spare them. However Heath tells him no and he begins to pick which one of them he will kill, however he is interrupted when Paul Monroe grabs a Savior by the foot and uses him as a shield from the Saviors bullets.
Negan tells his men to stand down and when he does this Paul leaps out of a trench and kicks the nearest Savior in the face. Paul orders Rick and the others into a trench and proceeds to fight his way towards Negan. When Paul reaches Negan he manages to disarm him and hold him hostage. Paul stalls the Saviors until Ezekiel and his men arrive, Negan breaks free from Paul and runs to a truck, where he retreats back to The Sanctuary with his men.
Negan is later seen back at The Sanctuary where he gives the Saviors a speech about them being the dominant force in the world and that they need to remind people of that and then states that they are going to war.
Days later, Rick’s army arrives to the Saviors base and demands that Negan come out. Initially, Negan is amused by this and begins to taunt him. Rick reveals that they know there are women, children and others inside who aren’t part of this fight, he offers a chance to surrender and let them live; for the rest, he reaffirms his old saying: “You kill and you die.”
Negan plays along with it and asks what will happen if he refuses. After hearing that whatever happens, happens, Negan thinks for a split second and blatantly refuses Rick’s offer. He muses that if he thinks the army he’s assembled “can actually accomplish something… that’s fucking rich.”
He briefly entertains the idea of letting Rick’s plan go through only to reveal a wildcard; after the ambush at Alexandria, Negan ordered Gregory kidnapped and brought to him. Afraid of what Negan might do, Gregory quickly pledges his allegiance (and that of the Hilltop) to Negan and the Saviors.
Even then he is furious, as only eight people accept the ultimatum and leave. Negan berates Gregory for this and kicks him off the balcony. He refuses Rick’s offer once more and his snipers begin to fire at the militia. Negan asks Lucille if she “believes this shit” and retreats from the bullets and falling glass. He calls Dwight, ordering him to bring the men from the outposts back to help drive off Rick’s army.
Dwight agrees but due to the commotion, Negan doesn’t notice the former’s hesitation to immediately act. As more men rush outside, Negan orders them to start shooting the army before all their snipers are killed. He notices that all their snipers are taking cover and is initially confused as to why Rick’s militia are shooting not the snipers, but the windows.
He then notices the large herd of zombies that are rapidly approaching the walls. He looks outside the fence and tells Dwight that “I hope you’re wearing your shitting pants.”
Suddenly, Holly drives through the fence, destroying a portion of it and letting the herd inside. Negan frantically orders his men back inside the foundry, but notices that Holly is still alive from the crash. He sees a zombie about to kill her and dispatches it. As she looks up, Negan smiles and says that she wasn’t going to get off that easily.
As the zombies converge inside the courtyard area, the Saviors retreat back inside the foundry to develop a new strategy. Negan delivers an analogy to a group of Saviors about how you can destroy a man “by fucking his vagina,” meaning that the best way to destroy a man’s heart by destroying the woman he loves; he clearly believes this to be Holly since Rick “was going to drive a car at us… you wouldn’t let him sacrifice himself to tear our gate down.”
She corrects him by saying he’s got the wrong woman; Rick loves Andrea and she herself was in love with Abraham, the man Dwight killed. Negan refuses to listen, insisting that she is the one who killed Connor “and a terrible liar.” He then orders her taken away and goes off to clear his head.
Later, Negan is seen outside with more Saviors trying to clear the courtyard of all the zombies, swearing that if any of them die he will fuck them up.
Eventually, too many roamers pour in the fence and Negan’s group retreat back inside once more. Negan realizes that if the herd keeps them stuck inside for more than one day, they will all be dead and he orders squads outside every two hours to clean up the infestation by any means necessary. He goes to interrogate Holly some more, but catches David in the middle of trying to rape her.
He demands that he get away from her and grabs him by the collar, angrily reminding him one of the Savior’s main rules: “no rape,” thus proving Negan does hate sexual violence. As punishment for him breaking it, Negan proceeds to stab David in the neck and apologizes to Holly, telling her that the Saviors aren’t monsters.
After killing the Savior, it is presumed that Negan got word of one of his outposts being overrun by Rick’s army and sent more to fortify the remaining ones. This in turn led to Ezekiel’s army being eradicated in a failed attack. Negan also finds a way to eliminate all of the zombies that had flooded into The Sanctuary’s courtyard, for he is later seen heading towards Alexandria.
When he arrives at the safe-zone, he throws a grenade over the wall and it detonates, demolishing one of the houses and getting Rick’s attention. He threatens that there is more where that came from and insists that he’s there to parlay.
To support his claim, he has a blindfolded Holly brought out of his truck and offers to release her back to Rick. Rick agrees to talk only when Holly is safely back inside, to which Negan agrees. This is later shown to be a ploy as it’s revealed that Negan had Holly killed and she later reanimated. As the Alexandrians are distracted by this revelation, Negan orders his men to surround Alexandria and throws another grenade over the wall.
Negan is happy seeing all the destruction and chaos. He asks Lucille if seeing him use the grenades makes her jealous of not being inside to take part in all the mayhem and wishes that he was inside as well watching them all burn.
One of his Saviors is then shot through the eye, and gunfire erupts from behind several buildings. Surprised by this, Negan orders his men behind one of the trucks. He asks for one more grenade to use as cover and tells his men “the last boat is leaving… you’d better fucking be on it.”
He manages to escape and they are able to make a fast exit. When a Savior makes an offhand comment about retreating, Negan retorts that this wasn’t a retreat. Pointing towards the smoke coming from Alexandria, he comments that this means they’ve won.
After successfully bombarding Alexandria, Negan is seen leading his men back to Sanctuary when he sees a herd of roamers attacking several people from Alexandria. He orders them to kill the roamers and wonders aloud why they are out here beyond the wall.
Nevertheless, he orders Eugene and the others to be taken back with them.
Later, Negan somehow finds out that Eugene was making ammunition for Rick’s army and goes to see him. Flanked by Dwight and Carson, Negan demands for Eugene to begin producing ammo for the Saviors. When the latter refuses, he threatens Eugene, saying he could iron Eugene’s face or castrate him.
He insists that he doesn’t want to do this, but remarks he does things he doesn’t like all the time. Eugene still refuses to betray Rick and Negan leaves Eugene, reminding of the castration threat. After ordering Dwight to lock Eugene up and to check on the others, Negan returns to his wives.
The next day Negan reveals to the Saviors that he’s come up with a brilliant plan that will help them win the war. He has assembled a group of roamers inside the courtyard to demonstrate his idea, exclaiming “they are the lynchpin of our plans going forward.”
Reminding them about the fever that comes from getting bit or from any other injury caused by a roamer, Negan approaches one with Lucille. After apologizing to Lucille, Negan begins to rub it all over the roamer, caking the bat with guts and the bacteria that causes the fever. Holding up the “new and improved” Lucille, he says that even the slightest touch from Lucille will now essentially be a death sentence.
He orders the Saviors to do the same to their weapons and then hit the road. Arriving at the Hilltop later that day, Negan and his men hide inside the forest just outside the Hilltop. He then issues the order that they’ll attack at sundown.
Hours later, Negan and his troops arrive at the Hilltop gates, demanding to see Rick. Kal is atop the wall and threatens them by saying they won’t survive what’s behind the walls. Negan tells him to bring Rick but Kal says “you’re talking to me.”
Insulted, Negan has one of his men shoot Kal off the wall. Once again, Negan demands for Rick to show himself. After no response from him, Negan orders his men to further gunk up their weapons, saying they’re going in. He goes up to Dwight, making sure his arrows are covered. Dwight offhandedly talks back, but Negan dismisses it.
He warns Rick one more time what will happen and then orders a truck to ram into the front gates. The truck gets shot up, but Negan issues another to take its place and has motorcycles come in as well. The Saviors pour into the Hilltop and begin to kill off the residents.
As gunfire continues to erupt towards them, Negan and Dwight get separated from the other Saviors. Negan is unaware that Dwight is loading an arrow to kill him when he spots Rick away from the other survivors.
He tells Dwight to shoot Rick; no matter where. Dwight is hesitant to do so, but Negan demands why he’s waiting and screams at him to shoot Rick. Dwight finally does so, hitting Rick in the side. After this, Negan declares that without Rick, the rebels are nothing, and that the game is over.
Negan and Dwight retreat back to the rest of the Saviors, hoping to devise a plan of attack against the remaining survivors at Hilltop. When night completely falls on the colony, Negan is almost shot by one of the Saviors, who states he couldn’t see properly in the darkness. Negan says that it is not that dark and asks one of his Saviors the status of the battle.
The Savior tells him most of The Saviors are now re-grouped and they are ready to get back on the defensive and Negan orders him and the rest of the men to get ready for their attack on the Hilltop mansion.
When they begin their attack, they are immediately surrounded by many of Rick’s forces, who manage to cause Negan to order and retreat and head back to The Savior camps on the hillside near Hilltop.
After his and The Saviors’ retreat, Negan is seen back at the camp alongside Dwight, who questions if camping so close to Hilltop is a good idea. Negan says that they are doing it and remarks that he sometimes wonders if Dwight has ever had a brain in his head. He elaborates by saying that Rick’s forces won’t have enough manpower to counterattack and that because Dwight shot Rick with an arrow, his death will cause the remaining forces to bow back down to Negan and he says that he will be their Savior again, as long as they let him urinate on Rick’s dead body.
Seeing the look on Dwight’s face, Negan says that there’s nothing weird about it, since Rick has ruined everything. He is then informed that Carson has escaped with Eugene. Negan tells him not to worry about it, and that they will deal with them later.
He arrives at Hilltop gates, and shoots twice into the air. He claims that he’s there to accept their surrender and asks them to send whoever is now in charge out. He swears the area he’s in will be a safe zone and there won’t be any bloodshed.
After getting impatient, Negan threatens to come back inside when Rick exits the Hilltop. Bowled over with shock to see him still alive, Negan turns towards Dwight for an answer but Rick tells him to look at him.
Overcoming his initial shock, Negan asks Rick to surrender, to let things go back the way they were, but Rick refuses. He repeats that he only kills people to make an example and threatens Rick that he will do so again if pushed too far, but Rick replies by saying he’s the stupidest fucking person still alive.
Taken aback, Negan asks what he’s talking about. Rick goes on to say that they should pool their resources and people together. Negan doesn’t believe him, saying that with the system he is been using saves lives. Rick tells him in the current situation, the only ones who are winning are the undead; the only way to get through this is by working together.
Negan takes this all in and Rick says that they can take their supplies, but they must give the survivors something in return: make supplies of their own to give or trade for others via a barter system. A fog seems to lift from Negan’s mind and he finally sees what Rick has been talking about, realizing that his actions and methods have only helped himself while the communities he’s been threatening have suffered.
Negan says he’s been wrong all along and that Rick is right. Rick then slashes Negan’s throat with a knife, responding “Good.”
Caught by surprise, Negan begins bleeding out while Rick begins to address the remaining Saviors. Negan then tackles Rick and begins beating him. Despite Rick putting up a fight, Negan catches one of Rick’s legs and breaks it.
Laughing, he passes out due to blood loss. He eventually wakes up inside one of the rooms in the Hilltop and sees Rick standing over him. He admits to Rick that during the conversation Rick had with Carl, he was able to only catch bits and pieces of it. He knows that Rick decided not to kill him, but asks what was going to happen next. Rick reveals that he will gonna keep Negan alive so he can see how much he was holding the survivors back, telling he will rot in jail until he dies an old man.
Two years after the war, Carl goes to the basement of an unknown house and talks to a figure in the shadows. Saying how he, Mikey and some other boys went to a girl’s house after class, and that she showed them her breasts. He says it was cool and all but he kind of had a crush on her, but after this he’s not sure, remarking how he doesn’t want to have someone who does that sort of thing.
The figure says that nothing is wrong with the girl and suggest Carl not hold this one instance against her. He then says to Carl that he enjoys the talks, that it’s good for him to keep track of the time and days passed. Carl says he’s leaving, before he leaves, the figure asks him if, after all this time, all the things they’ve shared and the talks they’ve had, Carl still wants to kill him. He turns around and faces the person behind bars, simply saying: “Yes, Negan. You know I do.”
Negan asks how he was supposed to know that Carl wanted to kill him and tells him not to insult his intelligence. Negan says that he thought the two of them were friends to which Carl walks away, making Negan retreat into the corner of his cell.
Negan says to Rick that his least favorite part of the day is shitting in a bucket but it’s also his favorite as Rick has to be the one to come get it. Rick says that he’s only bringing him food and that someone else will be out to clean his bucket later.
He asks if Rick is taking Carl to the Hilltop, slightly shocking Rick. Negan says that him and Carl are friends and that Rick couldn’t break that bond. Negan asks if the creaking he can hear is a windmill, making Rick say that life would go on without him just as he said it would.
Negan tells Rick that he’s just getting things ready for him, and that he won’t be in his cell forever. Rick says that he knows Negan will die behind bars, Negan states he won’t and that deep down, Rick knows he should have killed Negan.
Rick asks him if he noticed that he doesn’t use profanity all that much anymore and asks why that is. Negan says he doesn’t see the point and that it is best to save his energy. Rick tells him that’s not why, it is because Negan has been neutered like a dog and has no fight left in him.
Magna and her group later come down to see who was in the jail. When they walk down the stairs to where Negan is being held, Negan grabs the bars to his cell and asks if they’re here to rescue him, saying that they are animals. This shocks Magna and her group.
He begs to be released and claims Rick is a monster who locked him up and tortured him for speaking out against him. However, Magna doesn’t believe him, having seen actual victims of torture. Negan admits he was lying but had to give it a try. Magna and her companions leave the cell.
Negan is bathing in a small tub provided for him outside of his cage. He is being guarded at gunpoint by two men as Olivia cuts his hair. The two share uncomfortable words about his scars as she does so. Andrea enters to assure that everything was good to which Negan responds the one thing he has never been accused of is being good.
The two men then take the tub as Negan dresses and Andrea orders him to go back into his cell with her gun drawn. Olivia struggles with locking the cell but eventually believes to succeed. The two women then also leave and he sighs, leaning against the bars. But much to his surprise, the door swings open, having been left unlocked.
Later on, Rick goes downstairs, and much to his shock, Negan is sitting inside his cell, with the door open. Negan sarcastically welcomes him home. Rick reaches for his gun, only to be taunted by Negan about his leg and his “grandpa” appearance.
He then questions Rick about the gun, since he could have easily sneaked behind and subdued Rick, but instead he decided to stay, as to make Rick trust him a little. He goes on and say that he could have booby-trapped the safe-zone, he could have started a fire in the house to kill Rick and Andrea while they’re asleep or that he could have simply raped Andrea without anyone knowing.
Much to Negan’s surprise, Rick still says that nothing has changed and that he has no trust in Negan. Knowing that nothing he says will work, Negan proceeds to taunt Rick about the reason why he’s keeping him here, only to prove to himself and no one else that he has mercy, and that he wants others to believe he’s a good person and the only one who can fix the world.
After a tumultuous community meeting regarding Rick’s proposed plan regarding the Whisperers, Rick goes to Negan’s cell and asks for his help. He fills him in on everything that has happened since they’ve come into conflict with this new group.
Negan advises Rick to keep his group happy, even if that means lying to them, touting his expertise as leader of the Saviors, some of whom disliked him. Rick leaves, and Negan dons a grin. When Negan hears the chants and cheers of Rick’s name at a later town meeting, Negan smiles and says, “atta boy.”
Later on, Negan is approached in his cell by Brandon Rose, who has the keys to the cell and wants to release Negan so they can inform The Whisperers of Rick’s plan to attack them, and they can come back to kill Rick and the other members of the community. Negan is skeptical that they would leave the Safe-Zone alive, though Brandon assures Negan that a group from the Hilltop are preparing to leave as well with Negan and Brandon can smuggle themselves out.
Negan tells Brandon that he’ll think about it. When Rick and Michonne arrive after being told that the keys are missing, they find an empty cell.
Negan and Brandon, having escaped the Safe-Zone, meet up in the woods where the latter gave Negan his jacket who remarked he feels naked without it. Brandon presses Negan to contact the Whisperers, with Negan pointing out that Brandon’s plan is flawed, for now Negan has his freedom and Brandon has no leverage over him. Negan orders Brandon to lead him to the Whisperers, making it clear that he is the one in charge.
As they make their way to the border, Brandon’s complaints irritate Negan, who bluntly expresses his dislike for the boy. The pair reach the border where Brandon’s mother’s head was placed by the Whisperers at which point Brandon breaks down, Negan responds by insulting him, though Negan appears to show empathy by apologizing and embracing him.
Brandon expresses his desire of revenge on both Rick and the Whisperers by pitting the two sides against each other, Negan says that is the plan, before plunging a knife through Brandon’s heart. As Negan walks into the Whisperer’s territory, he tauntingly tells Brandon’s corpse that it was his plan, not his.
Negan engages in some “friendly” conversation with Alpha. After a while, she asks how he survived so long. He tells her he was with another group, but they “booted him out”. She asks him if he’s looking for revenge on these people. He says it’s not the kind of thing he’d ask for on a first date. Alpha asks him to stop, but he continues making sexual remarks, leading to Alpha punching him in the face, prompting Negan to apologize, saying he can tell he crossed a line.
Beta appears, pinning Negan up against a tree. He tells them about his encounter with Michonne, Aaron and the Militia. Negan admits he lied, saying when he is scared he starts lying.
Alpha orders him to explain himself. He doesn’t, saying Beta is scary, and to just kill him if that’s what they’re going to do. Alpha asks him if he’s scared, to which he replies no. He says he lived longer than he expected to. When Alpha asks him why he came, Negan says he has a lot to offer her.
Alpha and Beta continue to debate on how to handle Negan, with the later stating his disapproval for allowing him to live despite him deceiving the Whisperers of his true nature as an escaped prisoner and that he doesn’t understand the nature of their ways. Negan states his willingness to learn but also questions on how the Whisperers recruit others when they trust so little in reference to Beta’s attitude towards him.
Beta becomes enraged by Negan’s statement but Alpha pulls him aside and asserts herself in suggesting whether Beta questions her judgement and leadership, questioning if it his time to become Alpha, asking him if he’s challenging her. Beta quickly lowers on one knee and apologizes for his actions, asking for forgiveness which Alpha grants him before asking him to leave her with Negan.
Negan applauds Alpha confronting Beta as awesome, before bowing down to Alpha himself, requesting acceptance which she grants him. Negan jokes about how the experience gave him an erection as Alpha returns Negan’s knife to him saying that he can stay and that he should learn and follow the Whisperers rules, however doubting his survival. When Negan requests a skin suit, Alpha responds he must earn the privilege.
Negan is later seen participating with the Whisperers in various activities such as loading cargo onto carts, feeding horses, sleeping in sleeping bags alongside other Whisperers and shooting a boar with a long bow as the days transpire.
After shooting the boar Negan boasts proudly of his achievement which leads him to being reminded by Alpha in being silent and not raise noise. One day as Negan hacks at a fallen tree he is approached by a Whisperer informing him of nearby roamers and that he shouldn’t draw any attention so they can pass before passing a group of Whisperers preparing a skin suit.
As Negan carries logs of wood he is grabbed by a roamer to his surprise. The Whisperers refuse to help, stating that if he is strong he will survive much to Negan’s annoyance. Alpha then promptly drops Negan’s knife close to him, requesting Negan to prove that deserves having his property returned to him. Negan is then able to dispatch two roamers with the Whisperers in awe of his skills, however Beta scoffs at his achievement.
Later that night, Alpha requests Negan to join her for dinner which notably upsets Beta. As Negan prepares his sleeping bag, Beta orders Negan to sleep on the other side of camp and not with Alpha. Negan mocks Beta under his breath. As Negan looks for a place to sleep he hears out cries for help to which he runs over to and is shocked to discover two male Whisperers attempting to rape a female Whisperer. Negan steps in to protect the female, calling the male pair “sick fucks”. Before Negan attempts to murder one of the assailants, Beta knocks him over the head.
Beta defends the men by claiming they were simply “living their lives” and that interference only denies the right for the victim to defend themselves thus proving their strength. Alpha concurs, saying that despite understanding Negan’s actions that interference is not their way. Negan becomes outraged by their reasoning for such atrocities, causing him to be “punished.”
Later seen sleeping outside the camp with no protection as his form of punishment, Negan mutters his disdain for the Whisperers, calling them weirdos.
Alpha approaches Negan, stating him to have proven himself as an asset and that he has gained her respect and trust. However, she also fears that Negan doesn’t belong with the Whisperers.
Negan mockingly suggests that he belongs because they need him as he expresses his hatred for the barbarity that Alpha tolerates and that she should be ashamed of herself for letting the horrors continue.
She defends herself by saying if the weak are protected they will never become strong. Negan counters by saying protecting the weak is the basis for civilization and by not doing so makes the Whisperers nothing but animals, to which she declares they are, and that civilization is a myth and Negan must stare into the ugliness to see the truth. Negan is unswayed, declaring Alpha’s reasoning as bullshit.
He argues hurting people for pleasure as a form of “instinct” makes you a monster that should be executed on the spot. Given Negan’s own commitment of atrocities, he defends his actions as being for the greater good and never for pleasure, exempting himself as a monster.
Alpha declares that in nature only the strong survive, and attempts to further her point but becomes emotionally shaken and attempts to leave. Noticing this, Negan orders her to come back and talk to her. Negan says that Alpha doesn’t have to worry about displaying weakness by crying in front of him as he doesn’t want to assert himself as the next Alpha unlike other Whisperers who would if they noticed and that she has Beta to protect her.
She disagrees that Beta protects her to which Negan suggests otherwise, calling her a hypocrite and that she wouldn’t survive as long as she has without Beta protecting her. Alpha attempts to assert that her strength and authority is what creates order among the Whisperers before breaking down into tears when she states how the thought of letting Rick’s group take her daughter, Lydia, would make her stronger and that there was no other way to live in this world. “I… I miss her so much”, says Alpha, finally expressing her love for Lydia.
Realizing how exposed she made herself to Negan, Alpha declares herself as weak and not fit to lead. Negan, surprised by Alpha’s emotional outburst, begins to lament on the loss of someone close to him before the apocalypse started and how much it broke him, causing him to lose all sense of feeling.
He declares his emotional insensibility to be his strength and the reason he has survived this long. Negan claims how this helps in him committing atrocities in order for the greater good whilst not feeling remorse for the pain he causes; “It just is what it is. It’s survival”.
Negan compares his emotionally severed connection to the world with Alpha’s facade and argues she’s only pretending to be emotionally detached.
Wowed, Alpha suggests that Negan does in fact belong with the Whisperers to which Negan suggests as well.
Negan then proceeds to slash Alpha’s throat with his knife before revealing he doesn’t want to be with the Whisperers. She falls to her knees in shock, bleeding out.
He delicately lowers her onto her back and then slashes her throat several more times until he holds her head in his hands. He tells the head to wait until Rick sees it.
On patrol, Magna spies Negan approaching with a bag. She yells for Dwight, who wants Magna to shoot him but she refuses. Since Negan is unarmed and seemingly poses no immediate threat, they agree to take him back to Rick. Negan tries to grab Lucille from Dwight’s back, but Dwight doesn’t let him. Negan teases him, asserting that he will prove his trustworthiness, and saying “You’re going to fucking give her to me.”
Later, Negan shows the head to Rick and Andrea, who are very hesitant to believe and trust him. Negan reassures them that he only wants trust. He says Rick’s way of thinking is inspiring. He says he could’ve taken several chances and attacked Rick, but he didn’t. He wants to fight with him, not against him. Rick finally agrees to let Negan out of the cell, but not in a community. He will live in an outpost, alone, with only enough food and weaponry to keep him surviving. He is not allowed these freedoms yet, though. He is going to be monitored for a long time and will fight in the front lines against the Whisperers. He will earn his freedom after the war, unless he slips up, in which case he will be immediately killed. Negan is later present when the group discuss where to station themselves. He is also seen travelling with the Militia to patrol.
Negan is seen patrolling with Dwight. He asks Dwight for a gun, but Dwight refuses. He proceed to tease Dwight about Sherry until Dwight shouts at him to stop. Laura runs up saying they’ve got movement and possible contact. Negan stands back as the Militia fire at horde of zombies and Whisperers approaching, however moves to action when a soldier is attacked by a Whisperer. He defeats the Whisperer and grabs the fallen soldier’s gun, but is snuck up upon by a zombie, but the zombie is killed by someone unknown, just in time. He now fires at the approaching horde. Later, as Dwight is attacked by Beta, Beta is struck over the head by an assailant revealed to be Negan, who promises to kill Beta.
Negan fights with Beta, slamming his gun into his back, and Beta cutting Negan’s forehead. When Beta disarms him, Dwight tosses him Lucille, who Negan hits off Beta’s back. To Negan’s anguish, Lucille breaks in half by the force of the blow. Tears well in Negan’s eyes as he runs to kill Beta, however he is forced to recline when he’s attacked by two zombies. During this time, Beta escapes.
After the battle, Negan buries Lucille as a way to properly lay to rest the person he named her after: his wife. Negan openly mourns her, apologizing for failing to bury her previously and be a good husband as well as naming the bat in honor of her. Negan then arrives at Alexandria with the rest of Militia, knowing that he doesn’t belong and no one cares about him as other members are embraced.
Negan is hated by Carl, and this is demonstrated when Carl risks his life to get revenge, by sneaking into Negan’s truck in order to kill him. It appears though, that Negan likes and admires Carl because of how hardened he is. It is shown that he may even have some higher opinion of the child, such as respect, as he is shown to be sincerely concerned and apologetic after making fun of his exposed gunshot injury. Carl returns Negan’s admiration for him by accompanying him throughout the Savior’s base without even trying to run or take action, also questioning the leader of his wives actually being his. Negan may very well be catering Carl to become a protege of some sort, as he is shown to be more impressed by the boy rather than angered by his violence against his men. However after Carl shot Lucille (Negan’s baseball bat covered in barbed wire), Negan demanded Carl’s head or he’d kill everyone else in the safe zone.
In Issue 127, two years after the end of the war, Carl has regularly visited Negan in his makeshift prison. He tells Negan about a girl he has a crush on, and Negan thanks Carl for visiting him, saying that Carl’s visits help him keep track of the days. However, he asks Carl if, after all of their discussions, he still wants to kill him, to which Carl responds, “You know I do”. Negan is shocked, offended, and upset, though it is more likely he was upset due to this closing off a potential path of escape.
Dwight and Negan seem to have a tense relationship, as both seem to dislike the other to a point. However, Dwight’s fear of Negan keeps him in line, as it is implied that Negan himself caused the deformity on his face. This is seen when Negan comments on Dwight’s return and how he can always try next time to attack the Alexandria Safe-Zone, which resulted in heavy casualties and Dwight’s capture. Dwight shows a look of disgust towards Negan after this. Dwight also seems to be intimidated by Negan, as he decides not to tell him about Paul’s escape, in fear of Negan’s wrath. Dwight’s frustration grew when Negan, after playing ping pong, provoked Dwight by saying him that he would “ping pong his dick” with Sherry, causing Dwight’s bearing to finally break and assist the alliance. At the end of All-Out War, Dwight takes Negan’s position as leader of the Saviors and turns him over to Rick, most likely severing their relationship completely. When Negan met Dwight again, Dwight order Magna to kill him but refused to. Dwight is place in charge with watching Negan now. During a fight Negan saves Dwight’s life from Beta.
Rick has shown nothing but anger and rage at Negan. Negan, on the other hand, has a deep held respect for and acknowledgement of Rick’s abilities. Although he acts like a laid-back bully, rather than a psychotic murderer around Rick, Glenn’s gruesome death was proof to Rick of the violence and brutality that Negan and his Saviors are capable of. This leads Rick to realize that striking back immediately will most likely result in the destruction of the Safe-Zone, leading him to choose a passive course of action until he can stand a chance to avenge Glenn’s death. His first step was to allow their prisoner, Dwight, to be set free so that Paul could follow him to their base. After returning Carl unhurt (after implying to Rick that he had done something to the boy), Negan tried to assure Rick that it was a gesture of good faith and shows that he could be reasonable as long as Rick was compliant. Although Rick was grateful, he made it clear that things hadn’t changed between the two of them, to which Negan didn’t seemed surprised.
Although Rick bitterly despises Negan, at the end of “All Out War” Rick decides to keep him alive and incarcerated, not wanting to go down to his level by committing murder again, saying Negan will rot in jail until he dies an old man, all the while watching how the survivors are thriving without him. After the time skip when Rick visits Negan in jail, he belittles him and mocks everything he’s become.
After Negan is freed, he travels to the Whisperers’ camp and returns with Alpha’s head. He argues with Rick that he is an asset, in that he uncharacteristically withheld the opportunity of taking control of an army and exact revenge. Given the situation, Negan states he cannot return to incarceration. Rick grudgingly agrees to free Negan and let him live at an outpost alone. He says that he will never trust him, however Negan is visibly pleased.
When the Whisperer’s herd invades Alexandria, Rick and Negan pull together with the rest of the community to defend their home. Negan even saves Rick’s life when the latter becomes surrounded. Together, Rick and Negan take refuge in an abandoned house. Given the situation and how others fled in fear, Negan notes how alike he and Rick are in the face of danger and that they should get along better. Rick bitterly states “that ship has sailed”.
As time passes, Negan asks Rick what was the worse thing he has ever done. Disinterested at first, Rick eventually gives his answer that the worse thing he had ever done was live while countless others he knew did not. Reacting profoundly to Rick’s response, Negan openly admits his disconnection to humanity as he began viewing everyone he met as weak and a liability and how Rick helped him change his perception. Negan then states the worst thing he ever did was leave his wife to rot after not possessing the courage to put her down once she had turned.
More time passes as the invading walkers are being split apart by the joint community’s efforts to manage the herd. Rick suggests he gather weapons and help, Negan however offers to assist as sending Rick would be suicidal given his injured leg. As they’re about to kill some walkers, Negan joyfully exclaims how the two are working together.
“No, I have never been accepting of Negan’s truce. I crowned myself king of this Kingdom in order to make the lives of my people as good as they can be. Negan and his Saviors… I wish to be rid of them. Your friend Jesus knows how deep my hatred for these people burns, how I’ve simply been waiting for the right moment to strike against these devils. Your son’s experience provides me with more than enough information needed to launch an assault. I thank you and again, I am truly sorry for what you had to endure to retrieve that information.“
—Ezekiel to Rick and Jesus about Negan’s rule[src]
Ezekiel deeply hates Negan and wants him dead, as he stated that Jesus knew how much hate he had for the Saviors. It is also mentioned that he never accepted Negan’s supply truce
Maggie deeply hates Negan for killing Glenn, and assisted Rick in the war against the Saviors. Maggie’s reaction on Rick not killing Negan is unknown, but it is implied she understood by not wanting to kill people if necessary. After the time skip, Maggie reveals that she still believes Negan should be executed.
Gregory is shown to be terrified of Negan and his group, to the point where he avoids as much confrontation as possible between the Saviors and the Hilltop. Negan expected Gregory to force the Hilltop Colony residents to leave the war, but it was only eight members instead, which caused Negan to shout out at Gregory in anger. After that, he kicked Gregory off the building, calling him “pathetic.”
“Now you listen to me. You’re not going to survive this. Even if you kill me… they’re still going to mow you the fuck down. Assuming you don’t want to die as much as I don’t fucking want to die… Where do we go from here?“
Paul has a significant role in planning to overthrow The Saviors reign of tyranny and kill Negan. He has a strong dislike of Negan, yet has only seen him in person a few times. When Negan was about to execute Rick and the group at the gate of Alexandria-Safe Zone, Jesus managed to save them all by attacking The Saviors on his own before holding Negan at the gunpoint.
Negan is greeted by Spencer when he visits the Safe-Zone several times. During the most recent visit, Negan takes a bit of a liking to him after hearing how the Safe-Zone was formed and all the commodities the Safe-Zone offers. Spencer tells Negan that Rick is a bad leader and proposes that Negan put him in charge once Rick is killed. Negan is disgusted by Spencer for waiting until Rick was gone to tell him this. Negan taunts Spencer, saying that Rick is willing to put the good of others before his own feelings, and then brutally kills him.
“Lets leave him to his dick and his thoughts… while he still has them.“
—Negan to Carson and Dwight about Eugene.
Negan and Eugene have a poor relationship. During All Out War, Eugene is captured by Negan who threatens to cut off Eugene’s testicles if he doesn’t make bullets for him. Eugene refuses, expressing his loyalty to Rick. This annoys Negan, who makes further threats, but Eugene never obliges.
Negan and Mark have a bad relationship, it is assumed that Mark and Amber were in a relationship before she became one of Negan’s “wives” so after she did and Negan demanded that she could not continue her relationship with him, he began to carry on the relationship with Amber in secret. Once found out Negan punished Mark awfully by scarring half of his face with a hot iron. It is likely that, similarly to Dwight, Mark now despises him for the disfigurement of his face.
Amber is one of Negan’s wives, though she does not love Negan, she has to pretend, for her and her boyfriend’s protection. When Amber slept with her boyfriend, Mark, behind Negan’s back, Negan punished Mark and burnt his face, similar to Dwight and his relationship with Sherry, another wife of Negan.
Negan takes Holly captive after thinking Holly is Andrea. After Negan finds out Holly isn’t Andrea he keeps her prisoner. When David tries to rape her Negan kills him telling her that his group is not monsters. Negan later kills Holly, having her zombiefied, and then leads and attack on the Alexandria Safe-Zone.
“Oh, don’t be such a crybaby. The fucking world ended. Everyone’s mother is dead, you pussy. Besides… we’re on our way to talk to the people who cut your mom’s head off… have some motherfucking perspective.“
—Negan to Brandon telling him to get over his mother’s death.[src]
Brandon and Negan first meet when the former goes down to Negan’s cell to help him get out, and go to the Whispers base and alert them about the war between Alexandria. After Brandon tells Negan his plan, Negan then seemingly tells Brandon that he likes where this is going and he has to think about it. When Rick and Michonne and alerted by Paula that the cell door keys are gone, they race to see if Negan is still there. When they get there he is gone.
However, their relationship takes a turn for the worst when Negan starts to dislike Brandon, due to his treacherous intentions toward Alexandria. When Brandon tearfully mourns Tammy, Negan tells him that he is a coward and that they’re going to meet with the people that killed his mother in the first place. He hugs Brandon, but then kills him by stabbing him in the chest, showing his contempt for Brandon himself.
Alpha and Negan had an interesting relationship. When they first meet, Negan declares his love for her, and his respect for her as a leader quickly grows. She returns her respect to the fearless and jolly Negan.
Negan continues to constantly make advances on Alpha despite the latter being completely unamused and annoyed by them as well as his charismatic exterior. When Negan makes an explicit advance, Alpha strikes him, promoting Negan to see that he crossed a line.
When Beta appears, he asks Alpha if he can kill Negan due to him lying about his true nature and how he almost died as a result, though she doesn’t allow him. Alpha taunts Negan about being scared, but he says he isn’t. He tells her that he has a lot to offer her.
Over the next many of days, Alpha slowly begins to trust Negan in his abilities and in acting as a possible member of the Whisperers such as when she invites Negan to dine next to her and Beta one night.
Negan internally begins to question the respect he held for Alpha when he witness the inhumanities she allows to run rampant in her group. When Negan expresses his outrage to Alpha of her allowing rape of the women in the group in a chance to test one’s strength to then later mock their way of life, this adds a strain on the relationship. Negan further calls out on Alpha for presenting a false facade of strength and how she needs constant protection in order to maintain her role, this causes her to confide in him about missing her daughter and how that maybe Negan does in fact belong with the Whisperers. Negan’s opinion on Alpha takes a turn south when he realizes that she forces a facade of stoicism, believing civilization was always fraudulent and that mankind is nothing more than another wild animal. This directly conflicts with Negan’s worldview and admiration of civilization, and thus Negan concludes Alpha is not quite what he thought her to be.
Hence, Negan severs the relationship when he brutally murders her and decapitates her head, saying he doesn’t want to be with her group before proudly stating “Wait until Rick gets a look at you” when holding her head.
Negan and Beta have a hostile and scornful relationship. Beta sees Negan as threatening and weak, and doesn’t have much respect for him. He asks Alpha if he can kill Negan, though Alpha doesn’t allow him. Beta, having implied feelings for Alpha, begins to grow jealous of her fondness for Negan, and views him with disdain. Negan thinks Beta is awesome for his size and dual wielded knives at first, but later begins to dislike Beta for the way he is treated by the giant.
Later, after Negan kills Alpha, Beta is furious at Negan and plots to avenge Alpha. Negan’s dislike for Beta soon turns into pure enmity when Negan’s weapon of choice, Lucille, is broken after beating Beta with the bat several times causing it to shatter into wooden shards. As a result, both severely wish death upon the other.
Lucille was Negan’s wife before the apocalypse. While its shown that Negan loves his wife deeply, he used to cheat on her. When she is diagnosed with cancer, Negan is upset and blames himself for not being a good husband. Negan names his baseball bat after her. In Issue 162, Negan has shown to still miss and grief for her, apologizing for naming a baseball bat after her, and that he never got to bury her. Negan later admitted, in Issue 164, that the worst thing he ever did was not put down and bury Lucille, showing just how much he loved his wife, and how much he misses her, even after all the time that has passed since she died.
Negan was originally called Nagus by Kirkman: “Every now and then I just make up a word and then I look it up and it’s a name. So he was Nagus for a long time, and then I realized that the Ferengi high commander on Deep Space Nine was called the Grand Nagus. And I was like, ‘Oh, that’s where I got that! Oh, okay. Uhh, maybe he’s Negan.’ So that’s how that happened.”
Another idea for the name was “Negus”, emphasizing how negative it sounded.
Negan’s character was not supposed to appear in issue 100, following Glenn’s death. 
Originally, Glenn was going to be put in a situation where Rick was forced to kill him in order to save his son. Kirkman was not satisfied with this route, and thus Negan was born.
Negan’s appearance and character were also based off of an unknown actor who Kirkman refused to reveal, just in case that actor wanted to portray him and could not.
Charlie Adlard has confirmed that Negan is based on actor Henry Rollins, who is presumably the actor mentioned by Kirkman.
Rollins auctioned for the role of Negan in the TV Series, but the role was given to Jeffrey Dean Morgan.
Negan’s main weapon of choice is a baseball bat wrapped in barbed-wire, which he calls, “Lucille”, the same name his wife had.
Negan’s attachment towards Lucille is shown to be deranged. Apart from claiming that it’s saved him more times than he can remember, he also says that it’s “the only bitch I’ve ever loved” and disturbingly admits that he occasionally has sexual thoughts towards Lucille, and even acting on these thoughts.
Until Issue 158, Negan was never seen carrying or using a gun. However, while he primarily used it as a club to knock down Beta, he did fire it.
Negan was a fan of Neil Young, and presumably saw him on tour.
Negan was originally planned to be killed off shortly after his introduction in Issue 100, however Kirkman said he liked Negan “too much” to kill him off. He was originally supposed to die by the hands of Rick in the end of Volume 17: Something To Fear, appearing in only five or four issues. Rick would’ve delivered Negan’s decapitated head to Maggie in a box saying, “I’m sorry”. 
In addition, the story arc was supposed to end when Maggie takes over Hilltop Colony.
Negan is notable for using excessive profanity when he speaks, even to his own men.
Negan’s prequel story Here’s Negan shows that he used this excessive profanity even before the apocalypse, when talking to his wife and his students.
At first, it was implied Negan was some kind of cult leader, as the Saviors believed that Negan spoke through all of them. Though the term cult may not apply to the Saviors, they are most definitely the followers of Negan to an almost religious level.
This is heavily supported in #105, as it is revealed that he runs the Saviors as a cult would entail, complete with the followers bowing at his entrance and chanting to his words.
In Issue 105, a very rare glimpse of Negan’s sympathy is shown after he makes light of the disturbing gunshot injury to Carl’s eye, making the young boy cry. He apologizes for this with what appears to be sincere concern and admits how easy it is to forget that he is just a child.
Negan exhibits several symptoms of what is known as a God complex, living a life of total and uninhibited dominion over any form of life he sees, people who will follow his every command.
Whether or not they choose to follow him willingly never seemed to be an issue, that is, until Rick Grimes began to lead a revolt against him.
Negan despises sexual violence. This is shown in #117 when he kills David for attempting to rape Holly, and in #156 when he tries to stop two men from raping a woman in the Whisperer camp.
Negan is the second major recurring antagonist in the Comic Series, and also has the longest lifespan.
Negan, Dwight & Laura are the only named Saviors to have appeared on more than one issue cover.
A fan asked via Reddit which are the hardest characters to write, and Kirkman answered that “Negan is a blast”.
Negan’s backstory will be revealed through Image+, all-new monthly magazine published by Image Comics. It is titled “Here’s Negan” and includes 48 pages of story.
Negan is the first recurring antagonist to kill another recurring antagonist.
Negan holds the most appearances in the comic book out of any character introduced in the third compendium.
Negan appears on variant covers for a single issue of five Skybound comic book series under the caption “Negan Kills…”. Those series are Green Valley, Manifest Destiny, Thief of Thieves, Birthright and Horizon.
In Issue 162 it is revealed that Negan believes in an after life. More specifically in Heaven and at least an undesirable place which is possibly Hell.
From Issue 100 to Issue 126, Negan appears to wear a woman’s jacket due to the side of the zipper. It is fixed in Issue 153 as he appears with the zipper on the other side.
When Negan gutted Spencer, the hand that didn’t hold the knife (the left hand) was drawn as a right hand, clenched in a fist, despite the knife being held by his actual right hand.
“I appreciate everything you’ve done for me. Giving me a home. Letting me take over the church, giving me a place to serve the lord. Now I want to serve in another way. I don’t think it’s enough to protect the souls of our people. I’ve done that and I feel I’ve done a good job. But I’m able… able to do more… able to really protect my flock. I feel like I could be of use to you… as a soldier. With your blessing… I’d like to start training with the others.“
Gabriel Stokes is a main character first encountered in Issue 61 of Image Comics‘ The Walking Dead. He is a preacher who came across Rick Grimes and his group after leaving his church, where he had been hiding from the undead. Gabriel traveled with the group to Alexandria, where he became the head priest of the church located there. After overcoming his aversion towards violence, Gabriel lost all hesitation towards killing walkers, and has now joined Rick Grimes’ military against The Whisperers. However, despite his desire to help the community, the early attack from The Whisperers made fear over take him, leading to his death at their hands before he could signal the rest of the militia.
Gabriel Stokes was the reverend of a regional community church. Not much of his personality or life before the outbreak has been revealed. The only detail given by the reverend was when he admitted to Rick and the rest of the group that during the initial zombie outbreak, he locked the doors to his church due to his own cowardice and allowed a whole group of survivors to be killed by roamers.
Gabriel claimed he had been living in the church’s safety since the beginning of the epidemic, but the validity of his story, especially considering that it had been a full year since the outbreak began when the group encountered him, is questionable.
Forced from the church due to dwindling supplies, Gabriel set out into the surrounding countryside and eventually ran into Rick Grimes and his group while they were on the road.
The group encountered Gabriel on the road at a chaotic time, in the aftermath of losing the prison to the Governor and during the heartbreaking dilemma involving the twins. Thus, the survivors were initially very suspicious of his presence and story, and did not trust him due to their weariness of other human survivors and conflict among the group. Gabriel tried to comfort them with his obvious appearance as a religious man, but most of them visibly expressed open distrust or disbelief of his presence and mannerisms.
The moral dilemma involving Ben and Billy, and Dale‘s eventual fatal bite allowed Gabriel to blend into the group without too much difficulty as Rick and the other leaders were focused on the more pressing matters at hand. When it was discovered that Ben had killed Billy, Gabriel conducted prayers for the burial of both of the children.
Eventually, Gabriel led the survivors to his church for shelter while searching for the missing Dale, who had disappeared the night before. Rick eventually confronted Gabriel in the church, accusing him of being somehow involved in the disappearance of Dale and threatened him with violence. Gabriel then revealed his true story before meeting the group in tears. He expressed extreme remorse and guilt when he explained that he only survived several months alone in the church by turning away his followers and any other local civilians when the zombie attacks started. His main focus, he tried to emphasize to Rick, was to try and keep some spiritual faith for himself and the survivors, a sentiment which unfortunately was largely not shared.
It did not take long for the group to soon discover a group of human Hunters were stalking them. The conflict escalated when Glenn was shot in the leg from afar when he and the others tried to rescue Dale, who was discovered partially mutilated in the front of the church entrance.
Gabriel was soon forced by Rick, Andrea, Michonne, and Abraham Ford to accompany them in finding the whereabouts of the Hunters, as he was the only member of their group who was familiar with the local area. When the group found the Hunters, Gabriel watched in horror as the group, led by Rick, brutally mutilated and murdered them in violent retaliation for their stalking and near fatal attacks on Dale and Glenn. Gabriel vocally expressed shock and outrage at their murder but Rick told him he was no better than them for turning people away from the church, silencing the reverend into submission.
With no other choice, Gabriel followed Rick and the group on their journey to Washington, D.C., despite admitting extreme disagreement with the group’s violent actions against the Hunters.
He traveled successfully to the Alexandria Safe-Zone and was soon identified by Douglas Monroe during the introduction interview as the man to run the local Church, which had survived intact. When the walls expanded and the church became accessible, he began to run daily masses. He seemed to be doing well in adjusting to living within the Community, aside from the packed living conditions of living with the group in Rick’s house for the first few nights.
Gabriel became convinced that God led him to the Community so he could eventually preach at the new church. He eventually believed and tried to get the rest of the survivors exiled from the Safe-Zone because of what they did to the Hunters, but Douglas Monroe did not agree with Gabriel’s belief that the groups actions were evil and decided to ignore his request.
In Issue 82, when the zombies breach the Safe-Zone, he’s seen in his church, crying. He finally gets over his fear and lets Eugene Porter and Nicholas in before the zombies reach them, the opposite of what happened the first time at the onset of the outbreak.
In Issue 84, after watching Rick and Michonne fighting endlessly against the zombie horde, it may have inspired the men. Eugene and Nicholas get over their fears and go out to help Rick and Michonne. They also eventually convince Gabriel to stop hiding and help. While he’s shown clearly afraid, he still joins the group and aids them during the fight. He, along with the others, survive and win the zombie attack. Although he’s left stunned, most likely by his actions or that he survived the fight.
Gabriel has had little participation in the war against Negan. However, he serves as the priest for the funeral of Abraham (who was killed by the Saviors). He survives the attack on the Alexandria Safe-Zone, and moves to the Hilltop, along with the rest of the group and survives the events of the conflict.
Gabriel has now returned to Alexandria to resume his duties as the town’s priest. He was present at the funeral of the members of the communities that were killed by Alpha. Gabriel later appears at an Alexandria meeting and is shocked when violence breaks out among the citizens. When Rick announces that he plans to take action against the Whisperers, Gabriel is amongst those cheering and chanting his name.
As the Militia take position, ready to face the Whisperers, Gabriel climbs a nearby water tower to take patrol. He struggles to climb, but eventually makes it up. As he looks through the scope of his sniper rifle, he is shocked to see a large group of Whisperers approaching. Gabriel runs towards the ladder, pleading to the Lord for help, in his panic he falls backwards off the ladder and tries to catch himself on a ring by using his foot, which snaps his ankle nearly clean off. Dangling upside down he is met by a voice proclaiming “I will save you”. This voice is revealed to be Beta, who proceeds to slash Gabriel’s stomach open, telling him that he should have whispered as he marched onward towards Alexandria. Gabriel is then devoured by walkers, stripping him nearly to the bone on the upper half of his body.
Himself (Indirectly Caused, Accidental)
Gabriel panics when he sees the large Whisperer army coming toward him. In a rush to climb down the ladder, he falls and gets his leg caught and broken, trapping him on the ladder.
Gabriel is stuck upside down on the ladder begging for someone to help him. Beta says that he will, right before stabbing him in the gut. Gabriel quickly bleeds out and the Whisperers leave him to be devoured by the oncoming walkers.
At first Gabriel and Douglas seemed to have a good, friendly relationship as Gabriel took the role as the priest of the church. But Gabriel felt disgusted by Rick and the others actions, brutally killing Chris and the other hunters and told Douglas that he felt as though Rick and the others don’t fit in with the rest of the community and he suggests should be kicked out of the safe-zone. Douglas is shown to be shocked and slightly angered by what Gabriel says and tells him that the people in the community have done the same to build and protect the place, himself included and asks Gabriel not to make him ask Gabriel leave his home, this seemed to strain the relationship between the two although this could be explored further as they weren’t seen interacting again.
Gabriel and Eugene seemed to have a stable friendship. While looking for Dale the two debated with one another about the existence of God. Once the Alexandria Safe-Zone was overrun, Eugene and Nicholas begged Gabriel to let them inside the church to hide. Hesitating at first, but not wanting to cause more deaths by locking people outside like Gabriel had done in the past before the group met him, he let both Eugene and Nicholas inside.
Rick and Gabriel have a strained relationship, at first Rick didn’t trust Gabriel and was on guard while travelling to Gabriel’s church. Rick became very suspicious after Dale was kidnapped and like Andrea believed it was related to Gabriel. Rick pinned Gabriel against the wall at his church and Gabriel burst into tears revealing how he had survived by locking his church doors and ignoring the people begging for help. Rick believed his story and after Dale was returned by the hunters and he revealed that their camp was in a house Father Gabriel helped the group find the hunters base. But Gabriel watched in horror as Rick and the others slaughtered the hunters for eating Dale’s leg, shooting Glenn and eating many unnamed people, including their own children. Once arriving at the Safe-Zone, Gabriel feels like Rick, and the others, do not fit in and are dangerous and tries to persuade Douglas to throw them out, Douglas angrily refuses to do so, but, it is assumed that Rick is unaware that Gabriel had asked.
However, it now seems as if Gabriel and Rick have established a good relationship when Gabriel thanks him for all he has done for him and even volunteers to help, Rick accepts this and welcomes him aboard saying thank you in the process.
At first Andrea and Gabriel have a strained relationship, believing he was involved with Dale disappearance acting very hostile towards him. Andrea eventually trusts Gabriel and at Alexandria attend his services at the church.
Gabriel knew Dale for only a little while. Gabriel offers Dale to say a few words for his adopted sons which Dale tells him off. When Dale was kidnapped, Gabriel assisted with trying to find him. The group initially blames Gabriel for Dale’s disappearance. Gabriel is seen at Dale’s funeral.
Abraham distrusts Gabriel when they first met checking him for weapon and believes Gabriel is leading them into a trap, which Gabriel makes a joke about, making Abraham angry. But he is thankful for leading him and the group use his church as shelter. Abraham was outraged about Gabriel’s comments about the hunters. Gabriel later held a funeral service for Abraham.
Gabriel and Rosita seem to have a stable relationship, at first Rosita doesn’t trust him and is scared when he makes a joke about leading them into a trap. At his church Gabriel offered her a extra blanket which she is thankful. At Alexandria, Rosita attends Gabriel’s service at the church.
Gabriel and Dwight seem to have a good relationship as Dwight is training him; he’s shown to give Gabriel compliments on his training but worries that Gabriel will falter when he finds out that they are starting to attack human targets.
Gabriel was originally supposed to be named James.
Gabriel is the only confirmed priest who is encountered within The Walking Deadcomic series.
During the events of “No Way Out”, Gabriel has to endure the exact same situation he’s been through in the beginning of the apocalypse: being locked in his church with survivors outside begging for help, although this time, he overcomes his fear and lets the survivors in, unlike the first time.
In the Letter Hacks of Issue 158, it is suggested that Gabriel’s death might have been one of the most unpleasant ones yet.
Benanti remembers being “very serious” and “a bit of an ugly duckling” as a child, and was intensely interested in musical theatre, saying she “came out of the womb as a 40 year old”, being interested in Sondheim at an early age, distancing her from other children. (In 2008, Benanti told The New York Times that she drew on this loneliness in her portrayal of the neglected Louise in Gypsy.) Though her parents refused to let Laura audition for professional theatre, Laura appeared in several high school and community productions, including Evita (as Peron’s mistress), Follies (as Young Heidi), and Into the Woods (as Cinderella). At 16, Benanti played the title role in her high school production of Hello, Dolly! and won a Paper Mill Playhouse Rising Star Award for Outstanding Actress in a high school production. She graduated from Kinnelon High School in 1997.
In 1998, Paper Mill’s then-artistic director Robert Johanson recommended Benanti for the role of Liesl in a Broadway revival of The Sound of Music. She auditioned for the show’s producers and was considered too mature-looking to play Liesl, but, after several call-backs, was signed at the age of 18 to play one of the nuns and to understudy Rebecca Luker as Maria. Benanti played the role for two weeks during Luker’s vacation, and, at 19, took over the role when Luker left the production. Michael Buckley of Playbill later wrote that Benanti “was an absolutely wonderful Maria […] As do others, I believe that had she opened in the show, Benanti would have been an overnight sensation.” When she was cast in The Sound of Music, Benanti had attended New York University for two weeks; the dean recommended she go on leave to take the job.
The injury was misdiagnosed and Into the Woods producers asked Benanti not to mention her injury; when she began missing performances due to neck problems, rumors spread that Benanti was behaving unprofessionally, something that she calls “really hurtful”. She says, “I had a serious injury and there was absolutely no way I could have done the show. I tried to. I tried to go back and do it but I physically couldn’t.” Benanti was eventually replaced in the show by Erin Dilly. Eight months after her initial injury, Benanti was rediagnosed and received surgery that could have damaged her voice but was successful, though as of 2005 she still experienced neck pain and myelopathy.
Three weeks after undergoing spinal surgery, Benanti started previews in March 2003 for the Broadway revival of Nine, in which she played Claudia, a movie star who inspires Guido, a director played by Antonio Banderas. She left the show in September 2003. Benanti appeared in the World AIDS Day concerts of Pippin, Children of Eden and The Secret Garden. From April 2006 to December 2006 she played Julia Sullivan in the Broadway musical The Wedding Singer.
In addition to stage roles, Benanti was a regular on the short-lived FX Networks sitcom Starved (2005), which received mixed reviews but which Benanti described as “a good experience. I got a lot of camera experience, which was something I just hadn’t had.” In 2006, she appeared in two films: Take the Lead, in which she reunited with her Nine co-star Antonio Banderas, and Falling for Grace as “Princess Alexandra”.
In 2008, Benanti had a recurring role on the ABC television series Eli Stone. She appeared in the pilot for the TV show as well.
In 2011 she was cast in the NBC series The Playboy Club, which was canceled after three episodes. Benanti played the wife of Dr. Atticus Sherman on episode 11 of season two of The Big C, entitled “Fight Or Flight”.
In 2014 she was cast as country singer Sadie Stone in the ABC musical drama series Nashville for its third season, recording and performing several songs during her arc.
In 2015, she joined the cast of Supergirl, where she has a recurring role as Alura In-Ze, Zor-El’s wife and mother of Kara and Alura’s twin sister General Astra, who wants to take over earth as its new ruler and destroy her niece Kara.
A songwriter and guitarist, Benanti has written songs privately since at least the early 2000s; in 2005, she said that she was working on a folk-rock solo CD, though “Musical theatre is my first love[…]I want to take my music and orchestrate it in a kind of old fashioned style, and take some standards and ‘popularize’ them—do a true crossover. I’m working on it.”
In Constant Search of the Right Kind of Attention, a live recording of Benanti’s concert engagement at 54 Below, was released by Broadway Records in September 2013.
In Constant Search of the Right Kind of Attention: Live at 54 Below (2013)
I Like Musicals – Single (2016)
The Sound of Music (1998 Broadway Revival Cast Recording)
Swing! (1998 Original Broadway Cast Recording)
Into the Woods (2002 Broadway Revival Cast Recording)
Benanti met Chris Barron, lead singer of the Spin Doctors, in the early 2000s. They married on July 25, 2005 but by the end of the year were going through what Benanti has called a “terrible divorce.” They were divorced in 2006.
At the 2005 World AIDS Day “dream cast” concert of The Secret Garden she met actor Steven Pasquale. In September 2007 they married. On July 8, 2013, they made the statement “After almost six years of marriage, Steven Pasquale and Laura Benanti are amicably filing for divorce. They remain loving and committed friends.”
On June 12, 2015 she became engaged to Patrick Brown. The two were married on November 15, 2015. She announced her pregnancy on August 11, 2016, saying “Coming this winter [#BabyGirlBrown]”. Benanti gave birth to her daughter, Ella Rose, on February 14, 2017.
Weronika Anna Rosati (Polish pronunciation: [vɛrɔˈɲika ˈrɔsatʲi]; born 9 January 1984) is a Polish actress and a member of European Film Academy. She began her acting career in Polish soaps. In 2005, she starred as Dżemma in her first theatrical feature film Pitbull. A year later, she launched her international career with a small uncredited role in Inland Empire directed by David Lynch. Since then she has appeared in many critically acclaimed Polish and international productions. In 2013, she has received her first Polish Academy Award nomination for Best Actress for her role in Obława (2012). A year later, she starred alongside Agnieszka Grochowska in Obce ciało directed by Krzysztof Zanussi. She also had a recurring role in the HBO TV series Luck (2012).
Weronika Rosati was born in Warsaw, as a daughter of Polish-Italian father Dariusz Rosati (birth name Gaetano Dario Rosati), a professor of economics and former member of the European Parliament, and his wife Teresa, a fashion designer. Weronika Rosati spent her childhood in the United States and Switzerland. Rosati and her family came back to Poland in 1990.
As an actress, Weronika Rosati debuted in the Polish Television series Klasa na obcasach in 2000. Then she performed in many other Polish soap operas, including: M jak miłość, Samo Życie, Pitbull and Majka. The last one was based on the Venezuelan TV series Juana la virgen. In 2012 she appeared as Naomi in the US TV series Luck.
Rosati was in relationships with Polish journalist Max Kolonko, Polish rapper Tede and Polish film director Andrzej Żuławski. Esther, one of the characters in Żuławski’s book Nocnik, was allegedly based on Rosati. Since 2013, the actress was in a relationship with Polish actor Piotr Adamczyk. They broke up in May 2015.