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|Actor|| Jensen Ackles|
Hunter Brochu (Young Dean in 1.01)
Ridge Canipe (Young Dean in 1.18 & 3.08)
Brock Kelly (Young Dean in 4.13)
Chad Everett (Elderly Dean in 5.07)
Nicolai Guistra (Young Dean in 5.22 & 7.10)
Dylan Everett (Young Dean in 9.07, 10.12 & 11.08)
Anthony Bolognese (Young Dean in 12.22)
|Dates||January 24, 1979 (born)|
|Location|| Age 4 – Lawrence, Kansas |
Present – Lebanon, Kansas (HQ)
Yeah, that's revenge. It'll get you out of bed in the morning, and when you get it, it feels great... for about five minutes. I've been there. Me and Sam – we have had our fair share of fights – more than our share – but no matter how bad it got, we always made it right because we're family. I need him. He needs me. And when everything goes to crap, that's all you've got – family. Now you might be a-an all-powerful being... but I think you're human where it counts. You simply need your brother.
– Dean Winchester, 11.23 Alpha and Omega
- 1 Background
- 2 Deaths
- 3 Michael's True Vessel
- 4 Pre-series
- 4.1 March 5th, 1861
- 4.2 November 1943
- 4.3 November 1944
- 4.4 April 30-May 2, 1973
- 4.5 Spring or Summer 1978
- 4.6 January 24, 1979
- 4.7 1983
- 4.8 November 2, 1983
- 4.9 1985-86 (approx.)
- 4.10 1989 (approx.)
- 4.11 1991 (approx.)
- 4.12 Christmas Eve 1991
- 4.13 Summer 1994
- 4.14 1995
- 4.15 1997
- 4.16 1998 or 1999
- 4.17 Sometime between 2001-2005
- 4.18 October 2005
- 5 Episodes
- 6 Weaponry
- 7 Trivia
- 8 See also
- 9 Dean in Fandom
- 10 References
- Born January 24, 1979; the same month and day as Jess. In an interview Eric Kripke said the reason they share a birthday was "...not a creepy, mythology, conspiracy reason. January 24th is my wife's birthday, and it's kinda my valentine to her."
- Son of John & Mary Winchester; older brother of Sam Winchester and older half-brother of Adam Milligan.
- Named after his grandmother, Deanna Campbell.
- Drives a black 1967 Chevy Impala which his father gave to him. It is later revealed that a young John Winchester initially bought the car in part because Dean, after being brought back in time by Castiel, persuaded him to buy it, as opposed to a van his girlfriend Mary Campbell (who would later become Mary Winchester) liked.
- Dean is a good mechanic. He single-handedly repairs the totaled Impala multiple times throughout the series and is a professional mechanic in the Wishverse of 2.20 What Is and What Should Never Be.
- He is also a good cook, as meals he has prepared are complimented by both Sam in 8.14 Trial and Error and Death in 10.23 Brother's Keeper.
- He always (until 5.02 Good God, Y'All) wears an amulet given to him by Sam as a Christmas present in 1991.
- He always (until between 5.07 The Curious Case of Dean Winchester and 5.08 Changing Channels) wears a silver ring.
- In seasons one and two, Dean alternates between wearing two bracelets. One is an African tribal bracelet and may either be a support bracelet from Invisible Children, or an elephant hair bracelet, which are believed to protect the wearer and bring them good luck and fortune. The other is a Buddhist mala, or prayer bracelet, whose beads carved in the shape of skulls are used by Tibetan monks during meditation as a memento mori.
- In 3.12 Jus in Bello we learn that Sam and Dean got matching tattoos depicting a pentagram that protects them from demonic possession.
- In 4.18 The Monster at the End of This Book Dean says that his favorite songs are a tie between "Ramble On" and "Traveling Riverside Blues" by Led Zeppelin
- Dean is Michael's true vessel, but he refused to say yes to Michael, which forced Michael to use Adam as his vessel.
- After Sam fell into Lucifer's Cage, Dean and Bobby parted. Dean then stayed with Lisa Braeden, putting a hold on his hunting career. After Sam's return from the Cage at Castiel's hand, Dean went back into the "hunting business."
- Following his abduction by fairies, Dean is capable of seeing all types of them who reside in the human realm as he was dragged over to their side and came back. In general, humans are incapable of seeing fairies, unless they want to be seen.
- Dean's most common catchphrase is "Son of a bitch."
- Dean loves pie, hamburgers, and diner/junk food in general.
- Dean has a love of the Magic Fingers bed relaxation system and memory foam mattresses
- In 10.03 Soul Survivor Sam says "I got your blood type" which could easily mean he got a compatible donor. Dean could accept type O - which is the universal donor and can be given to people with type AB, A, B or O. As John is AB, and whether Mary is A, B, AB or O, Dean could be type A, B or AB.
- In 2016 Dean killed Adolf Hitler.
- Dean dies over 100 times as part of Gabriel's time loop. Known causes of death include getting shot in the chest, being hit by a car, being crushed by a dresser, choking on a sausage, eating a bad taco, being electrocuted plugging in an electric razor, falling in the shower, accidentally being bludgeoned by an axe, getting shot with an arrow by Doris, and getting mauled by a dog. After Gabriel ends the time loop, Dean is shot by Cal and remains dead for six months until Gabriel sends Sam back to the Wednesday when he was killed, only without Cal.
- Dean dies when he is torn apart by a hellhound on May 2nd, 2008, when his crossroads deal expired. Dean is pulled out of Hell and resurrected by Castiel on September 18, 2008.
- Dean almost dies when Zachariah gives him Stage IV Stomach Cancer. Reversed moments later at Castiel's order.
- Dean dies when two angry hunters -- Walt and Roy -- shoot both him and Sam for Sam's role in starting the Apocalypse.
- Dean dies when Dr Robert injects him with something that kills him, in order to give him time to talk to Death. He is revived 7 minutes later.
- Dean dies after being stabbed in the chest by Metatron with an angel blade. Several hours later the Mark of Cain brings him back as a Knight of Hell.
- When Dean thinks Sam is dead, Dean overdoses on barbiturates and dies in order to talk to Billie the reaper. She tells him that Sam is not dead, and she is there to reap Dean and take him to the Empty. However, Dr. Kessler is able to successfully resuscitate him.
- In order to get out of a remote federal prison where they are being held for attempted assassination of the president, Dean and Sam must die. Dean asks Billie the reaper to let him and Sam die and come back one more time, and then she could take a Winchester for good. Being temporarily dead allows them to be transported to another room, and they sneak out once Billie brings them back.
- Dean dies after he injects himself with something that stops his heart in order to speak to the ghosts who are haunting a house. Sam injects him with a syringe full of another substance that is supposed to restart his heart, but it doesn't work. Billie shows up, and she brings him back, after a conversation in which she reveals that it is not his time to die yet.
Michael's True Vessel
- According to Zachariah, Dean is the "Sword of Michael" meaning that Dean is Michael's true vessel. His brother Sam is Lucifer's true vessel. The archangel Gabriel states that the Winchester brothers were always destined to be vessels, partially because of their bloodline, and partially because their relationship parallels that of Michael and Lucifer. Michael himself tells Dean that his line goes all the way back to Cain and Abel, thus explaining why Dean is destined to kill Sam.
Gabriel: Why do you think you two are the vessels? Think about it. Michael, the big brother, loyal to an absent father. And Lucifer, the little brother, rebellious of daddy's plan. You were born to this, boys. It's your destiny. It was always you. As it is in heaven, so it must be on Earth. One brother has to kill the other.
- Dean consents to being Michael's vessel in 5.18 Point of No Return; as Michael begins to appear, Dean reneges and kills Zachariah. He tells Sam that he changed his mind because he didn't want to let him down. Their half-brother Adam Milligan is taken as the vessel instead.
- In 13.23 Let the Good Times Roll Dean consents to being Apocalypse World Michael's vessel in order to battle Lucifer. He demands that he remain in control, but after Lucifer is killed, Michael reneges on their deal and takes over Dean's body. Michael suppresses Dean, but Dean fights back and Michael leaves him after about a month's timeBefore leaving, however, he leaves the "door" to Dean's mind open, which enables him to remotely see what Dean does and provides a way for Michael to later re-occupy Dean's vessel without his consent. This time, he creates an illusion in which Dean is happy (Rocky's Bar) to stop him from fighting back. Sam and Castiel enter Dean's subconscious, and help him repress and contain Michael within his mind.  After being knocked unconscious by the gorgon Noah Ophis, Michael is able to escape Dean's mind and possess Rowena, but he is exorcized and destroyed by Jack Kline. 
March 5th, 1861
Dean, along with Sam is transported back in time by Castiel to Sunrise, Wyoming to kill a phoenix and get its ashes to use against Eve. Sam retrieves the colt from Samuel Colt himself, which Dean uses in a showdown with the phoenix.
April 30-May 2, 1973
A 29 year old Dean is transported back from 2008 by Castiel. He discovers his mother Mary was a hunter, as were her parents. She was very capable but ambivalent about the life; she wanted to leave for a safe life with her boyfriend, a mechanic recently returned from Vietnam – John Winchester. She tells Dean the worst thing she can think of is having her children raised to be hunters. Mary and Samuel (Dean's grandfather) start hunting a demon, which is revealed to be Azazel. Dean goes to Daniel Elkins' house and steals the Colt, with the hope of killing Azazel and thus preventing the tragedies that have cursed his family. When Dean, Samuel and Mary encounter Azazel, he is very interested in Mary, and subsequently possesses her father. He kills both her parents and John, and then offers Mary a deal in return for John's life. Dean is unable to stop the deal, in which Mary agrees Azazel that can have access to her home in ten years time.
Spring or Summer 1978
Dean and Sam are taken back in time from 2010 by Castiel so that they can defend their parents from Anna Milton. Anna has come back in time to kill John and Mary, thereby preventing Sam's birth. Mary remembers Dean from his previous time travel, but John does not. The two are married, and Mary does not want their life interrupted by hunting, something she has left behind. She is persuaded to accept Sam and Dean's help when Anna goes after John, and the family retreats to a safe house. Once there, Dean tells Mary about her future, and reveals his true identity. He tries to warn her about the night in the nursery when she will be killed. Sam suggests that it is not enough for her to avoid the nursery. She must leave John so that Sam and Dean will never be born. Mary informs them that it is already too late: she's pregnant. Anna attacks, but Michael intervenes by using John as a vessel. He destroys Anna, then wipes the memories of John and Mary so that they will continue with their lives as before. He then returns Sam and Dean to the present, assuring Dean that he will one day consent to being a vessel.
January 24, 1979
Dean is born.
The Journal mentions that prior to Mary's death, Dean played t-ball.
November 2, 1983
Mary Winchester is killed by Azazel when she interrupts him feeding demon blood to Sam. John hands the infant Sam to Dean as the nursery burns and tells him to "Take your brother outside as fast as you can! Don’t look back! Now Dean, go!"
John leaves Lawrence with Dean and Sam before Dean's fifth birthday (see The Journal).
When Dean is "6 or 7," John takes Dean out shooting for the first time, using bottles as target practice. According to Dean, he "bullseyed every one of them." (Story told by Dean to Jo in 2.06 No Exit). Dean cites this story as one of the fonder memories of his father.
In 1.18 Something Wicked Dean recounts to Sam of an occasion when John is hunting a shtriga in Wisconsin and leaves Sam and Dean alone in a hotel room. Dean gets bored and goes out, and comes back to find the shtriga attacking Sammy. John returns in time to scare the shtriga off. Dean is haunted by his failure to defend his brother.
In 7.10 Death's Door, Bobby has a flashback to a sunny afternoon in "89-ish," when he took young Dean to a park. Ten-year-old Dean tells him, "Dad says I'm supposed to practice with the double-barrel," but Bobby insists that he gets to throw a ball around "like a regular snot-nosed little jerk."
When Dean is in sixth grade he makes his first sawed-off shotgun.
Christmas Eve 1991
Events told in flashback scenes in 3.08 A Very Supernatural Christmas:
Dean is left to babysit Sam (8 years old) while John is on a hunt, and Sam begins to interrogate Dean about what it is that their dad actually does. Dean responds "You know that. He sells stuff." When Sam moves on to asking about their mother, Dean gets angry and yells "Shut up! Don't you ever talk about mom! Ever!" before storming out. Upon his return, Sam reveals to Dean that he found and read their dad's journal, and demands to know if monsters are real. Dean finally resigns 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.
It is hinted at that Dean still believes that his father is a "superhero" at this point, and continually excuses his flaws, while the tension between Sam and John is clearly starting to take root.
In 5.12 Swap Meat we learn that Dean and Sam spent a portion of the summer being looked after by Donna, a maid at the Mayflower motel in Housatonic, Massachusetts, while their father was hunting. On one occasion, John was gone for two weeks. It was the summer before Sam entered sixth grade, and he assigned himself a summer reading list. Dean possibly had a crush on Donna.
Dean is 16.
- Dean: ... So, I picked up this crossbow, and I hit that ugly sucker with a silver-tipped arrow, right in his heart. Sammy's waiting in the car and, uh, me and my Dad take the thing into the woods, burn it to a crisp. I'm sitting there and I'm looking into the fire, I'm thinking to myself... I'm sixteen years old. Kids my age are worried about pimples, prom dates... I'm seeing things they'll never even know. Never even dream of. So right then I just sort of...
- Gordon: Embraced the life?
- Dean: Yeah.
In November 1997, John "parks" the kids in Fairfax, Indiana, where they attend Truman High School. While Sam is having trouble with a bully named Dirk McGregor, Dean gets a girlfriend, Amanda Heckerling; although he becomes uncomfortable when she wants him to meet her parents. When she catches him cheating on her with another girl, she challenges him, charging that his "cool" persona is a cover for his loneliness.
1998 or 1999
Dean is 19 or 20.
In 3.02 The Kids Are Alright, Dean says it has been "8 years ago," then edits himself to say it has been "8, almost 9 years." The episode is based in 2007, therefore, depending on when "8, almost 9 years" ago was precisely, he was either 19 or 20 at the time.
Dean goes on a road trip that was supposed to be "5 states, 5 days" while Sam (15 or 16) was "in Orlando with dad, wrapping up that banshee thing." However, Dean reveals in 3.02 The Kids Are Alright that he spent most of his time in Lisa Braeden's loft. "She was a yoga teacher. It was the bendiest weekend of my life."
Sometime between 2001-2005
During this time, as Dean tells Sam in 1.13 Route 666, he met Cassie Robinson while he and John were in Athens, Ohio for a hunt. She was "finishing up college" (she was therefore approximately 21 or 22) and they "went out for a couple of weeks." Dean was in love with Cassie, who was the first person he'd ever seriously dated (as Sam says "for more than one night") and the first person he'd ever felt that way about. When he found out he was leaving, he told Cassie the 'big family secret' about hunting because, as Dean says in the episode, he "just couldn't lie to [her]." Cassie, however, called him "nuts" and dumped him. This, as Dean also revealed in the episode, really hurt him, and he decided at that point that it was "stupid to get so close" and that he didn't need to open up to anyone.
Note: It is likely that it was around 2003 or 2004, during the "almost two years" that Dean did not speak to Sam, because Sam claimed that Dean hadn't told him anything about it. That means Dean was approximately 24 or 25.
Dean is 26.
In 1.01 Pilot, Sam asks Dean why he didn't go with John when he left to check out the hunt in Jericho. Dean explains that before he showed up in Palo Alto to get Sam from Stanford, Dean was "working [his] own gig... this, uh, voodoo thing down in New Orleans."
Sam asks, "Dad let you go on a hunting trip by yourself?" to which Dean replies, "I'm twenty-six, dude." This implies that before Sam left for college when Dean was 23 (see again Canon Discrepancies: How long did Sam spend at Stanford?), Dean had not gone on a hunting trip by himself. Considering the two men had not spoken in "almost two years," as Dean points out in 1.01 Pilot, it could mean that Dean hadn't hunted alone until he was 24 or 25.
When John Winchester goes missing, Dean goes to Stanford to enlist the help of the brother he hasn't spoken to for a couple of years. After spending an unsuccessful weekend trying to track down John, Sam returns to Stanford, despite Dean's obvious desire for him to stay. Sam's commitment to returning to shaken when his girlfriend, Jessica Moore is killed in the same manner as their mother. Sam joins Dean, and they go on the road with the aim of finding their father and killing monsters along the way. In particular, they are after the demon that killed Jess and Mary Winchester.
In season one, it is obvious that Dean is happy with his life as a hunter, and he tries to draw Sam back into the life: "Saving people; hunting things. The family business." To some extent, Dean sees himself as a soldier, and his father as his commander. Gradually, Sam and Dean become reacquainted with each other after their long separation – and often clash. In 1.06 Skin, the shapeshifter reveals Dean's anger at Sam going to college, while he had to stay and look after their father. He states that he knows eventually everyone will leave him. They clash over Dean's loyalty and obedience to John. In 1.09 Home, Dean first becomes aware of Sam's psychic abilities, when he has a vision of trouble at their old home in Lawrence, Kansas. In 1.10 Asylum while influenced by the spirit of Dr. 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, who insists he and John are both selfish because all they care about is revenge then later who 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 1.12 Faith, an accident while hunting a rawhead leaves Dean with a fatal heart condition when he is electrocuted, but he is saved by a faith healer 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 1.16 Shadow, as they prepare to battle Meg, Sam announces he will return to Stanford after the Yellow-Eyed Demon is killed, to which Dean says he wishes Sam would stay with him and keep hunting, even if they kill the demon that killed their mom, and Jess.
They come closer to this possibility in 1.20 Dead Man's Blood, when John reveals that there is a weapon that can kill the demon: The Colt. The Winchesters manage to acquire it from a group of vampires. The Yellow-Eyed Demon and his "children" Meg and Tom are quick to act, and begin killing John's friends and threatening to kill more until John gives them the Colt. John tries to trick them and is captured. In the season finale, the two Winchester brothers must rescue their father and face the Yellow-Eyed Demon, who possesses John. It is Dean who senses that something is wrong, when his father, uncharacteristically, praises him. Azazel is able to hold the brothers in check with his powers, and begins to torture Dean. The demon taunts him:
- "You know, you fight and you fight for this family, but the truth is they don’t need you. Not like you need them. Sam – he’s clearly John’s favorite. Even when they fight, it’s more concern than he’s ever shown you."
John manages to resurface and hold the demon in check. John pleads with Sam to shoot him with the Colt, but Dean begs him not to. The demon leaves John's body after Sam shoots him in the leg, and the three Winchester men drive towards the hospital. Suddenly the Impala is totaled by a demon driving a big semi-truck.
The season opens with Dean comatose from his injuries. He encounters a reaper, Tessa, who explains that Dean’s choice is either to stay as a disembodied spirit, and become the type of vengeful spirit that he hunts, or leave this world with her. Just as Dean is about to choose, he is returned to his body and healed because John has made a deal with the Yellow-Eyed Demon, trading his life for Dean's. Before he dies, John gives Dean a last, secret command – that he should save Sam, and if he can't save him, he should kill him. Throughout this season Dean struggles with this secret and his grief and guilt over his father's death. As much as he wants to, he has trouble admitting the secret to Sam. He becomes increasingly concerned about Sam's powers as the season progresses, but attempts to be supportive. During Sam's possession later in the season, Dean insists that Sam could not be responsible for the actions attributed to him, because in spite of Dean's own fears he believes in Sam.
Dean's police record begins to be a problem for the brothers this season. Dean is picked up in Baltimore on suspicion of murder, and the national authorities become aware that he is alive. They associate the crimes of the dead shapeshifter who took Dean's form in 1.06 Skin with the living Dean, who is now officially a fugitive. Matters become even more convoluted when Sam and Dean deal with another shapeshifter in 2.12 Nightshifter and end up holding people hostage to find it. In this episode they first become aware of Special Agent Victor Henriksen of the FBI who has been tasked with hunting Dean down. Their notoriety does allow the brothers access to a prison they are investigating in 2.19 Folsom Prison Blues when they allow themselves to be captured. They later escape.
Some of Dean's inner desires are revealed in 2.20 What Is and What Should Never Be, when a djinn attacks Dean. It uses a strong desire from Dean's subconscious (that his mother never died) to hold Dean captive in a dream world. There, Mary is indeed alive, Dean has a girlfriend and a job as a mechanic, but Dean and Sam are not close, and rarely speak. However, when Dean finds out that it is a fantasy and that all the people he has saved are dead in this reality, he struggles to escape it. He decides in favor of his life as a hunter, but he later admits to Sam that "I liked it there. I didn't want to leave."
In the season finale, Sam is kidnapped by the Yellow-Eyed Demon and pitted against the other Special Children. Dean and Bobby arrive as Sam is battling Jake. Jake comes up behind Sam and stabs him in the back with a knife. Sam dies in Dean's arms. Grief stricken, Dean makes a deal with a crossroads demon that echoes what his father did for him - Sam's life for Dean's, and Dean is given one year to live. Dean also agrees not to fight the deal, on pain of Sam's death.
In the climax of the episode, the boys battle the Yellow-Eyed Demon. The Devil's Gate in Wyoming is opened by Jake who using the Colt and demons and souls pour forth – including John. The spirit of John helps fight the demon, who is finally killed by Dean with the Colt. Sam and Dean share a silent moment with John before he disappears. The brothers then move forward with the knowledge that they have one year of Dean's life left.
In the third season premiere 3.01 The Magnificent Seven, Dean decides to make the best of his final year, indulging in many pleasures and refusing to even think about saving himself, while Sam tries desperately to find a loophole in the crossroads demon's deal. While searching for escaped demons to send back to Hell, Sam encounters Ruby, a mysterious blonde who assists him but who also informs him that, for some reason, demons are killing all of his mother's old acquaintances. Sam learns that Ruby is a demon, and she promises him help in freeing Dean from his contract. She "fixes" the Colt so that it can again kill "anything," and also shows them a knife in her possession that can kill demons. Later, they learn from her that all demons used to be human, but had their humanity burned away slowly in the fires of Hell. Dean begins to train Sam to fight demons alone once he is gone.
In 3.10 Dream a Little Dream of Me, Bobby falls into a coma, and Sam and Dean investigate the murder of a scientist. In the course of viewing Dean's dreams, it becomes clear that Dean believes that Sam was their father's favorite, but only thought of Dean as a tool. Dean encounters a future, demonic version of himself in a nightmare, which shocks him into starting to fight for his life and to realize he is not worthless. 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 to fight with when the hellhounds come for Dean.
In 3.11 Mystery Spot, Sam is forced to relive the same day, a Tuesday, repeatedly. On each new day, Dean dies a different way despite Sam's frantic efforts to save him. Sam realizes that the culprit is the Trickster, a villain from season two. 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's 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. He is warned by Ruby that he might not make it back from Hell.
In 3.12 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 comes to kill them. Ruby comes to help them, but is furious to learn 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 continues to search for a means to save himself from his fate, but ultimately is told by Ruby that there is no way to get him out of his deal. Shortly before Dean's contract comes due, he learns from Bela that Lilith, the demon pursuing Sam, holds his contract. 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.
As Dean and Sam confront Lilith and her demon forces in a last-ditch effort to protect Sam and save Dean's soul, Ruby appears and the three are chased into a room by a hellhound that has come for Dean. Dean quickly recognizes that Ruby's human host is now possessed by Lilith, not Ruby, but it's too late. The hellhound mauls and kills Dean in a gruesome fashion. Lilith flees, leaving Sam alone with Dean's mutilated corpse. In the last scene of the season, Dean is shown in Hell, suspended in a void by seemingly endless chains and hooks through his flesh, crying out in agony for Sam's help and yelling Sam's name.
The fourth season premiere, 4.01 Lazarus Rising, begins four months after the third season finale. Dean awakes to find himself in a coffin choking he manages to dig himself out and breaks into a nearby gas station where he gets some water, food and cash and a sneak peek of “Busty Asian Beauties.” Before leaving the store, Dean sees the television and radio flicker on, with static, and a powerful whine that shatters all of the glass and hurts Dean's ears. Dean calls Sam, but finds his number disconnected. He calls Bobby, who hangs up on him, so he hot-wires a parked car and goes to Bobby's house. After proving that Dean is really back, he and Bobby track down Sam in a town right near where Dean was buried — he's in a hotel with a girl, but he claims he did nothing to bring Dean back; he's in town because he is searching for a demon. The girl acts puzzled by all of this and leaves, while Dean tells Sam he remembers nothing from Hell. The Winchesters track down whatever force ripped Dean from Hell. 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 body, and Sam had lied to Dean when he told him that he didn't know where Ruby was and that he wasn't using his demonic powers. Dean, in turn, was lying to Sam about Hell; in 4.08 Wishful Thinking, Dean confesses that he does remember every second of Hell.
Later, in 4.03 In the Beginning, Dean is transported back in time to Lawrence, Kansas in 1973. There, he meets his father and mother, as well as his grandparents, and learns of a connection between Azazel and Mary, which explains why Mary seemed to recognize the demon hovering over Sam's crib (as seen in 2.21 All Hell Breaks Loose: Part One) and why her ghost apologized to Sam (in 1.09 Home). A causality loop is revealed in that the time-traveling Dean, by trying to stop Azazel in the past and change his future, actually made the demon aware of his family in the first place, setting in motion the events leading to the death of his parents, the corruption of his brother, and the life he tried to change, therefore setting up a predestination paradox. (However, it is implied by Castiel that the events would have happened anyway without him being there as they were already destined.) Upon returning to the present, Dean is informed by Castiel that Sam is "going down a very dark road," and that if Dean doesn't stop him, the angels will.
Dean follows Castiel's directions and encounters Sam using his powers to exorcise a demon, also learning of Ruby's return. He conveys the warning of the angels. After he and Sam stop a rugaru in Missouri, Sam decides to stop using his powers, which seems to satisfy Dean.
In 4.10 Heaven and Hell, Dean 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 put on the rack and "cut, carved, and torn" apart until there was nothing left of him, only to be made whole again just so the demons could start over on him. 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 it and torture them. Dean resisted for thirty years, then gave in and spent ten years torturing people in Hell to escape being tortured himself.
In 4.11 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.
4.13 After School Special included flashbacks of a teenage Dean and a pre-teen Sam while they are going to a high school. In this episode, we learned that Dean was as promiscuous as ever when he was younger. The girl he was currently dating told him that he acted cool when, in reality, he was a little boy who played with people's feelings to make himself feel better. Dean, clearly stung, from then on hated the school.
In 4.15 Death Takes a Holiday, Dean meets up again with the reaper Tessa. She awakens 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 she is taken by Alastair in his quest to break another seal, that involved killing reapers. The boys ask Pamela Barnes to help them spirit walk and leave their bodies 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 on reaping souls. However before Dean is able to return to his body, Alastair corners him, but he is captured by the angels and Castiel informs Dean that they have won this seal. As he awakes in his body, Pamela is dying from her injuries she obtained during a fight with a demon, while the boys were "out".
In the next episode 4.16 On the Head of a Pin, Dean is pressed into service by the angels, who need him to torture Alastair for information on who is killing angels, since Dean was his "student" in Hell. Dean refuses at first but eventually agrees. However, he only succeeds in getting Alastair to reveal that Dean 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.") The distraction is enough for Alastair 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, but Sam, having grown stronger, arrives, and uses his powers to torture Alastair in to revealing he did not know who was killing the angels. Sam killed him shortly after. 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 the angels' "brother" Lucifer from hell, which would start the end of days and destroy humanity whom they despise for being forced to "bow down" to and they believe is the reason God no longer seems to be concerned with them. He 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 up to such a task, telling Castiel to find someone else as tears run down his face.
To put Dean back on the right path, Zachariah, Castiel's superior, rewrites Dean and Sam's memories to remove their knowledge of supernatural creatures, making them believe they're average people working regular jobs. He then drops them in a haunted building. The brothers proceed to defeat the spirit that's haunting the building as Dean's boss, Zachariah restores Dean's memories to show him that hunting is in his blood, not simply something he was brought into by his father, and that he has an opportunity to affect the world in ways most humans will never be able to. This renews Dean's resolve.
In 4.20 The Rapture, Dean witnesses as Sam drinks the blood of a demon he is about to kill. Later in the Impala, Sam is waiting for Dean's rebuke. Sam tells him to get over it and Dean yells at him for drinking demon blood, before Sam gets a request from Bobby to head to his house. Once there, Dean and Bobby trick Sam and lock him in the demon-proof panic room for his own safety as he detoxes.
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, to which Castiel says "if that gives you comfort". 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 whether or not Ruby is corrupting him, if he is supposed to stop the apocalypse, and if Sam is turning into a monster. The argument leads to a fight that Sam wins. Dean yells at Sam by saying, "If you walk out that door, don't you ever come back," after which Sam leaves the room.
The angels take Dean to a "safe" room and Zachariah explains that they are preparing for the Apocalypse and will allow the final seal to be broken. They want Sam to kill Lilith as her death will break the final seal holding Lucifer, after which Dean will kill Lucifer and bring paradise on Earth. Dean is shocked and horrified that they would allow the Apocalypse. He asks Castiel for help, together they escape and meet Chuck to see where the final seal will be broken. As Castiel holds back the archangel, he sends Dean to stop Sam from killing Lilith. Ruby shuts the door on Dean as Sam kills Lilith. After the final seal is broken, Sam finds out Ruby has been working with Lilith since the get-go and manipulating him to kill Lilith to break the final seal to release Lucifer. Dean then enters the room and approaches Ruby. Ruby says "It's too late," to which Dean replies "I don't care," and stabs Ruby with her own knife with Sam's help. A portal opens for Lucifer while Dean and Sam can only watch.
The fifth season begins right where season four ends with the portal opening. As Lucifer escapes the brothers are teleported into an airplane by an unknown force. 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.
Dean and Sam fight the Horseman War in a town where the people think that their neighbors are demons. Dean worries that Sam cannot control his urge to drink demon blood and the brothers agree to go their separate ways because Sam is a liability with his demon blood lust. Castiel finds Dean and they capture the archangel Raphael to ask the location of God.
In the 5.04 The End, he finds himself in 2014, eventually meeting up with his future self, as well as the survivors, and victims of the Croatoan virus. Dean finds out that Sam let Lucifer into his body, and this was the reason the world was in such disarray. Later, the future Dean is killed by Lucifer, while in Sam's body. After being told by his future self to accept Michael into his body. Dean is transported back to his own time, where he comes face to face with Zachariah. He refuses to become Michael's vessel. In the end of the episode the brothers meet back up again, and decide that they should stay together, to "Keep each other human."
In 5.10 Abandon All Hope..., Dean and Sam get the Colt and head off to take on Lucifer alongside Castiel, Ellen and Jo. It is discovered that the Colt cannot kill Lucifer and Ellen and Jo lose their lives in the fight against a group of Hellhounds, which severely damages Dean’s spirits. Dean is further shown to be “broken” in 5.14 My Bloody Valentine when he is unaffected by Famine’s abilities and Famine tells Dean that he wants for nothing because he is “dead inside.” Dean’s so desperate he even begs for help from Heaven.
In 5.16 Dark Side of the Moon, Dean’s further pushed when he receives word from God through Joshua to “back off” and that God is not going to get involved with the fight against Lucifer. When a despondent Castiel returns Dean's amulet to him, deeming it worthless, Dean discards the amulet into the waste bin.
Dean eventually decides that saying “Yes” to Michael is the only he can do as he doesn't believe they can find a way to stop Lucifer and he doesn't believe in Sam himself. However, it is Sam’s faith in his big brother which eventually convinces Dean not to say “Yes” to Michael.
Eventually, Dean discovers that Lucifer can be locked back into Hell using the rings of the Four Horsemen of the Apocalypse but to do so, Sam must say “Yes” and then jump into the pit. Dean is extremely reluctant at first but then realizes that Sam is a lot stronger than he gives him credit for and he allows Sam to make this decision himself.
Sam says “Yes” to Lucifer in Detroit and is seemingly taken over to him. However, Dean has yet to give up on his brother and chases him down to Stull Cemetery to try and talk with Sam. An annoyed Lucifer severely beats him however Dean continues to call out to his brother, eventually causing Sam to regain control enough to pull both himself and Michael into Lucifer's Cage.
With the Apocalypse avoided and both Lucifer and Sam locked away in Hell, a distraught Dean sets about fulfilling the last promise he made to Sam: to live a normal, safe life with Lisa Braeden and to not find a way of bringing Sam back. Lisa comforts Dean and the they seem to have a try at being a normal family, even sitting down to a family dinner, unaware that outside the house, staring in through the window at them, is Sam.
In the first half of the season, Dean is in many ways the center of the action because Sam is soulless. Dean has been living with Lisa and Ben Braeden for a year. He works construction and drives a pick-up truck, having stored the Impala in the garage under a tarp. He embraces domestic life, and when asked about his past, Dean says on one occasion that he was in "pest control." He has nightmares, though, and keeps vigilant: there is holy water and a gun under his bed, and a devil's trap is painted under the rug by the front door. When djinn track him down and poison him in 6.01 Exile on Main St., he is saved at the last minute by Sam, who injects him with the antidote. Dean is shocked to see his brother; he is both puzzled and hurt to learn that Sam has been back almost a year. Sam has been hunting with their Campbell family members, in particular their resurrected grandfather Samuel Campbell.
Dean struggles with balancing his relationship with Lisa and Ben against the need to help his resurrected brother and to hunt. When Sam approaches Dean for help with a shapeshifter infant in 6.02 Two and a Half Men, Dean is hesitant to go, but Lisa tells him that he should. He proves to be a help with the baby, knowing how to put on diapers and get him to sleep. When he returns, Lisa encourages him to return to hunting full time. Dean does, unwrapping the Impala with a flourish and heading off to meet Sam. As he spends more time with his brother, Dean becomes more suspicious of his behavior and motives, but he is distracted in 6.03 The Third Man by Castiel's news of an angelic civil war with the archangel Raphael. There is also the matter of Bobby's deal with Crowley. Dean and Sam travel to Scotland during 6.04 Weekend at Bobby's to help Bobby regain his soul. Dean's fear of air travel made the journey difficult, but he made the trip to help Bobby.
Dean's relationships with Lisa and Ben and his own brother are severely strained in 6.05 Live Free or Twihard, when Dean is attacked by a vampire leader and turned. He goes to Lisa to say goodbye, frightens her, and shoves Ben away roughly when the boy gets too close. Samuel Campbell has a cure for vampirism, but Dean needs the blood of the vampire that turned him, so he goes to the vampire nest and slaughters them all with a machete. While there, he has a vision of the Alpha Vampire and his plan to build a vampire army. He takes the cure and undergoes an agonizing transformation back into a human. During the transformation, he remembers the moment he was turned and realizes in horror that Sam stood by and smiled while it was happening.
Dean avoids speaking with Lisa about what happened, but when they finally do speak in 6.06 You Can't Handle the Truth, Lisa ends their relationship. Left with only Sam and his guilt over endangering and then losing Lisa and Ben, Dean tries to find out what is wrong with Sam and how to fix it. When Veritas declares Sam to be "not human," Dean attacks his brother and knocks him unconscious. He calls Castiel, who diagnoses Sam as soulless. Though Dean distrusts Sam, he still sees him as his brother. He tries to find a way to return Sam's soul, but the answer eludes him, even though he goes so far as to work with Crowley in his search for Purgatory, hoping the demon will return Sam's soul. This hope is lost when Castiel incinerates the demon. Dean becomes increasingly disturbed by RoboSam's behavior and the thought of Sam's soul still in Hell. Finally, in 6.11 Appointment in Samarra Dean gambles with his own life, and then with Death, who wants the brothers to continue investigating the souls.
The second half of the season begins with Sam having regained his soul, and Dean worrying that Sam will remember his time in Hell if he tries to remember too much of the last year. Dean tries to hide the existence of his soulless self from Sam, but his brother finds out, and wants to make amends for what he did. They are soon distracted, though, by the arrival of a new threat: Eve. The mother of all supernatural creatures, she is released from Purgatory in 6.12 Like a Virgin and threatens to overrun the world with monsters. They research her and her possible weaknesses, and follow the trail of destruction she leaves behind. Dean is possessed by one of her new creatures in 6.16 ...And Then There Were None. The angelic civil war is also an obstacle, and sends them into an alternate universe in 6.15 The French Mistake and an alternate timeline in 6.17 My Heart Will Go On.
Dean gets to live out a cowboy fantasy when Castiel sends the brothers to the Old West in 6.18 Frontierland to search for phoenix ashes, Eve's weakness. They manage to get the ashes, and strike out after Eve in 6.19 Mommy Dearest. She has created a town of monsters, and they have little hope, but Dean, having drunk some of the ash, antagonizes Eve into biting him. She dies, but the victory of her death is overshadowed by her announcement that Crowley, who they thought was killed by Castiel, is still alive. Dean defends Castiel against Sam and Bobby's suspicions, but when they discover the angel has been spying on them, even Dean cannot deny that the angel is not being honest with them.
When they finally unravel Crowley's plan to open Purgatory and use its captive souls as a power source, Dean is shocked and horrified to discover that Castiel has been working with Crowley in secret for the last two years. Castiel is adamant that he needs his half of the souls in Purgatory to defeat Raphael, who wants to restart the Apocalypse, but Dean is resolved to stop him and Crowley. Crowley tries to hold Dean off by kidnapping Ben and Lisa. Dean saves them, but Lisa is gravely injured. Castiel, in a last act of friendship, heals Lisa, and at Dean's request erases their memories of Dean.
Dean's path is next blocked by Castiel, who knocks down Sam's wall to hold Dean back. Even so, Dean and Bobby resolve to stop the angel and the demon. They fail, however, and Castiel manages to claim all the souls in Purgatory for himself, and kills Raphael. A weakened Sam tries to kill the angel, but they discover that he is too powerful. Dean is confronted with the loss of someone that he considered a brother, and the terrifying prospect of a new, God-like enemy.
In 7.01 Meet the New Boss, Castiel spares the hunters, but refuses to heal Sam. As Castiel travels the world, wreaking havoc in his attempt to right the wrongs he sees, Dean despairs. He sees chance of stopping the angel, and instead resorts to drinking, focusing on the broken Impala, and worrying about Sam. As Castiel's actions become more erratic, Dean does come up with an option: binding Death, as Lucifer did. Dean, Bobby and Sam succeed in putting a spell on Death, but Castiel undoes it in a moment. Death does agree to assist in reopening Purgatory, but it is up to them to get Castiel to release the souls. Dean refuses to pray for Castiel to come, thinking there is no hope. Instead Sam prays, and eventually Castiel appears. Cas tries to apologize to Dean, but Dean is not forgiving. Cas returns the souls, and survives, but is taken over by Leviathans, which hung on inside him. In 7.02 Hello, Cruel World the leviathans escape in Castiel's body to a reservoir, and let themselves loose on the world. Castiel disappears beneath the water, and Dean finds Castiel's trenchcoat at the shore, and takes it with him.
Dean and Bobby take a disturbed Sam back to Bobby's place, and confront him about the consequences of losing his wall. Sam admits that he is seeing Lucifer, and cannot tell if he is out of Hell, or still there. Dean worries about Sam as he leaves to investigate the first of the known Leviathan killings. When he returns to Bobby's house, he finds Sam missing, and tracks him by his phone GPS. Sam's hallucinations manifested as Dean, and led him to a warehouse as part of an imaginary hunt. Tormented by his visions, Sam nearly shoots the real Dean when he arrives. Dean, with as much calm as he can manage, grabs Sam's injured hand, and uses the pain of it and his own experiences in Hell to convince his brother that this is the real world. When they return to the salvage yard, they find Bobby's house destroyed, and no sign of the hunter. Dean calls Bobby's phone, and leaves him a desperate, near suicidal, message, pleading for him to be alive.
The brothers are attacked by Edgar the Leviathan in the salvage yard, and are so badly injured that they are taken to the Sioux Falls hospital, which is also infested with leviathans. Bobby appears in 7.03 The Girl Next Door, and manages to get Dean, who broke his leg, and Sam away to hide at Rufus's cabin. As they heal, Dean continues to worry about Sam, though his brother insists he is well. When Sam disappears suddenly to investigate a case on his own, Dean follows his trail, and finds out that he was hunting a kitsune named Amy Pond who has been killing criminals. Sam met her when they were kids, before finding out what she was. He leaves her alive now because she was hunting for her sick son. Dean pretends to accept Sam's decision, but secretly goes after Amy and kills her.
In the weeks that follow, Dean's worry over Sam and the Leviathans, and guilt over the Amy situation, overwhelm him. He sinks into alcohol dependency, even drinking on jobs. When Osiris threatens to punish Dean for his past sins in 7.04 Defending Your Life, Dean gives in to judgment to prevent Osiris from revealing Amy's fate. Sam cannot understand, and tries to get Dean to open up, while also attacking Dean's alcohol use. Matters are complicated when two Leviathans masquerade as Sam and Dean in 7.06 Slash Fiction and go on a killing spree in hopes of exposing the brothers. Bobby sends them to Frank Devereaux, who gives them new fake IDs and insists that they hide the Impala, something to which Dean agrees with great reluctance. Sam and Dean are eventually caught by police, and the leviathans come after them. Dean manages to behead them with an axe, but not before the one pretending to be Dean reveals the truth about Amy to Sam.
The brothers separate for a time, but reunite to investigate a series of murders in 7.07 The Mentalists. Dean receives an unexpected message from Ellen through a real medium, encouraging him to talk to Sam about how he feels. Dean obeys, and tells Sam he feels justified in killing Amy, but guilty about lying to Sam. Eventually they move on, and take their annual pilgrimage to Las Vegas, but life takes another odd detour in 7.08 Season Seven, Time for a Wedding! when Becky Rosen kidnaps Sam using a demon love potion. Dean is forced to work with Garth, an unusual hunter, to get his brother back. In spite of his drugged state, Sam is able to help with the case, and Dean admits that Sam does not need him the same way that he used to. Sam suggests that Dean should be relieved, and that now he has a chance to look after himself instead. Dean does not seem comforted by the idea.
Investigating murders in New Jersey during 7.09 How to Win Friends and Influence Monsters, Sam, Dean, and Bobby, run across the trail of the Leviathans again. They are tampering with the food supply through the Biggerson's Restaurant chain, and Dean ends up drugged by a turducken sandwich, which blocks his emotional turmoil. After Dean recovers, they go after the leviathan test facility, but during their escape Bobby is shot in the head by Dick Roman. The boys rush him to the hospital, where an administrator asks Dean about organ donation. Dean is furious to the point of punching a wall. Outside the hospital, he sees Dick Roman. Dean taunts him, and promises vengeance. Bobby awakes briefly, gives the brothers a series of numbers, and dies.
The brothers retreat to Rufus's cabin to mourn. Over the next three weeks, Dean obsesses about the numbers, and agrees to split up with Sam on a case during 7.11 Adventures in Babysitting so that he can talk to Frank Devereaux about them. Dean has been losing track of time, and does not know that he gave Frank the numbers only four days before. Frank has identified them as map coordinates, and the two set up surveillance on the designated area. Dean passes out, and sleeps for thirty-six straight hours. When he wakes, Frank reveals that he lost his whole family to monsters, and advises Dean that he has two options: to quit, or to keep hunting, and smile while he does it. Dean considers Frank's words carefully, then sets out to find a missing Sam with Krissy Chambers. Dean gets similar advice from Eliot Ness in 7.12 Time After Time. Dean has a drunken one night stand with what turns out to be an Amazon in 7.13 The Slice Girls, and the two have a fast growing daughter together, who comes to kill Dean two days later. Dean tries to persuade her that she does not need to be a monster, but she does not relent, and Sam kills her. Dean's drinking slows after this, though he continues to carry Bobby's flask with him.
In 7.14 Plucky Pennywhistle's Magical Menagerie and 7.15 Repo Man, the brothers revisit their pasts, and Sam's condition gets worse. During "Repo Man," Dean gets kidnapped by the former host of a demon they exorcised while searching for Lilith and as a result of allowing the Lucifer hallucination to help him find Dean, allowing it a stronger grip on Sam's mind. By 7.16 Out with the Old he is unable to sleep, and in 7.17 The Born-Again Identity he is institutionalized after being hit by a car. Dean searches for a faith healer, and to his surprise finds an amnesiac Cas serving as one. He takes Cas to Sam with Meg in tow, telling Cas that his brother was hurt by Dean's friend, and that Dean has not been able to forgive him. At the hospital, Cas remembers who he is after fighting a group of demons, and Dean returns his coat. Cas takes on Sam's suffering, and remains at the hospital in a catatonic state watched by Meg.
The brothers reteam with Garth in 7.18 Party On, Garth, and Garth suggests that Bobby may still be with them as a ghost, tied to the flask. The same idea has occurred to the brothers, but both are reluctant to believe it Bobby is shown to be watching over and helping them and they are finally able to see him in 7.19 Of Grave Importance. Dean in particular is bothered by Bobby's presence, worrying that Bobby made the wrong decision in staying behind. Still, they work toward bringing down the leviathans, and manage to steal a tablet that is the Word of God from Dick Roman, and have a prophet named Kevin Tran translates it for them. Uncovering the tablet wakes Castiel, and Dean tries to get him involved in the fight, but Cas is hesitant and damaged and leaves.
The brothers work on a weapon to defeat the Leviathans based on the tablet, and secure blood from the Alpha Vampire, Castiel, and Crowley for it. Bobby meanwhile becomes vengeful, and asks the brothers to burn the flask, and send him away. They agree, and Dean burns it. He then asks Cas to transport him to the Impala, and tries again to get the angel to come with them in the attack on Dick as he is the key to finding the real Dick. Cas is afraid of doing wrong again, but Dean insists that either way he would rather the angel be with him, and forgives him for what he did. Castiel finally agrees and Dean, Sam, Castiel and Meg attack SucroCorp, using Meg and the Impala as a distraction. Dean faces down Dick Roman and finally kills him with Castiel's help, but as a side-effect, Dean and Castiel are sucked into Purgatory with Dick. Once there Castiel disappears on Dean, leaving him surrounded by monsters.
After a year in Purgatory, Dean escapes with the aid of a vampire called Benny Lafitte, who he subsequently restores to life with a ritual, but Castiels fate is initially unknown. Reuniting with Sam and Kevin, Dean learns that Kevin has discovered another Word of God tablet containing a ritual that could seal the Gates of Hell forever, but Kevin flees because he does not trust Dean to keep him safe. Despite this, Kevin and Dean eventually make contact again after Dean saves Kevin from Crowley with the aid of the returned Castiel, Kevin continuing his research under the protection of Garth, who has taken over Bobby's former role as Hunter coordinator. Although Dean and Benny grow more distant after Sam learns of his existence, Dean stands by Benny when another hunter accuses him of murder.
Following a meeting with their temporally time-displaced grandfather, Henry Winchester, Dean and Sam take custody of the archive of the Men of Letters, an organization dedicated to recording the supernatural before their destruction in the 1950s. With the archive resources and Kevin's translation of the tablet, Sam sets out to complete the three trials to seal the Gates of Hell, which include killing a hellhound, delivering an innocent soul (Bobby) from Hell unto to Heaven, and curing a demon. However, Dean stops Sam when he learns that the trials will kill him, shortly before renegade angel Metatron seals off Heaven using spell to banish all the angels from Heaven and leaving Castiel human.
In order to save Sam's life, Dean manages to make contact with a fallen angel who introduces himself as 'Ezekiel', who manages to trick Sam into agreeing to act as his Vessel while in his coma, allowing Ezekiel to heal Sam's injuries and recharge his own 'batteries' from inside Sam. With Castiel reduced to a human state and on the run from the other angels, Dean orders him to stay away so that Ezekiel can focus his energies on healing Sam while Kevin Tran studies the angel tablet to find a means of reversing Metatron's spell. However, things become more dangerous when the fallen angels begin to fight amongst themselves and Abaddon sets out to take over Hell while the Winchesters hold Crowley captive.
When Castiel regains his powers by stealing the Grace of another angel, he learns that Ezekiel is actually the renegade angel Gadreel, who was banished to Heaven's prison for past mistakes. Taking complete control of Sam, Gadreel kills Kevin and flees, forcing Dean, Castiel and Crowley to collaborate to reveal what has happened to Sam so that he can expel Gadreel from him. Disgusted at Dean's lies, Sam loses his trust in his brother, forcing Dean to work with Crowley to find Cain and receive the First Blade and the Mark of Cain, the only weapon capable of killing Abaddon. Dean is able to kill Abaddon, but is killed himself in a later confrontation with Metatron, with the Mark's influence causing him to transform into a Knight.
When season 10 starts, in 10.01 Black, several weeks have gone by. Now transformed into a Knight of Hell, Dean disappears from the Bunker, leaving behind a note for Sam, which says only, "Sammy let me go." While Sam and Castiel try to figure out what happened and where he is, Dean is busy hanging out with Crowley at bars, singing karaoke, sleeping with women, and getting drunk. He also kills several demons who had been Abaddon supporters. When Sam gets captured by Cole Trenton, and Cole tries to use Sam to lure Dean, Dean makes it clear that he does not care what happens to Sam, and that he will not be coming to Sam's rescue.
In 10.02 Reichenbach, Crowley (thinking Dean would make a good partner in running Hell) convinces Dean to agree to kill a human for the client of one of his crossroads deals. However, when Dean instead kills the client, Crowley realizes that Dean is out of his control. Crowley then finds Sam, and gives him Dean's location. Sam finds him, and reminds him that they know how to cure demons. Dean, however, says that if he had wanted to be cured, he would not have left. Sam doesn't give up and tries to persuade Dean to let him attempt the cure, but Dean mocks him. As Sam pulls out the handcuffs, tear gas is thrown through the window, interrupting them. While Sam is on the ground outside coughing, Dean fights Cole. He defeats him easily, but leaves him alive in order to make him have to live with his failure. Sam takes advantage of Dean's distraction by throwing holy water on him. As Dean falls to the ground in pain, Sam is able to put the binding handcuffs on him.
By 10.03 Soul Survivor, they have returned to the Bunker, where Sam has handcuffed Dean to a chair inside a Devil's trap in the dungeon. Sam begins injecting Dean with purified human blood, which Dean reacts to with great pain. Throughout the process, he continues to taunt Sam mercilessly. Sam perseveres, despite not knowing if the cure is working or not. Eventually, the human blood makes Dean human enough to be able to slip out of the handcuffs and the devil's trap, and he chases Sam through the Bunker, trying to kill him with a hammer. He almost succeeds, but at the last minute, Castiel finally arrives, and is able to stop and subdue Dean. They return him to the dungeon, where they are able to finish the cure successfully. Although Dean is human once again, they know that because the Mark is still there, it will continue to be a problem.
While Dean no longer has access to the First Blade, he still finds himself struggling against the Mark's influence. In 10.06 Ask Jeeves, he kills a shapeshifter, and then proceeds to shoot it several more times after it is already dead. In 10.09 The Things We Left Behind, he has a nightmare in which he is kneeling on the floor in a room full of bodies, covered in blood with a knife in his hand. It turns out to be prophetic - the nightmare becomes reality when loses control and single-handedly kills several men after they attack him. When a shocked and horrified Sam says, "Tell me you had to do this," Dean can only reply, "I didn't mean to."
In 10.10 The Hunter Games, Castiel brings Metatron to the Bunker so they can question him about the Mark of Cain. When Castiel and Sam are elsewhere in the Bunker, Dean locks himself in the dungeon with Metatron and begins torturing him with an angel blade to force information out of him. When the others realize what is happening, they run to the dungeon, and Castiel breaks the door down. Sam pulls Dean away from Metatron, who warns Dean that he is only going to get worse. Dean later admits, "I was going to kill him, and I couldn't stop myself." When Castiel asks him to go talk to Claire, he is ambushed and almost kills his attackers, but manages to resist.
Charlie returns in 10.11 There's No Place Like Home, and she explains to them that she has been split into two - good Charlie and bad Charlie. They are connected, if one Charlie gets hurt, the other one will also get hurt. When Dark Charlie confronts Dean, a fight ensues, and Dean breaks her arm. He continues to beat her until she is semi-conscious, until Sam, carrying Good Charlie in his arms, yells at Dean to stop. Dean, snapping back to his senses, realizes what he is doing and steps back. He watches as the two Charlies merge back into one, his face etched with remorse. Back at the Bunker, a battered Charlie tells him that she forgives him, even though he doesn't forgive himself.
After a spell reverts Dean's body into that of his 14-year-old self in 10.12 About a Boy, he discovers that the spell also removed the Mark. For this reason, he briefly considers remaining as a teenager, but ultimately changes back in order to save Sam, Tina, and himself. After working a case involving a ghost in 10.13 Halt and Catch Fire, Dean tells Sam that he's done trying to find a cure for the Mark of Cain. He doesn't believe there is one, and he can't continue to rely on false hope. He vows to continue to fight and work cases, saying that is where he finds his peace.
When Cain resurfaces and starts killing humans in 10.14 The Executioner's Song, Dean resigns himself to confronting and killing him. Sam, Castiel, and Crowley lure Cain into a Devil's trap in a barn, and Crowley hands the First Blade over to Dean, who takes it with apprehension. While the others wait downstairs, Dean goes up to face Cain, and they fight. Because Dean is desperate to not fully give in to the powers or influence of the Mark, he is easily overpowered, and Cain gains the upper hand. He tells Dean that their stories are very similar, and by killing him he would be doing Dean a favor. If he let Dean live, he would inevitably end up killing those he cares about - Crowley first, then Castiel, and then Sam. The act of killing his brother would be the one he would not survive. When Cain goes to kill Dean, Dean manages to grab a knife from Cain's belt, and uses it to cut Cain's hand off. In control of the Blade once more, he desperately asks Cain to tell him that he will stop killing people - or that he even can stop. When Cain refuses, Dean kills him, devastation written all over him. When he meets up with the others, he gives the Blade over to Castiel instead of Crowley, and then collapses into Sam's arms.
Dean goes to a bar in 10.17 Inside Man and is attacked with a spell by Rowena, who is shocked when he survives, completely unaffected. Dean corners her, and she tells him that he is a bad influence on her son - Crowley. Later, he meets up with Crowley and they have drinks and talk about how they have changed, and what family means.
In 10.18 Book of the Damned, Sam and Dean get a phone call from Charlie. She has managed to find a book called the Book of the Damned that might contain a cure for the Mark of Cain, but is being chased by several men who are able to track the book. They meet up at an old hunting cabin, and when Charlie hands Dean the book, he becomes entranced by it. Unnerved, he hands it back, saying that he doesn't think it's a good idea for him to touch it. After some research, Dean discovers that the men who are after Charlie are members of the Styne Family, who have used the Book in the past for evil purposes. He decides that using the book is a bad idea. He tells Sam and Charlie that the book is calling out to him, telling him to use it, but not for good. He insists that they destroy it, but Sam argues that it is their only hope to save Dean, and he'll do anything he can to do so. Dean goes to a convenience store to get some snacks, and while there runs into Jacob Styne and another man. They attack Dean, but not before telling him that the Book does in fact contain a cure for the Mark. Dean escapes after shooting one of them to death, unloading an entire clip to do so. He goes back to the cabin, giving a few seconds warning to Sam and Charlie. He tells Sam to burn the book, and as the Stynes break into the cabin and attack, he watches as Sam throws a book on the fire that he believes to be the Book of the Damned.
In 10.19 The Werther Project, Sam starts to work with Rowena without Dean's knowledge, and sets out to look for a codex which allow them to translate the Book of the Damned that he was supposed to have burned. When he goes to look for it, Dean catches up with him, and says he wants to help with the case. Sam agrees, though he doesn't tell him what they are really looking for. Sam finds the box containing the codex in the basement of a house, but when he tries to open it, he releases a deadly spell that was put there by Cuthbert Sinclair of the Men of Letters. The spell, which makes people hallucinate and drives them to suicide, makes Dean hallucinate that he is back in Purgatory with Benny. There, Benny tells him that he would be doing Sam and Castiel a favor by killing himself. Dean knows that this is not the real Benny, and says that although he would do it if he really had to, the Mark won't let him die. He wakes up from his hallucination in time to save Sam, who was also hallucinating and on the verge of death.
After investigating a murder in 10.21 Dark Dynasty that they find out was committed by one of the Stynes. When Dean is attacked by Eldon Styne and another man, he is able to defeat them and brings Eldon back to the Bunker's dungeon. While Sam is out of the room, Eldon tells Dean that the Book is protected by magic and cannot be destroyed. When he confronts Sam about this, they get a panicked phone call from Charlie, who has been working on translating the Book of the Damned. She is trapped in a motel bathroom, and Eldon Styne, who had escaped from the Bunker by ripping his arm off, is attempting to break in. Dean, realizing the extent of Sam's secret campaign to save him, angrily criticizes him for lying, and getting Castiel and Charlie involved. They arrive at the motel to find Charlie's body, dead in the bathtub. This causes something inside of Dean to snap. In 10.22 The Prisoner, after telling Sam that he should have been the one to die instead of Charlie, he goes on a hunt for the Stynes. He goes to the Styne estate in Louisiana, where he single-handedly kills at least 15 people. Then he returns to the Bunker, where three more Stynes are stealing things and ransacking the place. He kills them all, including a teenager who pleaded with Dean not to kill him, trying to explain that he was nothing like the rest of his family. When Castiel arrives, a confrontation ensues, ending with Dean severely beating Castiel and nearly killing him. As Dean leaves, covered in blood, he warns Castiel to stay away from him.
Dean wakes up on a motel room floor in 10.23 Brother's Keeper, looking awful as he takes a swig of beer and tells himself, "I'm good." He tries to work a case, but ends up getting another hunter, Rudy, killed. When he goes back to his motel room, he sees the images of both Rudy and Castiel in the mirror. He then proceeds to thoroughly trash the motel room. He goes to an abandoned Mexican restaurant where he summons Death, who he asks to kill him. Death tells him that he can't - the Mark won't let Dean die. Although Death could remove the Mark, he won't, because the Mark acts as a lock which holds back the Darkness, an evil primal force that God himself banished. However, Death offers Dean an alternative - he will take Dean somewhere where he can't hurt anyone. Dean calls Sam and tells him it's time to say goodbye. Sam rushes to the restaurant, where he is shocked to see Death. Sam tries to reason with Dean, telling him that he doesn't need to die, but Dean says that it isn't his death that is the way out, it's Sam's. They fight, and Dean wins. Defeated, Sam finally agrees that Dean must be stopped, and is willing to die in order for that to happen. Death hands Dean his scythe, and Dean tells Sam to close his eyes. Before Sam does, though, he pulls out a few old photos of Dean and Mary, and Dean and Sam when they were kids. He tells Dean to let them be his guide when he finally finds his way back - to remember what it was like to to be good, to love, and to be loved. Sam closes his eyes, and Dean swings, but goes over Sam's head and kills Death instead. He helps Sam up, and as they prepare to leave, a lightning bolt strikes Dean's arm, removing the Mark. Just as they get outside, multiple lightning bolts hit the ground, and columns of black smoke emerge from the holes in the ground and start moving toward them at a breakneck pace. Sam and Dean try to drive away but reverse into a pothole. Trapped, they watch as The Darkness engulfs them.
In 11.01 Out of the Darkness, Into the Fire as the black, swirling cloud surrounds the Impala, Dean vanishes and reappears next to an unfamiliar woman - the Darkness. She thanks him for setting him free, and tells him that they will not harm each other. She reveals the Mark of Cain on her collarbone and informs him that they are bound, and they will always help each other. The next thing Dean knows, he is waking up in a deserted field, where Sam finds him. They head to the nearest town and find that there are dead bodies everywhere, and that there is something that appears to be infecting people, turning them into rabids. They meet up with Deputy Jenna Nickerson and head to the local hospital, where they find more rabids. They also find a man and his newborn daughter. Unfortunately, he has been infected, so he turns the baby over to Jenna. While they are in the hospital, the building becomes surrounded by rabids. In order to get Jenna and the baby out to safety, Sam uses himself as a decoy to draw the rabids away from the others. Just before Dean, Jenna, and the baby reach the building's exit, they run into the baby's father, who tells them, just before he dies, that the child's name is Amara. Dean takes Jenna and Amara to Jenna's grandmother's house.
In 11.02 Form and Void, Dean is heading back to the hospital, when he gets a worried phone call from Jenna, who tells him about the strange things that Amara appears to be able to do. He turns the car around and goes back to find Crowley there, posing as a Catholic priest. Dean and Crowley go outside to talk and return to find that Jenna has killed her grandmother. Dean goes to check on Amara, and realizes that she has the Mark of Cain on her collarbone, in the same spot that the Darkness had it. Dean begins to suspect that she is the Darkness. When Dean asks Jenna why she killed her grandmother, Crowley says that it's because she does not have a soul - Amara consumed it. While Dean and Crowley are distracted, Amara mysteriously disappears.
Sam and Dean start to look for information about the Darkness in 11.03 The Bad Seed, and for any leads on Amara's whereabouts. They also track down Rowena, in order to force her to remove the attack dog spell she had placed on Castiel. In 11.04 Baby, Dean learns about the visions Sam has been having, and that Sam thinks that they are from God. Sam also confesses to Dean that he had been infected by a rabid at the hospital, before he was able to find a cure.
While investigating what appears to be a ghost case in 11.05 Thin Lizzie, Dean interrogates Lizzie Borden superfan Len Fletcher. Through talking to him, Dean realizes that Amara had been in town, and had consumed Len's soul, along with those of several other people. Even more surprising to Dean is the news that Amara is no longer a baby - she is now a 12 year old girl. Sam and Dean continue to look for her in 11.06 Our Little World, trying to find more people who have had their souls removed in order to track her. After Len turns up dead, they figure out that demons are also going after the soulless people. They find another soulless person, Goldie, who has just been arrested, and set up a devil's trap in her jail cell. When a demon arrives, saying he must clean up the messes that were made by his boss's daughter, he tries to kill Goldie, but is stopped by the devil's trap. Through interrogating the demon, Dean realizes that Crowley has Amara. Sam is able to pinpoint a location that is likely to be where Crowley and Amara are, and after some debate, they decide to go there to kill her, despite not knowing how strong her powers are, her weaknesses, or if she can be killed. When they arrive, they are able to enter the building (an abandoned asylum) with ease, but run into several demons inside and get separated. Dean finds Amara's room and goes in to find her (now a teenager) waiting for him. Dean apologizes for what he is about to do, but before he can do anything, Crowley emerges from behind Dean and pins him against the wall. He makes the decision to kill Dean, but as he says this aloud, Amara hits Crowley over the head with a heavy object, and then uses her powers to force him to drop the knife and pin him to the wall. She threatens Crowley and demands that Dean be allowed safe passage out. Then she orders him to leave her room. When they are alone, Dean approaches Amara with Ruby's knife, but she scoffs at him. He can't take his eyes off of her and stares at her in a trancelike state as she reveals that she is God's sister. She tells him that he was the first thing she had seen of God's creation after her release, and that he represents that creation to her. She says that soon she will be ready to settle a score - the oldest score. Dean can't seem to move, until Sam bursts in, which seems to break the trance. As Amara throws Sam back into the hall, Dean charges at her, but she hurls him back. He falls to the floor, and watches her leave.
In 11.07 Plush, Sam tells Dean that the visions he has been having are about Hell, and Lucifer's Cage. He doesn't know if the visions are from God, and he doesn't know what to do about them. When he wonders aloud if it means that he has to go back there, Dean says no, and that it's not going to happen. Sam brings it up again in 11.08 Just My Imagination, but Dean refuses to go along with it, saying that there is always another way. Sam asks what that other way is, but Dean doesn't have an answer.
They continue to argue about it in 11.09 O Brother, Where Art Thou?, when Dean finally agrees to try and find out if it's even theoretically possible to safely talk to Lucifer without opening the cage. When they ask Crowley, he tells them that there might be a way. He captures Rowena and they convince her to help them. Sam stays with Rowena while Dean goes to investigate a massacre at a church. He tells Sam over the phone that he suspects that Amara was behind it. Sam gives Dean updates on the research to find a way to contact Lucifer, and Dean tells Sam not to do anything without him there. As Dean leaves the church, a strange sensation comes over him, and the sounds around him become muffled. He looks around but doesn't see anything, so he goes to a park. Sam calls him and he is about to answer, when the sensation happens again. This time, he turns around to find an adult Amara standing behind him. She touches him on the shoulder, and transports him to a remote wetland. There, she tells him that the things she has been doing has been to get God's attention. She says that she only has a bad reputation because God was afraid that she would make a better creation than his, and that was why she was exiled. Dean asks her what she wants, what her plan is. She replies that she was the beginning, and she will be the end. She will be all that there is. When Dean compares her with God, she says no - he is the Light, and she is the Dark. Dean then tries to stab her, but the knife's blade shatters instead. She tells Dean that she can't be resisted, and moves forward, her hands cradling his face. She opens her mouth as if to suck out his soul, and Dean just watches, once again in a trancelike state. After a few seconds, she either changes her mind, or is unable to consume his soul, and kisses him instead. After the kiss, he pulls back, confused and slightly alarmed. Amara tells him that is the future, that he is the one who set her free, and they are bonded. Dean protests, saying that it was an accident, but Amara insists that it was destiny. He had the Mark of Cain, and she is the original Mark. She tells him that they will be together, that they will become one. A horrified Dean tells her that that is not going to happen. Several angels arrive then, and tell Amara that she must surrender to Heaven. If she resists, every angel will smite her in a single, unified blow. Dean tries to dissuade them, due to the fact that a lot of people would die, but they do not care. Amara kills the angels, and as the skies darken with the impending wrath of the angels, she transports him back to the park, to safety.
In 11.10 The Devil in the Details, just after the angels’ smiting attempt, Dean drives back toward the spot where he and Amara had been, to check and see for himself if it had worked. However, when he gets close, he starts to feel ill and is forced to pull over and get out of the car, where he promptly vomits. Castiel finds him, and after a quick examination informs Dean that he has smiting sickness - he cannot get any closer. If he does, it will only get worse, and he will die. Castiel insists on going alone, as angels are not susceptible to smiting sickness. Dean goes back to the Bunker, but Sam isn’t there. Crowley calls him, and informs him that Sam is in Hell, with Lucifer. He tells Dean to go to a warehouse in Nebraska. Billie lets him inside, and then opens a door to Hell. There, he meets up with Crowley and Rowena. Dean and Crowley put a witchcatcher around her neck, forcing her to work on the spell to put Lucifer back in the cage. Not long after, Castiel arrives, with a message (“I AM COMING”) carved into his chest by Amara, who survived the smiting. While discussing this, they start to hear the sounds of Lucifer attacking Sam. Dean bolts for the cage, Castiel right behind him. When Lucifer sees them, he snaps his fingers, and they are instantly transported into the cage as well. Castiel lunges at Lucifer with an angel blade as Dean rushes to Sam’s side. The four of them fight until Rowena finally finishes the spell, and Lucifer vanishes in a burst of bright light.
Soon after, in 11.11 Into the Mystic, Dean goes back to the Bunker during a case to retrieve gold blades which are needed to kill a banshee. He is surprised to find Castiel there, going through all the files. Castiel tells Dean he is looking for a spell that can draw Amara out, adding that he had her in his sights and he should have killed her. Dean then admits that he has had two opportunities to try and kill her, but he couldn’t do it. Castiel tells him that he and Amara are connected because of the Mark, but Dean argues that it’s more than that. He admits to feeling a sort of attraction to her. He doesn’t know if he can resist it, and that scares him. Castiel promises Dean that they will figure it out. Later, after they finish the case, Dean mentions to Sam that he thinks there was something a little off about Castiel. Sam doesn’t think it’s anything too serious, but suggests they keep an eye on him.
In 11.13 Love Hurts they head to Ohio to work a case involving a curse that is transmitted by kissing. Once a person is cursed, they are killed by a creature called a qareen, which takes the shape of a person's deepest desire. Dean curses himself to distract the qareen from killing its other victim, and while he and Sam look for the creature’s heart (which is not located in its body), the qareen approaches Dean in the form of Amara. The qareen tells Dean to give in to the love he feels for Amara. She tries to kill him until Sam is finally successful in stabbing its heart. Later, Dean confesses to Sam that the qareen had appeared to him as Amara, and is surprised when Sam isn’t surprised. Sam tells him it isn’t his fault, he never had any choice. Dean then admits that although he wants to kill the Darkness, he can’t. Sam tells Dean that it’s okay.
While researching ways to kill Amara in 11.14 The Vessel, they come across what is known as the Hand of God. It is a piece of the original Ark of the Covenant, touched by God himself. They track it through history to a WWII submarine that went down in 1943, and convince Castiel to time travel with Dean to the submarine to retrieve it. Dean successfully gets on board, but Castiel is unable due to the angel warding on the hull. Dean gets the Hand of God, but right before he gets teleported out and back to 2016, the Hand of God is used by Delphine Seydoux. When Dean lands back in 2016, he finds out that Castiel has in fact been possessed by Lucifer. When Lucifer takes the Hand of God and realizes that its power has all been used up, he starts to punish them, stopped only by Sam, who uses an angel banishing sigil to blast him away. Dean vows to hunt Lucifer down and save Cas. They work a few more cases in [[11.15 Beyond the Mat] and 11.16 Safe House when they have no luck finding anything useful that will help them in their fight against Amara, or the search for Lucifer.
In 11.17 Red Meat, while hunting werewolves deep in the woods, Sam is shot in the torso. Along with two others, they try to make their way back to where the car is parked, miles away, but Sam’s injury is severe enough that he is slowing them down. They find an empty cabin, and Dean leaves Sam with the two hikers while he looks for sticks to make something to carry Sam back on. When he comes back in, he finds Sam on the floor, all signs indicating that he is dead. Devastated, Dean at first refuses to leave Sam’s side, but ultimately, the pleas of the hikers convince him to help get them to safety. He leaves, promising Sam he’ll be back. The trio find their way to the road, and Dean flags down a Sheriff. He tries to leave and go back to Sam, but the Sheriff won’t let him. Dean punches the sheriff in an attempt to escape, but is tased and brought to the hospital. There, he becomes desperate and decides to talk to a reaper. In order to do so, he downs a handful of barbiturates, overdosing. He collapses on the floor and starts to seize. Dean, in ghost form, watches as the doctors surround his body and attempt to save him. Billie the reaper arrives and refuses to make any deals with him. She tells him that Sam is not dead, but that Dean’s time is up. However, the doctor is able to bring Dean back to life. Soon after, to his great relief, Dean gets a phone call from Sam. Later, Sam asks Dean what he did when he thought he was dead, but Dean avoids answering, saying that he knew he wasn’t dead.
In 11.18 Hell's Angel, Crowley calls Dean and tells him that he’s found a Hand of God, and to meet him in St. Louis. Once there, Crowley tells that he possesses the Hand of Joshua, and will give it to them if they expel Lucifer from Castiel’s vessel, and return him to the cage. Dean and Sam tell Crowley they’ll need Rowena to do so, but Crowley tells them that Lucifer snapped her neck. They then argue about whether Lucifer should be dealt with before or after Amara, as he might be useful in defeating her. Crowley quickly gets tired of their arguing and stands firm that he will not give them the Horn of Joshua until Lucifer is back in the cage. Outside, they see the sky is full of lighting and swirling dark clouds. Dean apprehensively says that he thinks it’s Amara. Then, the words “BACK FROM THE DEAD FERGUS” appear on the wall, letting them know Rowena is still alive. They meet up with her in an abandoned church, where they summon Lucifer. When he arrives, they trap him in a ring of holy fire, then use a sigil to bring Castiel out. Dean tries to tell Castiel something, but before he can, Lucifer comes back. When some of the other sigils start failing, Crowley, as a last resort, goes inside Castiel’s vessel to try and talk to Castiel himself. However, it is unsuccessful - Castiel doesn’t want to expel Lucifer. The Holy Fire goes out, and Lucifer is able to get the Horn. He begins to torture Sam and Dean, until Amara comes in. Lucifer uses the Horn against her, but it doesn’t work. Amara is unharmed, and she disappears with him.
In 11.20 Don't Call Me Shurley Sam and Dean become trapped in a police station surrounded by a uncomfortably familiar mysterious fog, which starts to seep in through the building’s vents. Sam accidentally breathes it in and becomes infected. Seeing this, Dean refuses to go on without him, and willingly takes a deep breath of the fog as well. When trying to infect himself doesn’t work, Dean desperately and angrily yells out to God to stop it. Then, Dean notices something glowing in Sam’s pocket. He reaches inside and pulls out the samulet. Going outside, they see everyone who had died in the street walking around, bewildered and confused, but perfectly fine. They make their way down the street, unsure of what to expect. Then, they see him. They stop, stunned. Chuck turns around and comes over, saying that they should probably talk. In 11.21 All in the Family Dean refuses, saying that he isn’t going anywhere with him, he doesn’t even know if he is really Chuck. Chuck snaps his fingers and transports them all back to the bunker. Kevin Tran’s ghost appears from behind Chuck and tells them it’s alright, and to trust Chuck. Chuck sends Kevin’s ghost to Heaven. Dean and Sam watch, flabbergasted, as it finally becomes clear.
Sam is beyond excited to talk to God, who prefers to go by Chuck, but Dean is much more withdrawn, not understanding how Chuck could just have left humanity to deal with everything by itself when he was really needed. Chuck says that he needed to let people find their own way. Being over involved was not helping anyone. Later that night, in the bunker, Dean is on the computer looking for any leads on Amara, when he has a vision of her inside the bunker, telling him that she misses him and that she knows her brother has resurfaced and that he should tell him that Lucifer (and his vessel) aren’t doing so well. The next morning, Sam finds out about another town that experienced the mysterious fog, where thousands of people died, everyone except for one person. They go to the town, where they talk to the survivor, Donatello Redfield, and figure out that he is a prophet. Dean sees another vision of Amara, telling him that she needs to see him. They bring Donatello back to the bunker to see Chuck, then go off to meet Metatron at a bar, who tells them that Chuck has no intention of taking Amara down - he will sacrifice himself. Dean meets Chuck in a park and asks him why he’s giving up. Chuck plans to make a deal with Amara to have himself put in a cage as long as the world is unhurt. He tells Dean that if that doesn’t work, he and Sam will step up - it’s why he saved Dean - Dean is the firewall between the light and the darkness. Dean argues that it’s Chuck who must do it. Back in the Bunker, they agree to let Metatron in on their plan, as his knowledge may be useful. Dean meets up with Amara in a forest, and once again she asks him to join her. However, she quickly realizes that he has betrayed her - this meeting is a diversion to distract her while the others rescue Lucifer. She goes to try and stop them, leaving Dean unharmed.
In 11.22 We Happy Few Sam, Dean, Chuck, and Lucifer, decide to put Amara back in the cage, after talking about how outright killing her would disrupt the balance of darkness and light. To increase their power to do so, they decide to bring in Crowley, Rowena, and more angels. Crowley recruits demons, Lucifer recruits the angels, and Rowena recruits several other witches. They come up with a plan to attack her, weakening her enough so that Chuck can put her back in the cage. At the abandoned power plant where this is all to take place, Dean finds out that the plan involves Sam taking on the Mark of Cain, something he immediately objects to, but his protests are brushed aside. Rowena telepathically lets Amara know where they are, and when Amara arrives at the power plant, the attacks begin, from the witches, demons, angels, and Lucifer. She and Chuck argue, until she admits defeat, and requests that he kill her. However, when she realizes that he is about to imprison her instead of killing her, she fights back with renewed vigor. She rips Lucifer out of Castiel’s vessel and injures Chuck. She tells Dean and Sam that he is dying, then vanishes.
Castiel wakes up a few minutes later in 11.23 Alpha and Omega, much to Dean’s relief. Chuck also wakes up, and tells them that Amara was right, he is dying. Outside, they realize that the sun is dying as well. Back at the bunker, Chuck finally agrees to help kill Amara. He says that the darkness can be killed by light. A plan is devised to create a bomb using souls. Sam and Dean head to a haunted asylum to raid the souls of the ghosts there, and when they return, Billie the reaper appears and wants to know what they are doing. When they tell her, she offers to help them by letting them use the souls that are in the Veil. With Billie’s help, Rowena is able to build the bomb. Dean is chosen as the one to bring the bomb to Amara, as he is the one with a personal connection to her. However, Rowena tells him that he will not just be carrying the bomb - he will be the bomb. Resigned, Dean agrees. After he has said his goodbyes, Chuck transports him to Amara. There, Amara knows about the bomb - she knows what Dean is trying to do. Dean tells her that Chuck doesn’t actually want her dead, and to put aside their differences. Amara summons Chuck, they talk, and Amara heals him, which makes the sun shine again. Chuck and Amara are planning to go away together, but before they do so, Amara tells Dean she wants to to give Dean what he needs the most. Later, somewhere in a dark park, Dean hears a woman calling for help. As he rushes over, he sees who it is, and stares at her in shock. It is his mother, Mary Winchester.
The season 12 premiere 12.01 Keep Calm and Carry On begins immediately after the events in 11.23 Alpha and Omega, with Dean staring in disbelief at what appears to be his mother, Mary Winchester. Once he establishes she is really his mother, they sit on a park bench and talk until morning. Dean then takes her back to the Bunker where they discover blood on the floor and no sign of Sam or Castiel. Cas returns to the Bunker where Dean introduces him to Mary, and they begin the search for Sam. Cas tells Dean about the woman waiting for them in the bunker so Dean hacks traffic cams and finds the SUV that kidnapped Sam. They track it to the SUV's driver, and then to a vet who treated Sam for a gunshot wound, who gives them the phone number of the woman who kidnapped him - Lady Antonia Bevell. Dean calls her to let her know they are coming to rescue Sam. Toni sends Ms. Watt to meet them -- she crashes into the Impala and fights with Dean and Cas, almost beating them. Mary kills her with Cas' angel blade, then becomes upset over taking a life and her sons becoming hunters. Dean comforts her, saying he believes what he and Sam do has made the world a better place to live.
Dean is working with Castiel to search for Sam in 12.02 Mamma Mia, and struggles with the return of his mother Mary. She overhears his conversation with Cas, and Dean tells her he's glad she's back but feels she needs time to adjust. Mary worries that Sam won't be able to forgive her for her deal with Azazel. Cas calls with a possible location for Sam and texts Dean the address. Mary insists on coming along and Dean argues against it, but loses and Mary joins him. In the car, Mary tells Dean about her time as a hunter, how she was good at it but also realized that all hunters end up dead. Dean tells her about how she died, how it caused John to become obsessed with hunting and raise him and Sam in the life, and how Sam wanted out, but when John went missing, they realized they only had each other. They arrive at the house and join Cas, and while searching the grounds Dean comes across a sigil and disappears. He reappears inside the house where Toni catches him and shoves him into the basement with Sam and threatens to torture him so that Sam will give up information on the American hunters. Mary appears and threatens Toni with a gun, tossing handcuff keys to Dean who releases himself and Sam. Mary and Toni fight but are interrupted by Mick Davies, who apologizes for her behavior and states that the British Men of Letters want to work with them instead.
12.03 The Foundry begins with Mary finding a case in Minnesota where people are found dead after reporting hearing a baby crying. Sam expresses concern over Mary's desire to get back into hunting but Dean is all for a "family hunting trip". Mary struggles with her lack of knowledge about the technological methods the boys use and the aftereffects of the attack. While salting and burning what they think is the ghost's bones, Sam remains concerned about Mary but Dean still believes she's just "adjusting". They return to the room to find Mary gone and upon discovering she's returned to the house, they return to rescue her but she's been possessed by the actual ghost. The ghost tries to make her kill Dean but she resists it and releases him. Dean keeps the ghost occupied while Sam finds the bones and burns them, which releases Mary and the ghosts of all the children in the house. Back in the Bunker, Dean apologies for taking over her case, but becomes hurt and angry when Mary says she has to leave to have some time by herself.
In 12.04 American Nightmare Dean, still upset about Mary's departure, travels with Sam to Mason City, Iowa, to investigate a person who died while being flayed by an invisible force and displaying signs of stigmata. As they discuss the victim, Olivia, with the priest who witnessed her death, Sam notices Dean is very short with him. They wonder if perhaps it was caused by a rogue angel, so Dean calls Cas to discuss the case. After hanging up with Cas, Dean texts Mary to check in on her and asks if he should still call her Mom. Sam returns and Dean briefs him on Cas' news -- the gates of Heaven are still closed, so it can't be an angel, and he and Crowley have teamed up to hunt for Lucifer, who has possessed the "Master of Butt-rock" Vince Vincente. Dean teases Sam when he defends Vince. They head to the morgue to examine Olivia's body, where Dean is dismissive to the medical examiner, and when Sam calls him out for being cranky, Dean denies it. They question Olivia's former employee and replacement, Beth, who's also a Wiccan, which causes Dean to believe she is responsible, but Sam disagrees. A grocery delivery guy is killed in the same fashion, and Olivia's case files show a connection to the Petersons, a "real Old-Testament type" family. They question the family, and afterward, Sam once again questions Dean about Mary's departure and how he's dealing with it, which Dean again brushes off. Discussing the case, Sam believes the ghost of their dead daughter, Magda, is responsible. Dean disagrees, believing Beth is the killer and leaves to track her down, leaving Sam at the farm. Dean questions Beth and determines she was not responsible for Olivia's death. He receives a phone call from Sam who tells him Magda is still alive before he is attacked and the phone disconnects. Dean rushes back to the farm in time to save Sam, who was about to be poisoned by the Petersons. Afterward, Dean receives a text from Mary where she apologizes for not getting back to him sooner and says that she will always be "Mom".
12.05 The One You've Been Waiting For finds Sam and Dean in Columbus, Ohio, to investigate a case of two people falling victim to apparent spontaneous combustion. While investigating the shop where the deaths occurred, Dean finds a hidden room full of Nazi paraphernalia. Meanwhile, Sam hacks into the shop's computer and discovers the victims were meeting regarding an antique pocket watch, and that the store owner had a whole business catering to "Nazi nutjobs". He finds out that the pocket watch used to belong to Hitler's inner circle, and the boys presume the Thule are involved. They call Aaron Bass to see what the Judah Initiative knows about any local Thule activity. Aaron tells them they've all come back to Germany regarding a mission called "Das Blut" (The Blood). They ask him about the pocket watch but he doesn't know anything. When news of another spontaneous combustion death pops up, they head to the crime scene -- the apartment of a young woman who managed to escape. They leave the apartment in time to see a cop car driving off, with a woman in the back screaming for help. The follow the cop car to a parking garage where they rescue the woman, Ellie, and tie up her captor for questioning. He is Christoph Nauhaus, the son of Commandant Nauhaus, a ranking officer in the Thule High Command. He explains how the soul of Hitler is trapped in the pocket watch "like a Horcrux", and the Thule plan to use it to resurrect Hitler, along with Ellie's blood, because she happens to be a direct descendant of Hitler -- "Das Blut". The boys convince Ellie to help them set a trap for the Thule, but while fighting Thule thugs, Ellie jumps out of the window and is captured by Nauhaus and Christoph. The boys head to a diner to research a tracking spell to find her, when Christoph arrives, having overheard their location while escaping execution. Christoph leads them to the location where the resurrection ritual is taking place. Handcuffing Christoph in the Impala, they plan their attack. Dean wants to use the Grenade Launcher but Sam refuses since they need to be stealthy; he promises Dean he'll be able to use it someday. The boys launch their attack but are captured and brought to the room where Hitler's soul has already been transferred into Nauhaus. Ellie is lying on a gurney, weak from blood loss. she staggers from the gurney, grabbing a gun and shooting one of Nauhaus/Hitler's flunkies. Dean uses the distraction to grab a gun and shoots the other flunkies, then shoots Hitler. They walk back to the Impala with Ellie, and Dean exclaims multiple times "I killed Hitler!". They release Christoph and take Ellie back to her apartment. Dean suggests heading for pie since he deserves it after... killing Hitler!
In 12.06 Celebrating the Life of Asa Fox, Sam and Dean are on their way home from a hunt in Brookings, Idaho, and stop by Jody's house in Sioux Falls for a visit. The girls are out of town at a Radiohead concert but Jody invites them in for pizza. Dean, of course, informs Jody that he killed Hitler. While eating, Jody receives a phone call which leaves her obviously upset. The boys ask her what's wrong, and she tells them a friend of hers died -- Asa Fox -- and they're having a wake tonight with a hunter's funeral the next day. The boys insist on going with her to support her, and also because they've never been to a hunter's gathering before. She tells them they'll have to get cleaned up before they spend five hours in a car together, as the gathering is in Manitoba, Canada. They arrive and meet Asa's mom Lorraine Fox and several hunters, amongst them Elvis Katz and Bucky Sims. Dean wanders into Asa's office where Sam finds him. Sam talks about how people tell stories about them, and when Dean mentions they're "kinda legendary", Sam says that Asa was too. Dean states that's how it usually goes for hunters, Sam questions it and Dean explains that they're not in the "live till you're 90, die in your sleep" business. Later, most of the hunters have left and only a handful remain. Bucky begins telling a story about Asa and reveals Jody and Asa had a relationship, when suddenly Mary arrives. Dean asks where she's been and she tells him she's been using John's journal to catch up on what she's missed, and that it was something she had to do on her own. Dean is annoyed, believing she was ignoring his texts and leaves to get some air. Outside, Billie appears, saying she's just finished reaping a soul from inside the house. Dean runs to the door to find it locked. Billie says the house is on lockdown, so he can't get in and no one inside can hear him. Dean makes a deal with Billie to get him inside, where he finds out Elvis has been possessed by a demon. They fight, but when Dean starts to exorcise it, the demon snaps Elvis's neck and leaves his body. The rest of the group joins him and works to trap the demon, but Dean discovers it has possessed Jody and stops Mary from killing her. The demon gets Bucky to admit to killing Asa as the group, taking turns with the Latin, manages to exorcise it. Afterward, Bucky explains he and Asa were hunting the demon, Jael. Asa wanted to chase him but didn't have his angel blade, and Bucky when wanted to go back to get it, they fought and Bucky pushed him, accidentally killing him. Dean accused him of stringing Asa up on the tree to try and frame Jael for his death, which Bucky admitted. The next morning at Asa's hunters funeral, Billie appears to collect on the deal: Mary. She tells Mary she knows she's all alone - Which Dean argues - and offers to take her back to Heaven. Mary turns down the "offer", but when Sam asks if she's coming home, she tells them she needs just a little more time, and Dean offers to buy her breakfast with all the bacon.
12.07 Rock Never Dies begins with Dean sitting in the Bunker's Library playing Words with Friends with Mary. Sam accuses him of taking advantage of her lack of technical skills until Mary plays a high point word against him. Sam asks how she's doing and Dean says she's "dealing," when Cas calls. Dean asks if he's still working with Crowley - "Unfortunately". Sam asks if there's any news on Lucifer, and Cas tells them to check the news which is flooded with news about Vince Vincente getting his band "Ladyheart" back together. Dean wonders how Vince can be Lucifer since Rowena damaged him. Crowley explains it is unlikely a Ladyheart revival is happening without outside influence and tells them to meet them in LA. As the boys drive to LA, Dean is complaining to Sam about having to go, recalling the last time they were there hunting a vengeful spirit (from 2.18 Hollywood Babylon). He realizes Sam has headphones in and asks him what he's listening to. Sam says it's a history podcast and protests when Dean suggests letting him listen; Dean pulls out the headphones to discover Sam is listening to Ladyheart and teases him about it. Sam protests that it's actually research and makes Dean listen to it. They meet Cas and Crowley at Vince's hotel. Crowley is certain Lucifer is still possessing Vince and, having acquired the key, suggests searching his room. They discover Vince/Lucifer has been reading rock star biographies as if he's researching how to become famous, and Cas finds a bloody tooth. They hear a woman, Roseleen Greenfield, has been admitted to the hospital after carving "Vince Vincente" onto her chest and they question her, asking if Vince forced her to do it. She claims she did it to make him happy and tries to leave to get to a secret Ladyheart show. To discover where this secret show is, Sam and Dean arrange to meet with Vince's PR person but she refuses to tell them where it is. Tommy calls Cas after Lucifer kills Russell Lemmons and lets them know where the show is. Sam and Dean clear the concert-goers from the venue and fight Lucifer, draining him and causing his vessel to disintegrate. Lucifer leaves Vince, killing him. Outside the club, Dean thanks Cas and Crowley for fighting Lucifer before the show, and while they didn't catch Lucifer they saved the crowd so he's calling it a win. Sam disagrees, saying everyone who died that night, including Vince, is on them because they let Lucifer out and that he threatened to possess someone even bigger. Dean assures Sam they will stop Lucifer because that's what they do.
Sam and Dean run into Castiel and Crowley posing as FBI agents while investigating the death of Wallace Parker in 12.08 LOTUS. Parker, a powerful CEO, was obviously Lucifer's latest vessel and wasn't able to hold him, and it's obvious that Lucifer is choosing powerful people to possess. Back at the Bunker, Sam is researching people in power looking for Lucifer's next victim. He notices a picture of the Archbishop of St. Louis with Parker. In the picture he is wearing a large cross, but in a new picture the cross is missing, and Sam discovers that all of his future public appearances have been canceled. They head to the Archdiocese to investigate, where they find everyone has been killed except for one priest who tells them they realized the Archbishop was possessed and tried to exorcise him, which failed. Among the dead is the Archbishop, meaning Lucifer has moved on. Back at the Bunker, Dean powers down the wards to allow Crowley to report big news on Lucifer. Crowley had received intel that Lucifer's latest vessel is President Jefferson Rooney. They strategize how to get close enough to the President to exorcise Lucifer from him. Cas is suddenly overcome by a burst of activity on angel radio, saying a Nephilim has come into being but with much more power used to create it than from a typical angel - Lucifer. Dean comments that he didn't know Lucifer was dating. On their way to Indianapolis to intercept the President at a fundraiser, Sam, Dean, and Cas are stopped by Rick Sanchez and the Secret Service, who try to take them into custody. From behind, a black sedan stops and a man exits with a grenade launcher, destroying the government agent's vehicle and knocking them unconscious. The man tells Cas to wipe their memories and introduces himself - Arthur Ketch, British Men of Letters. Dean, of course, doesn't trust him, so Ketch shows them the high-tech weapons he has, including the Hyperbolic Pulse Generator. Dean borrows the Pulse Generator, saying the BMoL have to trust them first. Crowley discovers Rooney/Lucifer's secret girlfriend - Kelly Kline - and teleports her to a hotel room where they convince her that Lucifer has possessed the President and have her call him to arrange a meeting. Rooney/Lucifer arrives and Sam uses the Pulse Generator to pull Lucifer from the President, while Rowena casts a spell to send him back to the Cage. Rooney collapses and is unharmed but while Sam and Dean attempt to revive him, they are taken into custody by Sanchez and the Secret Service for attempting to assassinate the President.
12.09 First Blood opens with Sam and Dean being taken to a "black site" for questioning and imprisonment, and they are placed into separate cells with no windows. When questioned, they say nothing so they are left in isolation, the only contact being meals served through a slot in the door. Dean finds a loose screw in his cot and uses it to mark the passing days. After about two months, the guard places a meal in Sam's door but he doesn't come to get it. Looking through the slot, he sees Sam unconscious on his cot. The guard opens the door and discovers Sam is dead. They open Dean's cell and finds him dead as well. In the morgue, Dean suddenly sits up, gasping and coughing. Sam is already up and asks Dean if he's good - "I've been better, but I've been worse." They hear footsteps approaching; Dean gets behind the door and grabs the coroner as he enters. Sam asks him where they are but the coroner doesn't know - he's always blindfolded when he's brought in. Escaping outside, Dean uses the coroner's cell phone to call Castiel. Sam finds a map in a vehicle parked outside and discovers they're in the Rocky Mountain National Park in Colorado, and they ask Cas to pick them up. Ditching the cell phone, they head off into the forest. Rick Sanchez discovers they are missing and gathers troops to follow them into the forest. The troops catch up to Sam and Dean, but they manage to capture one of them, take his rifle, and use his radio to threaten Sanchez - "We're not trapped out here with you, you're trapped out here with us." As darkness descends, Sam and Dean find an abandoned cabin. In the cabin, Dean finds a bear trap, which he places in front of the cabin and covers with leaves. Sam lights a lamp, which draws Sanchez and the troops to the cabin. Sam, hiding under the floorboards, takes down several while outside, Dean takes down a few more. Then Sanchez steps in the bear trap where Dean captures him and Sam joins him. They explain that the President was possessed by Lucifer and they saved his life. Sam and Dean leave Sanchez in the trap, warning him not to come looking for them. They find the freeway, where Mary and Cas are waiting for them, explaining they were able to find them with assistance of the BMoL. They leave in Mary's car, which suddenly loses power and stops. Billie is there, and Dean reveals that in order to escape the black site, Dean made a deal with Billie - they would get to die and come back one more time, but in exchange, at midnight a Winchester must die. Mary volunteers and draws her gun to shoot herself when Cas kills Billie with an angel blade.
In 12.10 Lily Sunder Has Some Regrets, Sam and Dean are in the Bunker discussing the search for Kelly Kline and Mary's return to hunting. Sam asks Dean if he's talked to Castiel but Dean is still angry with him for killing Billie, not because Cas cares about them but because of the consequences of killing her. Cas, overhearing, says he will deal with any consequences should they occur, but for now he has to leave to assist an angel friend of his who called for help. Sam offers to go with him and Dean agrees, wishing to prevent Cas from "doing anything else stupid". In the Impala Cas and Dean are not talking but Sam finally gets Cas to talk about his friend, Benjamin. They arrive at the location and find Benjamin has been killed. Dean finds an angel blade but Cas says it's not Benjamin's which seems to indicate another angel attacked him. Cas hears a call over angel radio from another angel he served with, Ishim. They meet at a diner; Cas goes in alone where he also finds Mirabel there with Ishim. Dean gets tired of waiting outside for Cas so he joins him and the other angels in the diner, Sam following. Ishim sends Mirabel outside to look for any others. In the diner, Sam and Dean get annoyed with Ishim taunting Cas. Cas stops them from arguing as it's more important to figure out what happened to Benjamin. Ishim agrees but suggests going to his safehouse and goes outside to get Mirabel. Cas, Dean, and Sam follow Ishim out just in time to find Mirabel dead and Ishim fighting with Lily Sunder. Cas rushes to help Ishim and recognizes Lily. Dean and Sam draw their guns on her but she blinds them with a spell and gets away. At Ishim's safe house, Cas explains to Sam and Dean how they know Lily - a long time ago, they were sent to kill an angel and a Nephilim, who was Lily's daughter. She is using some sort of magic to stay alive and exact her revenge. Sam and Dean agree to talk to her since she doesn't want to hurt them. They find her, and Lily explains she wants revenge on Ishim because he was obsessed with her, so when she didn't return his affections, he killed her human daughter, claiming she was a Nephilim. Dean tries to call Cas to confirm but he's not answering, so he returns to the safehouse while Sam stays with Lily. Back at the safehouse, Cas is greatly weakened by healing Ishim's wound from his fight with Lily. Dean finds him and tells him Lily's daughter was human and that he thinks Ishim is playing them. Ishim returns and when Cas confronts him, Ishim tries to turn Cas against Dean. Dean attacks Ishim, who throws him against the wall, then begins to fight with Cas. Dean draws an angel banishing sigil and threatens to use it, but Ishim tells him that using it would probably kill Cas in his weakened state so Dean stops. Lily and Sam arrive; Sam rushes to Dean and Lily fights Ishim, finally using her power to hold him long enough for Cas to kill him. Cas apologizes to Lily and tells her that if she decides she can't forgive him, he'll be waiting. Back at the Bunker, Dean tells Cas he's not weak for being their friend and explains that he's not mad about him killing Billie, he's just worried about the consequences. Cas acknowledges his concern but still does not regret doing it even if it costs him his life. Dean then asks him what he's going to do about Kelly and the Nephilim she's carrying. Cas says that while he knows a Nephilim is dangerous, he's not sure he can kill her. Dean asks what they're going to do, and Cas suggests they drink and hope they can find a better way.
12.11 Regarding Dean finds Dean chasing a man through a forest at night. Catching up to him, he confronts the man but is suddenly blasted by purple light and knocked out. He comes to the next morning in a park, having no idea where he is or how he got there. His phone is broken so he borrows one from a passing jogger and calls Sam, who asks where he's been and where he's at. Dean notices a waffle house and tells Sam to meet him there. Sam arrives at the restaurant and asks him what happened but Dean has no recollection of the previous night and assumes he blacked out. Sam, upon finding out Dean's phone is broken, says he'll text Castiel to let him know to contact him instead of Dean in case he gets a lead on Kelly Kline. Dean does not recognize Kelly's name until Sam reminds him she's carrying Lucifer's baby. When Dean tries to get Sam to have some waffles, he tells Dean they have a case to work which he also doesn't recall. As they're leaving, a woman walks up to Dean, obviously recognizing him but he does not remember her, which earns him a slap on the face. In the morgue, they review the autopsy report and discover one of the items removed from the victim is a hex bag, indicating a witch was involved. Returning to the Impala, Dean first forgets which key to use, then forgets to put it in reverse, and even briefly forgets his name. Back at the hotel, Dean claims to be okay but Sam wonders if he was hexed and starts quizzing him about the names of items in the room, which Dean falters on. Sam calls Rowena, who upon hearing about Dean's failing memory believes he may have been hit with a memory curse, and the cure requires killing the witch who cast it. Sam and Dean begin to retrace Dean's steps from the previous night in order to find the witch, which leads them to a glyph on a tree and the dead body of the man Dean was chasing the night before. Sam takes a picture of the body and the glyph and they return to the hotel room. Rowena arrives and recognizes the witch and the glyph. While Sam leaves to confront the witches and retrieve the spell to cure him, and Rowena prepares to cast the spell, Dean looks in the bathroom mirror and tries to recite his and his family's names, but soon forgets even that. When Sam is captured by the witches, Rowena and a now completely amnesiac Dean leave to rescue him. Dean wakes up alone in the car where Rowena has left notes directing him to grab the gun and witch-killing bullets. He enters the house and uses them to kill the witches. Using the witch's grimoire, Rowena reverses the memory spell and Dean's memory returns.
In the style of Quentin Tarantino's "Reservoir Dogs", 12.12 Stuck in the Middle (With You) begins with Dean, Sam, Mary, and Castiel in a diner with another hunter Wally, who has asked for help taking down a demon. During the attack, they discover the demon is more powerful than they were led to believe and has two other demons with him. The demon stabs Cas with a spear while Wally is killed by one of the other demons, and Dean kills a third that was threatening Sam. They call Mary and head to a barn where she has taken a now gravely-injured Cas. When they arrive, she tells them the demon had yellow eyes. Dean goes to Cas to ask him what happened, and Cas tells him about the spear and that he believes it may have been poisoned. Suddenly, Crowley appears, telling them they're all going to die because they have taken on not just a demon but a Prince of Hell, Ramiel, and that Cas was stabbed by the Lance of Michael which kills angels slow and painful - and there is no cure. Dean tells Crowley to shut up and help them or leave, and Crowley disappears. Dean asks Cas how he's doing, and Cas pulls aside his shirt, showing the rot from the Lance's wound has spread. He tells them they should go and when Dean protests, Cas tells them they are his family and he loves them, and begs them to not make him spend his last moments watching them die. Dean refuses, saying they don't leave family behind and that they'll stay and fight. They prepare a trap made out of holy oil. When Ramiel enters the barn, they light the holy oil and demand a cure for Cas, but he says there is no cure. He then accuses them of stealing from him, which Dean denies. Ramiel uses the Lance to blow out the holy fire and fights Sam and Dean. In the fight, Sam takes the Lance from Ramiel and kills him with it. As Cas' condition deteriorates, Crowley appears, grabs the Lance and breaks it in half, releasing the magic and curing Cas. He wonders what Ramiel meant by his accusation, but Dean dismisses it. Picking up the pieces of the Lance, he says "Let's go home."
In 12.13 Family Feud, Dean is on the phone with Castiel, who reports no leads in finding Kelly Kline. Sam has found another case involving the murder of a teacher at a Des Moines museum and Dean calls Mary to see if she wants in on it. Mary begs off, saying she's in a hotel in Newark recovering from the last case with Ramiel. On the way to Des Moines, Sam tells Dean of another teacher murdered in Andover, Massachusetts, under similar circumstances to the one in Des Moines, and that it's too bad Mary didn't want to join. Dean feels there's something off about her but Sam disagrees. In Des Moines, they talk to the museum curator who explains there has been yet another murder. Dean asks if there have been any new exhibits and she takes them to the lab where a new exhibit has been uncrated. Dean checks the EMF meter, which is off the charts, which leads them to believe it's a ghost. One of the exhibits in the lab are artifacts from a sunken ship called The Star, which Dean remembers was the ship Gavin MacLeod was supposed to die on. Dean calls Crowley to ask if he knows where Gavin is, but Crowley demands they find Kelly Kline first. They turn to Rowena asking for her help, telling her Gavin is her grandson. They pick up Gavin at the bus terminal and ask him for information on The Star, introduce him to Rowena, and then take him to the museum lab. Gavin looks through the list of artifacts and discovers a locket belonging to his fiance Fiona Duncan is among the items, and they determine she must be the ghost, tethered to the locket - but when they look for it, the locket is missing. They talk to the curator, who tells them another school group which had recently visited the lab. Sam, Dean, and Gavin head to the school in time to stop another teacher's murder, then have Gavin summon Fiona's ghost. After talking to her, Gavin tells Sam and Dean that she boarded the boat looking for him, where she was abused, and their teacher who was also on the boat said she deserved it, hence her vendetta against teachers. They determine the only way to stop her is to send Gavin back to his time to protect Fiona and prevent her from becoming a vengeful spirit, which Gavin agrees to do. Back in the Bunker, they use Henry Winchester's time travel spell to send Gavin back to his time. Checking the news, all of the teachers who were previously murdered are alive. Mary returns and tells the boys she's been working with the British Men of Letters.
In the Season 14 Premiere 14.01 Stranger in a Strange Land, Michael (Apocalypse World) continues to possess Dean as he travels the world looking for someone/something worth saving for his "better world". Dean reappears at the end of 14.02 Gods and Monsters in the dilapidated church where Michael performed his experiments after Sam, Bobby (Apocalypse World), and Mary take down a pack of Michael's augmented werewolves, and has no idea why Michael left.
When Dean returns to the Bunker in 14.03 The Scar, after he teases Sam about his beard, Sam asks if he's okay. Dean says he's good, doesn't know why Michael left, and as for his memory, he can't remember anything that happened while Michael possessed him, that it was "just a blink", and he's just really happy to be home... Then he sees the Map room has been inundated by the AU hunters. A hunter calls Sam "Chief" and Dean is about to tease him about that when Jack and Cas enter, overjoyed to see him. Dean excuses himself to clean up and returns to his room. Angrily whipping off the clothes Michael dressed him in, he turns to a mirror and notices a scar on his upper arm. After showing the scar to Sam and Cas, he asks Cas to look into his memories to see if they can determine what happened. Cas touches his head and sees memories of Michael's questioning and experiments, but when he touches the scar itself, he sees Michael on the ground being stabbed by a double-pronged spear wielded by an unknown hooded figure - the same person and spear that killed Kaia in the Bad Place. They call Jody to ask if there had been any disturbances at the rift in the boatyard but she hasn't seen anything. However, when Dean describes the scar, Jody knows what they are talking about as she has several beheaded bodies with a similar scar in the morgue. Sam and Dean load up and head to Sioux Falls to investigate.
When they arrive, Jody welcomes Dean back and compliments Sam's beard, much to Dean's chagrin. She points out the crime scene on a map and they head out. They discover a clearing with vampire heads stuck on pikes, probably belonging to the bodies in Jody's morgue, and the clearing looks just like the one Dean saw when Cas touched the scar. Suddenly they are attacked by the hooded figure with the spear. During the fight, the hood comes off, revealing someone that looks just like Kaia, who then turns and runs away with the spear. Dean finds her tracks but Sam stops him and tells him he believes the vamps were hunting her instead and were sent by Michael -- Jody had tested the bodies and they didn't react to dead man's blood. Dean does not care and continues to follow the tracks, which leads them to a cabin. Dean sees Dark Kaia and knocks her out, but the spear is not in sight. He ties her to a chair and they begin questioning her. She explains her and Kaia were connected and her death was an accident -- she meant to kill Claire. They ask her why she's here; she looks at Dean and says "because of him". Dean tells her he's not Michael anymore which she acknowledges, saying he's much weaker. Dean tells her she's still scared but she says she's not scared of him, she's scared of Michael's vampires which are hunting her. Jody wants to take her to the station for safety but Dean wants to "break her" so she will tell him where the spear is.
He kicks Kaia's chair against the wall and demands answers. Dark Kaia refuses and accuses him of being no different from Michael -- using threats and violence to get what he wants. She reminds him of the incident from 13.09 The Bad Place where Dean forced her into the Impala at gunpoint. She tells Dean his anger and impatience come from fear of Michael and tells them about her confrontation with Michael. Michael tried to take the spear from her, knowing it was the one thing that could hurt him, and she stabbed him with it. Michael's vampires arrive and burst into the cabin to take Kaia. Sam, Jody, and Dean try to fight the vampires but they are too strong. Dean shoots the leg out from under Kaia's chair to free her; she runs to get the spear and kills the vampires before disappearing again, spear in hand. In the Impala on the way back to the Bunker, Dean admits to Sam that his time with Michael was not a "blink" and he doesn't remember anything Michael did with his meatsuit because he was drowning, fighting for air the whole time and trying to escape but he was not strong enough. He blames himself for everything Michael has done because he said "Yes".
In a return to the MOTW format, 14.04 Mint Condition opens with Dean in his room watching 'All Saint's Day' and avoiding the mass of AU hunters in the Bunker. Sam comes to check on him and to tell him of a new case - a comic book store employee beaten up by a Panthro action figure. They head to the store, where Dean nerds out over a life-sized talking 'David Yeager' (Hatchet Man) figure. Posing as insurance agents, they question the clerk Samantha Juarez regarding Stuart Blake, the guy who was attacked by the action figure, and she directs them to Stuart's mom's house where he lives in the basement. They question Stuart about the attack and he claims he made it all up, then kicks them out when they attempt to question him further. Stuart's ex-girlfriend is Wiccan so they figure she might have cursed him. While waiting in the Impala for Stuart and his mom to leave so they can check the house for hex bags, Dean asks Sam why he doesn't like Halloween, but before he can answer, Stuart's mom leaves and Sam comments that Stuart changed his story because of all the brutal comments on the video. Suddenly Stuart emerges from the house screaming for help and bleeding from multiple cuts. Dean runs inside to investigate and is attacked by a floating chainsaw which barely misses him, embedding in the wall next to his head.
Stuart is in the hospital, his mom at his bedside talking to the boys and thanking them for saving his life. She says she needs to go home to get his favorite pillow but they convince her to stay until he wakes up. They leave the room to discuss the case in the hall, where Dean reveals that he didn't find any hex bags but the EMF was going crazy, so it must be a ghost. Sam suggests Dean stay to keep Stuart's mom from leaving so he can check the house. Stuart's friend Dirk Winchell arrives to check on Stuart, and he and Dean begin to bond over their love of the 'All Saint's Day' franchise of horror movies. Dean receives a call from Sam; he's calling from the comic book shop where he and Samantha were just attacked by the Hatchet Man figure which has been possessed by the ghost of Jordan MacNeel, the recently deceased owner of the shop. Sam tells his brother that the possessed figure is on his way to the hospital to finish off Stuart. Dean draws a salt circle around Stuart's bed while giving Dirk "the talk", explaining that Jordan is coming to kill Stuart. He tells Dirk to get inside, while he heads out to find Jordan/Hatchet Man. In Stuart's room, the lights begin to flicker and drawers open and shut, causing Dirk to panic and run. Dean finds an ax in a fire box (he starts to break the glass and then realizes he can just open the door to take it). Dirk rounds the corner to find Stuart's mom screaming as she's confronted by the Hatchet Man figure, and he tells Jordan/Hatchet Man that he knows he's there to kill Stuart but he'll have to go through him first. Jordan/Hatchet Man starts coming for him and Dirk runs. He ends up in the morgue and meets Dean, when Jordan/Hatchet Man rises from one of the morgue gurneys. Dean approaches him with the ax and tries to talk him out of attacking, but he pushes the button -- "Time to slice and dice" -- and attacks Dean, who loses his ax in the fight. Just as Jordan is about to strike him with the ax, Dirk stabs Jordan with a knife. Jordan attacks Dirk, and Dean tries to attack Jordan but is captured, and Jordan starts to strangle him. Just then, Sam and Samantha burst in the door telling Dean to get the shop keys -- they belonged to Jordan and it's how he's moving around. Dean fishes them out of Hatchet Man's pocket and tosses them to Sam, who places them in a bowl and sets them on fire, burning Jordan's ghost and saving Dean.
On the drive back, Dean thanks Sam for finding the case and getting him out of his post-Michael funk. Sam tells him he needs to stop hiding in his room, that the things Michael did are not on him. Dean agrees to help out more. He asks Sam again why he hates Halloween and Sam finally tells him about an incident at a Halloween party when he was a kid. Dean tells him he needs to get over it and that next year they're getting matching Halloween costumes ("Rocky and Bullwinkle", "Shaggy and Scooby").
14.05 Nightmare Logic finds Sam and Dean heading to Claremore, Oklahoma, after Maggie misses a check-in while on a hunt, and her body-cam shows she was attacked by a ghoul. She was following a lead from an online post where some kids were studying and were attacked by what they called a "walker". They enter the crypt where Maggie was attacked but find no blood, meaning she is probably still alive. A gardener finds them in the crypt, and Sam tells him they're from the Historic Preservation Society and asks to speak to the owner. The gardener takes them to the main house where they talk to Neil who is excited over the prospect of the property being declared a historical site but wonders how many people it takes, as their colleagues have already arrived -- Mary and Bobby (Apocalypse World). Mary takes Sam aside to talk, while Dean and Bobby question Neil, who tells them he's not the owner and escorts them to Mr. Rawlings, who is unconscious and bedridden, and also looks like the ghoul who appeared in Maggie's video. Sasha Rawlings, the daughter, enters the room and the boys question her about her father, but she really doesn't know much because she just came down to take care of his affairs. They start to ask more questions but she asks them to leave. They meet Bobby and Mary by the Impala where Bobby briefs them on his investigation into the elder Rawlings: he's not a ghoul, and the standard tests ruled out shapeshifter and demon. Bobby then argues with Sam over having sent Maggie on this case by herself before she's ready and says he's not a real leader. Mary stands up for Sam and suggests they split up to look for Maggie. Dean and Bobby split off, and Bobby asks Dean if he thinks he was too hard on Sam. Dean tells him Sam is doing the best he can and working his tail off. They find an old shed and Dean goes in to investigate and finds a body. He turns to look for Bobby, who has disappeared, and is attacked by the "ghoul" who turns into a cloud of dust when Dean stabs it. Bobby reappears and asks him what happened.
Dean returns to the house to find Mary and Sam talking to Sasha, who was attacked by what appeared to be a vampire while investigating noises coming from the attic. Dean tells them he found a dead guy in the shed, and Sam shows him a burned ID card -- he and Mary had found a pile of ID cards in a pile in the woods, partially burned. The ID picture matches the guy Dean found in the shed; something is killing hunters. Mary, alarmed, asks where Bobby is and Dean tells her he went to get something from the truck. She rushes outside to find him. Sam wonders if the dad is like Fred Jones and is creating the apparitions, but Sasha says her dad has never shown any psychic abilities. Sam goes to investigate the attic while Dean stays with Neil and Sasha. Dean and Sasha talk about her troubles with her dad; she blames him for her mother's suicide. Dean counsels her to "let it go", that he tries to do the same every day. They walk to the room where Neil is attending to Mr. Rawlings. Dean notices bags of blood attached to him and asks Neil if Mr. Rawlings is getting a transfusion. Neil stammers and says his iron is low. Dean, suspicious, asks Sasha to make him a sandwich as a ruse to get her to leave the room, and Dean draws a gun on Neil, realizing he's a djinn. Dean asks him why he's killing hunters and Neil says it's because he asked him to; he thinks Dean is Michael (Apocalypse World) and was testing him. Michael made him a deal: kill hunters in exchange for upgraded powers. When Neil realizes Dean is not Michael, he attacks Dean and attempts to read his mind, but sees something that distracts him enough for Dean to escape and hit him with a metal bookend. Before Dean knocks him out, Neil reveals Michael has laid many traps for him and his family. Dean empties a clip into him. Later, Dean removes the IVs from Mr. Rawlings and tells Sasha he'll recover as soon as the djinn's poison leaves his system.
Back at the Bunker, Maggie is welcomed back and Dean tells Sam he was the one that did this, that he saved her and brought her home.
Later, Sam and Dean make calls to all the hunters they know to warn them about Michael's traps and super-charged monsters. Sam reiterates to Dean that none of this is his fault, that Michael used him and they will find him and kill him.
In 14.06 Optimism, Dean finds Jack in the kitchen adding a ton of sugar to his coffee. Dean comments on his sweet tooth and Jack explains that since he lost his Grace, everything tastes different. Dean asks him where Sam is and Jack says he and Charlie Bradbury (Apocalypse World) went on a case while Dean was on a run to Bobby and Mary's place. Dean remarks that they just left Jack at the Bunker all alone, and Jack explains that Sam wanted someone there when Dean got back. Sam is, of course, worried about Dean, who is not surprised. Jack tells him that no one blames him for what happened with Michael but Dean still blames himself. Jack still has a cough and when Dean comments on it, Jack says maybe he's allergic to sitting around doing nothing. Dean asks him what he wants to do, and Jack says he wants to hunt. He's been on hunts with Castiel. Dean informs him that while Cas says he's doing well, Cas is an insurance policy on those cases and Sam is just trying to keep him safe. He says Sam's a smart guy (cut to Sam in the car with Charlie using a fidget spinner incorrectly and giggling). Jack shows Dean a possible case in McCook, Nebraska, where Winston Mathers was found dead with human bite marks present, and others have gone missing as well. Dean says Sam isn't going to like Jack going on a hunt, but Jack counters that Sam isn't there and that since all hunters have to have partners, Jack could be Dean's on this hunt. Jack says he feels a desperate need to do something since he had the opportunity to kill Michael and didn't. Dean reluctantly agrees and calls Sam to let him know.
Their first stop in McCook is Winston's favorite restaurant (as stated in his obituary), Dick's Red Rooster Diner. There they question the waitress, who gives them attitude until Dean slips her some money, after which she reveals that he was courting Harper Sayles. They interview several other people about Harper, who all state how sweet and popular she is but also how much bad luck she's had in both love and life. Dean congratulates Jack on finding a case and treats him to some pie. Jack asks Dean about "courting" and Dean says he'll give him "the talk" later, but now they have to find Harper. Jack wonders if maybe she's not human, and Dean says that's what they're going to find out. When Jack asks how, Dean asks him if he's ever read a romance novel.
Cut to the library where Harper works. Dean enters and begins questioning her brusquely and making her uncomfortable. Jack enters and interrupts them by asking for a book about the area's history, and when "bad cop" Dean protests, "good cop" Jack tells him she doesn't appear to want to talk to him and he can't make her without arresting her. Dean tells him to back off, and Jack counters with "No, YOU back off... OLD MAN." Dean visibly reacts to the term (out of his "bad cop" character), claims "This isn't over" and leaves, giving Jack a bit of a dirty look as he does. Harper is impressed and grateful to Jack for intervening and says she has the perfect book for him -- at her apartment. As Dean sits in the Impala, muttering "old man, my ass", he watches as Harper and Jack exit the library and are accosted by another library employee, Miles, who jealously questions her about taking a stranger to her apartment. Harper and Jack leave anyway, and Dean starts to follow Miles, who heads around the back of the library to dump trash. As Dean is rounding the corner he hears a shout and trash cans thrown, but when he gets there he finds Miles lying on the ground, dead.
Dean texts Jack and tells him to call him. Jack excuses himself to use the bathroom and calls him. He explains that Harper passed all the tests so is not a monster, and he's 99% sure she's in love with him. Dean tells him that's not how it works and he's sure she's not in love with him, but Jack counters that if she actually is, he needs to know all about sex, GO. Dean tells him Miles is dead and they have bigger things to worry about, that something is stalking Harper or those around her... and the line goes dead as Dean is attacked. Jack exits the bathroom, where Harper apologizes for being so intense and asks if they should go get coffee... when Dean bursts through the door. He and Jack explain that they're there to save her. Harper asks what they're going to save her from, when something starts bashing at her door, growling. Dean sees a picture of Harper's boyfriend and recognizes him as the thing that attacked him -- her boyfriend Vance is a zombie. Vance bashes through the door and Dean fights him, allowing Jack and Harper to escape. Suddenly Vance stops fighting Dean, stands with a blank look on his face, and runs out the door. Dean follows him to the library, where Harper has let him in and revealed she is a necromancer who killed Vance to keep him from leaving her for college and turned him into a zombie... and he needs to kill and eat Jack to maintain his body. Dean sneaks in, finds Jack, and tells him that the only way to stop a zombie is to drive them back to their grave and use a silver stake to keep them there. Working together, they trap Vance using silver handcuffs but Harper escapes.
Back in the Bunker, Dean and Jack are discussing the case. Jack asks him if since Vance is back in his grave, he can't hurt anyone, and Dean says the stake through the heart will keep him there. Jack then asks, "So that's... love?" Dean laughs and says that love can actually get crazier than that, and with Harper still out there it might get crazy yet. He then tells Jack he did good, which Jack uses as evidence that he should be able to go on hunts. Dean tells him it's not about being right, that he'll make mistakes but it's how he handles himself after making them and learning from them. Jack responds "and not beating yourself up about them." Dean smiles and agrees, and says he'll talk to Sam when he returns... but Jack starts coughing violently and collapses on the floor bleeding from his nose and mouth while Dean looks on helplessly.
14.07 Unhuman Nature picks up with Dean and Sam waiting in the hall outside Jack's room while Castiel attempts to heal him. Cas tells them he did what he could but he doesn't know what's wrong with him. They hear Jack fall from his bed and rush in, finding him on the ground and foaming at the mouth. They rush him to the hospital where the doctors begin to treat him, as Sam, Cas, and Dean look on, worried. The doctor emerges and tells them that all of the tests they've run on Jack have come back negative but his body is in systemic failure and they don't know why; they need to run more tests. Dean, talking to Sam, wonders how many more tests they can run, and Sam believes there isn't anything else the hospital can do for him -- they've never seen anything like Jack and they obviously can't tell them what he really is. Dean suggests taking him home and finding another way to treat him, like calling Rowena, and Sam says he's already called her. They put Cas' trenchcoat on Jack and, telling the doctors they're going to get a second opinion, they take him back to the Bunker.
After much convincing from Sam, Rowena attempts to cure Jack while Dean, Sam, and Cas wait in the hall. She tells them because he's a Nephilim, his Grace is what holds his human and angel sides in balance and without it, his cells are destroying themselves. Cas offers his grace but because Jack is part archangel, Cas' grace isn't strong enough. While Rowena is explaining this, Dean's vision begins to blur and the voices echo, but only for a moment. He recovers in time to hear Rowena say Jack's condition will be the end of him.
Dean brings Jack some milk and a sandwich and finds Jack packing; since he's dying, he wants to experience life before it's over, and he doesn't want to waste time arguing since he knows Dean will disagree. Dean asks "Did I say I disagree?".
Dean walks into the Library where Sam, Rowena, and Cas are attempting to find something to help Jack. Cas has found books on archangels but nothing about nephilim. Rowena has talked to "the greatest minds in witchcraft" but they don't have anything either, to which Dean quips "well then they're not the greatest minds, are they?". Sam says he talked to Ketch who has a line on a shaman, Sergei, but as Sam starts to explain, Dean's vision and hearing begins to blur and echo again briefly. Sam says he has the location of the shaman and Cas offers to go talk to him, as Jack enters the room, packed and ready to go, and tells them they're heading out. Dean tells them they're "taking Baby out for some exercise" as he and Jack leave.
Their first stop is a burger place and as they're leaving, Dean tosses the keys to Jack and tells him he's going to drive. When Jack says he doesn't drive, Dean says "Now you do." Dean patiently teaches Jack how to drive Baby, and as Jack gets more comfortable, turns on the tunes. Dean asks him how he feels and Jack says "It's like I'm you!" to which Dean responds, "No, you're not!" Jack exclaims that it's the best day ever and Dean laughs as Jack speeds down the road.
They stop on the side of the road to eat the burgers, and Dean asks him what he wants to do next, suggesting a nearby bar with little class but high hookup potential, but Jack has a different idea -- fishing. Sitting by a creek, Jack said he wanted to do this because Dean had once said he and his father did the exact same thing and it was one of his happiest memories. Dean claimed he never said that but Jack told him it was the way he said it -- he could tell. He goes on to say that the stuff he'll miss isn't going places like Tahiti or the Taj Mahal, but spending more time with Dean, that it's time together that matters. Dean is visibly choked up, as Jack says "I've had a good life, Dean."
Back at the Bunker, Cas has returned from the shaman with a spell and a portion of archangel grace. Rowena begins to perform the spell as Dean, Sam, and Cas observe. As Jack ingests the grace, Rowena recites the spell. Jack's eyes flare, he stands... then suddenly collapses. While Rowena works on him, Dean laments taking him out but Sam and Cas disagree, saying the trip with Dean made him happy, that he did more for him that either him or Sam. Rowena approaches and Dean asks her what they can do, and Rowena tells them they can watch over him and stay by his side... as he dies.
14.08 Byzantium picks up immediately afterward, as Dean, Sam, and Cas stand at Jack's bedside. Jack asks them not to be sad, that maybe this is how things are supposed to be. Dean angrily disagrees, saying this isn't a part of some damned plan and stalks out of the room. He paces the hallway and punches the wall. Cas joins him in the hallway to check on him. Dean tells him he can't go back in, but Cas tells him that Jack needs him. Dean goes back in the room but it's too late -- Jack is gone. The three stand in the hallway and talk about next steps. Dean suggests a wake and a bonfire, hunter style; it's what Jack would want. Sam turns quickly and walks away. Cas starts to follow him and Dean stops him, saying he needs space and they're going to give it to him. Dean goes to the kitchen to call Mary to tell her about Jack but gets her voicemail, so he leaves a message, asking her to call back and that it would be nice to talk to her. He finds Cas and asks him if he's seen Sam. Cas had just watched him leave the Bunker. In Cas' car on their way to find Sam, Dean asks Cas why he let him leave. Cas says he told him to give Sam space but Dean says he meant there in the Bunker, not actually leaving. They find Sam sitting by the Impala next to a grove of trees. Dean rushes to him, demanding to know if he made a deal, and Sam, confused, said he was trying to build a pyre but the ax broke while he was cutting down a tree. He is upset because he couldn't even do that for him, that he should have tried harder to save him. Dean tells him that at least he was there for him. Cas says Jack's death doesn't feel right - that Jack shouldn't have been taken before him. Sam asks what they should do, and Dean says "Say goodbye.. tomorrow. Tonight, we get loaded." Back at the Bunker, they drink, talk, laugh, and share memories... and eat nougat candy bars.
Dean wakes the next morning after having passed out on the table, and hears voices from the library. He staggers out where Sam and Cas are talking to Lily Sunder, who has aged significantly after giving up using angel magic. Dean asks what she's doing there and Sam tells him he called her. She knows more about angels than anyone, and he thought maybe she can read Donatello's notes from the Angel Tablet. She looks at his notes and unfortunately can't read them, but offers to use her angel magic instead. Since it draws power from the soul, it can be used to save him and keep him alive. Dean disagrees with the plan but Lily explains that it will only use a very small portion of his soul. Dean asks what the point is, Jack is already dead and his soul is gone, but Cas believes that if his soul is in Heaven he can pull it back to his body long enough for Lily to teach Jack to use her magic to stay alive, but only in trade for their help to get her soul into Heaven. After killing as many angels as she did, she's pretty sure her soul is not welcome there. Sam, Dean, and Cas discuss her offer, and how to get her soul to Heaven. Dean suggests maybe Billie/Death or Reapers could help but Cas says they aren't the ones who weigh souls -- Anubis, the Egyptian Guardian of the Dead, was appointed to the job after God left. Dean and Sam prepare to summon Anubis, but Dean is still against using Jack's soul and doesn't trust Lily. Cas joins them; Dean asks him if he's found Jack's soul but Cas says Angel Radio is playing a distress signal -- all the gates of Heaven are open and that means bad things are happening. Sam tells him to go and they'll pray for him when they're ready. Lily provides the instructions for her spell while Dean paints the summoning circle. When he's done he apologizes to Lily but wants to know why she stopped using her magic, why she's letting herself die and risk going to Hell. She explains that when Ishim took her daughter, she swore she would kill him even if it took her entire soul, but it didn't. She still has a tiny piece left, and her daughter is in Heaven.
Dean and Sam begin the summoning. Anubis appears and recognizes them, saying he's seen their files. Sam says they've never met although they've died -- many times. Anubis says he's a "back of the house" guy, that Death and the Reapers get all the face time. He asks them what they want, and Lily asks him to weigh her soul so she knows where she's going. Anubis reluctantly agrees and produces an abacus with white and black beads. He takes Lily's hand and places it above the abacus, where the beads move back and forth, finally stopping with more black beads than white -- Lily's soul is going to Hell. Sam tells Anubis to change it, but he claims he can't. Dean tells him that he's not going anywhere then, and Sam explains they have bound him in a circle of palm oil. Anubis says he still doesn't have the power, that THEY are the only ones that can decide that, by their actions and decisions in life, and they can try to keep him there or kill him, but that won't change Lily's fate and may affect theirs. Sam breaks the circle and Anubis vanishes.
Sam asks Lily if she'll still do the spell, but she says that wasn't the deal and she has to go. Dean yells at her -- "He's OUR KID!" -- and accuses her of losing so much of her soul that she's not even human anymore. If she was, she wouldn't be able to stand someone else feeling the pain of losing a child as she did. Lily stops, and changes her mind, agreeing to help them. Jack's body is placed on the table in the Library, and Dean prays to Cas to let him know they're ready, as Lily begins the spell. Jack suddenly sits up, Sam hands him the spell and tells him to read it. When he's done, his eyes flare as his soul reenters his body. Dean asks him how he feels. Jack says he feels good and they both hug him. Dean turns to thank Lily, and discovers she has died.
Later in the kitchen, Sam, Dean, Cas, and Jack are having burgers and beer. Dean tells him how glad they are to have him back, and now that they know where Michael is, things are starting to look up.
It's Christmas Eve in the midseason finale 14.09 The Spear, and thanks to Garth acting as a mole, the boys have a line on Michael's location: Hitomi Plaza, a high-rise office building in Kansas City, Missouri. Sam is concerned over putting Garth in harm's way but Dean reminds him that they're finally a step ahead. Ketch calls and lets them know he's found the Hyperbolic Pulse Generator -- the "egg" -- but was attacked and forced to drop it... in the mail. Unfortunately, the post office is closed due to the Christmas Holiday and the package is stuck in Joplin, Missouri. Since the post office is closed, the opportunity exists to break in and pick it up. While discussing this, Garth calls to tell them that Michael sent some of his people find someone at an old recycling plant north of Omaha, to get a weapon -- a spear. Also, he managed to overhear Michael's plan to attack and turn everyone in Kansas City, on Christmas Eve at midnight. With this news, they decide to divide and conquer: Sam and Jack will go to Joplin to get the egg, and Dean and Castiel will go to the recycling plant to find Kaia's Spear, then they'll meet in Kansas City before midnight to stop the attack.
Dean and Cas arrive at the recycling plant, and Cas comments on Dean's recent upbeat mood -- even being able to withstand the drive with a broken tape deck. Dean explains that he's fired up after getting Jack back, a no-strings-attached win. Cas reminds him that they have to deal with Michael now, and they're taking a big risk going after the Spear. Dean stops him and reminds him that Michael conned him and trapped him, drowning inside his own body. He didn't understand before what Cas and Sam went through when both were possessed by Lucifer but now he does, and he'll take it if they can trap him but he won't be truly happy until he's dead, preferably at Dean's own hand. Now that he has the chance to do that, he's good.
They make their way into the recycling building and find remnants of Dark Kaia's camp -- a sleeping area and a recently warmed pot -- but no sign of Kaia herself. Cas wonders why Michael's forces are not there since they had a head start, and asks if perhaps they've already captured her, but Dean says there's no sign of a struggle and she wouldn't have gone out without a fight. Dean tries to call Sam but there's no answer; Garth calls to tell him Michael left to back up his forces. Dean tells him those forces are not at the recycling plant and to call him if he hears anything else. They wonder if the recycling plant was a setup when Cas notices Kaia right behind them, the Spear pointed at the back of Dean's head. Kaia asks why they're here and what they want. Dean tells her she knows what they want, and when Kaia questions their ability to take it from her, Dean tells her they weren't planning to take it from her -- they came to ask. Dean turns to face her. Kaia says she will not give the Spear up. Dean moves towards her, causing the Spear to push into his chest, and he tells her that, in that case, she should just kill him. He says that the people he cares about, his family, are in danger from Michael, who tortured both of them. Michael is going to hurt and kill them, along with thousands of people in Kansas City, and the only thing that can stop him is her Spear. Kaia backs the Spear away from Dean's chest while he exhales in relief, and she asks what's in it for her. Cas asks what she wants, and she replies that she wants to go back to the Bad Place -- her home. She escaped there originally to get away from the monsters, but here is no different because Michael's monsters won't stop hunting her. Dean agrees to help her, but she still thinks Jack has his powers and can open the rift, and Dean lies and says he can. Kaia wants assurances but Cas says there aren't any, just as they have no proof she's not hiding something as well, and he still believes that she's hiding something regarding her desperation to return. Kaia explains there are people she is bound to protect in the Bad Place, and hands the Spear to Dean, telling him that if he doesn't return it she will hunt him down and kill him. Dean asks how he's supposed to find her, and she reminds him he did it before -- do it again. Dean's phone rings -- Sam -- and Kaia disappears. He answers the phone, where Sam explains Michael got the drop on them at the post office, destroyed the egg, and kidnapped Jack. Dean asks Sam how he escaped and when Sam says Michael just knocked him out and he doesn't know why he didn't kill him, Dean wonders if Michael is just playing them. Sam says he can't reach Garth and assumes Jack was taken to Kansas City, so he's headed there now. Dean tells Sam they have the Spear and will meet him there. Cas tells Sam not to go in alone and Sam assures them he won't.
Dean and Cas arrive at Hitomi Plaza with the Spear to find that Sam has already rescued Jack from Michael and fought a Michael-controlled Garth, and as they lock Garth (bound and unconscious) in the truck of the Impala, Dean chastises Sam for not waiting for them. Sam explains that he had no choice, and is dismayed that Garth drank Michael's grace, thinking Michael might have used him as an unwitting "double agent" to figure out where they were and get the jump on them. Dean conjectures that if they kill Michael it will cure Garth, and Sam mentions that other hunters are on their way to take care of the city, in case they can't beat Michael in time. Dean brandishes the Spear and claims he wouldn't bet against them and awkwardly attempts to twirl the Spear. Cas heals Jack's injuries from the fight with Garth, and Dean asks Jack about Michael, who tells Dean Michael is upstairs waiting for them. Cas figures that since Michael's monsters are all over the city by now, if he was even the slightest bit concerned about them, he would have sent his monsters to stop them, and Sam reminds them that Michael didn't kill him when he had the chance, so they can assume he wanted them to come there. Cas also reminds them that Michael will surely sense his approach -- so zero element of surprise, right into a trap by a full power archangel. "Impossible odds. Feels like home. Let's do it" Dean says, as Team Free Will 2.0 turn and march towards the battle with Michael.
Michael senses Cas' presence as expected and leaves the room. While he's beating up on Cas, Sam, Dean, and Jack enter. Dean hides in a closet with the Spear and rushes him while he's subduing Sam and Jack. They fight, but Michael overpowers him and Dean loses the Spear but while Michael is gloating, Sam manages to get the Spear back to him and Dean slashes Michael's arm with it, then backs him up against the outer glass. Just as Dean was about to kill him with the Spear, his vision and hearing blur again as Michael's current vessel collapses to the floor. Dean (now Michael) breaks the Spear and turns to face Sam, Jack, and Cas. Dean is locked away and Michael has taken over again.
Dean's weapon of choice is a stainless and custom-engraved .45 caliber Colt MK IV Series 80 1911 pistol with ivory grips, which John is also seen using in a flashback. Dean uses a Baikal sawed-off, double barrel, break action shotgun when he needs extra firepower. He has also been seen with a H&K G3SG/1 rifle in 2.05 Simon Said. Other small arms used by Dean include a Taurus PT99, a Beretta 92FS, a Smith and Wesson 5906 9x19mm pistol, a Remington 870 12 gauge shotgun, and an Ithaca 37 12 gauge shotgun. Dean is shown to possess a large machete in 1.20 Dead Man's Blood, and has used a knife in several episodes. Dean has also wielded a Desert Eagle loaded with wrought iron bullets in 1.18 Something Wicked and Tasers, which he and Sam used in the start of 1.12 Faith, when he electrocuted himself. Dean, along with Sam, John, and others, has wielded the Colt, a specially crafted Colt-Patterson model 1836 revolver made by Samuel Colt himself which, with Colt's special bullets, can supposedly kill anything in creation. Lucifer mentions that he is one of five things that the Colt cannot kill, but it is unknown who the other four entities are. Dean also frequently uses Ruby's knife, an "ancient demon-killing knife of the Kurds". As with any professional hunter, Dean relies on salt, pure iron, and exorcisms to further combat supernatural forces. When firearms and blades are scarce and Dean is in a dangerous situation, he uses a brawling style of hand-to-hand combat or improvised weapons from the surrounding area. During 4.16 On the Head of a Pin, Dean is shown with a number of torture implements, including syringes of holy water, although he does not like to resort to these measure unless he has no other choice. Starting in 5.18 Point of No Return, Dean has begun wielding angel blades, angelic weapons capable of killing both angels and demons. In 13.02 The Rising Son, Dean was able to use an angel blade against a demon in a similar manner to a throwing knife. In 13.23 Let the Good Times Roll Dean was able to wield an archangel blade against Lucifer and kill him due to Dean being the vessel of the Apocalypse World Michael at the time. In 14.09 The Spear, Dean wields Kaia's Spear with great proficiency against Michael and even while just showing off.
- In one version of the pilot script Sam suspected Dean of being a serial killer and the murderer of their father.S1Com, p. 14
- On the map of Winchester, UK, you can clearly see a place named Dean above it, spelling out Dean Winchester.
- Series creator Erik Kripke has said that Sam and Dean's names were a reference to Jack Kerouac's American novel On the Road, whose main characters are named Dean and Sal. Sal was changed to "Sam" because, according to Kripke, the name "Sal" is "inappropriate for a main character."
- Kripke has also stated that Star Wars was the major influence on the series, comparing Dean's character to Han Solo and Sam's to Luke Skywalker.
- Dean's Bedroom
- Dean's Hair
- Dean's Leather Jacket
- Winchester (family)
Dean in Fandom
- Fanfiction and Vernacular
- @SaltBurned - Dean Winchester Twitter RP account
- @imanaquarius - Dean Winchester Twitter/roleplay account
- valorslain - Dean Winchester Roleplay Tumblr Blog
- hellbitched - Dean Winchester Roleplay Tumblr Blog
- totaldeangirl - A community dedicated to girls into Dean
- dear_dean - A fan written advice column
- team_dean - A community for daily pictures of Dean Winchester
- dean_fic - A community for fic about Dean
- darkdean - A fic community for dark fics and fics with dark Dean
- Dean Minions - a Dean Winchester fan community
- Supernatural Twitter - a fan-created website following Dean, Sam, etc.
- 1.21 Salvation
- 4.03 In the Beginning
- 3.08 A Very Supernatural Christmas
- 6.09 Clap Your Hands If You Believe...
- 3.11 Mystery Spot
- 3.16 No Rest for the Wicked
- 4.01 Lazarus Rising
- 5.01 Sympathy for the Devil
- 5.16 Dark Side of the Moon
- 6.11 Appointment in Samarra
- 9.23 Do You Believe in Miracles?
- 11.17 Red Meat
- 12.09 First Blood
- 13.05 Advanced Thanatology
- 5.08 Changing Channels
- 5.13 The Song Remains the Same
- 14.02 Gods and Monsters
- 14.09 The Spear
- 14.10 Nihilism
- 14.14 Ouroboros
- 3.03 Bad Day at Black Rock
- 9.07 Bad Boys
- 4.13 After School Special
- 1.02 Wendigo
- 7.05 Shut Up, Dr. Phil