|Actor|| Jensen Ackles (adult Dean)|
|Dates||January 24, 1979- May 2, 2008 / September 18, 2008 - ?|
|Location|| Age 4 - Lawrence, Kansas|
Lisa Braeden's House (currently)
- 1 Background
- 2 Michael's True Vessel
- 3 Pre-series
- 4 Season 1
- 5 Season 2
- 6 Season 3
- 7 Season 4
- 8 Season 5
- 9 Weaponry
- Son of John & Mary Winchester; older brother of Sam and older half-brother of Adam Milligan.
- Named after his grandmother, Deanna.
- Dean drives a black 1967 Chevy Impala which his father gave to him.1.21 Salvation
- Dean is a good mechanic. During Seasons 2, he repairs the totaled Impala, and is a professional mechanic in the Wish Verse of 2.20 What Is and What Should Never Be.
- During Seasons One through Four, he always wears an amulet given to him by Sam as a Christmas present in 1991.
- In Seasons One and Two, Dean wears two black bracelets. They are African support bracelets from Invisible Children.
- In an interview Eric Kripke said the reason both Jess and Dean had the same birthday was "...not a creepy, mythology, conspiracy reason. January 24 is my wife's birthday, and it's kinda my valentine to her."
- In 3.12 Jus in Bello we learn that Sam and Dean got matching tattoos depicting a pentagram that protects them from demonic possession.
- Dean dies on 2 May, 2008 – Sam's birthday. Dean rises from his grave on September 18, 2008. 4.01 Lazarus Rising
- In one version of the pilot script Sam suspected Dean of being a serial killer and the murderer of their father.S1Com, p. 14
- In 4.18 The Monster At The End Of This Book Dean says that his favourite songs are a tie "Between Zep's "Ramble On" and "Traveling Riverside Blues."
- He is Michael's true Vessel, but he refused to say yes to Michael, which forced Michael to use Adam as his 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 - in part because of their bloodline, in part because their relationship parallels that of Michael and Lucifer.
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's 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 (diary entries)).
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.
When Dean is in sixth grade he makes his first sawed-off shotgun.<3.03 Bad Day At Black Rock>
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.
Disappointed with John's lying and absence, Sam gives Dean the present intended for his father: the amulet.
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 summer 1997 John, Dean and Sam are hunting a werewolf. 4.13 After School Special
In November 1997, John "parks" the kids in a small town in Iowa, where they attend Truman High School. While Sam is having trouble with a bully called Dirk, Dean gets a girlfriend, Amanda, 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.4.13 After School Special
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."1.02 Wendigo 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 shape shifter reveals Dean's anger at Sam's leaving for college. 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 for thwarting his attempts to find his father. In the following episode Sam actually does leave Dean, who tells him he was always proud of how he pursued what he wanted. Sam eventually returns to Dean.
In 1.12 Faith, an accident while hunting leaves Dean with a fatal heart condition when he gets 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."
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. Azazel and his 'children' Meg and Tom are quick to act, and hold a friend of John's hostage, offering to exchange him for the Colt. John tries to trick them and is captured. In the season finale, the two Winchester brothers must rescue their father and face Azazel, 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 Azazel, 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, 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 that, "Sam, I liked it there. I didn't want to leave."
In the season finale, Sam is kidnapped by Azazel 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 Azazel. The Devil's Gate is opened by Jake who using the Colt and demons and souls pour forth – including John. The spirit of John helps fight Azazel, 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 "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 anything. 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 "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 "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 2. It finally becomes Wednesday, but this time, Dean dies and doesn't come back. Sam spends months trying to hunt down the Trickster, who reveals that he'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 "Jus In Bello", the FBI and Agent Henrickson 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, "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 peak of busty asain 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 the episode "Wishful Thinking," Dean confesses that he does remember every second of Hell.
Later, in "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 "All Hell Breaks Loose, Part I") and why her ghost apologized to Sam (in "Home"). A causal 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 "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 "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.
Later on in the season, an episode aired with 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 "Death Takes a Holiday", Dean meets up again with the reaper Tessa. She wakens his memories of their previous encounter with a kiss. Dean confesses that there has been a "hole" in him since that time, and realizes that it is related to her. Soon after she is taken by Alastair in his quest to break another seal, that involved killing reapers. The boys ask Pamela Barns 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 "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 the episode "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 and her death will break the 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 Archangels, 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", 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 realises 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 Hell.
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 from Hell. 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.
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 also 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 "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 "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 the episode "Something Wicked" and tasers which he and Sam used in the start of "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. However, Lucifer mentions that he is one of five things that the Colt can not kill, it is unknown if the four other entities Lucifer was referring to were the four other Archangels (Michael, Gabriel, Raphael and Auriel) or the Four Horsemen. 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 "On The Head Of A Pin", Dean is shown with a number of torture implements, including syringes of holy water.