Dean Winchester - Season 5

Season 5

The fifth season begins right where Season 4 ends with the portal for Lucifer opening. As Lucifer escapes, the brothers are teleported into an airplane by an unknown force (later revealed to be God). Later, Dean is told by Zachariah that he is "Michael's Sword", meaning the Archangel Michael will use his body as a vessel to lead the forces of Heaven against Lucifer, 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.

In "Good God, Y'All!", Dean and Sam fight War, one of the Four Horsemen of the Apocalypse, in a town where the people think that their neighbors are demons. Once the brothers cut the ring finger off of War, restoring the town to normal, 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 bloodlust.

In "The End", Dean is transported forward in time by Zachariah, who wants Dean to see what the future will be like if continues to refuse giving his consent to Michael. He finds himself in the year 2014, eventually meeting up with his future self, as well as the survivors and victims of the Croatoan virus from Season 2. 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 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 again 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 the episode "Changing Channels", it is revealed to Dean and Sam by The Trickster (who reveals that he is the Archangel Gabriel) that their relationship (Dean the older brother loyal to an absent father and Sam the younger brother who is rebellious of the father's plan) mirrors the relationship between Michael and Lucifer, and has been told to the angels since the beginning to bring about Judgment Day.

In "Abandon All Hope", Sam and Dean plan to find Lucifer and kill him, with help from Castiel, Jo, Ellen and Bobby. They find out that the Colt is in the possession of a demon named Crowley, who gives the Winchesters the gun to kill Lucifer and end the Apocalypse. The Winchesters then find out that Lucifer is one of five things in the universe that the Colt cannot kill, when Dean tries shooting Lucifer in the head with no effect. Having lost another plan, Dean becomes more disillusioned and hopeless, and in "Dark Side of the Moon" where, after spending time in Heaven and finding out God doesn't see the battle with Lucifer to be his problem, begins to see little reason to deny his destiny as Michael's vessel, deciding to take on the role at the end of the next episode "99 Problems". Before doing so, though, he visits former girlfriend Lisa Braeden (Season 3 "The Kids Are Alright"), confessing that when he dreams of being happy it's with her and her son Ben, and promising to get them protection for what's to come.

During the series' 100th episode "Point of No Return", Dean was preparing for his possession by Michael before being discovered by Sam and Castiel, who take him to Bobby's house. They convince him to allow them some more time in order to research another method of stopping Lucifer; however, the unexpected resurrection of their half-brother Adam, planned to be Michael's vessel, forces Sam, Bobby and Castiel to keep Adam and Dean from Zachariah. When Dean escapes and tries to lure the angels, both Castiel and Sam leave to find him, allowing Adam to be taken by angels. Despite Bobby and Castiel's insistence in keeping Dean from Zachariah, Sam allows him to try to rescue Adam. With Castiel removed, along with angel guards, the brothers attempt to rescue Adam, but Sam's ambush of Zachariah fails and Zachariah causes internal damage to both Adam and Sam to coerce Dean to consent to Michael. Ultimately, Dean relents, but after Zachariah summons Michael, Dean taunts Zachariah into sacrificing himself in order to allow Michael in. Zachariah angrily refuses, and Dean kills him and rushes out, unfortunately leaving Adam locked in the room with the approaching Michael. As they leave, Dean admits that he would have accepted Michael, but because of Sam's faith, he decides that he will "take the fight to them".

After being trapped in "Hammer of the Gods" by a group of gods bent on using them as bargaining chips in the upcoming Apocalypse, Dean and Sam learn from Gabriel that the cage Lucifer was sprung from was still open and, if they could get all four Horsemen's rings, they could put him back in and trap him again. He also claims that Lucifer has no knowledge that he can be trapped again. In "The Devil You Know", the demon Crowley returns and leads Dean to a confrontation with Brady, one of Sam's college friends who, in fact, was a demon "Handler" for Pestilence. Despite being beaten badly, Dean and Crowley trap Brady and are eventually able to get the location of Pestilence.

In "Two Minutes to Midnight", the brothers go after Pestilence and, with help of a nearly-human Castiel, take his ring. During the trip, Sam tells Dean that he believes the only way to trap Lucifer is to say yes and allow himself to be possessed, believing that he can overcome Lucifer long enough to throw himself into the trap. Crowley then takes Dean to Chicago, where they have located the final Horseman. In the midst of a massive storm, Dean confronts Death in a pizza parlor. Revealing that Lucifer controls him due to a spell, Death agrees to give Dean his ring with the explicit condition that Sam say yes so he can lure Lucifer into the trap, and that Dean allow his brother to jump into the pit. Dean reluctantly agrees and gets the ring and instructions from Death for how to use the four rings. Upon returning, Dean claims he lied to Death, but upon talking to Bobby it becomes clear that their last best chance may be to let Sam say yes, with Bobby asking Dean if he was more afraid to lose, or to lose his brother.

In "Swan Song", Dean relents and agrees to let Sam say yes. As Sam prepares to drink demon blood to become strong enough to take in Lucifer, he makes Dean promise that he won't attempt to come after him once he has jumped into the pit. Dean objects, but Sam insists, begging that he instead go to Lisa and try to live a normal, happy life. Dean promises he will do so, and after drinking the demon blood, the brothers go to confront Lucifer in Detroit. Despite Lucifer's revealing that he did indeed know about the brothers' plan to trap him again, Sam says yes, believing he can overcome him nonetheless. After taking over and briefly knocking Sam unconscious, Dean opens the portal to Lucifer's prison, and Sam wakes up and prepares to jump in. At the last moment, though, Lucifer reveals himself, claiming that "Sammy is long gone". After closing the trap, taking the rings, and briefly taunting Dean, Lucifer disappears.

As omens begin to signal the final battle, Dean calls Chuck to try to pin down the location of the final battle, which will occur in Stull Cemetery back in the brothers' hometown of Lawrence. While Castiel and Bobby seem despondent, believing the battle to be lost and further confrontation pointless, Dean vows to go to the fight between Lucifer and Michael (now possessing his half-brother Adam), claiming at the very least he "won't let his brother die alone". As Lucifer and Michael prepare to fight, Dean interrupts and drives the Impala into the graveyard. He attempts to reach out to both Sam and Adam, asking for five minutes with Sam, but is dismissed by both. Bobby and Castiel suddenly appear, and Castiel throws a Molotov cocktail with holy fire at Michael, burning him out and buying Dean five minutes. It comes at a high price; an enraged Lucifer snaps his fingers, making Castiel explode for interrupting the fight. Lucifer and Dean begin to fight, with Dean taking a beating. Lucifer continues beating Dean and, with Dean backed against the door of the Impala, prepares for a kill shot. However, at that moment, he catches a glimpse of a toy soldier that a young Sam had stuck in the Impala's ashtray, and the memories of his brotherhood with Dean help Sam to overpower Lucifer and take control of his body. Sam reopens the pit, and though Michael returns and attempts to stop him, Dean watches as Sam pulls Michael into the pit, which closes as they both fall in, trapping both in Hell.

A fully restored Castiel suddenly appears, claiming to have been resurrected by God. He heals Dean and plans on returning to Heaven and bringing new order now that Michael is gone. Dean claims that he will go after God next, but Castiel claims, before disappearing, that Dean only got what he wanted in the end: no Paradise, no Hell, more of the same-freedom over peace. After an emotional goodbye with Bobby (it is said in Chuck's epilogue that the two will not see each other for some time), Dean returns to Lisa Braeden as Sam had suggested. Dean is last seen sitting down to dinner with Lisa and her son Ben. Unknown to Dean, a streetlight just outside the home goes out, and Sam is inexplicably standing beneath it, watching the home with a blank look on his face.