The journey of Dean Winchester is one of the most compelling on Supernatural. Forced to become an adult long before his time, his love and protective instincts for his little brother Sam have become both his burden and his greatest honor. While Dean is known for his humorous quips, he is also a man who often uses that humor to hide his emotions behind a tough exterior. Over the years, we’ve come to know Dean and appreciate the big heart behind the sarcastic veneer. As Supernatural prepares to wrap up its final season, we’re looking back at the journey Dean has taken from season one to now.
In the early days, Dean is the brother who is most at ease with the hunter lifestyle. Irreverent and good at killing monsters, Dean is most at home pursuing a case behind the wheel of his beloved 1967 Chevy Impala, Baby. Dean has a black-and-white sense of morality with regard to the monsters he gleefully hunts. But Dean isn’t just a sarcastic hunter with a whole lot of unresolved emotional baggage and a reputation as a ladies’ man. His heart is on display from the beginning. Having been raised by his father John to exact revenge on the demon who killed his mother, he fully bought into his father’s teachings and idolized him. This causes conflict with Sam, who wants to get away from the supernatural and live a normal life. Much of Dean’s emotional conflict comes from being torn between John and Sam, especially as Dean begins to process the way John’s parenting warped his life. Dean also must reckon with the lengths he will go to protect his family.
Having lost John when he sacrificed himself to save Dean’s life in “In My Time of Dying,” Dean has lost his sense of direction. He’s also carrying a big burden courtesy of what his father told him before he died: that if he can’t help Sam, he has to kill him. As is Dean’s way, he keeps this knowledge to himself. Dean has to reckon with what could happen if the premonitions surrounding Sam come to fruition. This is especially true when a possessed Sam kills a fellow hunter. In Sam’s moments of regaining control, he begs his brother to kill him, but Dean can’t bear to do it. In “All Hell Breaks Loose,” Dean’s worst fear is realized as Sam dies in his arms, stabbed by a fellow psychic child. In a demonstration of both his protective instincts and his self-destructive tendencies, Dean sells his soul to a Crossroads Demon to bring Sam back.
Season three follows Dean over his final year before his soul is claimed. At first, Dean adopts a “bucket list” approach while Sam desperately searches for a way to save him. Dean reconnects with Lisa and her son Ben, which shows Dean’s paternal side as he suspects the boy might really be his son. We even get a glimpse at Dean’s childhood in “A Very Supernatural Christmas,” proving that Dean never really had the chance to be a child at all. Dean’s ambivalence towards being saved ends when he sees a demonic version of himself in “Dream a Little Dream of Me,” and the back half of the season is devoted to Dean and Sam’s efforts to stop Dean from going to Hell. Their efforts fail, and Lilith masquerading as Ruby unleashes hellhounds that drag Dean to Hell as a devastated Sam watches.
But all is not lost for Dean, who wakes up from his ordeal physically intact (though not psychologically whole) in “Lazarus Rising.” It is revealed that it was the angel Castiel who brought him back and thus begins one of Dean’s most important relationships on Supernatural. At first, the two don’t see eye to eye: Castiel is a soldier of God, whereas Dean doesn’t want to be the tool of a being he didn’t believe in until recently. But Castiel begins to have doubts as Dean begins to see the angel as an ally. Dean also must face his time in Hell, eventually revealing to Sam that he not only tortured souls but also enjoyed it. This shame will follow Dean for a long time and once again demonstrates how difficult it is for Dean to forgive himself.
Lucifer is released, causing chaos. Dean and Sam are distant, and the brothers separate for a while as Dean admits he can’t trust Sam. Dean also has to decide whether or not to become Michael’s vessel to battle Lucifer as Lucifer tries to possess Sam. Ellen and Jo Harvelle are killed in “Abandon All Hope,” and Dean blames himself for what happened to his dearest friends. He also loses what little faith he had when it is revealed that God has no interest in stopping the Apocalypse. Dean almost says yes to Michael’s request, but when Sam proves his faith in Dean is unshakable, Dean regains his fighting spirit. Dean, Castiel, and Bobby face a now-possessed Sam, who manages to pull himself and Michael (possessing Adam) into the cage.
Dean is living a normal life with Lisa and Ben when Sam reappears. Dean struggles with whether to remain in his new life or rejoin Sam, but his hunter lifestyle begins to take root in him again. Sam is revealed to be soulless as he nearly lets Dean become a vampire, and the remainder of the season revolves around finding Sam’s soul. Dean is devastated when he discovers Castiel, who he says he considers a “brother,” is working with Crowley in order to finish the Apocalypse. Despite their status as enemies, Castiel still helps Dean by saving Lisa’s life and erasing her and Ben’s memories so they can live a happy life without Dean.
A newly all-powerful Castiel absorbs all the souls in purgatory, releasing the Leviathans in the process. Sam is also suffering from hallucinations due to remembering his time in Hell (which he hides from Dean in a patented Winchester move). Dean reckons with his guilt over the death of Jo Harvelle when he faces Osiris in “Defending Your Life,” showing just how much Dean internalizes his perceived failures. Bobby is killed by Dick Roman, devastating Dean as Bobby was a father to him. Dean must also care for Castiel, who doesn’t remember who he is. Castiel regains his memories and takes Sam’s on in order to atone for his actions, which leads to Castiel breaking down. Dean and Sam search for a way to get rid of the Leviathans and meet Charlie, another important part of Dean’s life. Dean and Castiel finally kill Dick Roman, but they are transported to Purgatory.
You can’t trap a Winchester for long, and Dean is able to escape Purgatory. Dean is angry to discover that Sam has apparently moved on, not even trying to look for him. Dean has flashbacks of losing Castiel, which haunts him. Sam and Dean experience a lot of tension over Dean’s anger at Sam for leaving him in Purgatory. Dean’s guilt over leaving Castiel behind only grows when a visibly weakened Castiel returns. Dean and Castiel discuss Castiel’s time as a godlike being, with Dean realizing how much those actions haunt Castiel. When a desperate Dean sees how sick the demon trials are making Sam, he begs for Castiel’s help. But Castiel is brainwashed by Naomi and doesn’t come, devastating Dean. Castiel begins completing angel trials to seal Heaven as Sam continues the demon trials, but both fail as Metatron uses Castiel’s grace to expel all the angels from Heaven after tricking him.
Sam is dying, and Dean is desperate. He enlists Ezekiel to heal him. Sam is unaware Ezekiel is in his mind. Dean has Ezekiel resurrect Castiel, but then kicks Castiel out as Ezekiel informs Dean that all the angels are looking for Castiel to get revenge and will bring Heaven down on them if Castiel is with them. Sam is upset about Dean not telling him about Ezekiel and tells him to leave. It is revealed that someone must take on the Mark of Cain to kill Abaddon. Dean agrees despite Cain warning of a terrible cost (another patented Winchester move). Sam and Dean argue, with Sam believing Dean selfishly brought Sam back just so he wouldn’t be alone. Dean is devastated to discover that Sam would not bring Dean back if situations were reversed. The Mark begins to affect Dean, and Sam realizes what the Mark will do to his brother. When Dean faces Metatron and dies, the “terrible cost” is fully revealed: Dean is now a demon.
Demon Dean is having the time of his life as Sam searches for him. But Crowley quickly grows tired of Dean’s antics and trades Dean for the First Blade. Castiel and Sam successfully turn Dean into a human again. The Mark continues to influence Dean, leading him to violently kill monsters. Dean nearly kills Dark Charlie, which he feels horribly guilty for despite the fact that she forgives him. The only thing Dean can do is resist his power, and Castiel is worried after Dean kills Cain. As they continue to look for a way to reverse the Mark’s effects, Charlie is killed while decoding the Book of the Damned, plunging Dean into grief over the death of one of his dearest friends. Dean loses control, nearly beating Castiel to death. He holds off just long enough to tell Sam and Castiel to leave – if Dean sees them again, he’ll kill them. Dean goes to Death, asking to die so he won’t hurt anyone else. He tells Sam that they both need to die so the world can be at peace. But at the last moment, Dean kills Death, and as Rowena removes the Mark, the Darkness is released.
It turns out the Darkness is Amara, God’s sister, who Crowley is trying to recruit to his side. Castiel agrees to be Lucifer’s vessel in order to stop Amara. Dean struggles with how he feels around Amara, and also works through his issues with Sam by forgiving Sam for leaving him in Purgatory. Dean also searches for a way to get Castiel back from Lucifer’s possession. But the biggest reveal comes when Chuck tells Metatron he is God. Dean realizes Amara wants to use him in her plans and tells Sam about the visions she showed him. Most of the main characters combine to try to stop Amara, but though she is weakened she does not die. She and Chuck reconcile with Dean’s help, with Amara rewarding Dean with the thing he wants most: his mother Mary Winchester, alive again.
Mary’s return brings up a lot of complicated emotions for Dean, as he has to learn more about who she is as a person. We also get a great mix of comedy and emotion in “Regarding Dean,” in which Dean begins experiencing memory loss as a result of a spell by a witch. The Winchesters and Castiel look for Kelly Kline and her unborn child, fathered by Lucifer. Mary is brainwashed by Toni, and in order to break the hold, Dean travels into her memories in 1983 in “Who We Are.” In an emotional monologue, he tells his mother all the ways in which she ruined his life. But in the end, he loves her and forgives her, which breaks the brainwashing and helps Dean heal. In the finale, Castiel and Crowley both sacrifice themselves to trap Lucifer in an alternate reality created by the Nephilim, but Lucifer manages to pull Mary into the other world with him. Dean now must mourn his mother and Castiel while dealing with the arrival of Lucifer’s son.
Dean is not happy about Jack’s presence, wanting to kill him immediately. After Jack saves Sam in “The Big Empty,” Dean grudgingly allows that maybe Jack can learn to control his powers. In “Tombstone,” Dean gets to live out his Western fantasies working the case, providing some levity. But the fun doesn’t last long as Jack accidentally kills a guard. Believing himself to be evil and irredeemable, he leaves the Winchesters and Castiel. Dean’s love of Scooby-Doo also leads to one of the most “out there” episodes of the series as the group finds themselves within a Scooby-Doo episode hunting ghosts. Dean and Ketch go through the portal to Apocalypse World, giving them only 24 hours to bring back Mary and Jack. Dean sees the alternate version of Charlie, and he saves her hoping to make up for his failure to save his Charlie. In a bid to defeat Lucifer, Dean agrees to be Michael’s vessel while remaining in control. But Michael reneges on the deal and fully takes Dean over before leaving.
But just as suddenly as Michael possessed Dean, he leaves, confusing Dean and those who love him. Dean also must deal with guilty feelings over what Michael did in Dean’s body, with Dean believing those deaths are on him because he allowed himself to be Michael’s vessel. Jack begins to feel the effects of his human and angel sides fighting each other. Dean works with Castiel to find a way to save him when Jack dies from his injuries – but doesn’t know that Castiel traded his life for Jack’s with the Empty in order to do so. When they go after Michael, Michael reveals he let Dean go to break his spirit only to repossess him later. Sam and Castiel are able to trap Michael inside Dean’s mind. In “Lebanon,” John Winchester returns from 2003 via a magic pearl, creating an alternate timeline. They realize they must send John back to his time to fix the damage, leaving them to try and work out years of family strife.
After Michael possesses Rowena, Jack uses part of his soul to kill the archangel and absorb his grace. He begins to act in a soulless manner. The worst happens when Jack accidentally kills Mary Winchester. When the boys and Castiel try to bring her back, it is revealed that she is happy in Heaven with John, and a heartbroken Dean and Sam decide to let her stay there, giving her a hunter’s funeral. The Winchesters try to capture Jack, but Jack lashes out at the world, and God appears to help the Winchesters kill him. Dean takes on the task but finds he can’t kill Jack. God is highly displeased by this and decides he will simply end the world, killing Jack himself.
The Winchesters and Castiel must battle souls from Hell in order to save the world and defeat God. To close the rupture, Rowena sacrifices her life. Dean is angry at losing Rowena, and still blaming Castiel for Jack killing Mary, he lashes out. Castiel knows he is weakening and leaves. Both Dean and Castiel seem to give in to hopelessness about their situation, but each decide to keep fighting when they successfully complete cases where people are helped. Michael tells them how God can be trapped, which requires a special flower from Purgatory. Dean and Castiel get the flower after defeating the Leviathans, and their relationship is back on steady ground. God goes about destroying the other alternate realities as a resurrected Jack arrives home. Jack’s soul returns after he visits the Garden of Eden, and he tearfully apologizes for killing Mary.
After 15 years, it seems Dean Winchester is truly facing the end. Dean himself has always known his end would not be peaceful. As he told Cole Trenton, “I’m past saving. I know how my story ends – at the edge of a blade or barrel of a gun.” But Dean deserves to face the end absolved of the guilt and fear he has always carried with him. Even with all he has done to save both the world and individuals within it, Dean believes his past transgressions push the scales towards a negative effect overall. As Dean faces the end of the world for the final time, we can only hope that he will know he has always been enough – for himself, and for everyone else.