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The Gamblers 12

Dean and Jack

The relationship between Dean Winchester and Jack Kline is a complicated one. Originally a strained one due to Jack's parentage and the circumstances of his birth, it evolved into essentially a father and son relationship.


Dean originally viewed Jack as a dangerous being and blames him for the loss of Castiel, as Jack had been the one to convince Castiel to watch over his pregnant mother and leave Sam and Dean behind. Dean spent the months leading up to Jack's birth feeling upset and angry and viewed Castiel's running away with Kelly as the angel being manipulated.

Due to Jack being the son of Lucifer, Dean originally viewed Jack as a threat that had to be stopped from being born. After Jack was born, with Sam unwilling to kill him, Dean would keep an eye on Jack, threatening to kill him if Jack ever turned evil. Jack in turn sought Dean's approval and affection.

Over time, Dean and Jack's relationship evolved to be that of a father and son with multiple characters noting the parental bond between the two. At one point, God himself compared Jack dying at Dean's hands to be akin to a father killing a son. When Jack was dying, he chose to do things with Dean that Dean had enjoyed doing with his own father. Despite his words and his anger over Jack killing his mother, Dean's love for Jack was strong enough for Dean to spare Jack's life and mourn Jack's death when God killed him moments later.

After Jack's death, Dean proved to be the most willing to work with the demon Belphegor who used Jack's corpse as his vessel. Dean later told the demon that Jack was their kid, "sort of" and showed that despite everything that had happened, Dean didn't believe Jack deserved his fate.

After Jack's second resurrection, Dean was visibly pleased to see him, though he didn't hug Jack as Sam did. Dean shows no hostility in their interactions, but Jack recognizes that Dean is still angry and their relationship has changed. Even soulless, Jack is shown to still care about what Dean thinks of him and to hope to gain his forgiveness one day. They begin to grow closer again after Jack regains his soul, but their relationship isn't back to what it used to be though Dean calls Jack a good kid and goes so far as to bake him a birthday cake. Dean admits that he's trying, but what Jack did isn't easy to forget though Dean isn't as angry as he once was. Billie later reveals to Dean that it is Jack's need for Dean's forgiveness and the belief that he will only gain it by killing God that is driving Jack's sacrificial actions. Despite clearly being upset, Dean feels that Jack sacrificing himself is their only way to be free. In addition, Billie tells Dean that it is now up to him to guide Jack through the final steps in his destiny to kill God and Amara.

As the time approaches, Dean tells Sam that he doesn't consider Jack family anymore, not like Sam and Cas, something which Jack overhears and Dean makes a point to apologize for. Though he is willing to sacrifice Jack when the moment comes, Dean is shown to be one of the most desperate to save Jack when he realizes that there is a chance to do so.

After Jack's near-death and almost sacrifice, their relationship improves again with Dean excited about sprucing up the bunker for Jack after he becomes the new God and upset to learn that Jack won't be coming back. Dean later admits to Sam that he misses Jack and doesn't correct Bobby Singer when he calls Jack Dean's kid. This suggests that ultimately Dean forgave Jack and has come to see the young Nephilim as his family once again.

After Dean's unauthorized actions in the Monster Club Universe, Jack is annoyed that Dean broke his rule of no interference and Dean challenges him to throw Dean out of Heaven if he must. However, Jack relents and lets Dean finish what he started, even providing Dean with his journal and the Colt to give to his parents. When Jack first appears with Bobby, Dean identifies him as family to the Monster Club.

Season 13[]

When Jack was finally born, Dean's first response was to shoot him, only for Jack to unleash his powers in self-defense and knock Sam and Dean out. Dean's opinion on Jack didn't improve as he began hunting for the Nephilim. His distrust in Jack contrasts Sam's softer opinion, likely due to Dean's grief caused by losing Castiel again.

Dean does however, give Jack's mother a hunter's funeral alongside Castiel.

Jack soon learns that Dean still doesn't like him and makes a clear effort to emulate Dean in order to appear more likable. Dean is both annoyed and distrustful of Jack. Dean eventually admits to Jack that should Jack go dark side as Dean anticipates, he'll kill Jack himself.[1] Jack overhears an argument between Dean and Sam in which he learns of Dean's negative feeling stem from him blaming Jack for the death of Castiel. In turn, Jack sometimes believes he is evil because of Dean's words, but Sam does his best to cheer Jack up.[2]

He manipulated him. He made him promises, said paradise on Earth, and Cass bought it and you know what it got him? It got him dead. Now you may be able to forget about that, but I can't!
— Dean's initial opinion on Jack
The Big Empty 15

Jack on a case with Sam and Dean

Soon, Jack tells Sam of Dean's promise to kill him, even thinking he might be right about his ways. Jack continues to long for Dean's approval while Dean chooses not to baby him and make him do some of the work during cases, or in Sam's words, treat him like an intern. When Jack becomes dismayed by the lack of approval from the elder Winchester and keeps thinking about Dean's promise to kill him, Sam informs Jack that he can earn Dean's approval through effort, something Dean respects.

While confronting the shapeshifter Buddy, Dean and Jack are both chained up though Dean orders Jack to use his powers to free them. Jack, afraid his lack of control over his own powers may hurt Dean, refuses to obey the order. Jack instead uses his powers to prevent Buddy from shooting at Sam, which gives Sam the opportunity to shoot Buddy, thus solving the case they were working on. Afterwards, Dean praises Jack for his efforts and acknowledges that he finally did good as Jack smiled to himself at this praise.

With Castiel's resurrection and return, it appeared Dean gave up some of his disdain for Jack since he had partial role in it and he listed Jack as a member of the team. Dean even counted him as a member of Team Free Will and humored Jack on a hunter case but was ready to go along with as it allowed him to act like a cowboy. He was also surprised that Jack was right about it being a case though the monster was something else. Jack wanted to be useful and tried to help Dean by using his powers though unintentionally killed an innocent. Rather than scold Jack, Dean instead told Sam and Castiel to take him back to the Bunker while he deals with the threat. After completing the case, Dean even covered for Jack by putting the innocent's death on the monster. Jack was shown not to accept this and broke down that he might actually be evil but Dean said he wasn't as he admitted that he was wrong in thinking he was.

Jack: I was scared, I was upset, but why would I look for him? He's no one to me. You, Castiel, you're my family.
Dean: Yes, we are.
The Bad Place 03

Dean and Jack reunite

After learning that Jack apparently killed Derek Swan, Dean discussed killing him for it with Sam. However, Dean admitted that he actually liked Jack and saw it as a worst-case scenario that he must be killed. Once they found him, they confronted Jack over his action but he was revealed to be innocent and told them his true intention were to find their mother, which he was able to do letting them know their mother is still alive. When Jack called the Winchesters and Castiel his family, Dean instantly agreed that Jack was family. Dean then praised Jack's initiative in trying to rescue Mary as the latter smiled at his words. Dean continued to be this way when Jack refused to join the angels and wanted to stay with them instead.

During Devil's Bargain, Dean and Sam are told by Castiel that Michael of that world intends to invade. Dean realized Jack and his mother are in danger and they decide to capture Lucifer and open a rift to enter the Apocalypse World to save the pair. Dean shows he still sees Jack as part of the family.

In Good Intentions, Jack chooses to help defend Bobby Singer's colony from Zachariah and his angels because he knows its what Sam and Dean would do. He also knows that Sam and Dean would stay and fight and chooses to kill Michael to protect the people of Apocalypse World.

In Beat the Devil, Dean and the others open a rift and travel through Apocalypse World.

After finding Mary who takes them to a camp, Dean reunites with Jack and both witness Sam's return as well as the arrival of Lucifer.

In Exodus, Dean told Jack to not approach Lucifer as he didn't want Jack to turn evil.

During Let the Good Times Roll, Jack had a nightmare but Dean came in his room to comfort him on this and told him they were family. Jack went on more cases with Dean and the others. The bunker was attacked by Michael and Jack was alerted of this by Sam's prayer. He arrived in time to save Dean from nearly being strangled to death by Michael and almost acted on his promise to kill the Archangel but was prevented when Michael revealed his deal with Lucifer. Jack was later horrified to watch Michael take full control over Dean after he managed to kill Lucifer. Weeks later, Jack's frustration over his lack of powers is also attributable to him not being able to do anything to help Dean.

Season 14[]

During Gods and Monsters, Jack is still worried about Dean's possession. Jack is shown to have a rational side such as telling Castiel that to stop Michael, then Dean had to die since he knew the latter wouldn't want to suffer from Michael's influence.

During The Scar, Jack is reunited with Dean who he is happy to see and hugs out of joy but questions him on what became of Michael. While talking to a girl who was cursed that asked if Castiel was his father, Jack responded that he was one of them. This means he sees Dean as one of his father figures as well.

In Unhuman Nature, its confirmed that Jack and Dean's relationship has evolved to that of a father-son relationship. Sam tells Castiel that Dean has never forgiven himself for threatening Jack in The Rising Son and Castiel compares Dean's impending loss of Jack to a father losing a son. In order to help Jack get enjoyment out of his remaining days, Dean teaches him how to drive using the Impala and Jack has Dean take him fishing, something that Jack knew was the one thing that Dean had enjoyed doing with his own father.

In Byzantium, Dean is so devastated by Jack's deteriorating condition that he has to leave the room when Jack tries to comfort him and is further devastated that Jack dies while he's gone. While trying to get Lily Sunder to help save Jack, Dean explicitly calls Jack his son, asking Lily to not force them to go through what she did when she lost her child. Dean's impassioned plea succeeds in convincing Lily to help them save Jack who is happily embraced by Dean upon his resurrection.

After Jack accidentally kills Mary in Game Night, Dean reverts back to his original opinion that Jack is a monster that needs to be killed, albeit only because Jack no longer has his soul. Though Dean advocates for first locking Jack up in the Ma'lak Box and then killing him, Dean is clearly not pleased to have to do so though he finds it necessary and is driven at least partially by a need for revenge.

I understand. I know what I've done. And you were right, all along. I am a monster.
Jack to Dean
in Moriah

In Moriah, Dean prepares to kill Jack with a gun supplied by God despite the fact that it will also cost Dean his life. Dean refuses to be dissuaded, even by Sam who points out that Jack is in this position because he burned his soul up killing Michael to save them. When the time comes, Jack accepts his fate and even tells Dean that he was right all along and Jack is a monster. However, when it comes down to it, Dean is unable to kill Jack, even when God offers to resurrect Mary if he does so. God compares Dean killing Jack to a father killing his son and is enraged by Dean's refusal to do so, finally killing Jack himself. Dean is left devastated by the loss of Jack alongside Sam and Castiel, but is left with no time to mourn due to God unleashing chaos upon the Earth.

Season 15[]

In Back and to the Future, Dean proves more willing to work with Belphegor than Castiel despite the fact that the demon is using Jack's corpse as his vessel. Dean tells Belphegor that Jack was their son, "sort of" and that Jack didn't deserve what happened to him.

In The Gamblers, Dean is reunited with the resurrected Jack. After Sam hugs Jack, Dean grabs Jack and pulls him close to look Jack in the eyes, clearly pleased to see him again though Dean doesn't hug Jack. While talking with Jack about what has been going on, Dean shows none of his former anger towards Jack though he is surprised to learn that Jack can become powerful enough to kill God.

In Destiny's Child, though Dean remains cordial to Jack, their relationship is shown to be more distant than before, something that Jack recognizes is because Dean is still angry at him over Mary Winchester's death. Even soulless, Jack is shown to still care about Dean and his opinion of him and asks Castiel if he thinks he will ever earn Dean's forgiveness. Castiel suggests that with time, Dean may in fact be able to forgive him. When Jack's soul is restored, many of the memories he reexperiences include his relationship with Dean such as Dean teaching him to drive and them fishing together when Jack was dying and Dean aiming the Equalizer at him. When Jack expresses remorse for killing Mary and begs them for forgiveness, Dean is left speechless, particularly after Castiel explains that Jack's soul is back.

Okay, I'm just gonna say this, okay? Just get it out there. Jack. I'm trying okay? I really am. But what you did... that's not easy to forget. Now, I was angry with you... for awhile. And maybe I still am a little bit, okay? But I'm not gonna let some evil Mary Poppins take you out. Do you understand?
— Dean to Jack
in Last Holiday
Last Holiday 03

In Last Holiday, Dean's relationship with Jack appears to have improved since Jack got his soul back, though Dean isn't as close with him as he once was and Jack remains somewhat distant as he deals with the return of his soul and all that comes with it. However, Dean calls Jack a good kid to Mrs. Butters and they work together to escape and stop the wood nymph. Though Mrs. Butters expects Dean to help her kill Jack with the archangel blade, Dean refuses without hesitation and is instead upset that Mrs. Butters ruined the good thing that they had going by trying to kill Jack. While imprisoned together, Jack asks if Dean still thinks he's a monster. Dean explains that he's trying, but what Jack did isn't easy to forget. However, Dean is no longer as angry with Jack as he had been and he doesn't intend to let Jack get hurt. While working together to escape, Dean and Jack appear to have a moment more reminiscent of their old relationship when they both become excited by Dean's new plan to escape. Dean tells Mrs. Butters that Jack has to save the world and later bakes Jack a birthday cake.

In Gimme Shelter, Dean encourages Jack and Castiel to take a case while he and Sam are out searching for Amara, displaying a friendly attitude in the process and recognizing that Jack doesn't want to remain in the bunker alone after the Mrs. Butters situation. However, Jack later tells Castiel that he's convinced that Dean and Sam will only forgive him after Jack sacrifices himself to end Chuck and Amara.

I told him the truth. Jack killed your mother and all he wants is your forgiveness. And I surmise that the only way he can get that is ending God and freeing you from the... What did you call it? Hamster wheel. Was I wrong?
Billie reveals Jack's motivations.
in Drag Me Away (From You)

In Drag Me Away (From You), Dean is revealed to be aware of Jack's destiny to die killing God and Amara, having been informed of the truth by Castiel against Jack's wishes. Dean questions Billie on how she got Jack to agree to sacrifice himself and she explains that Jack is desperate for Dean's forgiveness for Mary Winchester's death. Billie surmised that Dean would only forgive Jack if he killed God freed Dean from being trapped in God's "hamster wheel." Dean doesn't respond to Billie's question about if she was wrong or not and she tells Dean that it is now up to him to help guide Jack since Chuck's book shows that Billie has no further role in the coming events until the end.

Dean later tells Sam the truth about Jack's coming death. While Sam is devastated and angry, Dean feels that it is the only way for them to ever truly be free even if it mean sacrificing Jack. However, while talking with Billie, Dean admits that he doesn't like every part of the plan despite believing it to be necessary.

Unity 07

In Unity, Dean continues with the plan against Sam's objections. When Sam reminds Dean that they don't give up on family, to Sam's shock, Dean tells him that Jack is not their family. Dean admits that he cares for Jack, but he states that Jack is not like Sam or Castiel, unaware that Jack is standing behind him and hears the whole thing. Dean tries to apologize to Jack a few times before pulling over and explaining himself, thanking Jack for what he is about to do. Their conversation is interrupted by a message from Castiel that Amara is holding Chuck at the bunker and that the time has come.

As Jack is in pain from the effects of being turned into a bomb, Dean supports him as he leads Jack through the bunker to the room where Chuck and Amara are waiting. In his rage and need for revenge, Dean is more than willing to sacrifice Jack which God reveals to Amara is what he was counting on: God's ultimate ending for the Winchesters is for them to kill each other over the plan to use Jack as a suicide bomb. However, Sam succeeds in talking Dean down, but Jack collapses as he begins to detonate.

In Despair, Dean is desperate to save a detonating Jack, stating outright that they're not giving up on him and ordering Sam to try to find a solution in Rowena's Journals. Billie appears, angry that they failed to go through with the plan and teleports Jack away as she can't stop the detonation.

After Billie reveals where she sent Jack and that he potentially survived, Dean reminds Billie that she told them that it was a suicide mission, but Billie points out that she only told them that it would be fatal. Dean and Castiel demand that Billie bring Jack back, but she refuses without the return of Chuck's Death Book. After Sam reluctantly gives Billie the book, Dean impatiently demands Jack's return. After Billie attempts to take Jack with her, Dean leaps to Jack's defense by grabbing Death's Scythe and attacking Billie with it, wounding Billie and forcing her to flee without Jack, the book or the scythe. Unlike Sam and Castiel, Dean doesn't immediately rush to Jack's side, but that's because he was flung across the room by Billie and had to recover from it.

In Carry On, Dean admits to Sam that he misses Jack. After going to Heaven, Dean is impressed and proud of the changes that Jack has made. Bobby Singer calls Jack Dean's kid while they talk and Dean doesn't say anything to the contrary, suggesting that Dean ultimately forgave Jack and came to see the young Nephilim as his family again.

The Winchesters[]

They're.. they're with me. This is Bobby and that's Jack. They're family.
— Dean introducing Bobby and Jack to the Monster Club.
in Hey, That's No Way To Say Goodbye

In Hey, That's No Way To Say Goodbye, when Jack appears in the Monster Club Universe with Bobby Singer, Dean introduces them both as family to the Monster Club. However, Jack is displeased that Dean broke his rule of no interference by nudging the Monster Club along to fight the Akrida. Dean angrily tells Jack that he can cast Dean out of Heaven if he wants, but the Akrida threatened both their universe and Sam who is still alive. After Bobby backs Dean up, Jack relents, recognizing that there is always another case for hunters even in death and in a more lighthearted moment, quips that "after this... it's time to get around to the "there'll be peace when you are done" part of the song." Jack also not only allows Dean to finish what he started, but he gives Dean his journal and the Colt to help Dean out.


  • Dean and Jack's relationship resemble that of Dean's relationship with his own father.
    • This is further seen, as Jack is considered by many characters to effectively be Sam and Dean's son, though Mary Winchester also called Jack her son in Unfinished Business. Rowena once stated Dean was one of Jack's "three fathers". In Byzantium, Sam and Dean outright call Jack their son and God compares Dean killing Jack to a father killing his son in Moriah. Ironically, the Winchesters had started out trying to stop Jack from coming into existence and Dean was the most against and threatening towards him but became the closest to Jack. In turn, despite their rocky beginnings, Jack sought Dean's approval and support.
    • In Ouroboros, Jack referred to himself as a Winchester.
    • In Carry On, Bobby Singer calls Jack "that kid of yours" while talking to Dean.
  • Both Dean and Jack have done similar acts.