so the first seal shall be broken when a righteous man sheds blood in hell.
and i want to postulate on this concept of the righteous man. both john and dean are considered by this prophecy to be "righteous men," and of course they are both candidates for michael's vessel. it's in their blood.
but at the same time, this is a destiny that must still be fulfilled. action is required to create a righteous man—aka, they have to be sent to hell in the first place. they have to become worthy of being michael's vessel through their participation in starting the apocalypse.
john dies in 201. he's at peace; he's accepted the terms of his deal, and he's accepted his fate. his soul and the colt for dean's life.
there are two conflicts presented across season 1:
the first is on the topic of revenge. ultimately, the conclusion is that revenge is pointless, it will lead to no positive outcome—the past has already happened, and once blood is spilled there's no getting out of it, no stopping. knowing what happened to her brother didn't make kathleen feel better about his death. max killing his family didn't make his pain go away.
the second is on the topic of family. it's a more subtle theme, i guess, suggesting that family will invite destruction to everyone around them. the tagline "the good of the many outweighs the good of the one" is proven to be erroneous and ruinous: by choosing the family, by choosing to protect loved ones, great harm will inevitably come to the outsiders. we see this foreshadowed in 111; we see this exemplified when dean shoots and kills an innocent man in 121.
so choosing revenge and choosing family are both bad choices. but the conflict of season 1 is revenge vs family—sam as the protagonist has to choose one or the other. he's not given a third option.
john, however, finds that third option. he abandons his quest for revenge by relinquishing the colt to azazel, and he abandons his family by sacrificing himself. the act of sacrifice is seen as a selfish one (see: crossroad blues), one committed by a man who cares more about his own feelings than that of the person he saved. this is the recurring narrative throughout seasons 2 and 3—it's not something that john did for his son, it's something he did for himself. and in fact, his act of sacrifice puts sam and dean in more danger by leaving them without a weapon to combat azazel and without any of john's knowledge about the demon or sam's fate.
he doesn't choose revenge. he apparently doesn't choose family. he found the third option: he removed himself from the story.
so he managed to choose both "correct" options: he avoided ruin by abandoning his revenge, and he avoided ruin by abandoning his family. and he went to hell.
he became a righteous man, set to break the first seal to the apocalypse.
dean ends up following these exact steps at the end of season 2—the difference is that doing so is dean's fate and not necessarily john's. the other difference is dean is not at peace with his decision to die. john went to hell but he had accepted it. he was ready and willing to go, and he took what was given to him. even in all hell breaks loose, he's happy and serene in death, in hell. it's his commitment to his actions that separate dean and john.
but dean, through sam's influence, second-guesses himself, and his own shame and hypocrisy stir within him doubt and uncertainty. he doesn't want to die; he doesn't want to go to hell. when he gets there, he screams out for sam, wanting to be saved.
dean breaks. john doesn't.
obviously dean going to hell and breaking the seal was part of his destiny—that much is obvious. but i think it's important that it's dean's actions and decisions that lead him down that path, that he's not a passive receptor for his fate. it doesn't happen to him; he chooses it. sam has to act and decide in order to fulfill his destiny, so dean should be beholden to that same thing. which is why i like this interpretation that it's this selfish sacrifice that creates a righteous man—by dean's own hands he creates his destiny and starts the apocalypse.
john was able to escape this because he's not faced with the same conflict dean is. he's able to find peace and take himself out of the story, choosing both "correct" options and being okay with those decisions. dean makes those same "correct" decisions as john (in dean's case, the conflict he is given is not revenge vs family but duty vs family, and he abandons his duty and his family all the same), but he lacks the conviction that john has. he can't remove himself from the story, he's filled with doubt and unresolved tension, he can't let go fully. there is no peace in dean's story, and the righteous man broke.
and as he breaks, so shall it break.
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