It's not Dean dying, he's been resigned to dying in the fight for a long time. It's something awful happening to someone else, probably Sam, and probably not a clean death.
Guesses: Somehow Lucifer shows up again and Sam has to say yes to Luci to take out Michael? Jack saves the world by burning out his soul and now he is the soulless big bad that Dean has to take out?
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It's not Dean dying, he's been resigned to dying in the fight for a long time. It's something awful happening to someone else, probably Sam, and probably not a clean death.
Guesses:
Somehow Lucifer shows up again and Sam has to say yes to Luci to take out Michael?
Jack saves the world by burning out his soul and now he is the soulless big bad that Dean has to take out?