NEVER WRITE FOR SUPERNATURAL! OR PUSHING DAISIES! BECAUSE YOU HAVE CRUSHED MY HEART INTO TINY LITTLE PIECES OF TINY CRUSHEDNESS!
I can name two Dean or another person instances, but I can't think of the third, or the "something intervenes and as a result someone else dies". Regardless, he does have massive "I'm supposed to be dead" issues, which, along with Sam being the only family he has and the whole "Your one job in life is to take care of Sam!" childhood indoctrination, was a big part of why he sold his soul.
There was also Dean being tired, and not thinking he was allowed to stop otherwise.
God, if it wound up being Bobby, that would break Dean. And Sam would be all "You wanted to throw away your life for me!" pissed off, plus have issues of his own, so he wouldn't be good at comforting Dean's massive guilt.
Plus, AAAAH, BOBBY! BOBBY IS NEVER ALLOWED TO DIE!
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I can name two Dean or another person instances, but I can't think of the third, or the "something intervenes and as a result someone else dies". Regardless, he does have massive "I'm supposed to be dead" issues, which, along with Sam being the only family he has and the whole "Your one job in life is to take care of Sam!" childhood indoctrination, was a big part of why he sold his soul.
There was also Dean being tired, and not thinking he was allowed to stop otherwise.
God, if it wound up being Bobby, that would break Dean. And Sam would be all "You wanted to throw away your life for me!" pissed off, plus have issues of his own, so he wouldn't be good at comforting Dean's massive guilt.
Plus, AAAAH, BOBBY! BOBBY IS NEVER ALLOWED TO DIE!