I was just re-watching Season 5, at the back of my head thinking about how Sam could have come back as himself, when they meet Jesse.

Jesse, more commonly known as the Anti-christ, can make things happen just by believing in them. As he matures, I'm sure that he'd develop his ability further to be able to do really anything he wants. As Cas puts it, he could wipe out the angels, so what makes pulling Sam out from hell impossible?

At the end of the episode, Jesse has become friends with Sam and Dean, so if somehow he caught wind that the guy who helped him was stuck in Hell, he might be inclined to save him, no? Just my two cents. Could just be reaching too far