Can't Keep a Winchester Down
From one demon, older and wiser, to a recently appointed Crossroads demon.
"Sweetheart, I know you're young and kinda new at this, but lemme give you the one basic rule of Hell: You can't keep a Winchester in the Pit."
"You heard me. It's been tried. Multiple times, with multiple Winchesters. And one way or another, they always get out. Does it mess 'em up? Yeah. Do they let themselves get carried away while they're down here? Hell, yeah. Does that stop 'em from finding some way to get out and get gone? Never."
"Well, obviously it wasn't done right before. Whoever brought them must not have-"
"I'm gonna say this once, girlie; Don't ever underestimate them boys or their pa. You wanna know who has? Well, here's the short list.
"Several pantheons' worth of pagan gods and goddesses, Azazel, Lilith, Ruby, Meg, Zachariah, Loki who also turned out to be Gabriel, Raphael, Crowley, War, Famine, Pestilence, the Mother of All, hell, even their own grandpappy, old Samuel Campbell. You know where all of those folks are? Dead. Or their existence is just entirely gone, wiped out like it was never there.
"And it ain't just Hell that can't keep their hands on the Winchesters. Death and Fate are getting damn tired of the boys constantly unraveling their carefully laid plans, and Heaven is a place they've visited far too often without actually sticking around.
"By our count, Samuel's died something like 12 times. And as for Dean, that boy's in the triple digits at this point. And, like I already said, it never stuck.
"Most of the supernatural things in existence have a hate on for those boys, and their heads are always gonna be number one on any monster, demon, or angel hit list. But they are still running around, saving the day against impossible odds, and not letting any damn thing control them or decide their fate.
"So you may have one of 'em on the hook right now, and it don't matter, 'cause I can promise you they'll wriggle off it somehow and leave you with nothing."