the righteous man shedding blood in hell - that's gotta be rare in and of itself..
if the final seal has to do with Sam, then they needed a righteous man with a relative that might go evil and break the final seal..maybe Dean (or maybe John) wasn't the first righteous person to ever sacrifice themselves to end up in hell..so either plenty of other people never broke, or they need someone with the right family members (evil Sam) for the final seal...
now, i'm more confused than the first time i thought about it...so many possibilities..

How would Azazel have known back then? Dean wasn't even born and Azazel had never even heard of Mary before. It's possible he formulated a plan after having met Dean- but still, how could he possibly know that Dean had been in hell, much less that he was the righteous man? He certainly didn't act like he thought Dean was at all important. Just like he's always acted. He's never been interested in Dean- only Sam.

fanfly, i knew you would disagree :D
great comments!

lol Not that it's totally out of the realm of possibility! I just can't see the possibilities right now. Because remember- YED John almost killed Dean in Devil's Trap. Why would he do that if he needed him in hell? Dean hadn't sold his soul yet- or John for that matter.

i think it's possible but...i don't think the breaking of the seals is what YED had in mind...that plan i think belongs to lilith alone.

good point fanfly!
but i'm thinking how many righteous men could there be who also happen to know how to summon a crossroads demon and strike a deal? gotta think the idea of a truly righteous man in hell would be a rare thing indeed

idk, lucy- That guy in Crossroad Blues- the one who sold his soul to cure his wife's cancer? Wouldn't he qualify as a righteous man? I don't think that it's so uncommon and would in fact be easier to trick a righteous non-hunter into selling his soul than a righteous hunter. Also seems like they'd be easier to break too.

yeah, you're right..i'm not arguing with that :D

Some people do believe that demons can move up and down the timeline, but I got the impression that Azazel really didn't know who Dean was.

As for there possibly being plenty of other righteous men in Hell, that's part of my argument as to why John was never tortured nor intended to break the seal, nor had anything to do with Lilith's plan in the first place. The angels would have had to intercede every time on a "just in case" basis. As soon as they found out why Lilith wanted Dean, they fought their way through Hell to save him. I think Dean was the first. :D

Wow lucysmileyface your mind can make take things way farther than mines can. (In a good way though)

I think he had a plan but not with Dean. I think he was more into Sammy (not in that way though or maybe he was I don't know XD) I don't think he had much to deal with Lilith either because she wasn't really suppose to be in charge now. Remeber Sam and the other Pyshic kids where suppose to be the leaders. Lilith came later because she was the runner up.