What do you think Mary's hunt for Azazael would have looked like compared to John's? I mean, she has the hunter background he lacked, but I'm not sure how much she could have done differently.
this is an amazing question.
i know we’ve already been talking about it a little bit in this thread here, but the idea is so great that it definitely deserves an actual considered response on just this topic. standard disclaimer that we don’t know anything about her, everything is equally valid, etc, whatever.
i don’t know how much mary’s hunter background would’ve really changed things, in the long run; john did manage to develop an unbelievably extensive list of connections, to the point where i feel like we could get an ep where dean and sam get a call from another “old hunter buddy” of john’s and it wouldn’t be out of place at all way out in s11.
i feel like mary’s background might show itself in different ways. like, for john everything is a fairy tale, so tracking down the mystical ~gun that can kill anything~ doesn’t seem all that different from tabulating demon signs. but samuel wrote off the colt as a myth, and mary might too, so actually facing down azazel might be harder for her than john. which reminds me, also, of john’s extremely meticulous approach to hunting, which seems like another personality difference. would mary have been able to work out the pattern? of course, she does have more information than john to start with, that she’s looking for a demon, where all john had to go on was the yellow eyes.
what mary did have that john didn’t have was the example that it was possible to hunt from a home base. there are probably unspoken drawbacks to having a home base, and i don’t know how feasible it would be with her being a single mother (samuel and deanna could’ve traded off hunting shifts when she was young), but i actually love the idea that mary would start looking for revenge for john and still try to keep it from sam and dean.
anyway the angels wouldn’t have that, and sam and dean would inevitably find out, and where sam and dean’s conflict with john was that he pushed them into hunting, i think their relationship with mary might strain under her refusing to let them hunt with her. (this is a great set-up for a reverse!verse featuring lucifer!dean and michael!sam, where dean longs to be able to protect his mom and sam is annoyingly always reminding him that it’s good that they get a normal life, that mom’s trying to keep them out of it.)
and of course, the psychological weight of her spouse’s death has reason to weigh on her even more heavily than it did on john–john drowns himself in alcohol and child neglect, so what does mary, who doesn’t just lose her husband and the normal life he represented but knows that it’s her fault for making the deal do? and how does she treat sam? in “home” she tells him “i’m sorry,” so she already knows that whatever azazel was planning, it’s to do with sam. does she treat him differently? if sam grew up shielded and sheltered (in a way) by john and dean, is he always able to feel his mother’s wariness of him now?
that dean raises sam is integral to defeating lucifer. so does this world just burn or do sam and dean’s all-new, still-terrible emotional scars balance out again? i feel like dean and sam would definitely have complexes about the idea of the “normal life,” even more than they do right now. if sam grows up thinking that the normal life is only for people who deserves it (and convinced, of course, that he’s unclean), maybe he never leaves hunting to pursue that for himself, maybe he thinks he doesn’t deserve it. does dean long for ben and lisa, or is he afraid of them, afraid of what losing john did to his family? when dean has a year left, does he keep hunting, or does he try to get out, try to experience what that mythic dream of suburbia feels like before he dies?
i like the way you played out the idea of mary letting dean die, because there is so much angst potential in that idea–what happens when dean comes back and realizes his mother didn’t make a deal for him, the way he’d be willing to do in a heartbeat for any member of his family? and she definitely has good reason to NEVER BE WILLING TO MAKE A DEAL AGAIN. EVER. but say that hell doesn’t want her anyway. so if the reason that azazel deals for john’s soul in s2 is because either john or dean could break the seal (righteous men), maybe mary, with lucifer blood, wouldn’t be asked to deal anyway.
so maybe it’s mary (or sam) who’s gravely injured by that truck, and it’s dean who makes that deal. or maybe mary dies at the beginning of s2 and life continues on until dean deals to save sam at the end of s2 because he can’t lose any more family. but i kind of like the scenarios where mary lives or gets resurrected, because she would be fucking furious. she’d make the last year of dean’s life hand-to-god hell. the last deal (her deal) they dealt with killed john. and of course this is her worst fear taken to an extreme, right? her son’s a hunter–he wouldn’t have known how to do this thing if he hadn’t been–and now he’s sold his soul. hopping spitting mad.
i also like the mary lives au au for a different reason, because i think mary would feel the exact opposite towards angels as you do. maybe her faith’s deteriorated in the last few decades, after the angels didn’t stop john’s death. or maybe it hasn’t. mary’s overtly religious/spiritual, as you say, and maybe she’d be easier to manipulate, the way sam is more susceptible than dean right up until uriel tries to bomb a town right off the map.
all in all this is a pretty horrible picture and everyone is probably better off if whatever parent the boys have left just kick it at the beginning of s2, but i actually think the mary lives au au might work itself out. linking that thing i wrote about vessel descent has made me think–what if sam is the true vessel, but to save him, mary says yes? and the scene in “swan song” is one of reconciliation and actual parent-child love (instead of pseudo-parent-child love) from mary to her sons? we even know what she’d say when she’d sacrifice herself to do away with the horrendous evil! “i’m sorry.” jesus, this is fucked up and somebody ought to write it