it's occurring to me that i haven't ever made a post laying out my thoughts on this so here goes:
i think john winchester was homophobic.
but that's the thing about the 1980s and 90s. like.... everything was homophobic. the TV was homophobic, the radio was homophobic, the government was homophobic, the schools were homophobic.
john was raising his kids during the height and aftermath of the aids crisis. even being about 10 years younger than dean and being raised in a blue state, the water i was swimming in was homophobic. every adult in my life was homophobic and they weren't even marine vets who *volunteered* for vietnam (read: heavily correlated with conservative views)
i think sometimes being in the 2020s when so much has changed (but not enough!) is that most of the homophobes I encounter these days are virulent. they're clinging to a hateful ideology with fervor even as it slips out of the cultural norm. they're vocal; they're saying slurs; they feel strongly; it's a big part of their personalities.
now, i don't think that's john winchester.
but it doesn't have to be. in order for john not to be raising his kids in a homophobic environment, he would have had to be intentional pro-gay counter talk. and he wasn't doing that. that requires an amount of care and attention to his kids' environment and emotions that john was demonstrably, canonically just not doing.
i don't see john going on big anti-gay rants and i don't necessarily see him threatening to kick dean out forever if he caught him with a boy. but we know he *would* kick dean out for some stuff so i'm not ruling out some kind of isolation based punishment. but like john doesn't have to be Big Homophobe by today's standards. he was just raising his kids absolutely horribly during a time when homophobia was a fucking cultural cancer.
all it would take to make john a homophobic parent is one or two comments from him - not even about dean or sam - but about gay people in general or some news story or some hate crime and boom, he's shown himself aligned with the culture. and the culture is homophobic.
that feels obscenely plausible to me.
dean was 15 when don't ask don't tell became the law. and that *incredibly homophobic* law was actually an attempt at reducing the amount of homophobic policies in the us military*. and you learn a hell of a lot before you're 15.......
and this is all stuff i think without taking into account most of supernatural and analyzing the behaviors of dean closeted winchester. i think there's a lot of reasons why dean's closeted. and he's not just about his sexuality but about so many of his other desires and wants - like his desire for a family, or a peaceful life not hunting, or feelings of worth beyond what he can offer of himself to other people. and i can tell you right now john had a big impact on dean not getting - and not feeling like he could even vocalize wanting - those ones. the sexuality part just doesn't even feel like a leap.
*don't reform the us military, disband it!