“john winchester did the best he could to raise sam and dean while being part of the life” john winchester burned his bridges with nearly every hunter he came across so severely that it led to sam and dean being almost completely isolated from the hunting community
dean: “what, was there an article in the demon hunters quarterly that i missed?” (2x02)
sam and dean, outside of the few friends john managed to keep over the years, have no connection to other hunters. john found out about the supernatural by himself; there was no hunter there to give him the truth is out there speech, mary died and over the next few weeks, he went looking for answers until he found missouri who filled in the blanks for him. but missouri isn’t a hunter so he was still by himself figuring it all out. he didn’t have a partner, a teacher; he entered this new world by himself and had to figure it out on his own, all with his personal vengeance that he didn’t want anyone else’s help in getting. he had a chip on his shoulder
and he raised sam and dean in a mimic of that isolation
throughout s1, we get a few name drops of people sam and dean reach out to to ask for help - caleb, who john goes to for ammo, jefferson who we never see, (1x10) and pastor jim who young dean is told to call if john doesn’t come back from the shtriga hunt and who he leaves them with after sam is hurt (1x18) (but that could be because of location since he lived three hours away from where they were). these are people john himself calls “our friends” (1x21). we also meet travis in 4x04 who they seem to have been close with - enough for him to know sam used to be a mathlete and for sam to doubt travis being unable to find someone - but haven’t seen for at least 10 years for an unknown reason. they are also, importantly, around john’s age; they’re his peers, people who have around the same level of knowledge as him
we also see a few people he never introduced them to; chiefly, missouri and daniel elkins. people who are older than john and people who are great sources of information when it comes to hunting. experts you could even call them. it’s even implied elkins was the one to teach john about the life because he has a journal just like john’s and leaves a message dug into the floor of a p.o box “just the way dad does it” and john himself says he taught him a lot about hunting (1x20)
at some point, john meets bobby and they go to his house in between some hunts. but they lose that safety, and bobby himself, all because of john. john and bobby have an argument and john takes them away from one of the few constants they have and they don’t feel secure enough in their welcome to reach out to him again until they decide the situation is life-threatening enough. but crucially, not life-threatening to them; they stayed away when sam started getting his visions, when dean was dying in 1x12, even throughout the whole season looking for john. it was only when they thought john would die if they didn’t do something more, when they were out of their depth and needed help, that they tried to reach out to bobby
(dean: bobby, thanks. thanks for everything. to tell you the truth, i wasn’t sure we should come
bobby: nonsense. your daddy needs help
dean: well, yeah, but last time we saw you, i mean, you did threaten to blast him full of buckshot. cocked the shotgun and everything
bobby: yeah, well, what can I say? john just has that effect on people (1x22))
john raised them to only trust each other, to only have each other’s backs. he kept them on the move, never putting down roots or building a connection with the people around them; he certainly never tried to introduce them to the community he knew existed. and he couldn’t even say that he didn’t know because he used to be close with ellen and bill. ellen and bill who ran the roadhouse. a place known to have hunters pass through. a place sam and dean have never heard of because john decided his feelings meant more than their safety
he never even mentions bill and ellen, not to sam and dean and not in his journal, because of his guilt over not saving bill and not wanting to face ellen, who by her own admission felt john “was like family once”
(he was probably seeing them as his own mirror; a partner and parent taken away and he couldn’t save them so now he’s doomed them to his life, never mind that it wasn’t the same circumstances and they were all aware bill could die hunting. he let his trauma and his guilt override ellen’s autonomy and decided to end their relationship so thoroughly he never even mentioned them again for at minimum a decade)
because of that, he also never mentions the roadhouse to sam and dean. but the roadhouse isn’t the only place of its kind; gordon says “look, you’ve got your roadhouse connections, i got mine” (2x10) and ellen says the roadhouse is full of other hunters with their own connections. there are places hunters can go to buy and exchange information, ask advice about difficult cases, just rest knowing there’s other people in the room who can watch your back even if you don’t trust them. they never know those hubs even exist. all because of john
he taught them the family business; he made them feel like they were the only people in the world capable of saving people, placed the fate of everyone on their shoulders and their’s alone; “‘course i know what you’d say … your happiness for all those people's lives, no contest. right? but why? why is it my job to save these people? why do I have to be some kind of hero? what about us, huh? … why do we have to sacrifice everything, dad?” (2x20)
the first thing we hear ellen say is “john, it's ellen. again. look, don't be stubborn, you know i can help you. call me.” she is begging to john to listen to her because she knows something that can help him kill the yellow-eyed demon. and john knows that, which is why he keeps the voicemail
but he didn’t want someone else to figure out how to kill the demon; he didn’t want someone handing his revenge to him. he wanted to do it by himself which is ultimately why he abandons dean and sam over and over again; he can say whatever he wants about keeping them safe and how dangerous the demon is - which dean literally calls out as a bunch of crap - but the real reason was because he wanted to do it by himself
because he was a selfish man; mary was his wife, the mother of his sons, and this is his pain
“you ever notice dad had a falling out with just about everybody?”