Here’s the thing: Sam was going to feel like a monster (a freak, an outsider) even if he’d never met Ruby.
Sam and Dean fit perfectly into sibling birth order roles people talk about when they talk about dysfunctional/alcoholic family dynamics. Dean is the Hero: his role, from the moment their mother died and John started taking them hunting, was to be the model child, to do things right and follow in his father’s footsteps. He downloaded John’s values system and priorities pretty much word-for-word and took it as his own. He acted as John’s proxy when John was away, he was
expectedrequired to be competent and responsible at an incredibly (inappropriately) young age. As long as he was there being successful (according to John’s values system: defending his family, saving people, hunting things, etc.), John could pretend the family was fine. And Dean would have done his part to avoid more conflict. That role isn’t easy, and I have heard some pretty convincing arguments that Dean’s designation as the Righteous Man was no less upsetting for him than it was for Sam to learn that he was Lucifer’s vessel. Children (humans) aren’t all good any more than they’re all bad, and an expectation of perfection is just as damaging as an expectation that you’re a fuckup.But I’m not talking about Dean right now.
Sam was cast as the family fuckup. In the dysfunctional family systems model, Sam is the Scapegoat. John cast him as angry, incompetent, and unreliable—an outsider in the family, a black sheep, a person whose job it was to take the blame for the dysfunction so the real source of the problem (John) didn’t have to seriously address his issues, and it has everything to do with Sam’s inability to value his own life and recognize the good in himself as an adult. In “Bugs,” Sam says that nothing he ever did was good enough for John, and that John has always been disappointed in him: “I didn’t wanna bowhunt or hustle pool – because I wanted to go to school and live my life, which, to our whacked-out family, made me the freak.” John cast him as the outsider in his own family. Which may have been true, in a way—it’s completely plausible to me that for whatever reason, Sam was just not wired to be a hunter. (To be clear, in most contexts I wouldn’t be on board with saying someone was or was not “wired” a certain way, but in the Supernatural universe things like bloodlines and destiny seem to matter. Which is why I think it’s worth mentioning that Sam, like John, unlike Dean, was probably meant to be a Man of Letters.) He’s a skilled hunter, but he’s never seemed tied to it in the way Dean is. Which, for John, would have been a problem: anything Sam did or said to question how they were being raised and why they weren’t being allowed to go to school would have been a threat to the precarious lie that John was a Good Parent doing the Right Thing. Or at least doing the Best He Could. By casting Sam as the “freak,” as the Problem Child with an axe to grind, he could distance himself from Sam’s completely legitimate problems with the way they were treated and brought up.
And it’s pretty clear they were, in fact, legitimate problems. In the few scenes where they appear together, John and Sam are fighting more often than they’re not, but they’re fighting in a way where Sam is fighting to get his father to see him, to recognize him and respect him as an adult and as a hunter. Look at this scene in “Dead Man’s Blood"—for context, this is when John had recently reappeared and is demanding their help but refusing to give them information about what’s going on. Sam stops both their cars in the middle of the road and demands an explanation, and this happens:
SAM: Last time we saw you, you said it was too dangerous for us to be together. Now out of the blue you need our help. Now obviously something big is going down, and we wanna know what!
JOHN: Get back in the car.
SAM: No.
JOHN: I said get back in the damn car.
SAM: Yeah. And I said no.
DEAN: Okay, you made your point, tough guy. Look, we’re all tired, we can talk about this later. Sammy, I mean it, come on.
SAM: This is why I left in the first place.
JOHN: What’d you say?
SAM: You heard me.
JOHN: Yeah. You left. Your brother and me, we needed you. You walked away, Sam.
DEAN: Sam…
JOHN: You walked away!
DEAN: Stop it, both of you.
SAM: You’re the one who said don’t come back, Dad. You closed that door, not me. You were just pissed off that you couldn’t control me anymore!There’s a lot going on here. Dean sort of sides with John, even though he’s just as curious about what they’re up to as Sam is, but his main goal is to try to get them to shut up and stop fighting. He also joins in the Winchester family bullshit chorus by belittling Sam (“tough guy”) while Sam is trying to stand up to John and demand respect if John won’t give it freely. John does not give him respect. First he tries to intimidate Sam, and then when that doesn’t work he resorts to emotional manipulation: “We needed you,” “you walked away.” He’s trying to make Sam feel shitty about what was a very healthy choice to walk away from a family that was constantly rejecting him and constantly demanding that he stay. What he tells Sam about himself is that he’s no good at hunting, he’s no good at being a member of the Winchester family, he’s no good, period. If John values Sam as a person, or even if he values his skills as a hunter, he doesn’t show it here. As far as we know, he never shows it. (His parting words to Sam basically amount to “Why do we fight so much? I did my best. Can we stop fighting now? Go get me some coffee.” Dean, by contrast, gets an “I’m proud of you” before he’s instructed to murder his brother. No apology for either one of them. Terrible parenting all around, but really different terrible parenting, which is what I think is interesting.)
Sam’s choice to leave the family and go to Stanford makes sense through this lens, and so does his guilt and ambivalence about it later: he leaves at least partly because the message he’s getting from John is that he’s not any good – or not good enough, not as good as Dean – as a hunter, so he takes John at his word and bows out of the whole deal. Only being told you’re not good at something (or that you’re wrong about something all the time, or whatever) isn’t the same as not valuing that thing. So he’s kind of nominally opted out of the hunting-and-family set of values and priorities, but actually doesn’t view his own choices as valid and feels all kinds of guilt about making them. Guilt that John and Dean are in no way shy about exploiting once he’s come back to the fold, as it happens. This is what I hear every time Sam says something like “you’ll never punish me as much as I’m punishing myself” or “I feel like maybe I’m never gonna actually be all right:” he’s internalized John’s and Dean’s idea of him as broken, monstrous, never good enough.
I guess you could, if you wanted to, read this whole thing straight: Sam sensed, even as a little boy, that Azazel had bled in his mouth and he was destined for demonic trouble later in life. But it makes more sense to me that, if the demon blood does have anything to do with Sam’s feeling of being “unclean,” it’s because of the way it informed John’s treatment of him. Because layered on top of all the more conventional family dysfunction, John actually saw his son as a monster. He told Dean he was probably going to have to kill Sam. Given how much John hated monsters in general and demons in particular, especially after Mary’s death, I have a hard time imagining that wouldn’t lead him to treat Sam with a certain level of revulsion. Kids are perceptive. Sam is perceptive. Even if John had been trying to hide it (which it doesn’t actually sound like he was, much, but who knows), there’s only so much you can hide in a closed society of three. John set Sam up to feel like a freak, a monster, an outsider, long before he made any choices as an adult to align himself with demonic forces or blur the lines between monster and human.
Yes, this. And further to that last point, John seeing Sam as a monster? When Mary died, John didn’t know wtf had happened. He didn’t know what she knew, neither about the supernatural nor about how to competently parent small children. John’s information about the devilish plot that killed his wife improved as the boys got older. His increasing knowledge, and his consequent increasing conviction of Sam’s monstrousness, would have coincided neatly with Sam’s increasing maturity, independence, and capacity for resistance to the family ethos.
The more Sam became his own person, the surer John was that Sam was a monster.