#5.20

anyway. the thing about john is that both the angels AND the demons wanted him to be doing all of that. they wanted him training and ruining his children. they wanted sam to be sharp and angry and resentful and they wanted dean to be hollow and broken and order following. (hell, chuck wanted it too.)

like in 2.21 azazel says this to sam:

AZAZEL: You’re tough. You’re smart. You’re well-trained, thanks to your daddy. Sam – Sammy – you’re my favorite.

throughout season 4, we see that the angels are testing dean specifically on how good he is at following orders - especially ones he doesn't understand or agree with (4.03, 4.07, 4.10, 4.15, 4.16, 4.17, 4.21, 4.22). summarized here (4.07):

CASTIEL: Tell me something, Dean, when your father gave you an order, didn’t you obey?

5.08 lays out the angels' vision for dean and sam's desired personalities from their upbringing:

GABRIEL: Why do you think you two are the vessels? Think about it. Michael, the big brother, loyal to an absent father, and Lucifer, the little brother, rebellious of Daddy's plan. 

so john could have moved his kids one town over in kansas and let them grow up and play sports and go to school dances and become a lawyer and a firefighter and that would have been more contrary to the schemes of all the sinister forces working around him than every single thing he did.

his kids didn't need to learn to hunt the supernatural. (besides the extra-canonical stuff in the john's journal book) nothing actually attacks or tries to harm his kids* until sam is twenty-two. (and the angels only come for dean after he DIES)

in fact, in 5.22, we learn that lucifer and azazel had sam surrounded by demons for most of his childhood** and no matter how prepared john felt he was and how protective of his family he thought he was being, he never caught on.

5.22

LUCIFER: Look closely. None of these little devils look familiar to you? SAM: That's Mr. Bensman... One of my grade-school teachers. LUCIFER: And that's your friend Doug from that time in East Lansing. And Rachel... your prom date. Sam Winchester, this is your life. Azazel's gang – watching you since you were a rugrat, jerking you around like a dog on a leash.

brady is actually the only demon we know of from sam's circle from after he leaves john.

5.20

BRADY: Brady hasn't been Brady in years. Not since, oh... middle of our sophomore year? SAM: What? BRADY: That's right. You had a devil on your shoulder even back then.

but the demons from sam's childhood don't actually seem to have been doing anything beyond watching to make sure sam stayed tough, sharp, smart, well-trained, etc. like brady only steps in and kills jess because,

5.20

BRADY: No, we could tell we were starting to lose you. You were becoming a mild-mannered, worthless sack of piss. Now, come on. We couldn't have that. You were our favorite. So I hooked you up with a pure, sweet, innocent piece of tail. And then I toasted her on the ceiling. 

2.21

AZAZEL: I mean, sweet little Jessica – she just had to die. You were all set to marry that little blonde thing, become a tax lawyer with two kids, a beer gut, and a little McMansion in the suburbs. I needed you sharp, on the road, honing your skills. Your gifts.

so, yeah, maybe there's a version where john tries to give them a normal life and the demons (or angels) intervene. but the version we have is the one where john was so hell bent, they never even got a chance. he played right into the demons' and the angels' plan.

the version we have is the one where john chose to have his son be bait (1.18, 1.20, 15.16), and shoot at gun at 6 (2.06) and leave him alone with one at 11 (1.18), and get enough of a criminal record to make any normal future at the very least humiliating, expensive, and deeply bureaucratically challenging. the version we have is the one where the most consistently harmful and damaging presence in his kids was not the supernatural but himself.

hell, the whole apocalypse plan in its entirety could be been thwarted by john teaching dean that his life mattered in and of itself and that his worth wasn't only found in making sure sam was ok.

the most powerful resistance to the schemes of the angels and demons, would have been john giving his sons a safe, stable, loving childhood.

*except you know all the monsters that attacked them on hunts john made them go on.

Most of them revolve around Diana Fowley. I knew was she coming and I’ve seen a lot talks about her. And here the thing, I don’t get what the big deal is. I don’t know if she comes up in later seasons but to me she is essentially the same as the British chick in ‘Fire’ season 1. Who personally I felt like Scully acted much more jealous and threatened by.

I kept on seeing people say that Scully is sooo jealous of Diana this episode and I just didn’t see it that way. Scully is on a case that is not originally an Xfile only to find out that there is this new person who is close with Mulder and who started with him on the xfiles. That is jarring but more than that neither Diana or Mulder are forthcoming about how they know eachother or the nature of their relationship. If it was me I’d want to know what the fuck is going on as well be a little uncomfortable at being left in the dark over such a thing. Especially by my partner. So no I don’t think Scully is jealous I think she is worried and confused.

Diana however is jealous and threatened by Scully. When hearing that Mulder is thinking about one of them Diana asks who. It’s her nervous face that the camera focuses on. She disagrees with scullys logical angle on the case and even goes as far to use them to make her self look better in the eyes of Mulder. She tries to drive a wedge between msr by talking about how exhausting and difficult it must be to work with someone like Scully, a close minded skeptic.

Which leads me to my second point. I was under the impression that Mulder was going to be enamored with Diana, the whole ‘one that got away’ type thing but it’s not. Mulder seems surprised and a bit cautious that Diana is around. I get the feeling that he doesn’t trust her and her presence unsettles him because if reminds him of a much different person. What is great about this episode is how immediately Mulder comes to scullys defense. Talking about her critical thinking is something he values after Diana comment on Scully. Once again showing her jealousy by states that maybe she should be in scullys place yet Mulder shoots her down, tells her he is fine without her.

And before you mention the end of the episode I think both Scully and Mulder have reasonable responses to Diana. When the boy says Scully doesn’t care what anyone thinks but Diana - it’s because all the secrecy around her makes scully feel like she isn’t to be trusted or that this thing that she’s spent five years of her life fighting for was given to the wrong person. Scully is more probably insecure than anything else. And Mulders attention to Diana in the end of the episode is because an agent was shot on duty, agent he was once close with and connected to the xfiles. Of course he’s concerned. Who wouldn’t be.

One thing I am noticing about Sam is that he is very anti-demon after season 4, which is understandable. We see this most strongly with Crowley in season 5, but it's not just Crowley—it's Meg too. And Sam and Dean also have many other reasons to hate Meg. But like Sam comments twice about how wary he is about them working with Meg in season 7, even if her only role is to keep watch over Cas at the hospital because they have no other options.

SAM I don't know. I mean, we can't just leave him. DEAN Well, we can't bring him with us. Everything on the planet's out for us, okay? Word gets out, we can't protect him. Not really. This is safer. Every demon who knows about Cas is dead. SAM Not everyone. Look, Dean, this whole "enemy of my enemy is my friend" thing feels kind of like a demon deal. DEAN It's not a deal. It's – SAM It's what? DEAN Mutually assured destruction. Look, man, I get it. She's not our friend. We don't even have friends. All our friends are dead.

It's funny because people often perceive Dean as this very dogmatic figure who can't handle the idea of working with demons and hates Ruby just because she's a demon, but he is the first person to trust a demon (the often forgotten Casey from 3.04). He never trusted Ruby, but he saved her bacon twice (3.09 and 3.10) because he actually does understand the concept "the enemy of my enemy is my friend". He shows this again with Crowley in 5.20 (an episode titled "The Devil You Know" which is rather pointed). Sam doesn't trust Crowley one iota. He tried to kill Crowley in 5.10 right after Crowley gave them the colt, and I actually think that interaction is what makes Dean decide Crowley can be trusted as an ally against the devil. In 5.20, Dean decides Crowley is on their side and agrees to go with him on a solo mission without Sam (because Crowley does not trust Sam not to shoot him) and Sam is so upset about it he vents to Bobby on the phone lol. (To Dean's credit, when Crowley tries to convince Dean to keep the Brady secret from Sam under the suspicion that Sam will fly off the handle, Dean refuses to lie to his brother).