#this is so fuckingl ong i think i deviated from the point lol

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One of the first times it really hit home to me how Dean can't win with Sam ever is during Faith.

I feel like because of the big deal made at the end of season 2 folks think Dean is the first one to ignore instinct and what he knew to be right just to save a family member but no, it was Sam.

And in that episode Dean is accepting he's going to die. That hey, he saved some kids, but something went wrong, he doesn't have much longer, and it is what it is. It sucks, but it is what it is. Sam was the one who couldn't stand that and decided to ignore his own instincts, and Dean's protests, and dragged him to Roy and pressured him in front of everyone to go up on that stage.

And then once they learned the cost of what Roy was doing, Dean had that weight on his shoulders that some poor bastard died just to save him, when he didn't even want to be saved in any capacity.

I think that was also the first time I had really understood and processed just how reckless Sam could be. You'd think he was the more understanding one but I think that's just that young 20's something, college boy earnestness but in reality, there's a reason why Sam and John are often grouped together instead of Dean and John. Especially when you think about how John sacrificed himself and burdened Dean with the guilt of having to take out his own brother if push came to shove.

And the fact that Sam continued to try to push Dean after John's death to talk about it, despite clearly seeing the signals that he doesn't want to or isn't ready at that point, is sad.

And THEN you pile all that on top of the guilt Dean already felt by pulling Sam from school and basically back into a life he had 'successfully' left [i say successfully because we learned later on that Lucifer and his cronies were essentially tracking his every move anyway] and because Dean had pulled Sam away from Jessica just for a few days, she died in that time.

Now, at the time, they didn't know it was part of a wider plan, but that doesn't matter. Feeling guilt is feeling guilt.

That was even brought up in 7.04, Defending your Life where Osiris calls Sam to the stand to try and get him to admit that Dean essentially ruined what would have been a promising future as a lawyer. By now we know that wouldn't have happened regardless because of the apocalypse stuff but that doesn't change Dean's guilt whatsoever.

And he really has no one to talk to about this. It's why in 4.16, On the Head of a Pin, that conversation Dean has with Cas after he's all beat up and stuff and talking about being disappointments to their fathers and the like, I really liked that heart to heart because he can't really talk to anyone else who is essentially on the same level as him: Guilt over ruined plans, shame, seen as nothing more than a tool, expectations they put on themselves through pressures of their family, so on and so forth.

There were two heart-to-hearts in season 4 that stood out to me, particularly because they were so early on in their time together: 4.07 and 4.16. Both times, they're on an equal plane while talking. Cas isn't standing in 4.07 but sitting next to Dean on an adjacent bench. And Cas in 4.16 is sitting next to Dean, who is in a hospital bed rather than standing by the door or something. And the conversation in 4.07 was one that he'd have to really trust Dean on because he was admitting he has feelings of doubt. He's barely known this man.

And I believe this guilt that Dean carries over a myriad of things obviously carries all the way to Season 15 where it's also manifested into existential dread.

It always frustrated me that for a good portion of time, Sam just never stopped to thnk about what Dean was constantly going through. There were some moments and some moments he acknowledged that Dean raised him and stuff but I don't think he ever fully understood and a lot of the times they talked about stuff, it came from a Sam-centric place and the outcome wasn't always favorable. Like OP says, Dean couldn't really win. Even sometimes with Bobby he'd lose and Bobby is their father figure.

It's why I loved the addition of Cas into the mix and was happy he stayed around because Dean needed someone on his level metaphorically and "role" wise.

It's why he was so angry at the end of season 14 and part of season 15 at Cas. At first it's like 'Oh he's mad because Cas omitted the truth about Jack and that caused Mary to die' but I think once Dean understood that Chuck had been pulling strings, that Mary was likely going to die anyway.

If you rewatch those episodes, especially beginning of season 15, Dean isn't mad at Jack. He's mad at Cas, and that's because that trust between them was broken. That trust that had been there since they met in season 4, that understanding they both had.

Obviously there had been trust issues in earlier seasons from time to time but that didn't change the fact that they were equal and by season 14/15 they should have trusted each other more.

Dean constantly had his trust broken, and whenever he would let one or two walls down [Cassie, Sam, Bobby, so on and so forth] he'd get hurt.

He's never had anyone in his corner.

You really just can't unsee it once you see it though, can you?

Sam starts blaming Dean for what he's going to do (work with Ruby) way back in 3.09 because Dean isn't going to be around to be Sam's mommy, which is going to force Sam's hand.

After Dean comes back, Sam actually blames Dean for him working with Ruby by saying Dean wasn't there to protect him (4.04).

Dean repeatedly begs Sam not to work with Ruby and is ignored repeatedly (3.03, 3.04, 3.09, 3.16, 4.01-4.04, 4.12-4.22).

After telling Dean to open up to him and trust him (4.08), Sam calls Dean weak and pathetic for being traumatized by hell and says Dean is holding him back and therefore deserves to be lied to because he can't be of use (4.14) Sam says it's not what he really thinks when they both know it is (and Sam repeats it to other characters in 4.16, and 4.18) and then he admits it's the truth again to Dean's face in 4.21.

Sam accuses Dean of not trusting him enough (4.21).

Bobby blows up at Dean for not supporting Sam enough and calls him a pansy after Sam strangled Dean near unconscious, and tells him family is supposed to make you miserable (4.22).

Dean tries to reach out to Sam and Zachariah and Cas actively prevent him from doing so (Cas only at first) (4.22)

Zachariah (5.01) and Cas (5.02) both tell Dean the apocalypse is his fault because Dean didn't reach Sam in time to stop him from killing Lilith.

Dean says Sam hurt him, Sam is the one Dean depended on the most and Sam hurt him in ways he can't even voice (5.01). Sam apologizes, but then in the very next episode, shoves Dean into a wall for not trusting him like Dean is crazy and irrational when Sam doesn't even trust himself (5.02).

Sam says he thinks they should go their separate ways and is shocked when Dean agrees easily. Dean says that he spends more time worrying about Sam than he does doing the job right and time apart would be good. Sam reiterates that he's sorry and Dean gently says he knows Sam is (5.02).

Cas asks Dean if he's okay even without his brother, and Dean says "Especially without my brother. I mean, I spent so much time worrying about the son of a bitch. I mean, I’ve had more fun with you in the past twenty-four hours than I’ve had with Sam in years, and you’re not that much fun. It’s funny, you know, I’ve been so chained to my family, but now that I’m alone, hell, I’m happy." (5.03)

Sam says he wants back in. Dean objects, on the basis that he thinks they're stronger apart. Dean says they're each other's weaknesses and it's being used against them (5.04, but the weakness line is repeated from 3.03 and 3.16).

Zachariah pushes Dean into a future 2014 where Dean never met up with Sam again, and as a result, Sam said "Yes" to Lucifer, and billions of people died. All because Dean didn't want to be around Sam after being hurt and never reconnected with him (5.04).

Dean reconnects with Sam (5.04) even though he clearly doesn't want to, because the first case we see them on again, Dean struggles to trust Sam and leaves to go drink alone because he doesn't want to be around Sam (5.05).

Sam says part of the reason he went off with Ruby was to get away from Dean, because Dean is smothering. Dean is the problem in the relationship, because Sam feels inferior compared to him. Dean apologizes for being too smothering (5.05).

What does all of this tell you? Dean can't win. Dean will always be the bad guy in the family. He loves too much, or he isn't loving enough. Sam needs him and Dean wasn't there for him and so Sam went down the wrong path, but also Dean is smothering and Dean being smothering is the reason Sam went down the wrong path. Sam is not a trustworthy person, but Dean doesn't trust him enough. Sam not being trustworthy is Dean's fault. Dean doesn't deserve trust, but Sam deserves Dean's trust no matter what and not giving Sam his trust is the worst possible thing in the entire world and also again makes him smothering. The apocalypse is Dean's fault. Every single thing Sam does every single mistake he might ever make in his life is always at least partly Dean's fault and Dean's responsibility.