What do you think Dean was specifically proud of though in relation to himself? Choosing not to let himself become a monster? Setting that limit?
I think he was proud of all the good he has done. In 9x10 he said he believed he was poison, and that he tried to tell himself that the good he had done outweighed the bad, but it's clear at the time he no longer believed it. I think once he was near the end, once he realized what true poison felt like, it was clear to him that he is nothing of the sort. He was proud of how brave he's been, of how many people he's saved, of how he's kept fighting despite all the trauma he has experienced...
I think he was just generally proud of himself, and that in and of itself is huge.









