Because at his core john is about love over everything else. When he looks up at his sons (yes, up, the fact that they’re both taller than him>>>>>), there is love seeping achingly from every single pore of his being even as he abuses them, as he destroys their souls beyond belief. He does it all entirely out of love. And he is so, so wrong for it. A part of him knows it. But he wants to keep dean alive, and he wants to keep Sam pure. And he loves them so much. And he damages them so horribly. John Winchester is the foundation upon which they are both built, they only become more of what he made them as the series goes on. Sam stops fighting it, Dean continues to mold into his image no matter how hard he tries to fight it.

Hell puts them both on steroids, but their individual trauma responses that influence this are the foundations that John built into them. No wonder azazel wanted sam to win so badly. John Winchester crafted his sons into alastair and Lucifer’s ideal victims, respectively, and dean was a better (worse) john than John ever was. John held out in hell. Dean acquiesced to his abuser despite all of his efforts to fight him, and he’s never been the same since.

Sam fought like hell, and he fought destiny, but at his core, he did what John always wanted him to by doing what dean wanted him to do, and then he stops fighting at all, loses the fire he showed john in adolescence that john immediately notices when he returns in s14.

And the sad thing is. They filled their roles so well that John is saddened by what they’ve become. He didn’t want dean to break. He didn’t want Sam to be dimmed. He’s sad to see what Sam is like in s14. In the process of recovering his wife, he ensured he would mold his sons into what he wanted them to be, and when he got what he wanted, he was devastated.

i'll never get over dean walking around wearing this too-big leather jacket cuz he's insane about his daddy and he needs to be as close to him as he can. it really is too big for him! how did anybody take him seriously?

Idk who owns the original pic but I updated it from 2023/2024 to 2024/2025.