Sam Winchester, hands down, every time.
I’m going to try and keep my reasons short, but I have a lot of Sam feels so who knows how this will turn out.
Firstly, I love Dean so much, he’s such a great character and person and for the longest time it was hard to distinguish whether i liked him or Sam better but the more I rewatched the series the more I realized how much I love Sam and I just want to give him a hug and tell him it’ll be okay.
Sam grew up a parentless child. John may have been alive, but he certainly wasn’t around a lot of the time and when he was he wasn’t too fatherly to Sam (or Dean). And even though Dean only got a few years with Mary, Sam literally has no memories with her as a child. We are painfully reminded of this in Dark Side Of The Moon, when Dean relives a memory of Mary making him a sandwich. While this is a touching scene for Dean, when I watch it all I can feel is sad for Sam, who never had these memories of a normal childhood, not even the small amount that Dean had. Plus there was the whole demon blood thing. He’s had it bad since day one. He’s been cursed since before he was born. He has every reason to complain, to give up. And yet he’s always, always, put others first. Whether it’s putting himself in between harms way and strangers (seen as early as Wendigo) or committing himself to an eternity in Hell with Lucifer to save the world, Sam never thinks of himself first. Like when he’s seeing Lucifer everywhere in season 7, but he doesn’t tell Dean or Bobby, because he thinks they have enough going on. He’s literally going insane and having hallucinations of the devil, and he didn’t think it was worthy of mentioning. He would run into a burning building to save complete strangers every single time. He’s had possibly the worst life ever, and he still managed to say “a lot of people got it worse”. And I just, I can’t even.
He has every reason to give up, he has lost EVERYTHING, he has been through so much that the average person would’ve thrown in the towel long ago. But yet he keeps going. And that is just incredible.
Sam hates himself. He may not express it the same way Dean does, or even as obviously, but he hates himself and he carries such a burden, still even now blaming himself for things that are not his fault. He blamed himself for Mary’s death, for Lucifer rising (yeah that one was mostly his fault), for Dean going to hell and thus starting the apocalypse… He literally has so much on his shoulders. He blames himself for it all and yeah he screwed up a fair bit but he was always trying to do the right thing. Up until season 5, he sees himself as this monster, this horrible creature that’s not even human, and because of that he sees himself as not deserving of the tiniest amount of happiness he has in his life (that comes solely from his brother). For the longest time, he just wanted to be saved. He wanted to feel like he had a chance, even though he knew he didn’t. He had nothing to do with the demon blood in his veins (before season 4), yet he acted as if it was some kind of punishment, something that he had inflicted upon himself just by being born. He didn’t deserve that, he didn’t deserve his mother dying, or his father dying, or his brother dying, or his girlfriend dying, his friends dying, or having to feel responsible for all that, feeling responsible for the end of the world, not having a normal family and childhood, not getting a chance in life, being tortured by Lucifer for months and months, he didn’t deserve any of that. He is a good person, yes he has flaws, yes he made mistakes, but he is a good person, who has been burdened with horrible things, yet he never complains, because he thinks he deserves it (also because he’s completely self sacrificing).
I saw a post recently that mentioned how Sam prayed well into his adult life, even in the face of such evil that he faced and all the horrible things that happened to him. He lost both his parents, never had a normal childhood, his girlfriend was killed, and yet he still had faith. He still prayed. He just sees the best in everything and everyone and because of that I want more than anything for him to have a happy ending. He deserves it so much.
Basically, to sum up (and I’m quoting someone else here) “Sam is every horrible mistake we’eve ever made and every soaring triumph that we could ever imagine staring straight back at us. He’s clumsy and messy and awkward but he tries. He wakes up every morning with the entire world weighing down on his bones and a life time of memories that threaten to swallow him whole and he tries.”