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Because he really doesn't, he's just some fag with a nice voice. He has things that gets under his skin and takes a personal dislike to but thats about as deep as it goes.
I'm not sure I'd call that a principled attitude, it could be that Jim is just as shallow as he presents himself.
Jim clearly started out with principles. He sounds like he's about to cry like a bitch in the video where he gave up on GamerGate, and in that video where he discusses sci-fi with JF he came off as having genuine wonder and interest in the ideas JF was presenting even though we all know how much of a sperg that froggie fuck turned out to be. Jim has become his own persona. Its ironic to me that he picked a faceless white manniquin with a baseball cap as his avatar, because now he truly has become that character instead of just being some dude with a mic hiding behind an edgy smiley face.
I'm also not fully convinced he's a boomer either. He acts like and has a point of reference consistent with any millenial I know that got raised on TV and movies instead of videogames.