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Not sure he's conservative, he's often just annoyingly contrarian - he really prides himself on being "that guy", and he's definitely a carrier of the Murc's Law virus. He's not exactly Patient Zero for it, or even the worst offender - David Brooks shares a lot of the blame, at least in more recent times. But he's up there with carrying the torch for it.
I've seen him do so much both sides nonsense. He is still clinging to Israel, FFS while acting like those that protest Gaza are actually antisemites. He keeps harping on the trans thing.
He's exhausting to watch and at this point, I'm mostly hate-watching him. And his guests at least on the panel make up an array of annoying choices.
But one thing he isn't, and it is not someone that really is going to the mat for Kamala or Biden. If anything, he's almost exactly the kind of guy that would love to gloat "told you so" about how Democrats can be disappointing, as if that's some big revelation, LOL.
You have a point, but the ways he's contrarian to me seem to indicate as stubborn conservatism lying dormant.