He's like an attention-NPC. He'll say whatever gives him the most attention. And he's masking his NPCness by speaking extra calmness and "asking questions" that aren't that questions. Once you've seen through this spiel, you can't help but cringe really hard at his monologues.
At least people like Joe Rogan are candid in their contrarianism - which increases my respect for him 10x even in things I don't agree with. And removes the cringe factor.
It's his front of being "the one journalist who's telling you the truth" combined with this (possibly sinister) narrative he's casually dropping that democracy is broken in the United States that's got my eyebrows raised.
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