Tim Pool, YouTube. Don't always agree with him, but he seems to sincerely strive for honest and accurate analysis. Plus, he drops so much content that actually uses excerpts from various news articles, that his channel doubles as one of the best news aggregators on the web, IMO. Easily half the shit I read about on any given day is from articles ol' Timmy turned me onto.
Razorfist (The Rageaholic), YouTube. My favorite conservative personality to watch. What I find to be the sharpest analysis from a conservative non-academic in front of a camera, and he gets extra points for accurately recalling politics from before last month and factoring that into said analysis. Also, you can tell he doesn't just wing his videos, which in and of itself isn't a selling point for me, but the style and wordplay of his writing are on point, and his pacing and overall delivery are fantastic. Kinda reminds me of a pissed off Denis Miller.
Don Lemon, Chris Cuomo, CNN, tied for third. I don't find these two personalities to be good sources for accurate news and analysis. I do find their over-the-top hysteria and performative self-righteousness, juxtaposed against a background of obvious bungles and cartoonish levels of ignorance absolutely f'in hilarious. There are times when I honestly have trouble believing that I'm not watching something intended to be comedy. 10/10, would absolutely recommend.
Sargon of Akkad, YouTube. Kind of a cliche pick for political YouTube personalities, I know, but the guy's sharp as shit and I enjoy his sense of humor. Plus, when he decides to deep-dive on a topic, dude seriously does his homework and shares a lot of interesting, often obscure information.
Tucker Carlson, Fox News. Sure, the guy looks like the archetypal prep school kid all grown up, and even kinda sounds like it when he speaks, but he generally seems to know what questions to ask to really cut to the quick of a conversation. Plus, who watches politics but doesn't like a show that's 90 percent 1 on 1 debates?