I don't think all of his takes are bad, he's just got a way of expressing them that makes him utterly irritating to agree with.
When I make a controversial point, and I know I am, I often try to make it as convincing and agreeable as possible so that people don't just outright screech at me (lawyer instincts unless I am actually angry at someone and just wanna argue), but I feel like bossman often makes his points in the most "I am right and there's nothing more to say" way, which pisses off our gaggle of anti-authority contrarians better than pretty much anything you could come up with.
The logical conclusion of this is a "choose the best interpretation" kind of deal: He either doesn't realize how he comes of, or he's so conceited about always being right that he doesn't care how others see him.