I think [1] is a balanced evaluation.
"...In short, Taleb resists categorization. If I had to pigeonhole him, I'd call him an anti-guru guru. That is, he mercilessly bashes other gurus, pundits and prophets and warns you not to fall for them. He depicts himself as a brave, lonely truth-teller in a world of fools and frauds. In so doing, he becomes a guru himself, with a cult-like following...
...even if you question what Taleb is saying—and you certainly should—he forces you to examine your own biases and assumptions. Yes, he can be irritating, but so are many of our most original thinkers..."
[1] https://blogs.scientificamerican.com/cross-check/nassim-tale...
Bullshit along the lines of: Did you know statisticians believe the normal distribution curve is infallible and perfectly describe real world scenarios? This actually false. Therefore, statisticians are stupid, and you're smarter than them for understanding otherwise. And I am smarter than everyone for having pointed it out.
He doesn't force you to examine your own biases and assumptions. He tricks you into believing that you have done so and have come out wiser. He's just yet another fool and fraud in a pit of fools and fraud.
Like, I wholeheartedly agree, he doesn't achieve good interviews by the quality of his questions.
Except... that he kind of does, in a weird way. Experts on the show are happy to use those questions as a launching point to correct whatever incorrect assumptions he had in asking it.
He's very good at getting people to open up and talk. Perhaps dumb questions play a role in that? Perhaps they make people feel comfortable by validating their expert status in the room or something, I don't know. But I do know that it seems to work. I also know he's a comedian. Comedy is fundamentally a weirdly manipulative art form... You carefully craft a set of jokes and then practice over and over again to make it feel like an organic, albeit funny conversation. Every little pause, intonation, turn of phrase, it's all intentional. So, being that he is a practiced comedian, it's possible some of that interview style is pretty intentional too.