I haven't looked much into his political thinking, but I could have guessed that he would be a supporter of Trump because Trump brings a lot of volatility to the system lol. He seems to use his statistical framework as a way to understand the world itself, not just the stock market, which is what I find the most interesting. And it has many similarities to Peterson's Darwinian view of Truth; Taleb says how the older something is, such as an idea, the more likely that it will last into the future. And this sounds exactly like what Peterson says about Truth. I just find the similarities interesting.

I think calling him a "Trump supporter" is going too far. I just listened to Skin in the Game on audio in my office (which was louder than usual, so I missed quite a bit) and what Taleb says about interventionists who act when they have nothing to lose applies to most politicians but not to Trump. Trump would lose if rich people who use Trump properties would lose, and thus has "skin in the game." HRC did not, Obama did not, most politicians do not. However, I'm certain there are things that Taleb would disagree with Trump about, such as environmental issues and possibly the handling of the Covid-19 virus. The MSM hates Taleb because he constantly says that they pretend to be experts on subjects that they are not experts on, so they return the favor by taking what he said out of context. Small articles and soundbites are not enough to really "get" what Taleb is saying.