I've been following this spat since it reignited several weeks ago, but also since Taleb first attacked Nate on Twitter back before the 2016 elections, and it has been the final nail in the coffin as to any supposed credibility Taleb commands.
The quandary that FiveThirtyEight and Silver are in is that the general public is stupendously bad with probabilities. Prior to the the 2016 election, Silver was personally being attacked, in some cases by major media organizations like the Huffington Post, and accused of tipping the scales towards Trump (for some inexplicable reason), since their models were giving him approximately a 1 in 4 chance of winning, since everyone knew it was a certainty Clinton would win. Then, in the months following the election, the narrative somehow switched, and the fact that Trump won despite only being given a 1 in 4 chance by FiveThirtyEight meant that Silver was now a hack and the model was wrong. This same criticism has been leveled by many right-wing media personalities, who had been trotting out Silver's 2016 predictions leading up to the election, as well as by the New York Times, whose own models were giving Clinton nearly a 90% chance of victory.
So now, fast forward to this year's election, Silver is doing his best to drill into people's minds that, yes, their model showed a Democratic win in the house as the most likely outcome, but that absolutely doesn't not mean their model says it is an absolute certainty, or that other outcomes would be unusual. It isn't covering his ass, its educating the public on how probabilistic statements work.
This is something Taleb should know. But Taleb has proven himself to be a hack and an intellectual parasite. He hasn't actually produced any ideas worth discussing since "Fooled By Randomness" which was nearly 20 years ago. Basically all of his works since then have been rehashing the same idea, or, as with Skin in the Game, pseudo-intellectual ramblings containing little to no interesting ideas, and what ideas do exist have been rehashed a million times by others.
Since then, he has taken to making ad-hominem attacks and nonsensical critiques on others in the public view, often on Twitter. I hate bringing up Trump, as it happens far too often in discussions these days, but some of his methods of "debate" are strikingly similar: strange monikers ("klueless Nate"), schizophrenic jumps between topics/arguments, often indecipherable language, and a ridiculous volume of output. All of this combines to mask the fact that most of the time, he isn't actually saying anything, or at least anything sensible, but by shouting loud enough, long enough, and purposefully making his point difficult to identify, it almost becomes impossible to argue with him, and a non-insignificant number of people will assume he is right.
Interestingly, I've also found many of his supporters to be similar to some of Trump's or other figures such as Musk. There is a cult of personality built up there where they have established the person as a visionary first, and therefore anything and everything they do or say is correct. Many of them parrot back the same, shallow catchphrases of his, that rarely contain anything insightful but are general enough that they can be thrown out in any situation: critics or dissidents are "Intellectual yet Idiots" or don't have "Skin in the Game". Note that the arguments of these critics or dissidents are almost never addressed.
Unfortunately, the spat between Taleb and Silver (which actually started back prior to the 2016 elections), is exhibit A in why Taleb is an intellectual charlatan, and shouldn't be given the time of day. Silver isn't some perfect person either, but in general he has been a reliable voice in the realms of political prediction, fairly forthcoming on shortfalls, and his most damning criticisms all seem to be built upon critical failures in the understanding of probability, or a willful misrepresentation of his results.