> But in this case I'm having trouble following what his criticism even is
A piece by Isaac Faber [1] from December last year clearly described what Taleb's position is. A summary paragraph towards the end:
> Here we can say, with some confidence that FiveThirtyEight predictions are not always reliable probabilities. However, they masquerade as one, being between 0 and 1 and all. This is Taleb’s primary argument; FiveThirtyEight’s predictions do not behave like probabilities that incorporate all uncertainty and should not be passed off as them.
Faber's piece was discussed on HN [2] soon after it appeared.
[1] https://towardsdatascience.com/why-you-should-care-about-the...