Could you point out specific holes in his arguments?
I find your comment to be too much relying on metaphors and not backed up with example or data and without any specifics?
E.g.
One of the recurrent themes in his books is how forecasters fail, and how when they fail they fail by huge margin.
In My experience I have found this ideas to be quite insightful.
Why do you think that his main Thesis about events with large impact and low expectation and their effect on our ability to make predictions is incorrect?
I agree that he himself gets involved in narrative fallacy and that his arguments could be more succinct and sans the Tony and other character that he uses in his book. But Maybe those are there for the hoi polloi and not for people who understand Machine Learning, Search and stuff.