The Black Swan is widely read for such an esoteric subject. My GF even quoted Taleb at dinner once. If I remember correctly, Don S. once said "Screw Taleb and the Black Swan he rode in on." I gather he doesn't like the book.
"Fat tails" are certainly taken into account in simulations. But, and I'm going against the grain here, using standard deviation calculations alone takes into account variance, but not kurtosis. Common thinking is that Kurtosis is nearly irrelevant in BJ. Obviously true using BS. Maybe not with counting. HOWEVER, the ridiculously complex options trading formulae work for card counting. That is the basis of Chapter 7 (I think) of
Blackjack Attack. I ran the sims in that chapter to see if the formulae match the sims, and they do.