> 71% chance of victory, which is anomalously low chance given current polling data.

Your question is based on 71% being low, which I don't think it's true. It's way way higher than I would expect or predict and certainly higher than what the polls indicate. Have a look at 538's methodology for creating it and also look at Nate Silver's article on how you shouldn't count Trump out yet.

As far as Taleb goes - who cares, the more people ignore him, the better.