Not to put too fine a point on it, but I bet all of my money he didn't predict Trump would win the Electoral College while losing the popular vote by millions. That article gives no hint he even knows it happened. Meanwhile, Five Thirty-Eight supposedly based most of the probability mass they assigned to Trump winning on a technical EC victory, and they said he had one chance in four (one in three earlier).

The fact that a 25% chance can happen with potentially devastating consequences is roughly why Trump the outsider might blow up America, though I'd give that no more than a 13% chance.