Earlier quoted context omitted.
I normally like Taleb's insights but it was obvious when following this that he (and Dinesh D'Souza) were ridiculously misconstruing Nate Silver's comment. Two outcomes being "extremely possible" in no way means they have a 50/50 chance of happening. It merely means that neither outcome has a low enough chance that you should assume it won't happen.
As the blog post rightly said, they present 538 present the forecast in a way that they are never wrong. I can see the point. I also fond the comparison of NFL vs. Senate forecasts meaningful. This kind of "forecasting" seems to be the current version of crystal balling and astrology. They (models) don't really know anything (no causation, and definitely nothing close to an actual model of the real world like in phys…
The whole point of probabilistic modeling is to replace absolute decisions like "right or wrong" by continuous weights on the possibilities. If you absolutely need a definite decision, you can sample a prediction according to the probability assigned by the model. If the true outcome is x and the model assigned it probability p, then that procedure is going to be wrong (1-p) of the time. You could define that number as the "wrongness" of the probabilistic model, as a continuous analog of the definite case.
The advantage of probabilistic modeling is that you can also ask how wrong the model expects to be and get a meaningful answer. If there are many possible outcomes and none of them very likely, any choice is going to be wrong a lot. But you should expect a good model to have a small difference between its expected and actual wrongness. One might call that value "honesty".