always regarded Taleb as a half-crackpot

My guess is Taleb wouldn't be offended by this, and would in fact argue that any serious intellectual should be viewed as a half-crackpot.

Serious intellectuals get some things right and get some things wrong, but they do their thinking independently and therefore their mistakes are uncorralated with others'. That means their input is a valuable contribution to an ensemble. You can make a very strong aggregate prediction by calling up your half-crackpot friends, asking their opinion, and forming a weighted average.

Pseudo-intellectuals, whom Taleb calls IYIs, are just regurgitating what other people say. That means their opinions are all highly correlated. The ensemble prediction obtained by asking a lot of pseudo-intellectuals isn't much stronger than the single opinion of just one such person.

There is an ethical component to this dichotomy. A serious intellectual is risking his reputation (being perceived as a crackpot) to add aggregate strength to the collective wisdom. In other words, the serious intellectual is accepting individual fragility to make the collective anti-fragile. In contrast the pseudo-intellectual seeks to protect himself from risk, while making the collective fragile, since the collective opinion of a group of IYIs is very likely to be wrong even if (especially if!) there are many IYIs and they all agree.

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.

Preferably to also confirm he wasn't making hundred other predictions that didn't happen.

Source for the 2008 crisis prediction would be his book The Black Swam (I remember checking the publication date when reading The Black Swan, since it did seem very prescient):

Globalization creates interlocking fragility, while reducing volatility and giving the appearance of stability. In other words it creates devastating Black Swans. We have never lived before under the threat of a global collapse. Financial Institutions have been merging into a smaller number of very large banks. Almost all banks are interrelated. So the financial ecology is swelling into gigantic, incestuous, bureaucratic banks – when one fails, they all fall. The increased concentration among banks seems to have the effect of making financial crises less likely, but when they happen they are more global in scale and hit us very hard. We have moved from a diversified ecology of small banks, with varied lending policies, to a more homogeneous framework of firms that all resemble one another. True, we now have fewer failures, but when they occur ….I shiver at the thought.

Banks hire dull people and train them to be even more dull. If they look conservative, it's only because their loans go bust on rare, very rare occasions. But (...)bankers are not conservative at all. They are just phenomenally skilled at self-deception by burying the possibility of a large, devastating loss under the rug.

The government-sponsored institution Fannie Mae, when I look at its risks, seems to be sitting on a barrel of dynamite, vulnerable to the slightest hiccup. But not to worry: their large staff of scientists deemed these events "unlikely".

There is no way to gauge the effectiveness of their lending activity by observing it over a day, a week, a month, or . . . even a century! (...) the real- estate collapse of the early 1990s in which the now defunct savings and loan industry required a taxpayer-funded bailout of more than half a trillion dollars. The Federal Reserve bank protected them at our expense: when "conservative" bankers make profits, they get the benefits; when they are hurt, we pay the costs.

Once again, recall the story of banks hiding explosive risks in their portfolios. It is not a good idea to trust corporations with matters such as rare events because the performance of these executives is not observable on a short-term basis, and they will game the system by showing good performance so they can get their yearly bonus. The Achilles’ heel of capitalism is that if you make corporations compete, it is sometimes the one that is most exposed to the negative Black Swan that will appear to be the most fit for survival.

source: http://www.fooledbyrandomness.com/imbeciles.htm