Back in the beginning of Trump's campaign, Nassim Taleb (judging from his Twitter presence) was conflicted about the only presidential candidate who was not a total all-tawk phony, who had enough fuck-you money to not be controlled by donors, who had skin in the game by funding his own campaign, and who embodied the ideas of anti-fragility (the more his enemies attacked him, the stronger he got). On the other hand, he felt that the only non-fake candidate was also a maniac, for reasons he didn't say -- maybe about protectionism, maybe about sending back the Syrian migrants, maybe feeling instinctively defensive as an immigrant, I don't know.
Now he's starting to defend the Trump phenomenon, not by outright endorsing him or anything like that, but by going on the attack against his moronic and dishonest detractors. He's also started pointing out how there are lots of folks in polite society who may not be open about their support for Trump, but will confess it after a few Christmas party drinks. A recent poll among Taleb's Twitter followers shows 59% support for Trump, with 46% willing to admit it without having to imbibe any Christmas party drinks.
To the untrained eye, Taleb the probability theorist is making a point about how messy it can be to estimate probabilities in a real world fraught by biases, like the social desirability bias. In this case, educated people are more likely to find it embarrassing to support Trump, so they'll lie more when called up by pollsters, and his true support level is higher than the polls say.
But to those familiar with Taleb's nature, he's clearly doing something beyond making an academic point -- he's cutting through mainstream bullshit to let people know it's OK to admit their support for Trump. After all, lots of like-minded people are either outright supporters, or are thinly closeted supporters. You're not crazy, so don't hide and be afraid as though you were crazy.
His recent efforts to really go to bat for The Donald seem to be related to Putin's favorable words about Trump, and Trump's reciprocation, hinting at a future where America and Russia are closer to being allies than enemies, particularly over foreign policy in the Middle East. Taleb is even more open about his man-crush on Putin, whom he says many Christians of the Levant, like himself, see as a protector of Orthodox Christianity in the eastern Mediterranean.
Taleb wants more of a regional role for Russia-Syria-Iran over the reigning Islamic fundamentalist axis of Turkey-Israel-Saudi Arabia. Israel supported Hamas in its early days in order to crowd out the secular nationalist PLO under Yasser Arafat, in the same way that we supported the various jihadist groups against secular strongmen. Israel is also friendly with the source of Islamic extremist ideology, Saudi Arabia. If Trump feels more friendly toward Putin and Assad than the Islamic whackjobs in Turkey and Saudi Arabia, then Taleb would welcome his role in the region.
Probably the only big reservation Taleb would have is about Trump going off on the Iran nuclear deal, thinking that Trump might attack one of the key members of the neo-Byzantine coalition. But he shouldn't worry: Trump only goes off on how our incompetent negotiators gave away everything and got nothing from "the Persians, who are great negotiators".
Trump may already know that Iran is far less aggressive than other Islamic states, and that Shia Muslims are far more tolerant and less fundamentalist than the Sunnis. He just has to put that to the side for the moment, while he whips up popular anger over how naive our stupid politicians are, and that we need more cunning negotiators on the American side in order to defend our interests against the equally cunning Persians.
So far Trump hasn't even hinted at attacking Iran, pushing for regime change, or anything interventionist like that. With Russia being their ally, Trump isn't reckless enough to start World War III over Iran, a death wish that he in fact accuses some of his GOP rivals of having (the ones who want no-fly zones in Syria).
If he gets along well enough with Trump, Nassim Taleb just might become our next Secretary of the Treasury -- imagine how much healing the financial world could undergo with Mr. Black Swan himself at the helm. Normally we'd have to add, "Well, at least we can dream," but in this election anything is possible. It would certainly fit with Trump's crusade to flush out the flunky sell-outs and put in outsiders who are smart, sharp, tough, and honorable stewards.