That's not Taleb's point at all, not even close. The point isn't about whether people take the risk or don't, the point is who is exposed to the risk. The CEO here had skin in the game. He may have been a cowboy taking needless risk, but if so he paid the price. Morally it's a very different thing from making the same set of decisions but never going down yourself.

The point of antifragility is the system benefits, even if the individual loses as happened here. The corruption is when the benefits accrue to one set of people and the risks somewhere else.