So yes, in retrospect he made some very basic errors. That said, it's pretty easy to call someone stupid after reading a long-form piece informed by a full indictment of their crimes produced by an intergovernmental criminal investigation and subsequent trial.

I have no experience in the matter, but I imagine that being the kingpin of such an organization tends to pull one's head in so many directions that it's easy for smart people to do dumb things unknowingly.