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So if rationality is about winning and Trump won, is he rational?
No, because rationality is systematic winning. And the main point here is “systematic". You could win sometimes in Russian roulette, but to play in it is not rational.
Systematic winning gives you opportunity to win constantly in many different games. Randomness and witchcraft give you a chance to win sometimes, but later you will inevitable fail.
Systematic winning is the ability to transfer expertise from one domain to another.
Trump surely has expertise in public stunts and PR. He knows how to appeal to suppressed emotions of crowds.
Bacteria could survive a billion of years in bottom of ocean, more than any multicellular life. But this winning is narrow.
The main question is in fact is human intelligence an evolutionary benefit or a curse which will destroy us quicker than any other large specie was destroyed in some type of a global catastrophe? Is our winning systematic at all, or just a long random flux?
Trump, probably not.
Scott Adams, probably not.
Peter Thiel, probably yes. He "bought" a big pile of utility and power for a million dollars and a minimal social-capital hit.