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"He's the single most monumentally arrogant SOB I've ever met, and I've spent nearly my entire career working for billionaires where hubris is commonplace. "

You've actually met the guy? Tell us more!!!

Please, do tell

I met him a couple of times. The first time was at a JDF fund raiser, way before he was even thinking of running for Mayor. He and his people were sitting at the table next to the one my boss had bought, and we ended up sort of caddy corner from one another. He wasn't rude or condescending in any way, but his arrogance still shown through. It was something about how he considered all questions of opinion over as soon as he told anyone what he thought. It was like once his bit was said, we were all supposed to say, "Well OK ... that's the answer then... I guess we don't have to worry about that anymore. Chicken or Steak? Well Mike says steak so I guess that's decided." and if someone then said chicken he would look at them like "what do you mean you want chicken... didn't you hear me say steak?"

The next time I met him he was exploring a run for mayor, and he stopped by our trading floor to take informal and off the record questions from us as a fact finder. He has some... I don't know what to call it exactly except charisma... but it's clear that the thinks the individual really has no business making decisions when an expert (like him or some other government hack appointed by him, or in the case of his company... hired by him) can make the decision for them. It's just the way he thinks the world should work.

Let the smart people decide, and the rest should just shut up and follow.