Trump is actually really complex, and imo, very interesting.
Yeah, he grew up with some money, but not much more than most high level politicians.
His parents sent him to military school at 13 because they thought he was acting out and rule breaking. His family money was very nice, but not robust....not NYC robust.
If you want to know what fuels him, it's the Manhattan elite. Despite being very rich, he wasn't accepted. He was from Queens, and didn't come from old NYC money. Even when he became very rich, they didn't respect him. When he became one of the richest people in NYC, they still didn't respect him - he's not one of them. He's always been brash, and self-promoting....the NYC elite didn't see him as their own.
If you want to understand Trump, even a little bit, read up on Roy Cohn. He was a bare knuckle, win-at-all-costs, NYC attorney who had some very big connections and was a major character. He liked to have public brawls, the more attention the better - bring a gun to a knife fight kind of guy. Very old-school NYC, not polite, not polished.
Trump is comfortable with confrontation. He likes it. It's the exact opposite of most politicians. He thrives in it.....everyone is playing into his hands.
