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Notes -
Important caveat I missed up front - I feel like Trump was like this before 2016.
I can understand why he might have a bit of a persecution complex since then.
I thought the usual argument there was that Trump has always wanted to be recognised and respected by New York high society, and he never has been. He's tried to use money and fame to buy his way in, but he's too fundamentally lacking in class or tact. I could imagine that, internally, what it feels like to be Trump is to be always excluded from the inner ring. He wants to get inside that ring, but no matter of power, not even being president, is enough to generate acceptance or respect.
The cartoon bit is important, I think. Trump is very rich and powerful, but Trump is also a clown in a way that real high society elites aren't. Trump's status has always depended on his ability to perform, the ability to get a crowd to hoist him on to their shoulders in a rush of popular enthusiasm. That's not how it is for the real upper class. The real upper class may be popular, but they don't need popularity, and in fact ought to mildly disdain it.
Money, fame and golfing ability. Elite golf is part of WASP high society (Steve Sailer has written a lot about this), and Trump embraced it and it embraced Trump (rejecting him only after January 6th). I don't think you are excluded from the inner ring if a club like Winged Foot not only grants you membership, but also tolerates blatant cheating.
I can absolutely imagine that Trump needed the single-digit handicap (which he earned legitimately when he was younger) to get into clubs that old money is allowed to shoot 90s at, but if the bluebloods see you as actively undesirable (at the time Trump was learning to golf, "undesirable" mostly meant "Jewish"), you need to be winning majors to get in with pure golfing ability.
This is a choice. Not many real high society elites make that choice, but the ones who do don't get kicked out of the club.
Trump doesn't need popularity for business reasons, he craves it for personal reasons. Fred Trump never courted popularity, and nor do most commercial real estate guys. Trumps third and fourth careers (reality TV star and politician) were choices made by a man who was already rich enough to do what he wanted.
Of course, the ultimate test of whether old money accepts you is who your kids marry, and the results for Trump are interestingly ambiguous.
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