Trump was always the butt of businessman jokes. He was never "america's darling". He always wanted to be in the club, to be seen as an example of business excellence, but the actual examples are generally pretty quiet and keep to themselves.
Donald Trump once owned a home in that town. He didn't hold on to it for very long, as Donald Trump was the butt of every joke those same financiers and their kids told growing up in the 90s and early 2000s. He realized that in the world of UHNW people, wealth is quiet and wealth also knows who's for real, and who isn't.
Turns out, a loudmouth who wears makeup and bankrupted 2 casinos isn't really wealth. Donald Trump was ran out of town because it was clear quickly that he was nothing more than a cartoon character.