This is one of my favorite Trump stories.

The tl, dr is that back in the day he had a chance to endear himself to the Manhattan elites. Instead, he let his stupidity, greed, and arrogance make him anathema to the people he was so desperate to impress.

https://www.forbes.com/sites/michaellisicky/2020/10/03/how-donald-trump-took-down-bonwit-teller-a-fifth-avenue-landmark/