It’s not just because he’s from NYC. It’s because he is rich, famous, powerful, and doesn’t give a damn whether people love him or not.
Also, Trump has known or met every so-called important person of the last 30 years. Apparently, he keeps a diary, lol, and so can dredge up every scurrilous piece of information on them at a moment’s notice. I.e.: his takedown of Bill Cosby.
Alinsky tactics: meet Trump!