It looks like Donald Trump and Chuck Shumer's wife (Iris Weinshall) go way back. In 1983 she was appointed Vice President for Economic Development (after her predecessor was fired) in New York. Starting pay was 50000 a year, not bad for a 27 year old.

https://www.nytimes.com/1983/03/24/nyregion/six-top-officials-discharged-by-new-udc-chief.html

It seems like Donald Trump was having trouble getting his development plans approved around the same time. Iris' boss William J Stern didn't like Trump very much.

https://www.timesunion.com/news/article/Trump-and-the-Cuomos-Powerful-friends-once-6886966.php

https://www.scribd.com/doc/304455552/donald-trump-mario-cuomo-letters#download&from_embed