In 1996, Harvey Weinstein had just become that guy in Hollywood after the success of Pulp Fiction which many studios passed up on but he wasn't the kingmaker yet. It is not as far fetched as people think that they knew each other. The Weinstein brothers were brothers from Queens who built their name distributing rare foreign films in the U.S, they had no real clout in the film industry until the mid 90s.
Jay is a well known drug dealer in mid 90s new york who has been hovering on periphery of the music industry since the late 80s, going on tour with Big Daddy Kane, been in music videos. Not saying it's true, Jay is not even close to being my GOAT rapper and I don't hate him or wish him any ill will but looking into how the Weinstein Brothers actually came up, their reputation from the start and it is not a stretch that they would be aware of each other at all.
Post War New York until the 90's was a very interesting place in terms of people from seemingly different walks of life, mixing. People who you would never expect were involved in the dope game. There are supermodels from that era who were moving drugs, you really think that the Weinstein's were just distributing foreign films in the 80's and early 90's. They are hustler's and hustler's tend to have a funny way of coming across other hustler's.