He comes from a once wealthy family with connections to the Rockefellers. His father was in the Kennedy administration, but Whit actually contributed to the American Spectator back in the 70s and 80s.
That was a very different era from the present, and I don't suppose he's especially conservative nowadays, but Stillman was definitely an exception in the film industry. More thoughtful than most movie people.
Wikipedia says his godfather was the man who coined the term WASP, and that's very appropriate if you know Whit Stillman's films. Wikipedia also has this gem:
From Wikipedia, the free encyclopedia
Not to be confused with Slim Whitman.
I agree wholeheartedly that Whit Stillman is a decent guy and a good filmmaker. His family was instrumental in getting JFK elected to the Senate, but it was a different Democratic Party back then.
Whit was born to fantastic wealth, but I don’t think he ended up with a lot of it. I think that after his parent’s divorce and business reversals that Whit found himself well off, but needing to make money somehow. I understand he sold his Manhattan apartment to raise money to make one of his films.
I like Whit. He’s a really decent guy, and I suspect he’s a lot stronger conservative than he can let on.