He said Mike Tyson shouldn’t have to go to prison for rape
In March of 1992, boxer Mike Tyson was convicted of raping 18-year-old Desiree Washington, a contestant for Miss Black America. Donald Trump said that, rather than going to prison, Tyson should be able to pay "millions and millions of dollars" to victims of rape, saying "a lot more people will benefit by what I’m saying than by throwing a man in jail, virtually with no money -- because by the time this ends he won’t have any..."
Tyson went to prison and still has at least some money.
He tried to create a reality TV show that reformed party girls
In 2007, Donald Trump worked with Fox to develop a reality series called Lady or a Tramp.
The show would send young, hard-partying women through charm school to reform their behavior, learning "the finer points of skills like flower arranging and needlework." Plans involved Trump potentially arriving from time to time to judge the contestants’ progress. Trump said, "We are all sick and tired of the glamorization of these out-of-control young women, so I have taken it upon myself to do something about it... I am creating a real-life version of My Fair Lady. This show is all about getting a second chance and transforming for the better; the idea is genius and the show will be huge."
Lady or a Tramp never made it to TV.
He examines the Miss USA contestants to pick the most attractive ones
Donald Trump is co-owner of the Miss USA pageant. According to former contestant Carrie Prejean, part of his role involves evaluating the attractiveness of contestants and separating the ones he finds beautiful from those he doesn’t. It’s called the Trump Rule, and according to Prejean, it's made some contestants break down in tears backstage.
Here is a recording of him doing it.
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Joe Oliveto is a writer for Thrillist. The New York Military Academy is directly across the street from his old high school, and he kind of maybe thinks Trump completely, totally exaggerated. Follow him on Twitter.