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."