Tyson was found guilty of raping 18-year-old Desiree Washington, a Miss Black America contestant, in a hotel room. After the 1992 verdict, Trump argued that Tyson didn't necessarily deserve prison time.
"I'm totally opposed to obviously what happened. I'm a very strong believer in harsh punishment," Trump said. "But we think it's probably, in this particular case, a lot more good can be done by having Mike Tyson pay a substantial award both to the victim subject to court approval and creating a ward for people that were abused or raped in the state of Indiana."
The next week, in an interview with NBC News, Trump seemed to blame the victim.
"You have a young woman that was in his room, his hotel room late in the evening at her own will. You have a young woman who was seen dancing for the beauty contest [the next day], dancing with a big smile on her face, looked happy as could be," Trump said.
Trump repeated his claim about Tyson's rape conviction in print, radio and television interviews. Trump's campaign did not respond when CNN asked about defending Tyson, proposing an alternative punishment and blaming the victim.
Trump's efforts didn't keep Tyson out of prison. He was sentenced to six years. He served three.
Tyson was an investment worth protecting for Trump: The young fighter had won some of his biggest victories at Trump-sponsored bouts in Atlantic City, N.J., earning the future Republican presidential nominee millions.
"Tyson was really the behemoth of the sport," said Seth Abraham, a former HBO Sports executive. "Understandably Trump wanted to have the Rolls Royce of the boxing business."
Along with the infamous promoter Don King, Trump brought Tyson to Atlantic City for four title fights in the late 1980s.
But for Tyson and Trump, the hot streak didn't last. By late 1990, "Iron" Mike had lost his crown and Trump's Atlantic City casinos were in the red
Tyson came out in support for Trump's candidacy in 2015, after which Trump expressed approval at a rally.
"I love it. He sent out a tweet. Mike. Iron Mike," Trump said. "You know, all the tough guys endorse me. I like that, OK?"