The Time Donald Trump Tried to Get Mike Tyson Out of Going to Prison for Rape

In October, GOP front-runner Donald Trump got a surprise endorsement from infamous boxer Mike Tyson. "He should be president of the United States," Tyson told the Huffington Post. "Hell yeah, big time!" Tyson said he liked Trump's business instincts: "The guy is winning fair and square, he's not bribing anybody."

Trump and Tyson are old friends who did business together in the late 1980s, when the real estate mogul promoted and hosted several of Tyson's fights at his Atlantic City casinos and even fashioned himself for a time as the boxer's "business adviser."  And in a largely forgotten episode, Trump came to the boxer's aid during one the darkest moments of Tyson's career—his 1992 conviction for raping a beauty queen. To save the champ from being locked up, Trump pitched a highly controversial proposal that would essentially allow Tyson to buy his way out of prison. To some observers, it looked like Trump was engaging in a form of bribery—or at least attempting to rig the system.

Over the years, Tyson's bouts had been highly lucrative for Trump's casinos, which paid millions in order to host the fights but reaped millions more in revenues from the surge in gambling that resulted during these highly anticipated events. In 1991, Tyson seemed destined for one of the biggest fights of his career, a face-off with then-heavyweight champion Evander Holyfield. As the groundwork was laid for this epic bout, it seemed like Trump might lose this event to his competitors in Las Vegas.

Then Tyson was arrested and convicted of raping 18-year-old Desiree Washington in Indianapolis.

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