The Trump Files: When Donald Tried to Shake Down Mike Tyson for $2 Million

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Until the election, we’re bringing you “The Trump Files,” a daily dose of telling episodes, strange but true stories, or curious scenes from the life of GOP nominee Donald Trump.
Donald Trump often promises to give money to charity, but he’s much better at handing out other people’s cash than his own. So it’s no surprise that Trump once tried to strong-arm boxing legend Mike Tyson into giving him $2 million, ostensibly for charity, in 1988.
That June, Trump hosted Tyson’s heavyweight fight against Michael Spinks in Atlantic City, New Jersey, holding it in an arena next to the Trump Plaza casino. It was part of Trump’s play to become a big-time figure in boxing, but his next move went even further. Less than two weeks after Tyson beat Spinks, Trump announced he was becoming a business adviser to Tyson. Any money he made from the arrangement, Trump claimed at a press conference, would go to charities for fighting “AIDS, cerebral palsy, multiple sclerosis” and “helping the homeless.”
Tyson’s life got increasingly chaotic after the fight. He told reporters he was “burned out” and announced his retirement at age 22. His marriage to Robin Givens was falling apart. (Givens later alleged that Tyson abused her while the two were married.) And he was in the middle of suing his manager, Bill Cayton, whom Trump helped push aside when he slid into Tyson’s circle. But despite the turmoil in Tyson’s personal and professional life, Trump wanted Tyson to fork over the payment for his expert advising services.
“As you are aware, I was very happy to beat Bill Cayton and reduce the ridiculous fees he was getting from you both on his management and personal service contracts,” Trump wrote in a letter to Tyson on October 21, 1988. “Not only was this time-consuming, but tremendous energies and knowledge were displayed—much as you display your energy and knowledge in the ring against an opponent. Over the course of your career, I have probably saved you substantially in excess of $50,000,000 and therefore, the $2 million contribution, all of which will go to worthy charities, is very reasonable. If you could ask your accountants to write a check to the ‘Donald J. Trump Foundation’, I will distribute the money in my name and yours and will let you have a list of the charities which benefited.”
It’s not clear whether Tyson actually made the payment. If he did, Trump might be the only person who benefited. According to BuzzFeed, which reviewed the Trump Foundation’s records in June, the $2 million donation never appeared.
But the demand clearly didn’t hurt Trump and Tyson’s friendship. Trump later publicly suggested striking a deal so Tyson could avoid jail time for rape, and Tyson, who is now Muslim, has even endorsed the GOP nominee despite his Islamophobic stances.