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.
Read the rest of "The Trump Files":
- Trump Files #1: The Time Andrew Dice Clay Thanked Donald for the Hookers
- Trump Files #2: When Donald Tried to Stop Charlie Sheen's Marriage to Brooke Mueller
- Trump Files #3: The Brief Life of the "Trump Chateau for the Indigent"
- Trump Files #4: Donald Thinks Asbestos Fears Are a Mob Conspiracy
- Trump Files #5: Donald's Nuclear Negotiating Fantasy
- Trump Files #6: Donald Wants a Powerball for Spies
- Trump Files #7: Donald Gets An Allowance
- Trump Files #8: The Time He Went Bananas on a Water Cooler
- Trump Files #9: The Great Geico Boycott
- Trump Files #10: Donald Trump, Tax-Hike Crusader
- Trump Files #11: Watch Donald Trump Say He Would Have Done Better as a Black Man
- Trump Files #12: Donald Can't Multiply 17 and 6
- Trump Files #13: Watch Donald Sing the "Green Acres" Theme Song in Overalls
- Trump Files #14: The Time Donald Trump Pulled Over His Limo to Stop a Beating
- Trump Files #15: When Donald Wanted to Help the Clintons Buy Their House
- Trump Files #16: He Once Forced a Small Business to Pay Him Royalties for Using the Word "Trump"
- Trump Files #17: He Dumped Wine on an "Unattractive Reporter"
- Trump Files #18: Behold the Hideous Statue He Wanted to Erect In Manhattan
- Trump Files #19: When Donald Was "Principal for a Day" and Confronted by a Fifth-Grader
- Trump Files #20: In 2012, Trump Begged GOP Presidential Candidates to Be Civil
- Trump Files #21: When Donald Couldn't Tell the Difference Between Gorbachev and an Impersonator
- Trump Files #22: His Football Team Treated Its Cheerleaders "Like Hookers"
- Trump Files #23: The Trump Files: Donald Tried to Shut Down a Bike Race Named "Rump"
- Trump Files #24: When Donald Called Out Pat Buchanan for Bigotry
- Trump Files #25: Donald's Most Ridiculous Appearance on Howard Stern's Show
- Trump Files #26: How Donald Tricked New York Into Giving Him His First Huge Deal
- Trump Files #27: Donald Told Congress the Reagan Tax Cuts Were Terrible
- Trump Files #28: When Donald Destroyed Historic Art to Build Trump Tower
- Trump Files #29: Donald Wanted to Build an Insane Castle on Madison Avenue
- Trump Files #30: Donald's Near-Death Experience (That He Invented)
- Trump Files #31: When Donald Struck Oil on the Upper West Side
- Trump Files #32: When Donald Massacred Trees in the Trump Tower Lobby
- Trump Files #33: When Donald Demanded Other People Pay for His Overpriced Quarterback
- Trump Files #34: The Time Donald Sued Someone Who Made Fun of Him for $500 Million
- Trump Files #35: Donald Tried to Make His Ghostwriter Pay for His Book Party
- Trump Files #36: Watch Donald Shave a Man's Head on Television
- Trump Files #37: How Donald Helped Make It Harder to Get Football Tickets
- Trump Files #38: Donald Was Curious About His Baby Daughter's Breasts
- Trump Files #39: When Democrats Courted Donald
- Trump Files #40: Watch the Trump Vodka Ad Designed for a Russian Audience
- Trump Files #41: Donald's Cologne Smelled of Jamba Juice and Strip Clubs
- Trump Files #42: Donald Sued Other People Named Trump for Using Their Own Name
- Trump Files #43: Donald Thinks Asbestos Would Have Saved the Twin Towers
- Trump Files #44: Why Donald Threw a Fit Over His "Trump Tree" in Central Park
- Trump Files #45: Watch Trump Endorse Slim Shady for President
- Trump Files #46: The Easiest 13 Cents He Ever Made
- Trump Files #47: The Time Donald Burned a Widow's Mortgage
- Trump Files #48: Donald's Recurring Sex Dreams
- Trump Files #49: Trump's Epic Insult Fight With Ed Koch
- Trump Files #50: Donald Has Some Advice for Citizen Kane
- Trump Files #51: Donald Once Turned Down a Million-Dollar Bet on "Trump: The Game"