Mike Tyson's Complicated Relationship With Trump, Explained

Similar to the surprising up-and-down relationship Donald Trump had with O.J. Simpson for many years, the former president was also close to Mike Tyson. In his 1990 memoir "Surviving at the Top," Trump defended the boxer who was known to be violent outside the ring. "He [just] grew up on the mean streets, where any sign of weakness could be fatal," Trump wrote about Tyson (via British GQ). The pair became acquainted in 1988 when the real estate tycoon hosted three of Tyson's matches at his Trump Plaza casino-hotel.

By July 1988 their relationship evolved, and Trump became the chief advisor for the heavyweight champion. "Mike Tyson has asked me, and I have agreed, to serve jointly, with regard to future decisions about Mike Tyson's career," Trump told The New York Times. This came on the heels of Tyson having a falling out with his former manager, Bill Clayton. However, their professional partnership was short-lived, and at one point Tyson levied serious accusations against Trump.

According to Trump, "Iron" Mike accused him of having an affair with his then-wife Robin Givens. This came after Vanity Fair published a photo of Givens wearing a "Trump Princess" hat that sparked rumors of infidelity. "Are you f***ing my wife? Everyone's telling me you're f***ing my wife," Trump recalled Tyson's questioning in the 2005 book "TrumpNation: The Art of Being The Donald" (via British GQ). "She's your wife, she's with you ... it's total bulls***," Trump responded. The boxing star believed him, and the two wound up staying on amicable terms for years.

Trigger warning: contains discussion of sexual assault. 

Donald Trump came to the defense of Mike Tyson during the most incendiary moment of the boxer's career. After the latter was convicted of rape in 1992, Trump voiced his displeasure with the verdict. "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 told NBC News at the time (via CNN).

That gesture was never forgotten by Tyson, and years later he showed his loyalty to Trump. The former heavyweight champion endorsed Trump for president in 2015. "He should be president of the United States," Tyson told Huffington Post Live at the time. The following year, when Trump was in the throes of a heated presidential campaign, Tyson spoke about how he related to his former business partner. "Now he knows what it's like when everybody is out to get you," Tyson told the New York Post in March 2016 while mentioning the backlash Trump had faced. "I think it's a pretty awesome thing that he's doing so well."

Trump mentioned Tyson at a campaign rally the next month. "Mike. Iron Mike. You know, all the tough guys endorse me," he told the crowd (per The Washington Post). Despite the endorsement, Tyson never voted for Trump in 2016 due to his felony record, but the pair stayed in touch.

Cameras caught Mike Tyson and Donald Trump sharing laughs together at UFC 287 in April 2023 — over three decades after their business partnership ended. The following month, Tyson was asked about his relationship with the former president when he appeared on the "PBD Podcast" with Patrick Bet-David. "People don't like [him], but Trump is the man," he said. "I've never had a bad moment with him," Tyson added. 

The duo were far more than celebrities who were cordial to each other at high-profile events. The "Undisputed Truth" author said that he visited Trump's home. "I just had dinner with him ... in Mar-a-lago," Tyson said. Melania Trump and Barron Trump also joined Tyson for the dinner, and the boxer described it as "off the hook." Bet-David mentioned how tall the teenage Trump had grown, but Tyson thought Barron's intelligence should be talked about more than his height as he gushed over the youngster's maturity.

A year after that interview, Donald made an overture to his similarities to Tyson when he posted a photo of him to Truth Social on May 29. In the snap, Tyson wore a shirt that read: "If You Don't Like Trump Then You Probably Won't Like Me... And I'm OK With That." Donald wrote "Thank you Mike!" alongside the snap. However, according to the Huffington Post, the image was photoshopped, and altered from a screengrab captured in a video Tyson posted earlier in the year.