“He should be president of the United States. Hell yeah, big time,” former heavyweight champion Mike Tyson told Huffington Post, endorsing Donald Trump back during the 2016 presidential election. This wasn’t the only time ‘The Baddest Man on the Planet’ has expressed his support for the Republican presidential candidate. 

“I always remember him from being a good guy, paying me a lot of money,” Tyson said during a 2022 appearance on the New York Post Sports’ podcast. But! Have you ever wondered why ‘Iron’ Mike was such a big Trump fan? Yes, Trump used to host Tyson’s fights back in the day! However, there’s more to the story. As Mike Tyson prepares to share the ring with Jake Paul on November 15th, let’s dive into the history between Trump and Tyson. 

Donald Trump’s unknown connection in Mike Tyson vs Mitch Green brawl

Tyson might have had the aura of a gangster, but the real gang leader was Mitch ‘Blood’ Green in the streets of Harlem. The duo had fought in 1986 when Tyson defeated ‘Blood’ via unanimous decision. Two years later, in the early hours of August 1988, Tyson and his sworn life-long deadly rival clashed in a surreal and infamous brawl outside Dapper Dan’s clothing store on 125th in Harlem. 

Tyson was there for business—he had dropped in to pick up his customized white leather jacket emblazoned with ‘Don’t Believe The Hype.’ By this time, Green was obsessed with getting a second go at Tyson. Lo and behold, after learning about Tyson’s visit to Dapper Dan’s clothing store in Harlem, ‘Blood’ showed up to confront Tyson, who had already become the undisputed heavyweight champion by then. 

There are several accounts of what happened next. Green, for one, claimed Tyson was the one who threw the first punch, while Tyson has maintained he was just trying to leave. The brawl sent both men to the hospital, although Green’s injuries were the worst. Tyson’s punches left Green with five stitches on his face and a closed eye. Tyson, on the other hand, had suffered a hairline fracture on his right hand.

However, this was enough for his upcoming fight at the time against Frank Bruno at Wembley Stadium to be jeopardized. That’s where Donald Trump came into the picture. Somehow Trump was involved in the fight and helped handle the negotiations surrounding the brawl. After the Dapper Dan brawl, he helped reschedule the lucrative Tyson-Bruno match.

Tyson’s broken hand meant the fight was off, with both parties losing time and money. Trump’s influence helped renegotiate and secure a new date, ultimately bringing the fight back to the Las Vegas Hilton in Las Vegas in 1989, where Tyson defeated Bruno. 

When did Mike Tyson hire Donald Trump as his adviser?

Mike Tyson hired Donald Trump as his adviser back in July 1988. This came after Tyson had knocked out Michael Spinks within 91 seconds during their fight in the same year in Atlantic City. In fact, after his victory over Spinks, ‘Iron’ Mike parted ways with his former manager Bill Cayton, ending their four-year contract.

Tyson sued Cayton, alleging that Cayton had exploited Tyson’s trust and youth. Regardless, after Tyson turned to Trump, then a real estate mogul, Trump confirmed the news in a New York Times report. “Mike Tyson has asked me and I have agreed, to serve jointly, with regard to future decisions about Mike Tyson’s career, including but not limited to the lawsuits going back and forth between Mike and his current manager, Bill Cayton,” Trump said. 

That said, Mike Tyson and Donald Trump clearly share a deep history with each other. Perhaps that’s the reason they often talk about each other. Coincidentally, Tyson has a big fight coming against Jake Paul in a few days while Trump is running for president. It would be interesting to see how they measure in their tests. What do you think about their relationship?