When Donald Trump billed Mike Tyson $2 million after surprising partnership fell through

Donald Trump and Mike Tyson have often publicly expressed their respect for one another. Nevertheless, an oft-forgotten element from their relationship is Trump seeking $2 million from 'Iron Mike' after their unconventional business partnership fell apart.

Back in 1988, boxing heavyweight kingpin Tyson procured Trump's advisory services in a multi-million-dollar arrangement. Per The New York Times in July 1988, Trump asserted that Tyson asked him for advice regarding future career decisions. Also, a boxing expert was to be hired to assist with the decision-making about Tyson's boxing career in particular.

Mike Tyson's litany of problems outside the ring reached a crescendo that year. A tumultuous relationship with then-wife Robin Givens, a vehicle accident, a street fight with Mitch Green, and other issues plagued him. Another NYT report hinted at a possible conflict of interest in the adviser role, with Trump reportedly earning millions as the live-site promoter for a trio of Tyson's title matches.

As reported by NYT in October 1988, Tyson and Trump were parting ways. Tyson, who was previously managed by Bill Cayton, gradually transitioned to polarizing boxing promoter Don King's roster. Many feared Tyson's finances would suffer with King as his manager.

Donald Trump demanded a sum of $2 million from Mike Tyson that month. Trump claimed he was an "adviser to nobody" and was his own adviser. He explained that Tyson sought his help to get out of his contract with Cayton.

Trump opined that his 'killer lawyers' coerced Cayton into relenting. In a letter, Trump emphasized that he helped save the pugilist "$50 million." He alluded to facilitating a sharp reduction in the percentages Cayton collected from Tyson's earnings. He implied that Cayton's cut from Tyson's boxing payouts was brought from 33 to 20 percent.

Also, Cayton's prior personal-services contract was sidelined, as Trump supposedly ensured that the manager gets a cut only from Tyson's boxing earnings. Apparently, if he'd bring 'Iron Mike' a client for another venture, he'd get a mere 10 percent cut.

With Tyson drifting toward King, Trump requested the $2 million sum from Tyson. An excerpt from Trump's comments read:

"When Mike asked me to help him get out of his contract with Bill Cayton, I told him, 'I can't do this stuff for nothing. I want either $5 million for myself or I want you to give $2 million to charity.' Mike agreed to the $2 million that would go to various charities in his name and my name."

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Mike Tyson supported Donald Trump in the 2024 U.S. presidential elections

During an appearance on Hot 97 back in 2015, former undisputed heavyweight champion boxer Mike Tyson asserted his support for the Republican Party's Donald Trump. The latter went on to win the 2016 elections and become the POTUS (President of the United States).

Furthermore, prior to this year's U.S. presidential elections, 'Iron' appeared on the It Is What It Is podcast and praised Trump. Tyson, who returns to the ring in a much-discussed fight against Jake Paul, implied that he supports the politician despite disagreeing in certain regards.

"Trump is going to win. Yeah, it'd be nice if he wins ... He is just a good man. Listen, I don't agree with all his sh**. Nobody agrees with all my sh**."

Watch Mike Tyson's assessment below (39:58):