The South Florida Sun-Sentinel relates that right before the Michael Spinks fight, Mike Tyson’s manager Bill Cayton received court papers at ringside. Tyson was suing to KO their contract, arguing that nobody told him co-manager Jimmy Jacobs was dying. The boxer contended that this invalidated his remaining arrangement with Cayton. During the post-fight interview, Tyson seemingly announced his retirement from boxing. Citing unnamed “sources close to Trump and Tyson,” The Village Voice suggests that the lawsuit culminated from months of discussions between the businessman and the boxer. One source insisted Tyson absolutely knew about Jacobs’s dire condition but needed an excuse to oust Cayton. Trump waited to strike until the Iron Mike was hot.

According to Trumped!, on the day of the fight, Trump comforted Cayton and assured the jilted manager, “Bill, I’m with you one hundred percent.” Less than two weeks later, on July 9, 1988, he publicly pointed the finger at Cayton, specifically the middle one. He informed The New York Times that he would assist Tyson in the lawsuit, slamming the management contract as “onerous and unfair.” He would further serve as the fighter’s advisor.

UPI explains that Trump had joined the board of the newly incorporated Mike Tyson Enterprises, a company devoted to advising Tyson on boxing and business decisions. After unveiling the new organization, Tyson un-retired from fighting. His enterprising new advisor was said to have enlisted the top-tier attorney who took over Tyson’s legal team. The parties settled out of court.

Mike Tyson writes in Undisputed Truth that even though his “social skills consisted of putting a guy in a coma,” he “was like a f***ing trained puppy dog around” Robin Givens. But the boxer was a snarling guard dog around dudes he thought knew her intimately, like when he allegedly threatened NBA icon Michael Jordan, who previously dated Givens. Boxing Scene reports that Rory Holloway, who managed Tyson for years, says in his memoir that the boxer began raging Jordan during a 1988 birthday party for Chicago Bears legend Richard Dent. Allegedly, Jordan was visibly frightened, so just imagine the abject terror Donald Trump might have felt when Tyson supposedly accused him of Michael-Jordan-ing his wife.

As Deadspin details, rumor had it that Givens was climbing Trump’s tower, and that Trump bragged about it. Writer Tim O’Brien claims in Trump Nation that “The Donald” told him Tyson showed up at his Fifth Avenue office not long after the Spinks fight. After 15 minutes of chit-chat, Tyson popped the question, “Are you f***ing my wife?” He also whipped out a Vogue magazine issue that showed Givens donning a hat from Trump’s yacht, Trump Princess. (There’s some photographic evidence that they boarded a yacht together.) “Now, if I froze, I’m dead,” Trump recalled of the encounter. So he strongly insisted the rumors were fake news. Satisfied, Tyson napped and drooled all over Trump’s office couch. Was this entire encounter fake news? Who knows?

The Village Voice notes that during the legal battle Donald Trump helped Mike Tyson wage against manager Bill Cayton, it came to light that Tyson once tried to force a kiss on a parking attendant and slapped her supervisor for intervening. The prosecutor dropped the charges after Tyson paid his victims in an out-of-court settlement. When Tyson was found guilty of sexual assault years later, Trump advocated making him pay with money instead of prison.

In 1992, an Indiana jury convicted Tyson of assaulting Desiree Washington, a contestant in the Miss Black America pageant (via History). Prior to sentencing, Trump began defending him in the court of public opinion, arguing that the boxer belonged between the ropes and not behind bars. Per the Associated Press, The New York Post quoted Trump as stating, “What has happened to him, the conviction, is already punitive. The victim has had the satisfaction of humbling him and being vindicated.” He thought Washington should be compensated financially with proceeds from a proposed fight between Tyson and then-heavyweight champ Evander Holyfield.

As documented by Fox 2 Now, Trump maintained that “a lot more good can be done by having Mike Tyson pay a substantial award both to the victim … and creating a ward for people that were abused or raped in the state of Indiana.” He argued his case in various TV, radio, and print interviews. However, Tyson received a ten-year prison sentence, with four suspended, and served three years.

When a 53-year-old Mike Tyson posted training videos in May 2020 to herald his return to the boxing ring, Donald Trump tweeted, “Keep punching Mike!” Those three words of encouragement arguably capture much of Trump’s approach to his presidency. It’s no secret that he cultivated a reputation for winging it — or rather West-Winging it — in the White House. Citing unnamed administration officials, Axios said in 2019 that the president explained his aversion to strategic plans by quoting Tyson, “Everybody has a plan until they get punched in the mouth.” Trump’s pugnacious debate style and 280-character ear bites on Twitter might remind you of the intimidating statements Tyson made during interviews and press conferences. Trump even poses in photos like he’s fighting.

According to GQ, Trump’s political pugilism was likely inspired by Tyson’s mind games. In his boxing days, Iron Mike ironically had a plan to punch people with his mouth. His sometimes deranged remarks were so over-the-top that the headline-hungry media obediently repeated them, terrifying many opponents. Tyson also spoke with his fists. Before his opening bell of the Spinks bout, Tyson struck fear into his foe by punching a hole in a dressing room wall, per TheIndependent. As Spinks’s manager looked on, Tyson warned, “I’m gonna hurt this guy” (via Sports Illustrated). Tyson’s psychological tactics impressed Trump so much that he wrote about it in Surviving At The Top and seemingly took a page from the boxer’s book as president.