Mr. Trump was behind some of Mike Tyson’s most high-profile boxing matches, advising and publicly defending the “iron fist” many times.

In the 1980s, after becoming one of New York’s biggest real estate developers, Donald Trump chose Atlantic City, neighboring New Jersey, as the site for his casino empire, capitalizing on the city’s casino-friendly policies.

He acquired many real estates, built the world’s leading large-scale, high-class casinos such as Trump Plaza, Trump Castle and Trump Taj Mahal.

Many of these projects later collapsed due to financial difficulties, but in a short time, Trump Plaza became the “boxing capital”. It all started when 19-year-old Mike Tyson knocked out John Alderson in just two rounds, in his second professional fight in 1985 at Trump Plaza.

Of Mike Tyson’s nine successful defenses of the WBC world heavyweight title in the years that followed, four were held at Trump Plaza.

Title defenses against Jose Ribalta in 1986 and Tyrel Biggs in 1987 were dramatic. In June 1988, Tyson knocked out Olympic gold medalist Michael Spinks in just 91 seconds, becoming a global celebrity.

Mr. Trump paid a record $11 million to rent the Boardwalk Hall right next to Trump Plaza to host the fight, which brought in $12 million in ticket sales and $15 million in casino revenue at Trump Plaza that night.

Tyson also earned about $22 million from this fight. “This is the greatest fight in the history of professional sports,” Mr. Trump said.

The fight was so successful that it sparked a partnership between the tycoon and Tyson. A month later, Mike Tyson terminated his contract with manager Bill Cayton and hired Mr. Trump as his strategist and financial advisor. Some sources said the two reached an agreement within hours of the fight with Spinks. Tyson also sued his former manager Cayton, accusing him of “ruining” his youth.

Trump claimed to have played a major role in all of Tyson’s decisions at the time, including his lawsuit against former manager Cayton. “I always remember him as a good guy, paid me a lot of money,” Tyson laughed, recalling Trump on the NY Post Sport podcast in 2022 .

In August 1988, Mike Tyson got into a fight with Mitch Green outside the Dapper Dan clothing store in Harlem, New York. Green, who was the boxer Tyson lost to in 1986, was also a notorious gangster.

The brawl could have ended Tyson’s career. Green needed five stitches to his face, while Tyson suffered a fractured right hand, leaving the world heavyweight champion in danger of losing his title defense against Frank Bruno at Wembley Stadium, England, scheduled for October 1988.

Mr. Trump then intervened, negotiating a deal to reschedule the fight and bring it to Las Vegas in February 1989, where Tyson defeated Bruno.

In 1990, Mike Tyson stormed into Trump’s office after Vogue reported that the tycoon was having an affair with the boxer’s wife, Robin Givens, a famous actress at the time. The story was recounted in a book by veteran NY Times reporter Tim O’Brien after interviewing Trump.

“Hey Trump, I want to ask you something, are you having an affair with my wife?” Tyson asked Trump in the tycoon’s Manhattan office, tossing a copy of Vogue onto the table. The magazine’s cover showed Givens dining with Trump on a yacht.

“Tyson, that’s bullshit. I assure you,” Trump calmly replied.

Tyson accepted the offer. The boxer then offered to sleep on the sofa in the tycoon’s office and promptly fell asleep, while Trump “was too scared to wake the boxer,” Tim O’Brien wrote.

Tyson was arrested in July 1991 for allegedly raping 18-year-old Desiree Washington, Miss Black Rhode Island, in an Indianapolis hotel room. A doctor confirmed that Washington’s physical examination within 24 hours showed signs of rape. Tyson claimed that he did not force her and that the incident was consensual. Tyson was convicted in February 1992.

Mr. Trump publicly defended Tyson, claiming that the boxer was the victim of blackmail. “I have never seen Tyson touch a woman indecently. In fact, the women around him harassed him more,” Mr. Trump said, calling for Tyson to be allowed to train and compensated with money earned from fighting instead of going to jail.

Tyson was eventually sentenced to six years in prison and four years probation in 1992 for rape. He was released early in March 1995.

Their relationship then received less attention, until Mike Tyson publicly endorsed Trump when he ran for president in 2015. At that time, Trump was widely sceptical, even ridiculed, for his style that was far from that of a traditional politician.

“Absolutely, Mr. Trump should be president. This country needs something new, run like a business,” Tyson told the media.

“Iron Man Mike endorses me. That’s great. The tough guys like me,” Trump responded to Mike Tyson’s endorsement in Indianapolis.

Tyson, now 58, has not publicly endorsed Trump in the 2024 election, but comments this year suggest the two remain on good terms.

Tyson expressed sympathy for Mr Trump as the former president faced multiple criminal charges. “The way they treat him in the press and the media? Think about it, the way they treat him in court? That’s the way they treat people of color,” Tyson said mid-year.