• Andrew Starc

Pugilist-In-Chief – Donald Trump's controversial ties to boxing and Mike Tyson

Donald Trump's business ventures have ranged from his iconic hotels and casinos to the downright bizarre.

He's flogged Trump Steaks, self-declared as "the world's greatest".

He's sold Trump Vodka that promised drinkers "success distilled" – a quality typically the opposite experienced under the influence of the Russian spirit.

He's even offered financial lifeline to homeowners with Trump Mortgage, under the personal guarantee of "Who knows more about financing than me?”

All these ventures, unsurprisingly, failed spectacularly.

However a business venture in which Trump met widely recognized success is boxing. He even became Mike Tyson's advisor, before the Baddest Man on the Planet accused him of sleeping with his wife.

As you'll see, Trump's history with boxing, like everything he does, wasn't without controversy.

How Donald Trump made boxing great again

Trump made his entrance into the grimy, notoriously corrupt boxing world in the 80's.

In 1984, he opened his first casino, Trump Plaza Casino, in Atlantic City, New Jersey – which was fast becoming the East Coast's answer to Las Vegas.

Realising the financial boon promised by an influx of boxing fans to the casino floor, Trump began hosting major title fights at a neighbouring venue, Boardwalk Hall. Soon, Atlantic City was challenging Las Vegas as boxing's premier destination.

His present day notoriety notwithstanding, Trump is widely regarded as a pioneer for boxing in New Jersey's gambling mecca – so much so that he was inducted into the Atlantic City Boxing Hall of Fame.

"Donald Trump had a very significant role in the 80's and 90's in establishing Atlantic City as a viable boxing destination," said Yahoo Sports reporter Kevine Iole in the UFC documentary Combatant in Chief.

Mayor of Atlantic City Sen. Jim Whelan, in an interview with The Philadelphia Inquirer, similarly praised Trump.

"He was very good for the sport, and that was good for the city. Trump was good at generating buzz and generating publicity. Fight night had made this town sizzle."

In 1987, Trump hosted six of the seven title fights in Atlantic City, including the heavyweight match-up between Michael Spinks and Gerry Cooney. Spending $3.2 million to host the bout, Trump's casino raked in $7.2 million from gamblers.

However the fight that really put Trump on the boxing map, and kindled his relationship with the Baddest Man on the Planet, was the hotly anticipated Tyson vs Spinks.

Donald Trump hosts Tyson vs Spinks in Atlantic City

Tyson vs Spinks was one of the biggest title fights in history – a "Once and for all" contest between two undefeated fighters, to unite boxing's many world titles.

Somehow, as is his wont, Trump insinuated himself onto center stage.

A hilariously bizarre promotional video, in which Tyson and Spinks take turns saying "Thank you Mr. Trump" while staring each other down, set the scene for Trump's pinnacle moment in boxing.

On 27 June 1988, before 21,785 fans at Boardwalk Hall and millions watching on pay-per-view, Mike Tyson made one of the most intimidating ring entrances in combat sports history.

As the jaunty beat of Spinks' entrance song fades out, a dark, menacing mood descends.

Tyson begins his walk to the ring, not to song as is convention, but to a baleful mix of deep base and metallic clanging.

"It's interesting to note that Mike Tyson selected as pre-fight music just noise. Every once in a while you hear the clanging of chains. I think that's what he has in mind to do to Mike Spinks' head," marvelled the commentator, in terror.

"Everything that Tyson does is intimidating. The electricity in this crowd is AWESOME."

Then, as Trump's name is seen boldly emblazoned around the venue, ring announcer Michael Buffer pays honor to the host of the evening, with an introduction dripping with Trumpian superlatives.

"He's a man whose success at business epitomizes the American dream, the author of the year's best-selling book The Art of the Deal. His vision and accomplishment make him the quintessential entrepreneur. Ladies and gentlemen, New Jersey thanks him – our host for this great evening of championship boxing, Mr. Donald J. Trump."

91 seconds later, Tyson knocks out Spinks in devastating fashion, sending him into retirement and cementing himself as the Baddest Man on the Planet.

Tyson vs Spinks established Atlantic City as the reigning capital of boxing, with Trump Plaza its most revered venue.

Tyson, 21-years-old at the time, summed it up as "a night of beauty," after reportedly receiving $11 million for the bout.

Trump, in characteristic superlative fashion, declared it "the greatest live gate in the history of professional sports," earning him more than $12 million, in addition to $15 million in casino revenue.

He lapped up the attention.

"I put on these fights because I'm a fan. I do it because I like it. It's exciting. People really react to it. You wouldn't see this kind of excitement at the opera or ballet," gushed Trump to the Inquirer post-fight.

Donald Trump's becomes Mike Tyson's advisor

"Mike Tyson has asked me and I have agreed, to serve jointly, with regard to future decisions about Mike Tyson's career," Trump announced to The New York Times in July 1988.

Trump was now advisor to one of history's greatest boxers, chiefly to help Tyson settle a contractual lawsuit against his manager. More importantly, the Brooklyn-born brawler was a cash cow for Trump, helping him rake in millions at the gate, and even more at the tables.

"Donald Trump was one of the first guys to really create a relationship with Mike Tyson," said Dana White in the UFC documentary Combatant in Chief.

The relationship, however, didn't last long – with Tyson accusing Trump of sleeping with his wife, TV actress Robin Givens.

Mike Tyson confronts Donald Trump about sleeping with his wife

Trump recalled the moment in the 2005 book TrumpNation: The Art of Being the Donald.

"He said, ‘Could I ask you, Are you fucking my wife?’ Now, if I froze, I’m dead...you would have zero chance. Here’s the heavyweight champion of the world, and he’s a solid piece of fucking armor."

Trump's answer wasn't revealed in the book.

Indicative of his paranoia, Tyson similarly confronted Michael Jordan over the same suspicions.

Donald Trump defends Mike Tyson after his rape conviction

It seems Trump didn't sleep with Tyson's wife, given their subsequent support for each other.

In 1992, when Tyson was convicted of raping an 18-year beauty-queen contestant, Trump rode to the defense of his heavyweight moneymaker.

He hosted a press conference in which he proposed Tyson provide financial recompense to the victim, in lieu of jail time.

Trump also shared his opinion of the case to NBC.

"It's my opinion that to a large extent Mike Tyson was railroaded in this case."

"You have a young women who was in his hotel room late in the evening at her own will...who was seen dancing for the beauty contest, with a big smile on her face, looked happy as can be."

Tyson was later sentenced to six years in prison, serving only three.

Donald Trump's recent relationship with Mike Tyson

In recent years, Trump and Tyson have taken turns publicly supporting each other.

Tyson endorsed Trump for president in 2016. While in May 2020, Trump tweeted his support for Tyson in the lead up to his comeback bout with Roy Jones Jr.

In September 2020, Trump hilariously retweeted a clip of Tyson confessing to Joe Rogan that he would often get an erection while boxing, describing it as "orgasmic."

How Donald Trump swindled $2.5 million from Bob Arum

The manner in which Trump did the dirty on famed boxing promoter Bob Arum is worthy of inclusion in The Art of the Deal.

In 1990, Trump's Atlantic City Casinos – Trump Plaza Casino and Trump Taj Mahal – were on the verge of bankruptcy.

Looking to change the odds, Trump made an audacious $11.5 million bid to host Hollyfield vs Foreman – a ridiculous sum given his casino's financial position.

Arum, who promoted Foreman, along with Hollyfield's promoter Dan Duva, accepted the bid. Wary of Trump, they included a rare "lock-box" clause in the contract, ensuring money from the fight couldn't be used to support his failing casinos.

"It was Trump throwing out these crazy numbers, and the people working for Trump telling him 'Donald, we can't afford this,'" recalls Arum in an interview with CNN.

Just days after the contract was signed however, Trump found a way to cheat the duo out of millions – and keep the fight.

On January 17, 1991, the first Gulf War broke out. Days later – two weeks before the fight – Trump sends Arum and Duva a fax, informing them he was enacting a rarely used clause in the contract.

"Dan got one and I got one from Trump's office saying, 'The deal is off [because of an] act of war,'" Arum told Yahoo Sports.

"We thought it was a joke, and I went to the press and said, 'There's no act of war unless and until Sadam Hussein lands troops on the beaches of Atlantic City.' But Trump insisted it was an act of war."

When Arum and Duva proposed moving the fight to Las Vegas, Trump threatened to sue. With the fight looming, and the prospect of a long legal battle, the duo were forced to except Trump's terms.

Hollyfield won the bout by unanimous decision, and Trump walked away with $2.5 million from Arum and Duva.

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