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Donald Trump was awful at boxing, too

(Originally Published: January, 2017 @

1988. Amid cries of conflict of interest, grown-up rich kid, real estate mogul, and future President of an increasingly dystopian United States, Donald Trump, announced that he was now “business and boxing adviser” for heavyweight champ Mike Tyson.

”Mike Tyson has asked me and I have agreed, to serve jointly, with regard to future decisions about Mike Tyson’s career,” Trump told the New York Times.

The self-styled adviser role flew in the face of legality and ethics as Trump, live-site promoter to many of Tyson’s bouts, would be in a position where he’d be negotiating with himself regarding site decisions and money issues pertaining to the young champ.

But there was no need to worry about conflicts because, as with most ventures outside of the narrow realm of real estate, Trump would fail fantastically. About 18 months after becoming Tyson’s adviser, “Iron” Mike would be led to defeat in Tokyo against mega-underdog James “Buster” Douglas. Not too long after that, “The Donald” would become just an afterthought in boxing.

All in all, Trump’s time as a major player in the sport lasted about five years, beginning with Gerry Cooney-Michael Spinks in 1987 and ending, for all intents and purposes, with Evander Holyfield-George Foreman in 1991. There were some ventures before and some after, but most of the heavy earning was done in that time span, when Trump was able to leverage his money and relationship with Don King into some highly profitable events for his Atlantic City casino interests.

As is usually the case with all things Trump, his successes came by throwing money at the project(s) (usually other people’s money) and blowing smoke up asses to secure the deals he wanted. Trump inflated purses for fights to lure them into his Atlantic City home base and away from fight capital Las Vegas. He made some quick scores with a few big fights in his time, innovating the moving walkway concept to take fight fans from the arena directly to his casino after the fight. His biggest stroke of genius, though, was a simple one—attaching himself to Mike Tyson, the biggest name in the sport at the time. The Trump-hosted Tyson-Michael Spinks heavyweight title unification bout in 1988 would be the biggest money fight in the history of the sport up until that point, bringing in over $70 million in revenue and, more importantly for Trump, a sizable uptick in earnings for his casino.

But, also in the modus operandi of Trump, when a short term windfall suddenly lost steam, he maneuvered to secure his investment, then bailed on his partners, leaving them to absorb all losses.

In late 1990, with two of his casinos in financial crisis, Trump bid $11 million to host the Evander Holyfield-George Foreman heavyweight title fight. It was considered a gross overpayment for the fight, perhaps spurred on by Trump’s need to roll the dice and come up with something big to save his distressed properties.

Just days after signing the deal in early 1991, though, the U.S. bombed Iraq to begin Operation Desert Storm and Trump seized the opportunity to invoke the “act of war” clause in the contract, insisting on a major cut to the agreed-upon site fee. With the fight date looming and under the threat of a Trump lawsuit should they try to move the fight to another venue, Holyfield’s and Foreman’s promoters, Main Events and Top Rank, were forced to settle for just about half of what Trump had been contracted to pay. On display here was another classic in the Trump repertoire—the strategy of violating contracts at will, knowing that the cost of a long legal battle would be greater to the victim than the money lost from Trump’s unethical restructuring of the deal.

“We just didn’t want to get into litigation over the money,” Holyfield adviser Shelly Finkel explained to the Baltimore Sun at the time.

“This was unprecedented,” Main Events’ Kathy Duva told CNN. “If your claim to fame is that you’ve taken money from other people and haven’t delivered what you promised, that doesn’t make you a genius businessman, that makes you a thief.”

Holyfield-Foreman would be Trump’s last major fight and, shortly after that, the slow unraveling of Trump’s Atlantic City casino empire accelerated.

But, Trump, gifted with a keen ability to see and exploit the greed and/or fear of potential investors, escaped his boxing failures unblemished, just as he escaped his myriad of other failures. Like most rich kids, Trump failed up. Using loopholes and general laissez-faire government policies put in place to favor the rich and powerful, he re-secured his empire and became the rich celebrity best known for being a rich celebrity.

And now he’s going to be the 45th President of the United States, officially taking office on January 20. Good luck with that, America.

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