Donald Trump and Boxing: The Art of the Double-Deal

By Paul Magno on July 18, 2017
Donald Trump and Boxing: The Art of the Double-Deal
His biggest stroke of genius was attaching himself to Mike Tyson. (Bettman/CORBIS)

“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…

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 the 45th President of the United States, bringing with him all of the madness and self-aggrandizement at the detriment of the big picture Trump usually brings to things he touches.

Good luck, America.

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  1. BS 04:22am, 07/21/2017

    Irish…Total BS. Look up Clarence George archives: Book Review Madame Bey’s ....

  2. Kid Blast 05:20pm, 07/20/2017

    Thanks Irish. I appreciate that.

  3. Irish Frankie Crawford Beat Saijo aka Gimpel 03:35pm, 07/20/2017

    Kid Blast- @Sorry I missed that one….I was under the impression that he thought highly of you and that you shared an interest in power lifting. If he pulled that shit he was way, way wrong.

  4. Kid Blast 02:21pm, 07/20/2017

    F—k that racist piece of slithery slime. He attacked my ethnicity. He was a true key board warrior but likely not so much if he had to talk tough in person.

  5. Irish Frankie Crawford Beat Saijo aka Gimpel 01:17pm, 07/20/2017

    It’s just come to mind that we haven’t heard from MAGA or Alt Knight lately. In their stead we have nonprophet who has come on here like Triumph the Insult Dog…..only this Triumph isn’t funny worth a shit! I don’t recall either MAGA or Alt Knight attacking another commenter on this site….ever! Alt Knight would defend when receipting for abusive posts but that was about it! Controversial things were posted, non-PC things were posted, sometimes off topic but mostly on topic especially when it came to Lightheavys in the Seventies and Eighties. Now we have this sik fuk telling @allen that he should “re-word” his comment to make it more agreeable to Triumph the Insult Dog!

  6. Irish Frankie Crawford Beat Saijo aka Gimpel 12:35pm, 07/20/2017

    -@nonprophet-There you go again feigning sanity….you psychotic fuk! Like when you come on here and give credit to Paul Magno or Caryn Tate when they have written something that you agree with….even then your prime motivation is hate toward those that might disagree with these writer’s positions on certain issues….because you are a hate filled, grievance ridden, maggotshit progressive….accept it….own it….. and you will be well on your way to self discovery. Which reminds me…why don’t you re-post that very thinly veiled threat directed toward Irish Frankie and another that you accused of being a racist on this site. Something about them deserving to be devoured by wolves and shit off a cliff! That’s archived here on Boxing.com in another blog.

  7. nonprophet 10:40am, 07/20/2017

    Thanks a bunch Irish Frankiewhateverthefuc…..

    It’s applaud you for your assistance in exposing your putrid racism, as well for as helping me to point out how ridiculously out of place your racist drivel has been on a boxing site.

    Sometimes, you come off as someone who actually knows a little something about boxing.  It’s just to bad that your racist tendencies prevents you from talking about boxing when you’re on a boxing site and leaving your supremacist claptrap out of the discussion. 

    Do that and you and I will be fine.

    Stormfront, (which you undoubtedly are familiar with) is the current go-to website for white supremacists.  Do us boxing fans a favor and stick with Stormfront to vent whenever you have an urge to spout the kind of racist garbage that you are well known for on this great site.

    Cheerio!

  8. Irish Frankie Crawford Beat Saijo aka Gimpel 08:20am, 07/20/2017

    @nonprophet-Boxing.com archives blogs and I refer any and all to the blog titled “The Ali-Trump Connection-July 7th 2017 and your psycho comments that accompanied that article.

  9. nonprophet 08:17am, 07/20/2017

    Kid…..ROTFLMAO!!!

    And based on similar stuff like that which I’ve heard from other trump supporters, the guy who told you that seems like one of the smarter ones!

    Wait until that MAGA chump finds out what his “God Emperor” trump has in store for him should trumpcare ever get passed.

  10. Kid 07:51am, 07/20/2017

    Yes, it’s great to have Paul on here. He can stir up things pretty well. Love it

  11. Kid 07:47am, 07/20/2017

    nonprophet , I had one moron Trumpster tell me yesterday the following:

    “Bout time we getting rid of Obamacare. Everyone I know’s covered by the Affordable Care Act always.”

    So help me God.

  12. nonprophet 07:12am, 07/20/2017

    GREAT WORK, Paul….absolutely spot-on.


    Unfortunately, it looks like we have a few Trump University certificate holders here today who are apparently waking up from yet another wet-dream about trump, their “God Emperor.”


    Of course we all know that they are the usual suspects:

    “Your Name” (is that the name trump printed on your certificate? );

    “Buster” (please don’t tell us your last name is “Douglas”);

    And last, and certainly least of all, the trump vodka-swilling, ever-demented king of all trump-whores, Irish Frankiewhateverthefuc?


    Bet each and every one of them thinks that trump is the Greatest Of All Time who would whup both Ali and Tyson just like the way he handled Vince McMahon a few years back.

  13. Kid 06:13am, 07/20/2017

    your name. Get back into your deplorable basket you red neck piece of slime. This is a boxing thread, not one for ridge running a-holes like you. So vanish.

  14. Your Name 05:48am, 07/20/2017

    surprised so many fight fans are left wing libs….who would have thunk it!!

  15. Your Name 05:46am, 07/20/2017

    wow magno I guess I should be scared huh? well you don’t know me so you have know idea what I’ve done and I ‘m not going to sit here and “brag” about how “bad” I am like you ! just because you say trump is a con man doesn’t mean s**t to me I mean who the hell are you to throw rocks at anyone what do you know ? did he con you? did he fleece you? I highly doubt it your just another lib trump hater so I have no use for you either pal! you know or a ‘tough” guy you sound like one of those lib snowflkes who need a safe space!! hahaha

  16. Paul Magno 08:47pm, 07/19/2017

    @Your Name….This “libtard” is a gun-possessing, survivalist, ex-fighter, ex-bodyguard living in the Badlands of Mexico smack dab in the middle of the Narco Wars….I just dislike career con men and rich boy sociopaths….and I dislike the weirdos and creeps who like people like that….

  17. Buster 07:21pm, 07/19/2017

    Do you want to know what Trump’s greatest accomplishment has been? He kept Hillary Clinton from occupying the White House. Anyone with any brains is so very thankful for that.

  18. Kid Blast 04:42pm, 07/19/2017

    Yes “your name” Trump is a fine president with a solid moral fiber.

    He is honest

    Always owns up when he is wrong.

    He is well read and understands the Health Reform from the inside out.

    He cherishes women especially if they are not bleeding.

    Has sons who are bright as new copper pennies.

    Has a son-in-law who will resolve the mid-east situation.

    Is very concerned about the climate and NATO.

    Has a great plan to deal with North Korea.

    Thinks Cuba is a part of the axis of death.

    Has a great staff

    Respects other Presidents

    And is never really wrong

  19. Your Name 04:28pm, 07/19/2017

    this magno character revealed exactly who he is in this article I see it all the time with these libtards I guess this moron paul magno wanted trump to allow himself to become a casualty in a bad deal huh? smart business people negotiate around losses something libs like magno frown upon trump outsmarted them all now I don’t know about you but that is the guy I want running our country!!! GO TRUMP!!!!

  20. Kid Blast 04:25pm, 07/19/2017

    Yes Tongue sandwich. Ugh

  21. Lucas McCain 02:25pm, 07/19/2017

    But I know you’re thinking “tongue sandwich”

  22. Lucas McCain 02:23pm, 07/19/2017

    He’s trying to look like a lover, but she (as always) wants to get a flattering portrait and is twisting away.

  23. Adlai 02:21pm, 07/19/2017

    Yeah, the passing years are funny that way.  (Cue the blowing sands shot!)

  24. Kid Blast 01:59pm, 07/19/2017

    What is Tyson doing to that girl?

  25. Irish Frankie Crawford Beat Saijo aka Gimpel 11:13am, 07/19/2017

    @Adlai-You got me there! BTW…do you realize that probably 90% of the people in this great country don’t have a fukin’ clue about your namesake who was the former Governor of Illinois and the UN Ambassador.

  26. Adlai 09:47am, 07/19/2017

    Frankie—did you write your last tuition check to Trump University?  Or send your grocery money in for Trump steaks?  Or cheer with your buds when Cheney assured us the trillion-dollar war in Iraq would pay for itself?  Fool me once, fool me twice, etc. etc. w/o end.

  27. Irish Frankie Crawford Beat Saijo aka Gimpel 06:35am, 07/19/2017

    In the photo above it looks like Trump on a double with Mike, Robin and her mom! BTW If you voted twice for Obama….if you voted for Hillary…..if you live in NYC and voted for DeBlasio….please don’t take this the wrong way, but there is no fukin’ earthly good to you!

  28. Nonymous 05:25am, 07/19/2017

    Trump = sewage

    The new norm is lying and that should sit well in the boxing world.

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