The History Of Mike Tyson And Donald Trump's Unlikely Relationship

Mike Tyson and Donald Trump came from opposite sides of the tracks but developed similar trains of thought, thanks to their childhoods. The Sydney Morning Herald describes Tyson as a shy, pudgy kid with pronounced acne and a lisp, who became a punching bag for bullies in the hard-knock neighborhood of Brownsville, Brooklyn. His mother doled out discipline by hitting him with a fireplace poker and electrical cords and gave him booze and drugs to get him to sleep. By puberty, he had been arrested 38 times. Suffocated by insecurity, Tyson became a fire-breathing boxer after trainer Cus D'Amato adopted him and taught him to see himself as an Alexander-the-Great-like conqueror (via GQ). "In my mind, I was a demi-god," Tyson later acknowledged. 

Growing up as a wealthy Queens native, Trump was told he was a "king" and a "killer" by his father, writes biographer Harry Hurt in Lost Tycoon. But father also demolished his confidence. A Guardian article by Tony Schwartz, who co-authored Trump: The Art of the Deal, paints Trump as someone who uses a wall of over-the-top bravado and bullying to hide that he's "the frightened child of a relentlessly critical and bullying father." Schwartz recalls Trump saying, "That's why I'm so screwed up, because I had a father who pushed me so hard." Trump and Tyson, seeming worlds apart yet possibly bonded by the planet-sized chips on their shoulders, would build a strange, sometimes strained relationship that may have shaped Trump's presidency.

It was the 1980s, an age of Rocky and high rollers. Mike Tyson was a Mr. T who showed no pity to the fools he punched unconscious. Donald Trump, while technically a Mr. T, didn't scream Clubber Lang so much as golf clubs. After becoming one of New York's premier real estate promoters in the 1970s (via The New York Times), Trump took a gamble in Atlantic City in a bid to build a casino juggernaut.

Showing shades of the wiliness that would help him bag half of the Empire State Building for free in the 90s, "The Donald" (by his own admission) tricked the Holiday Inn into paying him to construct Trump Plaza Hotel and Casino, which debuted in 1984, according to Philadelphia magazine. There, in July 1985, a 19-year-old Tyson would maul John Alderson (via Boxing Hall of Fame). In 1986, Trump Plaza hosted a ballroom bout between Tyson and unfortunate-casualty-to-be Jose Ribalta for a steep $100,000, which plaza president Mark Etess characterized as a calculated overpayment (via Chicago Tribune). This laid the foundation to build a rapport. Tyson won the World Boxing Council heavyweight title later that year.

Four of Tyson's seven title defenses took place at Trump Plaza as Atlantic City grew into a boxing mecca. According to Trumped!, a book co-written by former Trump Plaza Vice President Jack O'Donnell, "Donald was in awe of Mike's skill in the ring" and even made a point of watching his workouts and sparring sessions.

During the mid and late 1980s, Mike Tyson lost two dads. Per Sports Illustrated, in November 1985, his trusted trainer, manager, and adoptive father, Cus D'Amato, died. As GQ describes, D'Amato enriched Tyson's poor self-esteem by having him call himself a god and a warrior and would sit at his bedside to tell the sleeping boxer he was the greatest of all time. Life dealt another blow in March 1988 (the month after Tyson married Robin Givens) when Tyson's co-manager and fatherly mentor Jimmy Jacobs succumbed to leukemia (via The Village Voice).

Because Tyson didn't have the same father-son dynamic with his remaining manager, Bill Cayton, two Dons saw a new day on the horizon. The book Trumped! asserts that Donald Trump saw an opportunity to establish a more lucrative arrangement with Tyson if he played his cards right. So did promoter Don King, who had a reputation for failing to pay fighters what he owed them. King made the first move — purportedly with Trump's approval — by instigating a rift between Tyson and Cayton and ingratiating himself with Tyson's wife and mother-in-law.

Trump bided his time and eventually tried to outmaneuver King. When that plan imploded, he bent the knee instead, instructing Trump Plaza to obey King's every demand, even when that meant giving him and his crew 30 hotel rooms on the weekend of a Tyson fight. When he got 30 rooms, King would request 40 a day later, expecting to get them.

On June 27, 1988, amid tremendous turmoil, Mike Tyson and Donald Trump made history in Atlantic City. Sports Illustrated explains that while adjusting to married life, coping with the death of a second father figure, and trying to figure out who he could trust to manage his money, Tyson was preparing to trade punches with Michael Spinks.

As Bleacher Report notes, Spinks had already etched his fists into the annals of boxing by becoming the first light heavyweight champion to win a heavyweight championship. In 1985, he toppled International Boxing Federation (IBF) heavyweight title holder Larry Holmes but was forced to forfeit the belt for refusing a mandatory contest so that he could fight "Great White Hope" Gerry Cooney. Great white shark Tyson then won the IBF belt while Spinks proclaimed himself the people's champ. Both had unblemished records – Tyson with 34 wins (30 knockouts) and Spinks with 31 wins (21 knockouts).

Trump paid an unprecedented $11 million to host this date with destiny, which lasted all of 91 seconds. As the BBC points out, that worked out to $121,000 a second. Ringside seats sold for up to $1,500 a pop. It was a star-studded affair attended by the likes of Jack Nicholson and Muhammad Ali, who leaned in favor of a Spinks victory. But instead of floating like a butterfly, Spinks stunk like a beetle. Fear and ferocious punches overwhelmed him. In under two minutes, Tyson made over $20 million.

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.

The authors of Trumped! observe that in his crusade to become the Robin to Mike Tyson's Batman, Donald Trump undermined his advisor position by teaming up with the other Robin in Mike's life — Givens. Trump apparently got so chummy with Tyson's wife that folks at Trump Plaza gossiped they were having an affair (more on that later). As Tyson and Givens' marriage crumbled, Trump tried to insert himself as their go-between, which backfired. 

The Associated Press points out that Givens and her mother Ruth — who Tyson referred to as "Ruthless" (via ESPN) — had been pivotal in the decision to pick Trump as an advisor. So when Givens filed for divorce in early October, and Tyson sued for an annulment a week later (per UPI), Tyson and Trump were going through their own separation. This left a huge opening for Don King to become the boxer's right hand. In late October, Trump played the only card he had left and sought $2 million from Tyson.

Contradicting his earlier assertion that he would advise Tyson free of charge, Trump argued in a letter printed by the press that the boxer promised a charitable donation in exchange for his services. Trump requested a "very reasonable" $2 million check to the Trump Foundation, arguing that he saved Tyson $50 million through his involvement in the Cayton lawsuit. (The manager had agreed to reduce his cut of Tyson's earnings from one-third to one-fifth.) Whether Tyson complied is unclear.

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 end of Donald Trump's stint as Mike Tyson's advisor didn't end their friendship, observes GQ. In fact, Trump organized Tyson's title defense against Buster Douglas in Tokyo, which would go down as one of boxing history's biggest upsets. Per the Independent, Tyson slept on Douglas, slept with Geisha girls for weeks, and then got put to sleep on Feb. 11, 1990, when Douglas scored a tenth-round knockout. Immediately following the bout, Trump reportedly refused to see Tyson because the loss "might rub off. The same might happen to me."

According to The Philadelphia Inquirer, Trump had preemptively inked a $12.5 million deal with Don King to host a title bout between Tyson and an unbeaten Evander Holyfield. Since the Douglas fight was a bust, they scrambled to hatch a plan B. King pulled off an unbelievable coup, convincing boxing officials not to acknowledge Douglas' title win. He argued that the boxer benefited from a slow count during a knockdown and had actually been KO'd before Tyson.

The New York Times reports that on the day after the fight, Trump claimed to have arranged a Tyson-Douglas rematch with King, who — conveniently enough — was the promoter for both boxers. If so, it was scuttled when boxing officials declared Douglas the legitimate champion. Tyson, meanwhile, offered a sober assessment of the outcome at a press conference: "I lost. A loss is a loss. I wouldn't want a title or a changed decision" (via The Washington Post).

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.

Donald Trump wasn't the "Baddest Man on the Planet" during his 2016 presidential campaign, but he was branded some of the baddest things in the world. He was called "a race-baiting, xenophobic religious bigot" and a "proud sexual predator" and compared to an aspiring dictator. Perhaps worst of all in the world of civility politics, he was uncivil. Whether you believe all, none, or some of those assertions, it certainly made supporting Trump publicly controversial at best. Mike Tyson, however, seemed more than happy to tip his hat to the head of the MAGA movement. 

During an October 2015 HuffPost Live interview, Tyson declared that Trump "should be president of the United States." When asked if Trump had his vote, he gave an enthusiastic "yeah, hell yeah! Big time." He argued that the American people were sick of business as usual and suggested, "Let's run America like a business, where no colors matter. Whoever can do the job, gets the job." 

But his support ran deeper than politics. In March 2016, he said he could relate to the "hate" being shown toward Trump, remarking, "Now he knows what it's like when everybody is out to get you" (via The New York Post). In a 2019 interview, Tyson said he didn't like all of Trump's actions as president, "but I like Donald Trump." He added that despite his sexual assault conviction, Trump didn't disrespect him or reject his endorsement and only had "beautiful things" to say about Tyson.

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 The Independent. 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.