Donald Trump’s relationship with Vince McMahon and World Wrestling Entertainment (WWE) has evolved over decades, blending his business interests, entertainment presence, and eventual political career with the world of professional wrestling. Discover Trump’s deeper involvement with WWE and how his time in sports entertainment may have played a role in shaping his public persona.
Donald Trump’s decades-long relationship with Vince McMahon and WWE has intertwined business, entertainment, and politics. Photo Credit: WWE. Artwork by Pro Wrestling Stories.
Disclaimer: This article is not intended to be political. Instead, it focuses solely on Donald Trump’s history and involvement with WWE, highlighting key moments and contributions without engaging in political discourse.
Donald Trump’s Early WWF Partnership: A Wrestling Power Play
Donald Trump backstage at WrestleMania V with the late Ivana Trump, alongside then-WWF stars Virgil and "The Million Dollar Man" Ted DiBiase. Photo Credit: WWE.
Donald Trump’s association with WWE began in the late 1980s when his Trump Plaza in Atlantic City, New Jersey, hosted two consecutive WrestleManias. WrestleMania IV in 1988 featured a tournament to crown a new then World Wrestling Federation (WWF) Champion, while WrestleMania V in 1989 was headlined by the memorable “Mega Powers” match between Hulk Hogan and Randy Savage.
These events established Trump as a notable figure in the wrestling world.
Trump’s involvement with WWE went beyond just hosting events.
In a 2011 documentary, Trump expressed his interest in WrestleMania, highlighting the “great energy” that WWE has always had. He credited this energy to Vince McMahon, whom he described as “a very unusual guy” and an “amazing guy.”
Trump’s partnership with WWE was mutually beneficial. The events at Trump Plaza helped elevate WrestleMania’s status while also providing Trump with valuable publicity and aligning his brand with the popular world of professional wrestling. This early collaboration set the stage for Trump’s future involvement with WWE.
Jake "The Snake" Roberts’ Unexpected Moment with Ivana Trump at WrestleMania IV
Ivana (looking less than enthused) and Donald Trump take in the action at WrestleMania IV, held at Trump Plaza in Atlantic City, New Jersey, on March 27, 1988. Photo Credit: WWE.
During WrestleMania IV in 1988, Jake "The Snake" Roberts recalled an encounter involving his match with Rick Rude and an unexpected reaction from the late Ivana Trump, Donald Trump’s then-wife.
On his podcast, DDP Snake Pit, Roberts shared that while Donald was fully engaged with the match, Ivana seemed less interested, sitting ringside with her chair turned away from the action.
As part of his entrance, Roberts swung his snake, Damian, toward Ivana, startling her and causing her to push her chair back and fall over.
According to Roberts, the moment upset Ivana.
Roberts recalled, "I remember Ivana sitting at ringside, not even looking at the ring. She had her champagne glass with the little bottle in the cooler, and she turned her chair sideways. Don was going crazy for the match, but she wouldn’t even look.
“I came out on her side and took the snake and swung it at her, and she pushed her chair back, and she fell backward."
Roberts later found out from Donald Trump that Ivana was so upset that she wanted to hire guards to attack him.
“I found out later at WrestleMania 7 that she tried to hire two of her guards to come to my hotel room to beat the ******* **** out of me, and Donald affirmed it. Donald loves me. I don’t know if it’s just because of that, but I’m glad."
Though the situation was tense then, Roberts shared that there were no hard feelings between him and Donald Trump, who reportedly found the story amusing in hindsight.
Battle of the Billionaires: Donald Trump vs. Vince McMahon
Donald Trump shaves the head of WWE Chairman Vince McMahon after winning the "Battle of the Billionaires" at WrestleMania 23 on April 1st, 2007, in front of a sold-out crowd at Detroit’s Ford Field. Trump’s chosen representative, Bobby Lashley, assists with the shaving. Photo Credit: WWE.
Donald Trump’s most notable WWE appearance occurred at WrestleMania 23 in 2007, where he was involved in the “Battle of the Billionaires” storyline against then-WWE Chairman Vince McMahon.
In this storyline, Trump and McMahon each selected a wrestler to represent them in a match, with the stipulation that the losing billionaire would have their head shaved.
Trump’s representative, Bobby Lashley, won the match against McMahon’s representative, Umaga, leading to Trump participating in shaving McMahon’s head.
This storyline attracted significant mainstream attention and contributed to WrestleMania 23’s strong pay-per-view sales.
Vince McMahon’s Limo Explosion: Trump’s Reaction Revealed
Vince McMahon’s limousine explosion on WWE programming, June 11th, 2007. The dramatic stunt was so convincing that Donald Trump, watching the show, believed it was real and reportedly called WWE to check on McMahon’s well-being. Photo Credit: WWE.
In a 2008 interview on the Opie and Anthony Show, Triple H revealed an amusing anecdote about Donald Trump’s reaction to a WWE storyline. The storyline in question involved Vince McMahon’s limousine supposedly exploding on a June 2007 episode of Monday Night RAW, leading to McMahon’s “presumed death.”
Triple H explained, “What kills me is so many people [believed it]. I’m not kidding you, Trump called and was like, ‘Did something happen to Vince?'” He added, “That’s the magic of television.”
This incident occurred just a few months after Trump’s high-profile appearance at WrestleMania 23, where he was involved in the “Battle of the Billionaires” storyline with McMahon. Despite his familiarity with the WWE’s theatrical nature, Trump apparently fell for the staged explosion.
The revelation provides an interesting glimpse into Trump’s relationship with WWE and his understanding of the line between reality and fiction in professional wrestling.
It’s worth noting that this storyline of Vince McMahon dying was eventually cut short due to the tragic Chris Benoit double murder-suicide, which occurred shortly after the limousine explosion angle aired.
The Raw Takeover: When Trump "Bought" WWE’s Flagship Show
Donald Trump and Vince McMahon shake hands on WWE’s Monday Night Raw, June 22nd, 2009, during a storyline where Trump "purchased" the show. Photo Credit: WWE.
In 2009, Donald Trump was part of a storyline where he “purchased” WWE’s Monday Night Raw from Vince McMahon. The angle was designed to create buzz and draw attention to the show.
As part of the storyline, Trump announced that the episode would air commercial-free and that fans would receive refunds, which led to temporary confusion among some investors and briefly impacted WWE’s stock price.
McMahon eventually “bought back” the show at a premium, continuing the ongoing narrative between the two within WWE programming.
Breaking Down Each of Donald Trump’s Key WWE Appearances: A Timeline
A mock wrestling match between a fake Donald Trump, played by wrestler Ace Steel, and a fake Rosie O’Donnell, portrayed by Kiley McLean, took place on Monday Night Raw. The Trump impersonator won the match by throwing a cake in "O’Donnell’s" face and headbutting her. Photo Credit: WWE.
Donald Trump’s long-standing involvement with WWE is marked by numerous moments that merged his larger-than-life persona with the world of sports entertainment. Highlighting each of his key WWE appearances, the following timeline traces his journey from hosting WrestleMania to becoming a WWE Hall of Famer.
1988: Trump Plaza in Atlantic City, New Jersey, hosts WrestleMania IV. Donald Trump personally secured the event, which featured a tournament to crown a new WWF Champion.
1989: Trump Plaza hosts WrestleMania V, making it the only venue to host two consecutive WrestleManias. The event was headlined by the "Mega Powers" match between Hulk Hogan and Randy Savage.
2004: Trump publicly supports former wrestler Jesse "The Body" Ventura’s potential return to politics, pledging "100%" moral and financial backing.
2007 (January): A mock wrestling match between a fake Donald Trump and Rosie O’Donnell takes place on Monday Night Raw. A Trump impersonator wins the match after throwing a cake in "O’Donnell’s" face and headbutting her.
2007 (April): Trump features prominently at WrestleMania 23, accompanied earlier in the show by Miss USA Tara Conner. He meets The Boogeyman, a wrestler known for his worm-eating antics. He later partakes in the famous "Battle of the Billionaires" match, where his chosen representative, Bobby Lashley, defeats Vince McMahon’s pick, Umaga. After the match, Trump shaves McMahon’s head and receives a Stone Cold Stunner from Steve Austin.
2007 (June): During a Monday Night Raw episode, Trump drops $100 bills from the rafters, reportedly real money, much to the crowd’s excitement.
2009 (June): In a storyline, Trump "purchases" WWE’s Monday Night Raw and announces it will air commercial-free. This causes temporary confusion among investors, leading to a brief drop in WWE’s stock price. The storyline concludes with Vince McMahon "buying back" Raw for double the price, ending Trump’s short-lived ownership.
2013: Donald Trump is inducted into the WWE Hall of Fame’s celebrity wing for his contributions to the company.
Donald Trump’s WWE Hall of Fame Induction: A Blend of Showmanship and Controversy
Donald Trump speaks at the WWE Hall of Fame induction ceremony on April 6th, 2013. Photo Credit: WWE.
On April 6th, 2013, Donald Trump was inducted into the celebrity wing of the WWE Hall of Fame at Madison Square Garden in New York City. The honor recognized his contributions to WWE over the years.
WWE Chairman at the time, Vince McMahon, introduced Donald Trump to a mixed reaction from the crowd. McMahon referred to Trump as a "WrestleMania institution" and even quipped about his potential political future: “Donald might very well be a great president of the United States.”
McMahon also revealed their shared characteristics, stating, “Both of us are revolutionary businessmen, both of us have a very strong work ethic, both of us, as a matter of fact, followed our father’s footsteps... some say that uh, the two of us have massive egos.”
When Trump spoke, greeted by a bipartisan share of both cheers and jeers from the crowd, he began his acceptance speech by acknowledging his relationship with the McMahon family.
“Vince and I have had an amazing relationship for many years, many, many years, and it all began with WrestleMania number four in Atlantic City.”
He reminisced about his WWE experiences, notably the Battle of the Billionaires at WrestleMania 23.
“To this date, to this date it has the highest ratings, the highest pay-per-view in the history of wrestling of any kind. So, I’m very honored by that and perhaps that’s why I’m being inducted.”
In a moment of apparent sincerity, Trump expressed his gratitude for the WWE Hall of Fame induction, saying, “I consider this to be my greatest honor of all. I do, I really do.”
However, Trump couldn’t resist stirring up some controversy before leaving the stage, issuing a challenge: “I will challenge Vince next year to a fight and I will kick his *** if he wants. I will kick his ***.”
Trump’s induction into the WWE Hall of Fame solidified his place in the company’s history. His appearances with the company showcased his promo skills, which were later seen in other aspects of his public life, including his political career.
How Wrestling Shaped Donald Trump’s Political Tactics
The two "power couples" at the time, Donald Trump, Ivana Trump, Miss Elizabeth, and Randy "Macho Man" Savage, backstage at WrestleMania V, held at Trump Plaza in Atlantic City on April 2nd, 1989. Photo Credit: WWE.
Many observers have noted parallels between Donald Trump’s WWE appearances and his political career.
Some key similarities include the use of catchphrases and memorable soundbites, building a larger-than-life persona, engaging in public feuds, and utilizing “kayfabe”—the practice of portraying staged events as real.
Trump’s time in professional wrestling may have influenced his approach to political rallies and public appearances during his campaigns and presidency.
WWE’s Hulk Hogan Endorses Donald Trump at the 2024 RNC: A Wrestling Reunion
Donald Trump shakes hands with Hulk Hogan backstage at WrestleMania 4, held at Trump Plaza on March 27th, 1988. Decades later, Hulk Hogan spoke at the 2024 Republican National Convention, where he brought his signature energy by ripping off his shirt on stage in support of Trump’s presidential campaign. Photo Credit: WWE, CBS News.
In a convergence of professional wrestling and politics, WWE Hall of Famer Hulk Hogan appeared at the 2024 Republican National Convention to endorse Donald Trump’s presidential campaign.
Hogan, known for his larger-than-life persona in wrestling, brought his trademark energy to the convention stage.
He entered to his famous entrance theme, “Real American,” and delivered a speech that mirrored his in-ring promos, complete with his signature catchphrases and mannerisms.
Hogan drew parallels between Trump’s political career and professional wrestling, referring to Trump’s supporters as “Trumpites”—a play on his fanbase, “Hulkamaniacs.”
He even tore off his shirt to reveal a Trump campaign shirt underneath, reminiscent of his wrestling performances.
This appearance marked another chapter in the intertwined histories of Trump and professional wrestling. It showed how the showmanship and spectacle of WWE continue to influence Trump’s political style, even years after his direct involvement with the company.
Donald Trump’s Backstage WWE Moments: Secrets Revealed
Donald Trump takes the iconic Stone Cold Stunner from Steve Austin at WrestleMania 23. Photo Credit: WWE.
Despite WWE reportedly issuing a gag order to employees forbidding them from speaking about Donald Trump, some wrestling personalities have shared their thoughts on his contributions to WWE.
“I was at Ford Field, it was a ‘Battle of the Billionaires.’ There were two teams, and I was a special referee. We were backstage, and Vince comes up to me, unplanned, and says, ‘Hey Steve, I’m gonna see if we can get Donald to take a Stunner.’
I said, ‘Really?’
He goes over to Donald and says, ‘Donald, this is Stone Cold Steve Austin.’
Donald’s right-hand guy was there and said, ‘No, you don’t need to do that.’
But Donald looked at Vince and said, ‘You think it’ll help the show?’
Vince said yes, and Donald agreed to do it.
And then when it happened in the ring, I thought it was the worst stunner I’ve ever seen!”
"I don’t care what the news or the media says about Donald Trump. Donald Trump is one of the coolest, and he gets ‘it.’ Whatever ‘it’ is, Donald gets it, and he gets our business."
"I think many people give [Trump] a hard time and throw things at him that I believe are not true.
There are a lot of people who say, ‘Trump is a big racist.’
I’m a black man; I worked with him for several months and never felt that. I never came across that at all. I think he was a team player when he came into our field.
That was the largest WrestleMania in history at the time, and he played his part perfectly."
The Vince McMahon and Donald Trump Connection: From Wrestling to the White House
Donald Trump, alongside Vince McMahon, at a 2009 press conference. Their decades-long relationship is marked by deep business and political ties. Photo Credit: WWE.
The relationship between Vince McMahon, the McMahon family, and Donald Trump extends beyond professional wrestling. It also encompasses business and politics.
In 2007 and 2009, WWE made contributions totaling $5 million to the Donald J. Trump Foundation, coinciding with Trump’s appearances on WWE programming. The nature of these payments has been scrutinized, with WWE initially stating they were corporate contributions before later claiming they were personal donations from Vince and Linda McMahon.
Linda McMahon, former WWE CEO, ran unsuccessful campaigns for the U.S. Senate in Connecticut in 2010 and 2012. Her political involvement deepened when President-elect Trump nominated her to lead the Small Business Administration (SBA) in 2016. She served in this cabinet-level position from 2017 to 2019, supporting Trump’s economic policies.
The McMahons have been significant financial supporters of Trump’s political ambitions. Linda McMahon donated $7 million to pro-Trump super PACs in 2016 and has contributed $10 million to Trump’s current presidential campaign as of 2024, making her one of his largest individual donors. She has also expressed interest in serving in Trump’s cabinet again, should he win re-election.
This multifaceted relationship between the McMahons and Trump highlights the complex interplay between business, entertainment, and politics. While their support has been substantial, it has also raised questions about potential conflicts of interest and the blurring of lines between personal, business, and political spheres.
Trump’s WWE Legacy: Controversy, Criticism, and Acclaim
Donald Trump, pictured here with Vince McMahon on WWE’s Monday Night Raw, left a lasting impact on WWE through his high-profile contributions and appearances. Photo Credit: WWE
Some argue that his WWE Hall of Fame induction was more about his celebrity status than his contributions to wrestling.
Additionally, his political career has led some to question the appropriateness of his continued association with WWE.
In an August 2024 interview with Chris Van Vliet, WWE Hall of Famer and former Minnesota Governor Jesse Ventura spoke candidly about whether he ever considered a presidential run. He didn’t hold back when expressing his disdain for Donald Trump.
“If I had ballot access in all 50 states, and I were allowed in the debates, I’d be the next President of the United States,” Ventura said, emphasizing that he means in the present day.
“You see, I have an objection to one of these candidates. And I object to him – and I can say ‘him’ so you know who it is now – I can object to him because he is in the [WWE] Hall of Fame. And I’ve almost resigned from it on two or three occasions because of that.”
Ventura continued, “If I had ballot access in all 50 states, and I were allowed in the debates, I’d be the next President of the United States,” Ventura said, emphasizing that he means in the present day.
Donald Trump’s Lasting Legacy in WWE and Beyond
Donald Trump promotes WrestleMania IV with Hulk Hogan and Andre the Giant at Trump Plaza in March 1988. Photo Credit: WWE. Artwork by Pro Wrestling Stories.
Despite the controversy surrounding him, Donald Trump’s impact on WWE is undeniable. From hosting major events to participating in high-profile storylines, Trump’s involvement helped shape World Wrestling Entertainment’s mainstream appeal in the late 20th (then as the World Wrestling Federation) and early 21st centuries.
His induction into the WWE Hall of Fame in 2013 cemented his place in pro wrestling history, making him the first and only WWE Hall of Famer to become President of the United States.
Trump’s relationship with WWE represents a unique intersection of entertainment, business, and politics. His contributions to the company helped elevate its profile and brought mainstream attention to professional wrestling.
As his political career took center stage, the skills and techniques he had honed in the wrestling world appeared to influence his approach to campaigning and governance, for better or worse.
Whether viewed as a successful collaboration or a controversial association, Trump’s history with WWE remains an intriguing chapter in both the world of professional wrestling and American politics.
Regardless of one’s personal opinions on Donald Trump, there is no denying that he made an impact on the world of professional wrestling, leaving a legacy that continues to be discussed and debated to this day.
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JP Zarka is the founder of Pro Wrestling Stories, established in 2015, where he guides the site's creative vision as editor-in-chief. From 2018 to 2019, he hosted and produced The Genius Cast with Lanny Poffo, brother of WWE legend Macho Man Randy Savage. His diverse background includes roles as a school teacher, assistant principal, published author, musician with the London-based band Sterling Avenue, and being a proud father of two amazing daughters. He has appeared on the television show Autopsy: The Last Hours Of and contributed research for programming on ITV and BBC.
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