Donald Trump's History With The WWE Explained

Donald Trump, at one point one of the most controversial people to step foot in a WWE ring, became one of the most controversial people on the planet while holding office as the 45th President of the United States. He is perhaps the most polarizing figure in American politics, and he continues to cast a large shadow even though his time as president came to an end in 2020. He also has a long-standing relationship with Vince McMahon and the WWE to this very day. He has been involved with the company for more than three decades. His involvement includes multiple appearances at WWE events, including as a guest ring announcer, on-screen talent, and even as the "owner" of WWE's flagship show, "WWE Raw."

Trump's relationship with the McMahons has met no known speedbumps over the years. Major League Wrestling owner and former WWE writer Court Bauer, claimed on "Talk is Jericho" that the pair of billionaires having a "kindred spirit thing" and there is seemingly no end to the parallels between the two. Their strong personal relationship has led to Trump being invited back to the WWE time after time over the years, whether for an induction into the celebrity wing of the company's Hall of Fame, or for a rumored one-off appearance that would have made him the first sitting U.S. President to appear before a live crowd on WWE television.

Here are some examples and highlights regarding Donald Trump's well-established relationship with the WWE.

Relationship with Vince McMahon

The personal relationship between Donald Trump and Vince McMahon dates back to at least the mid-late '80s. McMahon had been the owner of his company, then known as the WWF, since 1982, the same year Trump made the inaugural Forbes list of wealthy people for the shares he possessed in his family's estimated $200 million net worth. Trump's Atlantic City boardwalk hotel and casino, the Trump Plaza, hosted back-to-back WrestleMania's in the late '80s, and the two seemingly became fast friends from there.

WWE media personality Renee Young caught up with Trump backstage on the night of his 2013 WWE Hall of Fame induction, where the future U.S. President elaborated on his relationship with McMahon and the company. "Well, there is a great energy," Trump said. "You are dealing with great athletes and I love sports of all kinds ... But there is a great energy that WWE has always had. And I think ... it all comes to fruition because of Vince, because he is a very unusual guy. Amazing guy." Trump went on to say he was open to a second WrestleMania match with McMahon, but such a match ultimately never came to fruition. 

Both Trump and McMahon also have several notable parallels, including but not limited to being the sons of successful businessmen and their controversial reputations in the public space, as summarized by Vince McMahon in his WWE Hall of Fame Induction speech on Trump's behalf in 2013.

Admiration for Pro Wrestling

Trump's willingness to work with McMahon in the late-'80s cannot be simply chalked up to the friendship between the two men — Trump is clearly an admirer of the art of pro wrestling. Trump's appearances on WWE television have shown him as a willing participant unafraid to engage with on-screen talent. U.S. Presidents having an admiration for pro wrestling is not a new phenomenon, as George H.W. Bush and Jimmy Carter were both notable fans. However, no president has had the direct ties to professional wrestling that Donald Trump has.

The sentiment on Trump from the wrestlers has been generally mixed over the years, but those who worked with him have had generally positive things to say about Trump as a fan and performer. "I think a lot of people give him a hard time and throw things at him that I believe are not true," WWE star Bobby Lashley said in a 2016 interview with Forbes. "There are a lot of people that say, 'Trump is a big racist.' I'm a Black man, I worked with him for several months, and I 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." Jim Ross, who eventually spoke out in opposition to Trump's politics, has also put a positive spin on Trump as a performer. "Donald Trump is one of the coolest, and he gets 'it,'" Ross said on an episode of "WWE Legends of Wrestling." "Whatever 'it' is, Donald gets it, and he gets our business."

Trump Plaza Hosts WrestleMania IV and V

Donald Trump, who made his initial fortune in real estate, opened his marquee Atlantic City property, the Trump Plaza Hotel and Casino, on May 15, 1984. In time, the casino became a destination for marquee combat sports events, hosting 19 professional boxing events between 1985 and 1998 in addition to WrestleMania IV (1988) and V (1989). Though both events were advertised as taking place at Trump Plaza, WrestleMania actually took place next door at the Historic Atlantic City Convention Hall as it was known at the time. However, Trump sponsored and paid for the event, which wrestling journalist Dave Meltzer said on an episode of "The Lapsed Fan" was WWE's primary motivation for downsizing the crowd by more than four times the previous year. Even still, Meltzer reported WrestleMania V set a live gate and pay-per-view buy rate record that held for a full decade, thanks in large part to the main event between Hulk Hogan and Randy Savage.

To promote the event, Trump teamed up with the WWF to host non-wrestling events to build to the shows, such as 5K runs and autograph signings, the latter of which has become commonplace the week of WrestleMania. "I just wanted a piece of [WrestleMania]," Trump said during an appearance on the WWE-produced documentary, "The True Story of WrestleMania." "Everybody in the country wanted this event and we were able to get it." 

Trump-sponsored WrestleManias came to an end after 1990. WrestleMania VI moved north of the border to the Toronto SkyDome, while Trump's secondary Atlantic City property, The Trump Taj Mahal, filed for bankruptcy in 1991, one year after opening.

Reality Television Parallels

Pro wrestling and reality television have several similarities. The parallels between the two worlds are so strong that a bevy of wrestlers have gone on to appear on non-wrestling reality shows over the years. Such similarities include the use of both scripted and unscripted content, character development, and audience engagement. Given his experience with pro wrestling, Donald Trump made for a natural host of NBC's "The Apprentice." The show features a pool of 14-18 contestants looking to "climb the corporate ladder" over multiple weeks. During the show's original run, the last remaining contestant would be awarded a one-year $250,000 starting contract to promote one of Donald Trump's properties.

With a decade-plus long run as the show's host, it is safe to say Trump's time working on reality helped shape his public persona. Trump was more than just the show's host; he was the main character. He adopted the catchphrase, "You're fired," which helped perpetuate his reputation as a no-nonsense businessman. The show also gave Trump a platform to make controversial statements within the context of the show, and his public perception was polarized than ever by the time his involvement with the show ceased for good. 

The way Trump used "The Apprentice" runs parallel to how wrestlers use their platforms to become bigger stars and relate to the fans. When the time finally came for Trump to step foot in a WWE ring, he made the transition from reality television to wrestling look almost seamless.

WrestleMania XX Cameo

One Trump appearance that is often swept under the rug is his appearance at WrestleMania XX at Madison Square Garden in 2004. During the show, WWE legend and former Governor of Minnesota Jesse "The Body" Ventura interviewed Trump, who was sitting ringside with his son, Donald Jr., in a brief segment. Unlike some of his later WWE appearances, the mention of Trump's name drew a mixed reaction from the New York fans in attendance. Trump, looking somewhat disinterested, had little to say, outside of remarking about his long-standing relationship with Vince McMahon. While speaking with Trump, Ventura hinted at a return to politics, and upon asking if he had Trump's moral and financial support, the future U.S. President replied, "100 percent."

"Donald was a friend," WWE executive Bruce Prichard said on his podcast, "Something to Wrestle with Bruce Prichard," speaking about how Trump's brief cameo at WrestleMania XX came together. "Especially in New York, he was a big deal. It was always nice to see him and nice to do stuff with him. He enjoyed it. He got the business and loved any opportunity that he could to promote himself." Much in the same way Ventura found political success six years prior, unbeknownst to anyone at the time, Trump found his own success 12 years later.

Connection to Jesse Ventura

There are plenty of noteworthy similarities between Jesse Ventura and Donald Trump. They are both brash, opinionated individuals. Both became anti-establishment political icons to their followers. They even used to be friends. However, the connection the two share in the world of politics runs deep. The fourth chapter of the Netflix documentary, "Trump: An American Dream," explored the connection between the wrestler-turned-governor and reality television star-turned-president. The documentary gave a synopsis of how Ventura became the unlikely 38th governor of Minnesota and highlighted how Trump's interest in the process caused him to run for president for the first time in 2000.

Both Trump and Ventura are former members of the Reform Party, a political party formed out of independent candidate Ross Perot's newsworthy 1992 presidential campaign. Through their political association, Ventura privately encouraged Trump to run for president in 2000 in the midst of a developing intra-party civil war between himself and allies of Perot. Ventura ultimately left the party, causing Trump to ultimately walk back his presidential campaign in February 2000. 

The Trump 2000 campaign has long since been overshadowed by his campaigns in 2016 and 2020, but the campaign was significant for being his first foray into national politics. Trump's association with Ventura and the Reform Party further highlighted a growing dissatisfaction with the two major political parties. Trump and Ventura have since had a falling out, with Ventura calling Trump "the conman president" on "The Issue Is: with Elex Michaelson" on Fox 11 Los Angeles.

Donald Trump vs. Rosie O'Donnell

Donald Trump's many feuds extend far beyond what is seen in modern U.S. politics. Trump has a long-standing public and personal feud with television personality Rosie O'Donnell that dates back to 2006. The feud started after O'Donnell made comments on "The View" about Trump's handling of the Miss USA beauty pageant, which he owned at the time. O'Donnell criticized Trump for not publicly addressing the controversy surrounding one of the contestants and accused him of using the pageant as a platform for his own personal gain. Speaking at a 2007 real estate conference, Trump used his platform to hit back at O'Donnell. "I called her a pig, I didn't say she was fat, because that's politically incorrect," Trump said.

The disdain between Trump and O'Donnell is as apparent as ever 17 years later. In an attempt to capitalize on the feud, Vince McMahon opted to have "Trump" and "O'Donnell" settle their differences in the ring on the January 8, 2007 episode of "Monday Night Raw." As has become par for the course in segments such as this, a pair of wrestling stand-ins portrayed both Trump and O'Donnell during the match. Former NWA Women's Champion Kiley McLean played the role of Rosie, while Ring of Honor superstar and friend of CM Punk, Ace Steel, portrayed Trump while donning a ridiculous wig. The match itself proved to be nothing special, and while the crowd rejected the match, Steel told SLAM! Wrestling that his portrayal of Trump earned him a contract with WWE.

Battle of the Billionaires

How WWE reached the conclusion of using Trump in "The Battle of the Billionaires" storyline on the road to WrestleMania 23 is not officially known. However, wrestling journalist Dave Meltzer praised the WWE in an appearance on "The Lapsed Fan" for using Trump's obvious star power with two rising stars in Bobby Lashley and Umaga. The storyline worked for its simplistic nature. Trump and McMahon, two rich men with matching egos and well-documented history between them, each picked a representative to compete on their behalf at WrestleMania. The losing billionaire would be forced to have their head shaved after the match. 

The stakes could not have been higher for either man, and particularly for Trump, whose hairstyle has long been a hot topic for entertainment media. Less than one month from the match, "Stone Cold" Steve Austin was appointed the special guest referee, which only added to the chaos. Austin once recalled the story of Trump being pitched to take one of Austin's patented "Stunners" after the match. "Boy, right then, Donald Trump's number one advisor, his right-hand guy at the time, gave him every single reason why he does not need to take the Stunner," Austin said on an episode of his podcast, "The Steve Austin Show." "Donald looked at Vince, and he goes, 'Sure, I'll take it.'" Trump's associate Lashley wound up winning the match while Trump landed some harmless ground and pound on his counterpart in the process. He then proceeded to assist Austin and Lashley with shaving McMahon bald before taking the Stone Cold Stunner in a fashion only Vince McMahon himself could rival.

Vince McMahon's Limo Explodes

WWE has gone to great lengths to tell a story, and once even attempted to fake the death of its own chairman as part of a storyline. As much as Donald Trump is credited as someone with an understanding of how wrestling works, the future U.S. President could not wrap his head around the idea of McMahon not dying in a fiery explosion on the June 11, 2007 episode of "Raw." Triple H appeared on the "Opie and Anthony Show" in 2008 and spoke to Sam Roberts about the limo explosion storyline. "What kills me is, so many people called," Triple H said. "[Vince] will probably be mad at me for saying this, but like, Trump called, and was like, 'Did something happen to Vince?' It's just the magic of television, you know what I mean?"

All plans were scrapped with the Benoit tragedy occurring over the ensuing weekend and McMahon returned to WWE television completely unscathed, contrary to what Donald Trump thought he saw. 

It wasn't the last time Trump was fooled by a storyline: He also recognized Ronda Rousey's on-screen WWE arrest in a document entitled, "PSA Celebrity Tracker," which included information on celebrities potentially willing to participate in a Trump-advertising campaign ahead of the 2020 election.

Trump Buys Monday Night Raw

Trump returned to the WWE in 2009, participating in a storyline in which he bought the "Raw" brand out from under Vince McMahon's nose. As part of the storyline, Trump appeared on the June 15, 2009 episode of "Raw," announcing that he had acquired the brand and would be taking over as its owner. Trump's purchase of WWE's flagship show was just for television, as he did not actually become the owner of "Raw." However, his brief time "in charge" of the show did yield one novel idea: a commercial-free show. Trump's involvement on the show combined with the promise of a commercial-free "Raw" resulted in the show posting its highest rating in seven years

By the end of "Raw," Trump anti-climactically wound up selling the show back to McMahon, putting an end to a storyline that seemingly had legs in just two weeks. Trump's involvement on the show during this time turned out to be the precursor to a larger storyline, with McMahon announcing just two weeks later that "Raw" would be receiving a new celebrity guest host on a weekly basis.

However, there is a possibility that the Trump angle was meant to drag on longer. After Trump "purchased" the show, USA Network published a press release to further the storyline, but quickly took it down after the WWE's stock price experienced a sharp drop.

2013 Hall of Fame Induction

Donald Trump joined the celebrity wing of the WWE Hall of Fame as part of a 2013 class consisting of headliner Bruno Sammartino, Mick Foley, Booker T, Trish Stratus, and Bob Backlund. Following a brief induction speech by Vince McMahon, Trump took the podium to a mixed reaction and spoke for three minutes on his relationship with the WWE. Trump spoke about meeting Andre the Giant for the first time and claimed his father congratulated him on bringing WrestleMania to Atlantic City in 1988. Trump then took the time to shout the members of his family, plug his projects and tease a rematch with McMahon for the following year's WrestleMania that never came to fruition.

Public opinion of the outspoken Trump became increasingly polarized after he announced his 2016 Presidential campaign, and even more so after he won the 2016 U.S. Presidential Election. As a result, there have been several cries from prominent wrestling personalities to remove him from the WWE Hall of Fame. Fellow New Yorker and Hall of Fame classmate Foley is chief among the people who have asked the WWE to remove Trump from the Hall of Fame primarily due to Trump's role in the January 6, 2021 insurrection at the United States Capitol. 

The WWE Hall of Fame is not reflection of wrestling's most prestigious talents and personalities, but rather a means for WWE chairman Vince McMahon to recognize those who worked for him he has an affinity for or simply wants to recognize. However, Trump's induction and inclusion in the Hall, even through turbulent times is a reflection of the strong relationship he shares with McMahon and WWE.

Linda McMahon's Cabinet Appointment

Following his election as the 45th President of the United States of America, Donald Trump appointed former WWE executive Linda McMahon to lead the Small Business Administration. She served in the role between February 2017 and April 2019. Much like Vince McMahon, Linda McMahon's relationship with Trump can be dated back to the days of WrestleMania IV and V. As a Republican who twice ran for U.S. Senate, McMahon shared the connection and commonalities with Trump necessary to garner the appointment. "Our small businesses are the largest source of job creation in our country," McMahon said in a December 2016 statement. "I am honored to join the incredibly impressive economic team that President-elect Trump has assembled to ensure that we promote our country's small businesses and help them grow and thrive."

As the head of the SBA, McMahon led efforts to streamline regulations and reduce the burden of federal regulations on small businesses and worked to increase access to capital for small businesses. She also promoted entrepreneurship and innovation by supporting programs that help small businesses start, grow, and expand. She ultimately stepped down as head of the SBA to chair the pro-Trump super PAC America First Action. Upon stepping down, Trump lauded McMahon's efforts in the role, referring to her as a "superstar" and "one of our all-time favorites." 

With Trump gearing up for another presidential run in 2024, it is not out of the realm of possibility that Linda McMahon could find herself working with Trump again in the not-so-distant future.

Rumored 2019 Appearance

Even after becoming the President of the United States, Donald Trump did not soon forget the WWE. There appeared the be a substantial amount of smoke regarding a 2019 appearance of Trump on WWE television, though there are plenty of conflicting stories regarding his role on the show as well as whether or not he was even invited to appear at all. WWE inked a deal with Fox in 2018, paying the company $1 billion over five years for the rights to "WWE SmackDown Live." With the show set to debut on the network in October 2019, Fox had plenty of incentive for Smackdown to make a strong first impression in the ratings. Tom Colohue of Sportskeeda Wrestling reported that Fox at least "floated the idea" to ask Vince McMahon to call in a favor to get Trump to appear.

Had Trump appeared on the show, it would have marked the first time a sitting U.S. President has appeared on a live, globally syndicated wrestling show. Journalist Brad Shepard also reported that WWE expressed a desire for Trump to appear on the annual Tribute to the Troops show in 2019, perhaps via satellite. However, Tribute to the Troops 2019 never aired on television, and Shepard has since taken the tweet down, though he added on his podcast that the former president's schedule was "too full" (h/t The Sun) to squeeze in an appearance for WWE. Ultimately, Fox and WWE were unable to bring Trump to television while he occupied the oval office, and a WWE spokesperson told Shepard the reports from him and Colohue were "completely false."

Sports Ownership Advisory Group

In response to the indefinite postponement of live sports and entertainment during the COVID-19 pandemic, U.S. President Donald Trump put together an advisory committee consisting of the nation's top sports executives to help shape his plans to reopen the economy. The larger committee — known as The Great American Economic Revival Industry Group, which formed in April 2020 — included longtime Trump confidant McMahon, who successfully put on a two-night WrestleMania without a fan presence the previous month, in the sports subdivision. Trump later referred to the committee as the "opening our country taskforce" and "opening our country council."

"We have to get our sports back," Trump said in a briefing following the announcement. "I'm tired of watching baseball games that are 14 years old. But I haven't actually had too much time to watch. I would say maybe I watch one batter then I get back to work." Other members of the committee included NBA commissioner Adam Silver, Dallas Cowboys owner Jerry Jones, and UFC President Dana White, among others. The group met at least one time virtually, according to NBA insider Shams Charania. McMahon's inclusion on the committee is a reflection of the mutual trust shared between him and the now former president, especially since Vince himself does not classify the WWE as a sport.

Unearthed Charitable Donations

The 2022 investigation into Vince McMahon's alleged sexual misconduct and probe into previously unrecorded company expenses yielded, to this point, the latest wrinkle in the Trump-WWE relationship. A report from the Wall Street Journal noted that McMahon contributed payments totaling $5 million to the now-dissolved Donald J. Trump Foundation in 2007 and 2009. The payments, which made the McMahon family the foundation's largest donors between 2004 and 2014, occurred in the same years Trump made his two storyline appearances for the company. The tax-exempt private foundation was created in 1988 allegedly to funnel donations and royalties received from Trump's book, "Trump: The Art of the Deal" into other charitable causes. The foundation dissolved at the end of 2018 after several legal violations came to light.

An attorney for WWE told the Wall Street Journal that those payments should have been cataloged as business expenses, because McMahon was a principal shareholder and the payments benefited the company. The WSJ also unearthed details from Trump's 2007 contract for the "Battle of the Billionaires match, which ensured that "under no circumstances would Mr. McMahon be allowed to shave his head, even if Mr. Trump's wrestler dropped dead in the ring[.]" Meanwhile, McMahon's attorney Jerry McDevitt downplayed claims that Trump's 2009 payment was a "bonus" like the future president boasted, clarifying that Trump was paid $100,000 in 2009 as the McMahons simultaneously donated $1 million to his foundation. 

The payments are illustrative of the seemingly unbreakable bond Trump shares with Vince McMahon and the WWE. It is a relationship built on years of loyalty between two kindred spirits who have done massive business together on more than one occasion.