There’s no good way to begin this piece, so why not start with an admission: One of the things I hate the most about professional wrestling, something that makes me sick to think of for too long, is how intertwined it is with Donald Trump, the 45th President of the United States. The fact that he’s “hosted” WrestleManias. The fact that he’s participated in WrestleManias. His place in the WWE’s questionably valid Hall of Fame. The way his presence in the White House, financially aided by a McMahon family that was rewarded with a cabinet position, hangs over the popular perception of the medium to the extent that “wrestling fan” and “Trump voter” are often synonymous to people outside of wrestling. All of it, as Vince McMahon once said, makes me want to puke.
It’s inescapable, the weight of this man, and it’s hard to know how to parse it. Does one look at Donald Trump’s relationship with the WWE merely as a facet of his image in popular culture? How it, like The Apprentice and years of tabloid and news coverage, trivialized how horrible he is and was as a man, let alone a businessperson? How it helped contribute to the notion of Trump as a titan of economics despite a litany of failed business ventures? How it continued to do the work of showing Donald Trump as a good sport capable of taking jokes about his hair when there were already several credible accusations of rape and abuse on his ledger? Or, when doing this, does one focus on the uncomfortable reality that watching WWE, beyond any quibbles about storylines, labor issues, or its response to the pandemic, is a tangible financial contribution to the fascist administration of this country?
This is not a “no ethical consumption under capitalism” situation, for those of you who are cringing. The McMahons were major donors to the Trump campaign in 2016, and now Linda McMahon, the former CEO of WWE and ex-head of Trump’s Small Business Administration, is the chair of America First Action SuperPAC, which is, according to opensecrets.org, the second largest fundraising and spending entity on the President’s behalf, trailing behind only Trump’s own campaign. Linda, despite resigning from the company over a decade ago to embark on a number of failed campaigns for Senate, is still a minority owner of World Wrestling Entertainment, holding 1.4% of voting shares according to 2016 SEC filings. That’s a small piece of the pie, but it’s also 566,670 shares of dividend-paying stock. At $0.48 a share, the $272,001.60 (just a baseline figure—she may have gained or lost more shares in the four years since those SEC filings, which are the most recent) dividend she’s receiving from her WWE shares in 2020 are a drop in the bucket so far as what she’s contributed to various republican causes this election cycle, but more than cover smaller contributions to Congressional candidates like Mary Fay (Connecticut), Cory Gardner (Colorado), Joni Ernst (Iowa), David Young (Iowa), and John Cornyn (Texas) made this year.
But it’s necessary, given my mandate as a narrative critic of wrestling, to narrow the scope somewhat. While tracking how many times the McMahon family and Donald Trump have swapped a couple million dollars here and there over the past three or so decades is of interest and does factor into this story, what I find most fascinating about Trump’s association with the WWE is how it came to cast him in an entirely different light than even his own television show. So let’s talk about that first, then come back around to facing the way the company and its owners’ relationship with Trump makes the notion of watching WWE morally challenging at best.
In the beginning…
The first thing you should know is that neither WrestleMania IV nor WrestleMania V were held at Trump Plaza, the now-defunct hotel and casino that was in its third year of operation the year Randy Savage won the vacant WWF Championship in a flat out awful tournament, beating “Million Dollar Man” Ted DiBiase, both the gimmick Vince McMahon would have given himself were he an able wrestler and a viable surrogate for Donald Trump. It was held in the Atlantic City Convention Center, a building WWE uses an extremely low angle photo of on its official venue page to make it seem attached to the actual Trump Plaza building. So far as convention centers go, it’s a fairly important one in American culture: in addition to being the site of the 1964 Democratic National Convention, it’s been a major music and sports venue for decades, even hosting the Beatles during their first American tour. In the case of WrestleMania and several major boxing matches, it was referred to as “Trump Plaza” because it was Trump paying the site fee, making his hotel and casino the primary sponsor.
I can’t find the data on how much Trump paid to bring WrestleMania IV to Atlantic City, but according to the Wrestling Observer Newsletter he put out $1.8 million for WrestleMania V, which was enough for McMahon to ignore that part of what tanked WrestleMania IV was the crowd of casino patrons not really getting into the likes of Butch Reed and One Man Gang. WWE has always been an able shill though, so both iterations of WrestleMania were casino themed, the words “Trump Plaza” uttered dozens of times, and, when Hulk Hogan cut his customary promos about the apocalyptic nature of Hulkamania, he made sure to mention that he’d save Donald Trump from drowning in the sea. A beautiful way to begin a relationship.
In the 90s, Trump’s relationship with wrestling was largely transactional. In 1991, he was one of the celebrity attendees at the inaugural World Bodybuilding Federation pay-per-view. A month later, the New York City Trump Plaza was played host to a Vince McMahon press conference about the federal steroid trial. I can’t find video, sadly, but according to Dave Meltzer, McMahon agreed to print the results of any steroid test he took from that point on in the newspaper (he didn’t) and claimed that the steroid trial was a good thing (it wasn’t) because it’d force the WWE to create a steroid testing program that would set the standard for the rest of pro sports (they didn’t). When Trump went to WWE shows, it was as a comped celeb, usually off camera. In the year 2000, at Madison Square Garden, tabloid cameras caught Donald and Melania trying to get out of the way of vampire character Gangrel’s red mist. According to a 2018 interview, Gangrel spitting the mist at Trump was a last minute rib on the part of McMahon, who deliberately put his germaphobic friend in that seat.
In one of his last appearances as a celebrity bystander, Trump was interviewed at WrestleMania XX by Jesse Ventura, himself something of a political huckster who, in 1999, advocated for a Trump presidential bid under the Reform Party banner. Held in Madison Square Garden to commemorate the first WrestleMania, Trump was in front of wrestling fans in his home town, and the reaction when he’s introduced as the host of The Apprentice, New York’s own, and all of that … is polite applause. The segment is nothing, really—Trump says that Vince McMahon has done “an unbelievable job” like he’s heading up a complete and utter failure of a governmental task force and says that he’d financially support and endorse Ventura’s return to politics, at which point Ventura says it might be time for a wrestler to go to the White House. “A wrestler in the White House?” Jim Ross asks. “Yeah, and maybe a billionaire as Vice President,” Jerry Lawler replies. Omens. Portents. All of them troubling.
The Battle of the Billionaires
It’s jarring, going back to the wrestling of 2007, a year WWE spent actively chasing the pop culture zeitgeist until the Chris Benoit double murder/suicide on June 22 ended all of that. John Cena opened up his year by feuding with Kevin Federline. The wrestling was reliably good. The world would not shut the fuck up about The Apprentice, specifically Donald Trump’s feud with Rosie O’Donnell, and Vincent Kennedy McMahon, showman and carnie that he was and is, heard a desperate public’s cry for something resembling a physical confrontation between the two and obliged, booking and promoting a match between the two to take place on Monday Night Raw. The angle, an intentionally bad match between two people dressed to roughly resemble two quasi-celebrities the tabloid press were obsessed with, impressed no one, though its cruelty towards Trump’s nemesis—backstage segments where the wrestler playing Rosie trucked her way through a Carvel ice cream cake while McMahon looked on disgustedly, McMahon making a point to mock O’Donnell’s queerness, not just in his comments about her “lesbionic fury,” but in booking a segment where she sexually harasses Maria Kanellis by dropping “vacation photos” on the ground so she can get a look at her butt, and two ice cream cake spots in the match, including one where Trump impersonator Ace Steele hits her in the face with a handful of Fudgy the Whale (chosen over Cookiepuss, I’d wager to bet, because whales are big, like fat people) with concussion force, while Trump got off with a lot of light jabs at his hair.

The match was terrible. Google it, and you’ll see that it pops up on lists with words like “worst” and “cruelest” in the title. Roundly lambasted, and justifiably so, it was nevertheless the opening salvo in a three month storyline that brought together a very 2007 assortment of characters, among them McMahon, Trump, Jonathan Coachman, Umaga, Bobby Lashley, and Eugene. But before we get to any of that, what must be confronted is how good Vince McMahon is in the first half of this feud. His Mr. McMahon character has one speed, but when he’s on, that speed is incredible, a real maelstrom of a bastard that you hate completely without getting into any of the very real reasons to find his success offensive. What the Trump vs. Rosie match did was create a way for Vince McMahon, five years removed from Steve Austin and still inexplicably over despite the dire nature of his endless feud against a reformed D-Generation X, to display insecurity.
It was 2007, Twitter wasn’t even a year old and Trump wouldn’t join the site until 2009, so FedExed letters were how rich people communicated with each other. After a gag where Trump’s secretary doesn’t know who Vince is, he gets a letter that roundly criticized McMahon not only for the segment, but for not knowing what his audience wants. It’s a vague letter, obviously not written by Trump himself, but here we have the makings of Donald Trump the babyface, a man who sees through Vince’s bluster and knows WWE could be doing better by its fans. This was 2007, early in the “WWE is shoving John Cena down our throats” era that lasted until Roman Reigns became the guy, so yeah, fans agreed. Vince responded to the letter by replaying the goddamn Trump vs. O’Donnell match while bragging about his genius, then by booking “fan appreciation night.” During that event, in the middle of McMahon trying to give away a blown-up version of his Muscle and Fitness cover, Trump appeared on the TitanTron.
This is how half of the storyline goes—McMahon works overtime to make himself a heel to an audience that has taken to bowing to him, then has to watch as his longtime friend puts zero effort into shooting a pre-taped promo McMahon can actually respond to. The cash drop, though, is a pretty stark departure for public portrayals of Donald Trump, a man who made his name as a ruthless business magnate who’d step on someone’s neck if there was a dollar to be made. The premise of The Apprentice was built around this, the appeal being in watching Trump be cruel to people (and later, celebrities) who were trying to please him. In a way, Trump’s character—and by “character” I mean the version of himself that he offered up to the public in the fiction that was his show—was a take on “Million Dollar Man” Ted DiBiase, only culture had turned to favor the mega-rich so much that people ate it up. Across the divide from him was Vince McMahon, a cartoon showman with Jack Donaghy’s disdain for his audience and Jack Donaghy’s genius for television. On paper, this is a heel vs. heel feud, two of the most hatable men in the history of television battling it out to satisfy their own egos. Trump’s letter is important because it establishes that he cares about the audience as much as he cares about the ratings. The cash drop, though the money wasn’t Trump’s, is the proof. Trump isn’t a sympathetic figure by any stretch of the imagination—his catching COVID-19 couldn’t render him worthy of compassion, so why would this?—but it made him better than McMahon, another conniving billionaire whose idea of giving to the fans was a his magazine cover.
Trump sends another letter, saying that he’s got a business proposal for Vince. That business proposal, of course, is the Battle of the Billionaires, an honest-to-goodness match against McMahon on McMahon’s own turf, WrestleMania. This is where things start going downhill, as WWE puts as much effort as they can into making Trump seem like a virile, tough customer. He comes to the ring with different women on the WWE roster, several of whom were in Playboy, in case you weren’t sure whether or not Donald Trump could fuck. He’s maybe the most wooden person to’ve ever appeared in a wrestling ring, walking around like Dr. Evil, stepping on all of Vince’s lines, speaking in the short, clipped, meaningless phrases he does to this day, promising another cash drop, only for Vince to say that he had Trump’s stagehands barred from the building, because Trump’s power over the world is such that he can hire stagehands to rig such a stunt in a venue he didn’t pay for. McMahon begs off of the match, kayfabing that he got injured during his Hell In a Cell match when really, man, imagine Donald Trump trying to work a wrestling match. McMahon proposes the two pick representatives, Trump proposes hair vs. hair and shows that he’s a good sport about people making fun of his hair, which is something that he’d do on The Tonight Show with Jimmy Fallon before the 2016 election, by showing Vince how real it is. After revealing that the reason he was mad about Trump vs. O’Donnell was because the fake Rosie was better looking than the real one, McMahon agrees, see you in Detroit.
A brief aside about Detroit playing host to this match. Two billionaires using a city frequently derided for its ruined buildings, its crime rate, and its poverty. In 1997, ground was broken on Comerica Park, the baseball stadium that sits kitty-corner from Ford Field, where WrestleMania 23 was to be held. Ford Field was built in 2002. The stadiums, which brought the Detroit Tigers and Detroit Lions downtown (the Tigers played in Detroit’s Corktown neighborhood and the Lions in the city of Pontiac), kicking off a nearly two-decade long systematic gentrification of the city that accelerated in 2010, when mortgage company Quicken Loans began buying and renovating aging office towers within visual distance of those arenas. The promise of all of these things was that it would revitalize the city, the stadiums (both of which were publicly financed) meant to attract big, gaudy events like All Star Games, Super Bowls, and WrestleMania 23, Quicken to bring jobs to the area. Detroit filed for bankruptcy in 2013 and an emergency manager was put in place by the state’s millionaire governor Rick Snyder. Snyder’s power to appoint an emergency manager, who had the power to circumvent publicly elected officials, was one of those small coups that rarely make it beyond the notice of locals, as a ballot proposal failed in the general election and was later passed by the state’s Republican legislature. Kevyn Orr, Snyder’s appointee, hired the law firm he used to work for to handle the bankruptcy, proposed selling artwork from the Detroit Institute of Arts, shut off Detroit residents’ water for non-payment, and cut pensions for city employees.
If that seems pointless to the discussion at hand, okay, but there is a significance, I think, to two rich men making a playground out of a city victimized by white flight and on the verge of committing human rights violations in order to become fiscally conservative. Maybe I feel that way because Detroit was my home—WrestleMania 23 was held in Detroit ostensibly as a tribute to WrestleMania III (and because Ford Field was new)—but the estimated $27.9M and the boon to Detroit’s growing tourist economy (people from the suburbs and elsewhere coming to the ever-gentrifying heart of the city for a fun event) was like vapor. How WrestleMania 23 “supported the equivalent of 334 full-year jobs” feels like how the President generates “jobs,” an intentionally robust but meaningless figure when you’re parting those numbers out across thousands of struggling people working temporary or gig economy jobs that go away without the same ballyhoo. In wrestling, in WWE in particular, what gets the credit for all of this is the main event of the show. John Cena vs. Shawn Michaels may have gone on last, but Trump vs. McMahon was the main event, two billionaires bringing relief to a city ravaged by other members of their cohort.
Besides the metaphorical implications of the match and its location, the angle went to pot because Trump couldn’t hold up his end of the bargain, leaving McMahon too twist in the wind. He made fun of Britney Spears for shaving her head. He did Photoshop promos where he intimated that he might give Trump dreadlocks. Those pictures hung in every makeshift locker room office Vince had for weeks. Meanwhile, he and Trump chose their representatives, Umaga and Bobby Lashley, the later of whom gave us the ultimate nightmare of Trump saying “ECW” a few times during his pre-tapes. It’s weird watching this play out in one go, because by most metrics, everything is going extremely well—Lashley is so over as Trump’s representative that there are big-time “BOBBY, BOBBY” chants during his brawls with Umaga, and the angle spilling over onto ECW and SmackDown didn’t exactly exhaust it, as Umaga trucking Jeff Hardy and Rey Mysterio did the work of rebuilding whatever he’d lost as a consequence of his feud against John Cena earlier in the year. But everything the company did outside of building the confrontation between Lashley and Umaga had an air of desperation to it. McMahon’s promos took place with barber poles and hair cutting implements in the shot, there were videos of celebrities weighing in on who they’d rather see bald (most of them went Trump, for the record), The Rock cut a rare promo about the match, Eric Bischoff and Mick Foley were teased as special refs when all Bischoff wanted to do was tell McMahon off and all Foley wanted was for McMahon to pay for a porno he watched in his hotel room. Finally, the ultimate hedge against the angle falling on its face at the show itself: the return of “Stone Cold” Steve Austin as the unbiased, impartial special guest referee, appointed in a 5-4 vote of the WWE Board of Directors (a number that allows one to assume that then-CEO Linda McMahon voted against her husband).
Trump’s face character is ridiculous throughout all of this. His most famous line in the angle is one where he tells McMahon “You’re a billionaire, I’m a bigger billionaire,” but my favorite is this ripped from the awful future line during his challenge to McMahon where he says that “a big newspaper” called him “the greatest” before wondering if his hair was fake. He later claimed that a poll of celebrities was taken and 95% of them wanted to see Trump beat McMahon. He specifically cited John Travolta saying that he “preferred Trump,” but in the video WWE played the week before, Travolta was asked who he’d prefer to see bald, the answer to which was Trump. It’s like watching the future, this utter bully of a man surrounding himself with women, making reference to news stories and polls that never happened, misinterpreting or editing things that did happen to favor him. The only pleasure to be found in his role is when Steve Austin confronts him, points out how stiff he’s been throughout the whole affair, and threatens to beat his ass. The much GIFed line where McMahon responds to the celebrity poll by saying that 95% of the fans might cheer for Trump, 95% of those fans being idiots, lands a lot softer now than it did then.
The more pushed into a corner McMahon felt, the more wrathful he got. This reached its apex when Eugene, a “developmentally disabled” wrestler portrayed by Nick Dinsmore, spilled a drink on McMahon, was booked in a match against Umaga, and had his head forcibly shaven by McMahon. Eugene is the worst thing the WWE has ever booked, full stop. I didn’t revisit any of it outside of this angle, but the gist of it was that Eugene was a massive WWE fan who, “despite his disability,” was a capable wrestler who often demonstrated that by stringing together sequences of major WWE finishing moves. Because he was developmentally disabled, he often couldn’t see when heels were taking advantage of him, which means that there is a lot of footage of Triple H, who had an inexplicably long feud against Eugene, doing this. Why Eugene was created, what purpose he served, and how he had a three year run on WWE television is beyond me.
When Linda McMahon ran for Senate in 2012, the Eugene character became a major point of contention for local journalists covering the race. Darian Times columnist Joshua Fisher wrote “While CEO of World Wrestling Entertainment, she created jobs that included making fun of retarded men, demeaning women and possibly encouraging steroid use — this does not even touch on how it possibly has influenced the future bullies of American schools” in an editorial about how the candidate would not sit for an interview with the paper. The WWE responded with a letter from the Stand Up for WWE campaign that claimed Fisher took Eugene out of context, claiming “Eugene, like most of WWE’s ‘good guys,’ overcame the obstacles, prevailed and was a hero to our millions of fans.” Hartford Courant columnist Colin McEnroe ran a blog post about Eugene featuring now down YouTube links to segments that featured the character that prompted Stand Up For WWE to issue a video titled “A truthful portrayal of the Eugene character” that was scrubbed from the official WWE website sometime in the last four years. A lot of Stand Up for WWE content from the years 2010-2012 has been made difficult to find on WWE’s website, but here, for kicks, is a 2010 video where Vince McMahon specifically defends the right of WWE fans to vote in response to the Connecticut Secretary of State banning WWE merch from the polls.
I will not post video or photos of McMahon shaving Eugene’s head. I have seen a lot of questionable, sketchy characters and segments in my time as a wrestling fan, but few of them caused me to feel ill. That one did, as Dinsmore threw himself into the role, screaming and crying as he was shaved in front of the world. When he showed up a week later with a Trump wig? The audience laughed at Eugene until McMahon started ordering him around like a manservant. Contrary to WWE’s 2012 press releases, Eugene did not triumph over the owner of the company—he was shuttled over to SmackDown and released in September, his usefulness as a prop for heels finally exhausted. In 2015, Trump mocked New York Times reporter Serge Kovaleski for his physical disability during a nationally broadcast speech. Again, the audience laughed. I guess this is just what billionaires do.
After all of this, WrestleMania 23. Breaking with tradition, WWE held the final press conference before the event at Trump Plaza in New York City rather than the event’s host city. Given his current antagonism against Donald Trump, it’s something else to hear Batista sound somewhat dejected as he cedes the mic saying “I’ll let you guys get on to the important stuff: bald billionaires.” In introducing Trump to the podium, Jonathan Coachman calls him “the embodiment of the American Dream.” How was the match? Who gives a shit. It’s a trifle, the best part of which is the relative silence that accompanies Trump down to the ring as money falls and four winners of various Trump-owned pageants cheer him on. He has nothing, y’all—no physical or verbal charisma, no awareness of what he’s doing or how he looks. He’s a space alien, a sack of meat filling out an overcoat, the weakest element of the match by a long shot. But he wins, he hits McMahon with what some would call a clothesline, he shaves McMahon bald, he takes one of the worst Stone Cold Stunners in history, and he saunters off until 2009, when he “bought” Raw, causing a 7% dip in WWE stock.
A Man of the People
Beyond this storyline, I can’t recall too many prolonged campaigns to present Donald Trump as a person who cares about anybody, let alone the unwashed masses who watch professional wrestling. Beauty pageants don’t do that. Hotels and golf courses and casinos don’t do that. Steaks and water and board games and books don’t do that. And I don’t think The Apprentice did, either, even when celebrities got involved and the money at stake went to charities instead of contestants. Only in professional wrestling can someone like Donald Trump get such a re-write of his character, an unearned reframing of his person as one who likes the same things you like, someone who wants the same things you want. A better product. A good time. Money. Here it is, take it and don’t think too hard about where it came from.
2007 is also the year the McMahon family or WWE (the company was listed as the donor but claimed it came from Vince and Linda) donated $4M to the Trump Foundation (in 2009, after Trump’s Raw appearance, they donated a further $1M). This was the beginning of a pattern of the McMahons donating large sums of money to various Trump entities, the most significant of which, of course, was his presidential campaign, its various arms receiving over $7M. While Forbes found other donations to the Trump Foundation that suggested the McMahons’ or WWE’s donations to the Foundation were appearance fees (though much smaller than what the WWE/McMahon donations insinuate would have been Trump’s payoff for his appearances), but the company denied it and the McMahons never publicly commented on the matter. As for what the Trump Foundation did with that money? Whew. In 2007 he used Foundation money to settle a dispute with the town of Palm Beach over the Mar-A-Lago Golf Resort’s flag pole by sending $100,000 to a charity for veterans as opposed to paying with his own money. He also used $20,000 that year to buy a 6-foot-tall painting of himself. At the end of 2006, according to the Washington Post, the Trump Foundation had $4,238 in the bank. The money that WWE or the McMahons put into the Trump Foundation paid for petty legal disputes and shows of wealth and prestige that were largely done under the guise of charity.
It’s incredible how much money the McMahons have been willing to dump on Donald Trump since 2007, but given how much Linda McMahon spent on two failed Senate bids (nearly $100M), what WWE or the McMahons gave to him in 2007 and 2009, and what Linda McMahon has given to Trump in 2016 and 2020 is a drop in the bucket. According to FEC filings from 2016, McMahon made 45 different donations to Republican candidates across the country, a pattern, as detailed above, she has continued this election cycle. Vince made far fewer donations in his name, the one presidential candidate receiving funds being Chris Christie. Stephanie and Paul Levesque also donated to Christie that year, all months after Trump announced his candidacy.
Linda, though, has been unapologetically on Trump’s bandwagon from the beginning. While she made a number of $2,700 donations to political candidates early in the election, it’s the polite thing political millionaires and billionaires do. On 12/31/15, she made a $200,000 donation to Future 45, a PAC that supported Donald Trump, donated millions to another Trump PAC, Rebuilding America Now, and gave a further $1M to Future 45 just as they launched a $10M television ad campaign on the eve of the election. Divorce her from wrestling all you want, but her money came from professional wrestling. It came from the toil of the wrestlers, crew, and staff who make their product possible, it came from stock offerings, it came from television rights fees, and it came from our wallets, from which we’ve given for tickets, merchandise, and access to the WWE Network.
Donald Trump is WWE’s President. They took him in and gave him a different persona. They put him on an unedited television show and let him play strongman at their expense. They’ve given him millions of dollars, worked in his administration, and chaired PACs that work on his behalf. As much as I hate the connection people make between the broad concept of wrestling fans and the narrower concept of Trump voters, WWE made that happen. And while Stephanie Levesque said in 2018 that WWE is “non-partisan,” the WWE is the McMahon family, and the fact that the only member of the McMahon family who continued to donate to political campaigns once it was clear that Trump would be the nominee was the one who unattached herself from the company due to her political ambition, does not absolve the company or the family who runs it from their role in creating the nightmare that we live in, especially given that her current job is to aid in perpetuating it.
This isn’t just right-wingers pasting CNN logos or Joe Biden’s face on Vince McMahon at WrestleMania 23, and it’s not just about money. 2020, to borrow a phrase, has been an unprecedented year for people who like wrestling at all levels. #SpeakingOut, WWE’s treatment of labor, Florida claiming that wrestling was an essential business during a pandemic, issues with the spread of COVID-19 at independent wrestling events—all of it has me questioning why we, why I, devote so much of our lives to it. This is the future professional wrestling wants for us. Why are any of us still here?