The week of April 3, 2016

How Donald Trump’s weird history with the WWE foreshadowed his presidential run

By Soyo Hong

The 2016 presidential campaign trail has oddly resembled a professional wrestling circuit. There have been epic feuds and heel-turning tantrums, candid interviews and unthinkable plot twists, with machismo abounding, unruly crowds gathering, and taunting insults regularly being hurled on national television. In fact, Donald Trump said the Republican debates were a “little bit like the WWE.

He would know. Trump, the current front-runner for the Republican nomination, has a strange, surreal history with World Wrestling Entertainment.

Ever the showman with a flair for the dramatic, Trump himself has twice received Emmy nominations for his reality TV show, The Apprentice, has made over a dozen appearances in TV shows and films, and at one point was the owner and executive producer of three of the most recognized beauty pageants in the world: Miss Universe, Miss USA, and Miss Teen USA. But it was in the world of professional wrestling, with its over-the-top characters, exaggerated displays of bravado, and athletic stunts, where Trump really came into his element.

Trump initially gained access to WWE in a way that’s not too far removed from how he entered politics in general—by cutting checks and slowly gaining clout and relevance. In 1988, for example, Trump sponsored WrestleMania IV—the biggest event of the year in sports entertainment—to promote the Trump Plaza hotel and casino in Atlantic City, New Jersey, and did so again the following year. It was the first and only time WrestleMania has been hosted in the same city on consecutive years.

Nearly two decades later, the blustering, insult-slinging Trump that we know today first entered the squared circle of the WWE. It was a bizarre sequence of events that started with a Rosie O’Donnell impersonator and ended with him allegedly acquiring the company’s signature weekly program and pledging to make it great again. And in retrospect, it was the perfect preamble to his presidential run.

Donald Trump and the WWE

Donald Trump vs. Rosie O’Donnell

Donald Trump’s real-life (and ongoing) feud with Rosie O’Donnell dates back to December 2006. Speaking out on The View after a Miss USA controversy, O’Donnell called Trump “a snake-oil salesman” and said “he’s the moral compass for 20-year-olds in America.”

Perhaps the trigger was that comment about 20-year-olds, but keenly recognizing some potential to shock, WWE staged a match between a fake Trump and a fake O’Donnell on Jan. 8, 2007, played respectively by Ace Steel and Kylie McLean. Vince McMahon personally introduced both characters, calling the fake O’Donnell “the double-chinned diva from The View, here in all her lesbionic fury.”

The only thing worse than that idea was its execution. After pulling out every fat lesbian joke in the book, fake Trump threw a Fudgie the Whale cake in fake O’Donnell’s face and landed a diving headbutt from the second rope, hitting hair-first—a hairbutt. The match, if you can even call it that, has been named one of the top 10 most cringeworthy moments in WWE history. You can actually hear fans chanting “Boring!” in the clip.

Donald Trump vs Rosie O’Donnell by sir-roddick

Giving the people what they want

A few weeks later, during an episode of Monday Night Raw on Jan. 29, 2007, Trump interrupted McMahon during a bit about Fan Appreciation Night, simultaneously embarrassing McMahon and positioning himself as a populist billionaire. “Vince, you claim you tell your audience what they want, what they like, and all of that nonsense. They want value,” Trump said from the TitanTron. “Who knows more about value than me, Vince?” Trump then proceeded to shower the audience in money, some of it real.

Years later, Trump claimed, “The fans appreciated Trump more than they appreciated Vince because I gave them a lotta money.”

Putting it all on the line

Bragging is like breathing for Trump; he does it constantly and effortlessly, every chance he gets. Unsurprisingly, we got a teaser of this behavior when he challenged McMahon to a showdown using terms not too far removed from the recent Republican debates. “I’m taller than you, I’m better-looking than you, I think I’m stronger than you,” Trump said. “You’re a rich guy; I’m a richer guy.” Eventually Trump taunted his way into a match with McMahon where they bet something that was invaluable to both of them—their hair.

Inking the deal

Trump and McMahon didn’t actually wrestle each other. That would have been painful to watch. Instead, they chose wrestlers to fight in their places. McMahon elected for a beast by the name of Umaga, while Trump had then-Extreme Championship Wrestling champion Bobby Lashley. The contract signing lasts an excruciating 22 minutes, but it’s worth it for this quip from McMahon: “You might have some support from this audience, but 95 percent of them are idiots!”

The Battle of the Billionaires

WrestleMania XXIII drew over $5 million in ticket sales and 1.2 million pay-per-view buys at $54.95 a pop from around the world. Trump’s Lashley won the match—after a run-in by Stone Cold Steve Austin as ref, and Trump got in “some of the worst punches in wrestling history” on McMahon. Trump took shears to McMahon as promised, but Stone Cold got the last laugh, delivering his signature Stone Cold Stunner to Trump.

Trump buys ‘Raw’

A couple of years later, on June 15, 2009, the billionaires’ feud resurfaced when Trump “bought” Monday Night Raw with an offer that purportedly “couldn’t be refused.” Trump immediately condemned McMahon that night for taking his audience’s loyalty for granted and pledged to turn things around in ways that only he could.

“You never really showed your appreciation for the Raw audience,” Trump said. “Never once did I see that appreciation. I’m gonna do stuff that’s never been done before, never been seen before. … My first act as owner is to do something unprecedented. Something you were too cheap and selfish to make happen, Vince. For the first time in its 17-year history, next week’s Raw will be presented live to the USA, commercial-free. … And guess what, Vince, I’m personally going to be at Raw next week to run things the way I want to see them run, meaning the right way.”

The following week’s episode was the highest-rated Monday Night Raw in seven years, but it came with a price. McMahon so convincingly sold the angle the previous week—even going so far as to issue a fake press release with USA Network—that WWE, a publicly traded company, saw its stocks go down nearly 7 percent the day after McMahon’s initial announcement.

Trump would ultimately “sell back” Raw, allegedly for double what he paid for it. “I’ve got a lot of people, a lot of friends, a lot of billionaire friends,” he told McMahon. “A lot of guys want to buy this from me, Vince. I could double my money anytime I want to sell.”

The WWE Hall of Fame

Solidifying his standing and history with the organization, Trump was inducted into the WWE Hall of Fame in 2013. During his induction, McMahon actually hinted at a Trump presidency:

“When you think about it, second only to me, Donald might very well be a great president of the United States.”

Donald Trump is not the first to mix politics and professional wrestling. Jesse “The Body” Ventura served as the governor of Minnesota from 1999 to 2003—and talked politics with Trump at WrestleMania XX in 2004—while former WWE CEO Linda McMahon unsuccessfully ran for a U.S. senate seat representing Connecticut in both the 2010 and 2012 general elections. (In the other corner, it’s worth noting that Teddy Roosevelt’s mantra, “Speak softly and carry a big stick,” could be the perfect tagline for a hardcore wrestler.)

If done right, there should never be a dull moment in politics or wrestling. The strongest personalities in both arenas use innate charisma and the ability to tell a compelling and convincing story: Franklin Roosevelt started his Fireside Chats to communicate directly to Americans and reaffirm their confidence throughout the Great Depression and World War II, while Ronald Reagan’s contemporaneous critics claimed he favored the emotional validity of drama over reason.

It’s the explosive combination of Trump’s larger-than-life persona and the WWE’s particular brand of braggadocio that makes him such a compelling character and candidate. Talking about his media strategy in his 1987 book, The Art of the Deal, Trump wrote: “The final key to the way I promote is bravado. I play to people’s fantasies. People may not always think big themselves, but they can still get very excited by those who do. That’s why a little hyperbole never hurts. People want to believe that something is the biggest and the greatest and the most spectacular.”

To some, Trump is the people’s champion (with apologies to the Rock): he’s the business magnate capable of making cash seemingly fall from the rafters; to others, he’s the ultimate heel—a villain of comic proportions. Either way, it makes for great entertainment.

Illustration and GIF by J. Longo