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Inside Vince McMahon’s Aspirational, Transactional, Utterly All-American Friendship With Donald Trump

Donald Trump and Vince McMahon at some WWE thing or other in 2009. I'm sure it was great.
Photo by Mark A. Wallenfang/Getty Images

This excerpt from We Promised You A Great Main Event: An Unauthorized History of WWE is published with the permission of HarperCollins.

Vincent Kennedy McMahon is a singularly fascinating individual, perhaps one of the most perplexing humans who has ever graced the face of the Earth. Stories about his proclivities and peculiarities—both apocryphal and verified—could fill their own book: he hates sneezing and considers it a sign of weakness. He was in his forties or later when he first learned what a burrito was, and that Asian pornography existed. He’s been known to deliberately step on a person’s feet or make a personal verbal attack on them in order to try and get them to stick up for themselves. He believes you can eat an entire box of Oreo cookies in one sitting with no ill effect; it’s having a few every day that will make you fat. He finds farts the most hilarious thing in the world, unless it’s a day when he’s tickled by poop. He yelled at a prospective screenwriter for using the phrase “to tell you the truth”—the implication being in Vince’s mind that the individual must have been lying to him during the rest of the conversation. 

He once tried to pitch his daughter two separate story lines involving incest: one that implied she was in a romantic relationship with her brother, and one where she was sleeping with him. She declined both. Howard Cosell, perhaps the most famous sportscaster of all time, told a story in his autobiography of McMahon calling him in 1984 to offer him a job as the WWF’s lead announcer. Cosell laughed, incredulous, and told Vince that he didn’t want to finish up his illustrious career “calling phony wrestling matches.” He said Vince must be crazy and turned him down cold. McMahon, in an instant, turned furious, yelling, “Fuck you, Howard! You’re making the biggest mistake of your life.” Howard recalled, “After I hung up, I thought McMahon was a real kook. I still do. But he’s an incredibly successful one.” A more succinct appraisal of McMahon would be difficult to find. 

Vince is ruthless both personally and professionally. If he feels a perceived slight, he has a long history of enacting his revenge fantasies on the air within his programs and inside the ring. When Rosie O’Donnell ran afoul of his good friend Donald Trump, he booked a match on Raw between a Rosie impersonator and a Trump impersonator (neither of which looked much like their real-life counterparts, apart from the Trump wig), with Trump going over. He booked a similar match between “Barack Obama” and “Hillary Clinton.” He cast geriatric actors to portray Hulk Hogan, Randy Savage, and “Billionaire Ted” when his two former top stars decided to sign with Ted Turner’s World Championship Wrestling (WCW). He’s hired former longtime opposition stars and paid them big money just to make them look foolish and diminish their value elsewhere. The many regional bookers, promoters, and adversaries who went up against McMahon hated his guts long before he eventually drove them all out of business. He has at one time or another employed just about every dirty trick in the wrestling and the promoter business in order to gain an upper hand, although that’s pretty much what you’d expect from any billionaire. Vincent Kennedy McMahon has kept an iron grip on his empire against all odds, but he wasn’t necessarily the born-into-this golden child you might expect given his promoter-family lineage. 

Vince Jr. was the younger of two boys born to Vince Sr. and his first wife, Victoria. Vince Jr. was born in 1945 in North Carolina, but Vince Sr. divorced Victoria in 1946 and departed with his eldest son, Roderick McMahon III. As a result, Vince Jr. didn’t meet his father until adolescence, instead growing up with several fathers and being raised under the name Vinnie Lupton. Vince Jr. said in a 2001 Playboy interview that the stepfather from which he took this surname, Leo Lupton, abused his mother, and subsequently beat Vinnie when he once tried to intervene on his mother’s behalf. Of Leo, Vince later said, “It is unfortunate that he died before I could kill him. I would have enjoyed that.” He also said in that same interview that he was sexually assaulted or molested as a child by someone very close to him. “You said the sexual abuse in your childhood ‘wasn’t from the male,’” said interviewer Kevin Cook. “It’s well known that you’re estranged from your mother. Have we found the reason?” After a pause, McMahon nodded and offered, “Without saying that, I’d say that’s pretty close.” 

Vince told Forbes that he grew up “dirt poor” and lived in a trailer park before finally meeting his biological father at the age of twelve. By all accounts, Vince was instantly hooked on the wrestling business, even wanting to become a pro wrestler himself before Vince Sr. forbade it.

After meeting his father, Vince would regularly make trips to MSG to watch the shows by his father’s side behind the scenes. Vince graduated from military school in Virginia, then got his bachelor’s degree at East Carolina University in 1968. He quickly came aboard his father’s business, eager to learn, and debuted in the World Wide Wrestling Federation as a ring announcer in 1969. It was off to the races at that point, as he became a play-by-play man in 1971 and continued to work hand in hand with his father. They clashed at times, as Vince Sr. was a traditionalist. Among other disagreements, Vince Sr. believed the role of a booker and promoter was to be behind the scenes and unseen at all costs—something Vince Jr. would eschew for the bulk of his time in the wrestling business. 

Linda Marie Edwards met Vince Jr. when she was thirteen years old and Vince was sixteen, as their mothers worked in the same building. Victoria McMahon became good friends with the Edwards family, and Vince and Linda dated throughout high school. Edwards’s stable home life was a balm to Vince, and he spent most of his free time there until heading off for college. He proposed to Linda after she graduated from high school, and they married in August of 1966, when Linda was seventeen years old. Linda attended East Carolina University alongside her husband, and finished college with a French degree and her teaching certification in just three years, so that she could walk in the same graduation ceremony as Vince. After Vince joined his father’s company, Linda worked as a receptionist and paralegal in Maryland, translating documents for a law firm and studying IP law, which would definitely come in extremely handy for the couple’s future in professional wrestling. 

In 1970, Linda gave birth to their son, Shane McMahon, and Stephanie McMahon was born in 1976. In 1980, Linda and Vince founded Titan Sports, which would eventually orchestrate the buyout of Vince Sr.’s wrestling company. Linda would eventually make her way onto WWE television—most notably as a wheelchair-bound zombie drugged by her real life husband and evil business partner, and recipient of some of the most gingerly applied wrestling holds in history. Outside of pro wrestling, Linda took part in various entrepreneurial and philanthropic efforts, and along with the success of WWE, the McMahons were real movers and shakers in Connecticut, their adopted home state ever since putting down the proverbial Titan Sports stakes (which eventually found its permanent home in Stamford). 

In 2009, Linda became a member of the Connecticut State Board of Education, appointed by then-governor Jodi Rell, and stepped down from that post the following year to begin the first of two attempted U.S. Senate campaigns. Running as a Republican, she was handed defeats in the 2010 and 2012 senatorial elections, reportedly spending tens of millions of dollars of her own money on the campaigns. After seeing her general-election political hopes dashed in two straight elections, McMahon became heavily involved as a donor and fundraiser for the GOP. Not surprisingly, the McMahons have donated several million dollars to Donald Trump and his various personal and political exploits, including a $6 million donation to a Trump campaign super PAC in 2016. Equally not surprisingly, Linda was one of the first people earmarked for a spot in Trump’s cabinet following his election. On February 14, 2017, Linda became the head of the Small Business Administration, and despite the subsequent mind-boggling picture of she and Vince in the Oval Office with their pro wrestling children and their children, she would eventually become one of the least controversial and least scandalized members of the entire Trump administration.

So now we really must talk about the McMahon-Trump relationship. Linda and Vince have a long-standing personal friendship with Donald Trump, dating back to the 1980s. The earliest notable on-screen collaboration between the Trumps and the McMahons came in 1988, when WrestleMania IV was referred to on-screen as being held at the Trump Plaza Hotel and Casino. Trump also appeared on-camera at ringside during the event, schmoozed backstage with wrestlers, and did it again the following year, when WrestleMania V was held at the same venue and Trump was interviewed at ringside by announcer Sean Mooney midway through the event. These were the formative events in the McMahon-Trump alliance, and the family have been friends with Donald ever since.

Much has been written about the relationship between the McMahons and Donald Trump over the years, but the underlying sentiment and belief is that the two showmen tend to have a lot in common in terms of showmanship under the guise of business—or vice versa. A sizable chunk of the American populace views the two men as billionaire hucksters of a sort, and huckster one-percenters tend to stick together. Personally, I believe the relationship is a bit more nuanced than that. 

Donald Trump and Vince McMahon see something in the other man that they desperately wish they could obtain for themselves. Vince McMahon has accomplished everything there is to be accomplished in a specific niche, but all of his other ventures have met with limited success or pointed failure over the years, especially when he’s tried to court a more mainstream audience. He’s always desired validation from the mainstream press and has either subtly or overtly desired to be seen as something other than a carny wrestling promoter. He’s hailed as a genius, visionary, and the largest mogul his field could ever imagine, but he desires nothing more than to be thought of as a self-made billionaire and genius, period, without the “wrestling” label appended to any of his superlatives. In Donald Trump, McMahon sees someone with his same mindset and mentality (to varying degrees) and his same love of bombast and showmanship, but someone who has always managed to convince the world at large of his business acumen, celebrity, and personality—someone who is Vince McMahon viewed from a different angle, but a Vince McMahon who has managed to attain the ultimate validation of mainstream acceptance: the office of the presidency of the United States. 

Similarly, when Trump looks at McMahon, he sees what he’s always imagined in himself: someone who has scrapped and clawed for every inch of his personal success and wealth; someone who has conquered his corner of industry and is hailed as an innovative genius, visionary, and ruthless businessman; and someone who is a big, strong, macho guy—a swaggering manifestation of excess and masculinity that Trump has always been single-mindedly focused on in endless interviews and speeches and braggadocio. Trump was handed immense wealth by his father and got a family doctor to write a note to avoid joining the military. He reportedly gorges on fast food and watches television most of the day, seething at people who call him out for what he perceives as petty slights. Vince McMahon, meanwhile, grew up in a trailer park, bought out his own father’s business, and has spent the past few decades working out hours a day, growing his business, and barely having time for sleep—not that he’d claim to need sleep, anyway. Vince has a full head of hair and bulging muscles and minuscule body fat. He fancies himself as being in control at all times, to the point where he has nearly mastered his own body’s compulsion to occasionally sneeze. That sure ain’t Trump. The two men recognize their ruthless showmanship nature in the other, but their yearning for what the other has is what drives them. If they weren’t friends, they’d be bitter enemies. If one of them didn’t exist, the other would create a hypothetical image of him in their mind to motivate them and propel them forward. 

Vince is seemingly motivated by this raging desire to break into a more respected business. Every time a non-wrestling website or publication spills any amount of positive ink or devotes any amount of space to something WWE did, the weekly shows will dedicate a short bumper to showing the headlines on screen, while lead announcer Michael Cole explains why the noteworthy news item was important. In the 1980s and 1990s, McMahon tried to start a movie production company, a bodybuilding league, a supplement company, and get into the boxing game (among other ventures). In the 2000s, he tried to start a mainstream football company (twice) and actually did start a movie studio. It’s his continued insistence that his company is an entertainment company, not a wrestling company. It rankles him that he’ll never get the mainstream respect he craves due to the very societal stigma associated with the fundamental nature of pro wrestling—and yet he is unable to break free from his status as a self-made billionaire who became rich and powerful by being better at promoting pro wrestling than anyone else in history.