Vince McMahon and the Damaging Impact of Failing Upward

In Ringmaster, author, journalist, and essayist Abraham Riesman takes on the admirable but unenviable task of chronicling the life of Vincent Kennedy McMahon, the billionaire owner and Don of professional wrestling. The book’s subtitle is Vince McMahon and the Unmaking of America. It’s a lot to pin on one man. That blame for the collapse of the American experiment could be somehow laid at his door is an assertion McMahon might snicker and then sneer at; it would simultaneously aggrieve and flatter him. “We have lived for a quarter of the century in the world Mr. McMahon made,” Riesman writes.

Now in his 70s, McMahon’s life has mostly resisted genuine attempts at biography. It’s strange, given that as of March 2023, he was running a publicly traded company that he had all but built himself and was valued at several billion dollars. This is perhaps because McMahon would pose a threatening presence to any writer. After a single question, he shut down an interview with a reporter from The New Yorker. He seemed poised to strike sports commentator Bob Costas during a heated interview for HBO in 2001. A much-promoted oral history of McMahon’s company, World Wrestling Entertainment (WWE), by I Want My MTV! authors Craig Marks and Rob Tannenbaum, has yet to appear.

Indeed, McMahon has betrayed little desire to be liked or accepted by serious-minded society. He seems to be both vastly more intelligent yet also more moronic than the average person. He might be playing 3-D chess, or he might be scribbling with crayons. It’s hard to say. Sportswriter Frank Deford described him as rude, loud, and almost childish. “Vince McMahon,” he concluded, “what a dick.”

McMahon was born in Pinehurst, North Carolina, in 1945. His father, Vincent J. McMahon, was a soldier stationed in nearby Wilmington. Although McMahon would only learn this later in his life, his grandfather was Jess McMahon, a well-heeled boxing and wrestling promoter operating in and around Manhattan. McMahon’s father and mother split before he was two. His mother, Vicki, re-married quickly, and he was raised by an abusive stepfather named Leo Lupton. Besides physical abuse, McMahon was also sexually abused by his stepbrother and, he has insinuated, his mother.

When he was 12, he reunited with his birth father, who had inherited his father’s promotion business by then. He incorporated it as Capitol Wrestling in 1957 before renaming it the World Wide Wrestling Federation (WWWF). The young McMahon took to wrestling immediately; “I loved it from the day I saw,’” he told one reporter. He married Linda Edwards in 1966, and the two set about fashioning themselves into aspiring entertainment promoters in the Northeast.  

If McMahon was skilled at one thing as a young businessman, it was failing upward. He had a hand in Evel Knievel’s failed jump of the Snake River Canyon in 1974 and the disastrous match between boxer Muhammad Ali and wrestler Antonio Inoki in 1976. Both were attempts to take advantage of the new technology of closed-circuit broadcasting. McMahon was failing publicly, but he was learning. In 1982, he purchased the newly rebranded WWF from his father and father’s business partners and busied himself with the friendless work of empire building. “I knew my dad wouldn’t have really sold me the business had he known what I was going to do,” McMahon would later say.

Over the next decade, McMahon led a scorched earth campaign against the regionalized wrestling promotions that had existed nationwide for decades and operated together as a loose confederation. No individual promoter got too rich or big, yet neither did they go out of business. McMahon changed everything; he hired away their star performers, outbid them for local television contracts, and brokered exclusive arrangements with their local arenas. He knowingly marketed to children, launching a line of action figures, a WWF-branded ice cream, and a WWF-themed Saturday morning cartoon. There were movies, albums, major network specials, and an insanely successful cross-promotion with a nascent MTV.

By 1988, professional wrestling in America was effectively a two-party system, with McMahon’s WWF competing against Ted Turner, the billionaire owner of World Championship Wrestling, in what came to be known as the “Monday Night Wars”. That McMahon fought with Turner, the media visionary who founded both CNN and TBS, was no accident. Since the late ’30s, success in professional wrestling has been about a willingness to embrace new broadcast technologies.

In his desperation to survive, McMahon undertook a second scorched earth campaign against all semblances of decency and good taste. It’s this era that fascinates Riesman the most. During this time, McMahon amplified everything to unheard-of volumes. He not only admitted openly that matches were pre-determined, but he also made them more violent, more juvenile, and the scene around them more sexist and racist than any promoter had previously dared. He remade himself into “Mr. McMahon”, the swaggering, callous corporate overlord.

For much of this time, his foil was the wrestler “Stone Cold” Steve Austin, with his shaved head, defiant attitude, and signature pair of raised middle fingers. Inside the ring, Austin was the ultimate non-conformist. Outside of it, he was a consummate company man. His secret for success, he later wrote, was “to develop a positive working relationship with Vince.”

McMahon also pushed harder to blur reality, with wrestlers’ personal lives seeming to bleed into their in-ring personas. It was shocking and often alarming, and it was must-watch television for much of the decade. By 1999, it had all become such a jumbled mess that when McMahon phoned the wife of wrestler Owen Hart to inform her that her husband had been injured in an in-ring accident that would soon prove fatal, she’d had to ask him, “Is this really a serious call? Or is this part of your production?”

Ringmaster ends not long after that phone call was made. The rest of McMahon’s story; the end of the Monday Night Wars, his company’s initial public stock offering, the high-profile flop of his XFL (the professional American football minor league), the horrific murders committed by wrestler Chris Benoit, and the McMahon family’s growing influence in right-wing politics (besides being major donors to Donald Trump’s 2016 presidential campaign, Linda McMahon served as Trump’s head of the Small Business Administration and now chairs the Trump super PAC, America First Action), are all condensed into a 20-page coda. It’s a curious choice on Riesman’s part, and it makes Ringmaster feel truncated. With its recurring episodes of murder, sexual impropriety, lawsuits, death, and obscene uses of power, McMahon’s life has all the makings of either a sizzling potboiler or a Robert Caro-sized megawork. In the end, Ringmaster is neither.

McMahon’s rocket ride from the trailer parks of Pinehurst to life as a billionaire power broker is an American story like no other. In many ways, the chaos he has orchestrated inside wrestling rings for the last five decades is the least interesting part of it. Riesman, unfortunately, spends too much time laying out wrestling storylines and developing a concept of “neokayfabe” – the idea that for wrestling fans, the surface fakeness of matches “encodes a deeper truth, discernible to those few who know how to look beyond what’s in front of them. To those fans adept at reading the signs, another narrative emerges, and another beyond that. Suddenly, the pleasure of watching a match has less to do with who wins than with the excitement of decoding it.”  This smearing of fact and fiction has bled into all facets of our lives, it is contended, but particularly into politics. (Riesman authored a recent New York Times editorial titled “The Best Way to Explain the G.O.P. Is Found in the W.W.E.”)

Riesman is an astute and intelligent writer and a keen observer of popular culture, but assertions that we’re all living in a neokayfabe world are overcooked and unconvincing. Wrestling fans have fancied themselves the ultimate insiders since at least the late-’20s. In 1941, Esquire’s Curt Riess called professional wrestling “the sport of the wise guys. The people who didn’t give a damn what went on before their eyes, who only wanted to know what was going on behind the scenes. The people with the backstage urge.” Riesman’s study of McMahon might have worked better as a work of straight biography. As polemic, it falls flat. Vince McMahon didn’t reshape America; it always fit him perfectly. “Vince was a businessman,” wrestler Adnan Alkaissy tells Riesmann. “He knows how to get the thing over and he wants to make money, and that’s the bottom line.”

In June 2022, it was revealed that McMahon paid out $12 million to silence employees with allegations of sexual misconduct within WWE. McMahon himself was accused of sexual assault. He resigned as CEO soon after, seemingly bringing his business career to a disgraceful close. When Ringmaster went to press, it appeared that this would be the end of the McMahon saga. “His time at the top was over,” Riesman writes in Ringmaster‘s introduction. But six months later, he was back as CEO, displacing his daughter, Stephanie, who promptly resigned from the company. In April 2023, it was announced that WWE was being purchased by Endeavor Group, the parent company of UFC, for $9.3 billion and that McMahon was being named executive chairman. McMahon’s career was not just back on track; he was richer and getting more attention than ever.

It was a talent he’d displayed several times in his life, a seeming knack for burning his own house down only to rebuild the ashes into something evermore gaudy and absurd. This capacity for failing upward, along with his defiant resistance to accepting even the faintest whiff of accountability for his actions, has brought McMahon his outsized success. On 3 April 2023, McMahon and Endeavor CEO Ari Emanuel appeared on MSNBC. Mustached, his hair dyed a glaringly deep shade of brown, it was McMahon like we’d never seen him; reborn, humbled, yet more puffed up than ever. “I would have bodyslammed him if he thought he was going to leave,” joked Emanuel. “I’m a visionary,” McMahon responded. He also made sure to remind Emanuel that he outweighed him by 100 pounds, should the two ever come to blows.

Perhaps McMahon’s full story will never be known. During the MSNBC interview, he confessed to having little interest in telling it himself. “I’m not sure of this legacy stuff,” he told reporter Scott Wapner. “I’m not going to write it, so, I don’t know.” When Wapner pressed, reminding him of the sale’s curious clause returning the WWE’s intellectual property to McMahon should it ever be sold again, McMahon first tried to deflect the question and then answered dismissively, “It is what it is.” Perhaps, he feels, his story is only just beginning. Perhaps the rocket ride isn’t over. God help us all.