How Wrestling King Vince McMahon Fought to the Top

From the trailer park to the wrestling ring — the billionaire promoter has led a fascinating life.

How Wrestling King Vince McMahon Fought to the Top

He’s taken chair shots to the face, stomped over his enemies (literally and figuratively) and built a professional wrestling empire. He might be the world’s most eccentric billionaire. He’s Vincent Kennedy McMahon, dammit, and these are 14 facts you probably didn’t know about him.

Although McMahon had appeared regularly as the villainous boss on the World Wrestling Entertainment’s “WWE Raw” and “WWE Smackdown” TV shows throughout the years, the wrestling mogul has shunned public interviews. He’s only given a few that shine a light on the real Vince McMahon, most importantly a 2001 print interview with Playboy Magazine and a 2001 radio interview with Howard Stern, both of which were given when he was 55 years old and were to mainly promote his football league, the XFL (much more on that later).

While McMahon may never write a tell-all book or give any more interviews, we do know a decent amount about the 72-year-old’s unusual upbringing, strange quirks and insatiable ambition. Here are 14 facts, stories and anecdotes about the world’s greatest wrestling promoter.

Growing up wasn’t pretty

Trump victory — Donald Trump shaves the head of McMahon after Trump's representative wrestler Bobby Lashley defeated Umaga at Wrestlemania XXIII in Detroit in 2007.

McMahon’s early life was rough. His mother had married five times, and the step father who stuck around, Leo Lupton, beat him.

“It’s unfortunate that he died before I could kill him. I would have enjoyed that,” McMahon told Playboy. “I grew up in a very volatile environment. My view was that if I took a beating and lived, I won."

But he isn’t looking for pity. “I still have that view. It gives me tremendous advantage because I’m not afraid of failure.”

He was raised in a trailer park

McMahon, O'Dell, Piper — McMahon, left, television host Nancy O'Dell, center, and wrestler Roddy Piper at the World Wrestling Entertainment SummerSlam in 2009.

McMahon was raised in an eight-foot wide New Moon trailer in Havelock, North Carolina.

McMahon told Playboy that while trailer park living had little privacy, he preferred it to his previous home in Manly, North Carolina, where he lived in a house with no indoor plumbing.

Given his humble beginings, his eventual success at building an entertainment empire is truly impressive.

And there were more obstacles....

He may have been molested by his mother

Today show — McMahon, during an interview on the NBC "Today" in 2007, urged people not to assume that steroids played a role in the murder-suicide of pro-wrestler Chris Benoit, his wife and 7-year-old son.

McMahon has a rather complicated relationship with his mother, Vicki Askew.

According to his Playboy interview, Vicki “was in the church choir. A real performer, a female Elmer Gantry. Very striking, with an excellent voice.”

When getting into the details about his past, and when asked if there was sexual abuse, McMahon said that it wasn’t from a man, adding, “That’s not anything I would like to embellish. Just because it was weird.”

Playboy then asked: “It’s well known you’re estranged from your mother. Have we found the reason?”

McMahon paused, nodded, and said, “Without saying that, I’d say that’s pretty close.”

McMahon does not directly say what happened. When Stern said (citing the Playboy interview) he was shocked to learn McMahon had been molested by his mother, McMahon replied, “I didn’t say that, that was the inference.” When pressed a bit more, he told Stern he didn’t want to talk about it.

More About His Mom

Vicki Askew is apparently still alive and in her mid-90s. She made a very brief appearance on WJACTV Johnstown to talk about a new tennis facility in Ebensburg, Pa., which was financed by the McMahon family fortune

When McMahon spoke to Stern in 2001, he said his mother didn’t get any of his money.

He was court marshaled in military school

military games — McMahon speaks during a news conference at Madison Square Garden in 2006 after Armed Forces Entertainment invited WWE to perform a series of wrestling matches for U.S. Troops in Iraq.

McMahon was accused of various troublemaking and was, according to him, the first cadet at Fishburne Military School to be court marshaled.

He was always in trouble, too. At military school, he once gave a colonel’s dog some laxative, which made it do some messy business all over the colonel’s carpet (Much later, a similar prank would be pulled on him: the late Owen Hart put some well-fed goats in McMahon’s office to poop all over the place). However, the charge didn’t stick as his teachers said the young McMahon didn’t deserve such a fate.

“The military changed their mind, and I will always remember that. Because it changed my life, will always be eternally grateful for that,” McMahon said during a TV documentary by Headliners & Legends in 2001.

You don’t need to be an academic to be a billionaire

hit man — WWE Hall of Famer Bret "Hit Man" Hart on his way to defeating McMahon at Wrestlemania XXVI in 2010.

According to McMahon, his GPA from East Carolina University was only a “‘2.001’” and it took him five years to graduate. While there, he majored in economics, and hated it.

“‘[I] sat in the back row, didn’t like the subject. It’s about numbers, not people,’” McMahon told Playboy.

That “2.001” wasn’t even easy to come by. McMahon said he had to go back to some teachers and pester them to change his grades because he couldn’t graduate with anything below a 2.0 GPA.

His early jobs were not glamorous

Dr. George T. Zahorian III, center, an osteopath from Harrisburg, Pa., poses with Vince McMahon, left, and wrestler Hulk Hogan in 1988.

McMahon’s first jobs included selling adding machines, paper cups and ice cream cones — jobs which he did not like.

“‘I would get up early and work a zillion hours, but it wasn’t for me. I mean, they want you to talk about the characteristics of the f***ing cup,’” he told Playboy.

Abandoning that job, he went to working at a pug mill. All the while, he had been pestering his father, Vincent J. McMahon, to work with him. McMahon Sr. owned the World Wrestling Federation promotion, then a relatively small promotion in the northeast. In 1969, when McMahon was around 25 years old, his father finally let him into the business.

He was ruthless in business

trial — McMahon with his wife Linda outside Federal Court in New York in 1994 as they await a jury decision on charges he fueled the sport's growth through widespread steroid use. He was acquitted on the conspiracy charges.

Vince Jr. was extremely successful and helped grow the WWF. But it wasn’t until he acquired the entire promotion in 1982 from Vince Sr., two years before the patriarch died, that Vince Jr. really started making waves in the industry.

“Had my father known what I was going to do, he never would have sold his stock to me," McMahon told Sports Illustrated in 1991. “In the old days, there were wrestling fiefdoms all over the country, each with its own little lord in charge. Each little lord respected the rights of his neighboring little lord. No takeovers or raids were allowed. There were maybe 30 of these tiny kingdoms in the U.S. and if I hadn't bought out my dad, there would still be 30 of them, fragmented and struggling. I, of course, had no allegiance to those little lords.”

McMahon did not adhere to old school wrestling’s unspoken rules. He poured money into producing television shows and broadcasted them deep into rival territories, and the WWF became the only nationally televised wrestling promotion. Wrestlers walked away from smaller territories for bigger paychecks and the chance to go from wrestling in high school gymnasiums to being seen on national television. Slowly but surely, McMahon crushed the competition.

By 1988, McMahon was estimated to be worth $100 million, at the very least.

Crushing the last competition

buying WCW — McMahon in 1991. Over the next decade he waged a war with the competing WCW and eventually squashed it.

By the '90s, there were only two wrestling promotions to speak of: the WWF and the newly founded (1988) World Championship Wrestling.

The two companies had a war for ratings, but WCW had been bludgeoning WWF in viewership throughout most of the '90s. It wasn’t until the late '90s and very early 2000s that the WCW lost ratings to the WWF, which ultimately led to McMahon buying a practically bankrupt WCW in 2001.

Actual numbers of the sale were never made public, but it’s speculated to be between $2 and $4 million.

Enter — then promptly exit — the XFL

McMahon listens as Minnesota Gov. Jesse Ventura talks about the new XFL football league during a 2000 press conference.

Hot off the 2001 purchase of WCW, McMahon decided to disrupt another sport: football. He launched the XFL, a new football league marketed as being an ‘extreme’ version of the NFL, where there was more contact, less penalties, and a bigger focus on player personalities. As a new league, the XFL couldn’t attract big name players or even NFL hopefuls. This is what the XFL pay structure looked like:

Quarterbacks made $5,000 per game
Kickers made $3,500
All other players made $4,500
There was a $2,500 bonus paid to each player for winning a regular game
A $7,500 bonus per player for a playoff win
The championship team would be awarded $1 million, to be split among the whole team.

To get some startup funding, McMahon partnered with NBC and together invested about $100 million. After just one season and a promising premier game, the XFL became a critical and Nielsen ratings failure. NBC and WWF had lost about $35 million each. It lasted only one season, broadcasting its first game in February, before the entire operation shuttered in May.

He’s a control freak

New Jersey Gov. Chris Christie, center, and McMahon pose with WWE personality John Cena, left, backstage at a 2012 news conference to promote WrestleMania XXIX.

McMahon is a bit of a control freak — so much so that he hates sneezing. According to Paul Heyman, a wrestling booker who currently manages Brock Lesnar in the WWE, McMahon hates sneezing because it shows a lack of control.

As he told Stone Cold Steve Austin during a podcast, Heyman was pitching ideas to McMahon when McMahon let out a sneeze. Heyman kept talking, until:

“I realized five minutes into the conversation he’s not listening to a word I’m saying. …He’s literally mumbling to himself. So I go, ‘You ok?’ and he goes [mimicking McMahon’s deep voice], ‘I sneezed.’ I should be better than that. I should be able to control that.’ I go, you don’t like sneezing? He goes, ‘In my world, pal, there is no sneezing.’”

He also noted that McMahon hates when other people sneeze, too, and they would leave the room to do so.

When Donald Trump ‘bought’ Raw, WWE stock dropped

Trump McMahon — Trump and McMahon in 2007, with wrestler "Stone Cold" Steve Austin, during a news conference for the "Battle of the Billionaires" match.

In 2009, McMahon ran a “Battle of the Billionaires” angle where Donald Trump went on “Raw” and said he had purchased the whole show.

The USA Network, WWE and McMahon took it even further, issuing a press release announcing that Trump totally did purchase Raw. Investors, who probably weren’t wrestling fans in the first place, thought this was legitimate. On the following Tuesday, WWE stock dropped 7 percent, prompting an apology letter admitting the whole thing was a publicity stunt.

Oh, and Trump shaved McMahon’s head at WrestleMania, because pro wrestling is strange.

His wife is head of the Small Business Administration

Linda McMahon stands with her husband and her son Shane McMahon, right, at Republican state convention in Hartford, Conn., during her unsuccessful run for U.S. Senate in 2012.

With good ties to Donald Trump and a background in politics — Linda had spent $100 million in self-funded runs for the senate in 2010 and 2012 — President Trump appointed Linda McMahon as head of the Small Business Administration.

Linda donated $7 million to pro-Trump super PACs during the 2016 Presidential Election.

He once declared bankruptcy

Muhammad Ali, standing on scale, gestures at his opponent, Antonip Inoki of Japan, during their weight-in prior to the so-called World Martial Arts championship in Tokyo in 1976.

Linda and Vince weren’t always rich. In 1976, the couple declared bankruptcy after amassing about $1 million in debt. How they got that debt is rather, well, McMahon-ish.

You know that classic Simpsons episode where Homer tries to jump Springfield Gorge and fails spectacularly?

That was based on a real-life event in 1974 when daredevil Evel Knievel attempted to jump Snake River Canyon located in Twin Falls, ID. The stunt was broadcasted live on television, and it failed horribly—Knievel’s ‘skycycle’ parachute deployed prematurely, and he ended up floating to the river below, narrowly avoiding drowning by landing right-side up (he was strapped to the vehicle). The debacle did not bring in a lot of money.

The promoter of the event? None other than Vince McMahon.

Then Another Big Business Mistake

Not long after, McMahon promoted a mixed-martial art ‘fight’ between Japanese professional wrester Antonio Inoki and Mohammed Ali, which was a dud. Ali wore boxing gloves and Inoki was hamstrung by a set of rules that left him mostly on his back and doing a few low kicks throughout the fight.

Both events pushed the McMahons into debt.

A glimpse at the McMahon Family Fortune

Of course, Vince McMahon is far from broke now: he’s worth about $1.51 billion. According to the Connecticut Post, his empire includes:

An $8 million estate in Greenwich, Conn
A $3 million penthouse in a Trump-owned condominium complex
$12 million spread out over 10 bank accounts in Vince’s name
$25 - $50 million in a Morgan Stanley money market account
$782 million worth of stock in WWE
Between $4.7 and $15 million in the public bond market throughout seven Connecticut cities and towns such as Danbury and Norwalk

A Parting Quote...