Men like Hulk Hogan, “Stone Cold” Steve Austin, Dwayne “The Rock” Johnson and John Cena can all lay claim to being household names. After all, even if you aren't a wrestling fan, you probably can recognize those names. But when it comes to having a legacy, nobody is more famous among actual wrestling fans than the owner of the biggest wrestling company in the world himself, Vincent Kennedy McMahon.
Vince McMahon took wrestling in the 1980s and launched it into the realm of mainstream entertainment. With constant great ideas, such as the invention of the annual worldwide phenomenon known as WrestleMania, McMahon would continually rebrand WWE to keep up with the demands of a changing fan base. Vince is simultaneously loved and hated for the empire he’s created. He is revered for keeping wrestling relevant for so long, but then also hated for the way he tries to stomp out any and all competition. McMahon may be the hardest working man in wrestling, but that doesn’t mean the man is not without his faults.
Vince McMahon has a knack for making questionable decisions which continuously come back to haunt him year after year. From smaller hiccups such as on-screen embarrassments to larger missteps which threaten to bring down everything he and the wrestling industry have worked so hard to build. There is no doubting that Vince McMahon can at times be reckless in the way he runs his business. Here are 15 of the worst moments in the career of the man responsible for the industry that we all love.
15 “Stand Back” Musical Performance
The 1980s was a glorious decade for many areas of the entertainment industry, professional wrestling included. We love to watch movies and TV shows from the era and laugh at the big hair and shoulder pads, and many of us get a kick out of how cheesy the music of that period was. Wrestling, WWE in particular, is not exempt from that comical scrutiny. The ‘80s brought wrestling fans WrestleMania, unstoppable heroes who got their superpowers from God, and women who still teased their hair high and wrestled in bathing suits.
During this time, Vince McMahon would make a horrible, horrible decision that would haunt him for the rest of his life when he staged a musical performance at the 1987 Slammy Awards ceremony. He gyrated his hips as he belted out the simple lyrics of his original song, “Stand Back,” as a sea of female dancers in sparkly dresses performed around him. McMahon even had some of the most popular WWE Superstars pretend (badly) to play the instruments behind him. It was quintessentially ‘80s and totally not tubular.
14 Winning the WWE Championship
Vince McMahon’s competition during the Monday night war, WCW, was partially written by another Vince who once worked for WWE, Vince Russo. Russo is frequently blamed for WCW’s downfall when he made himself the WCW World Heavyweight Champion, even though he wasn’t an in-ring performer. It forever tainted the lineage of that title and was one of the worst moments in WCW history.
A forgotten fact, though, is that Vince McMahon did this first on one of the earliest episodes of SmackDown. One year earlier in 1999, McMahon scripted himself to win the WWE Championship from his future son-in-law Triple H. For whatever reason, McMahon doesn’t receive nearly as much negativity for his decision, but it’s no less a crime against professional wrestling in the eyes of purists who have traditionally frowned upon the person running the company holding a World title, especially when that person isn’t an actual wrestler.
13 The Montreal Screwjob
In 1997 WWE Hall of Famer Bret “The Hitman” Hart was going into the annual Survivor Series as the WWE Champion, but he intended to soon leave the company for WCW. He let Vince McMahon know this and Vince wanted him to drop the title at Survivor Series to Shawn Michaels, a longtime rival of Hart. Hart didn’t want to lose the title to him in his home country of Canada, which is where the show was set to take place, so McMahon, Michaels and the referee went behind Bret’s back and threw the finish of the match. They claimed Bret Hart tapped out when he clearly didn’t and Michaels was crowned the WWE Champion.
There are multiple sides to the story, but in terms of how it affected Vince McMahon’s legacy the arguments are irrelevant. McMahon, Michaels, and the referee Earl Hebner became lifelong villains in Canada and for many years Bret Hart refused to work for the company. The blame, for the most part, falls on the boss and it will forever be a sore spot in Vince McMahon’s past.
12 Jim Ross’s Colon Surgery
Vince McMahon’s sense of humor is almost as legendary as the man himself, but it’s legendary for the fact that it’s universally seen as perhaps the worst sense of humor on the planet. Puke? Vince loves it. Farts? He loves those, too. Just about any bodily function is a surefire way to make the most successful man in the history of professional wrestling slap his knees. This has been very evident over the decades, but there’s no better (or worse) example of it than a certain skit from 2005 where Vince completely humiliates WWE Hall of Famer Jim Ross.
“Good Old” Jim Ross had only recently undergone colon surgery. Ross is one of the most respected men in the wrestling business, having built a career as the voice of Monday Night Raw for many years. For his extensive service, he was wished well following his surgery by WWE in the form of a skit where Vince McMahon pretends to pull random items from Ross’s behind. The entire (very lengthy) scene is filled with unflattering sounds and references which poke fun at all the things Ross became famous for. It was easily one of Vince McMahon’s most shameful moments, and sadly, is not the last time he mocked JR.
11 Mocking Shawn Michaels’ Religion
In 2006, D-Generation X was about to reform and lay waste to what was once the most popular stable in all of wrestling, but before that debacle came the rivalry between Shawn Michaels and Vince McMahon. In the weeks leading up to Backlash, Vince McMahon had been feuding with Michaels and making fun of his religion. Michaels was a born again Christian and his faith had been heavily discussed in storylines before, but it was about to be taken to a whole new level.
Vince McMahon did the only thing a man like Vince McMahon could do, which was to book a match for Backlash pitting himself and his son Shane against Shawn Michaels and his tag team partner, God. That’s right: Shawn Michaels would have to summon the almighty one unless he wanted to face the McMahons in a handicap match. The worst of it came just before the match when Vince pretended to welcome “God” to the ring (which was just a spotlight) and then invited God to dance with him.
10 Dropping the N-Word on Live Television
In the mid-2000s Vince McMahon was on fire, at least in terms of letting his unique sense of humor bleed into WWE programming, but I bet he wishes he could change his words in 2005. Vince McMahon was taking place in a backstage segment on a pay-per-view talking to then WWE Champion John Cena. McMahon, obviously attempting to seem “hip,” drops the N-word and then proceeds to walk past Booker T and his wife Sharmell, who are staring at him obviously baffled.
Many in the WWE Universe defended the segment as satire, but others were highly offended that he used the term at all. The scene was all but forgotten until Hulk Hogan’s previous racist comments were made public in 2015 and he was subsequently fired from WWE. The company came under fire for hypocrisy when the aforementioned skit was brought back into the limelight and McMahon received heavy criticism for his use of the term.
9 Firing CM Punk On His Wedding Day
When CM Punk left WWE in 2014 he doused that bridge in gasoline and tossed it a match. Rumors swirled about Punk being angry that his character wasn’t going in the direction he felt it should or that he was just generally burned out, and while both of those were true there turned out to be so much more to the story. One of Punk’s biggest complaints was that the company did a lackluster job of looking after the health of its wrestlers, citing his own mistreated staph infection.
Apparently, Vince McMahon tried for months to negotiate with CM Punk and talk him into returning, but Punk was having none of it. When McMahon finally decided to give up the fight and mail Punk’s release notice, the papers arrived on CM Punk’s wedding day. Punk declared this as a blatant kick in the pants, and while Vince has apologized and called the situation a coincidence, the legions of CM Punk fans weren’t buying it and have had Vince in the doghouse ever since.
8 Faking his Own Death
In 2007 the Vince McMahon character was a depressed wreck of a man. On one of the craziest episodes of Monday Night Raw to ever air, Vince shamefully walked his way past his entire roster of wrestlers to his limousine out back in order to leave the arena. When he stepped into his limo and shut the door, the vehicle exploded on live television. Well, technically the actual explosion was prerecorded, but it felt legit. Everyone knew it was all staged because the cameras glorified the moment by panning around to give us the full view, but it was one of Raw’s most shocking moments.
In a most unfortunate turn of events, only days later Chris Benoit brought about the darkest day in the history of professional wrestling. News broke two weeks after Vince McMahon “died” that Chris Benoit actually had died in real life, taking his own life after murdering his wife and son. The collective heart of the wrestling universe, talents and fans alike, were totally crushed and Vince knew there was no way to go on with this insane death storyline of his and it was immediately dropped.
The year was 2001 and pro wrestling, or at least WWE, was still on top of the world. As a big fan of professional football and being the risk taker that he’s always been, Vince McMahon had what he thought to be a genius plan: To do with football what he did with wrestling. The fanfare, the unabashed objectification of women through the use of its scantily clad cheerleaders, the over-the-top commentary, it was all there and ready to go complete with Vince McMahon introducing the show in his trademark guttural drawl. The XFL was born!
And just as quickly as it arrived, it was gone. The first night drew a respectable number in the ratings, but those viewers were fleeing for the hills once they had witnessed the train wreck that was Vince McMahon’s vision of football. The league ran for one season before was officially taken out back like Old Yeller. Can't fault him for being ambitious, but this has to definitely remain as a huge flop in McMahon's life.
6 His Illegitimate TV Son
This is an example of a brilliant long-term storyline, that fizzled into one of the absolute worst attempts at comedy ever to take place on television, Vince McMahon was once the center of an illegitimate child storyline. Following the failure of his faked death storyline, Vince still had intentions of following through with giving then WWE Superstar Mr. Kennedy a huge push as his illegitimate son, which was the ultimate goal of that angle.
Unfortunately, Mr. Kennedy would miss the boat again after being busted for a wellness policy violation and Mr. McMahon’s son would be revealed as the mini wrestler and token WWE comedy act, Hornswoggle. What followed was weeks of horribly unfunny skits of Hornswoggle making Vince McMahon completely miserable, until the whole thing was revealed as a sham.
5 The “Kiss My Ass” Club
Much can be questioned about the various storylines Vince McMahon has put himself into over the years. For example, he has curiously made out, and practically gotten to first base, with a vast number of WWE’s hottest Divas over the years including Sable, Candice Michelle and Trish Stratus. This, and the fact that he booked himself as WWE Champion, would make it seem as if the Chairman of WWE is very self-indulgent with his business.
Then you have Vince McMahon’s “Kiss My Ass” Club, a storyline where Vince would pull down his pants on live television and make his employees literally kiss his bare backside. It was a recurring angle that just wouldn’t seem to stop, and the fact that McMahon made a show out of flexing his buttocks muscles up close for the camera really made the whole thing feel like an uncomfortable excuse for the boss to expose his can to the world. Thankfully, it ended with The Rock shoving Vince’s face right between the cheeks of the 400-pound Rikishi.
4 His Jim Ross Impression
Sometimes Vince McMahon can seem like the most ruthless man on the planet. He’s one of those people you’re sort of friends with, but he knows no boundaries when it comes time to joke around. Seven years after Vince poked fun at WWE Hall of Famer Jim Ross’s colon surgery, things were about to get uglier when Vince shared a scene with his one-time screen partner, Hornswoggle.
During the time when Vince was under the impression Hornswoggle was his illegitimate son, Hornswoggle frequently grated Vince’s nerves acting like a baby due to his small stature, despite the fact that Hornswoggle was actually a grown man. But in 2012 they caught up with one another during a backstage segment when Vince decided to make an impersonation of Jim Ross again, this time playing up the fact that Ross has Bell's Palsy. This came not long after WWE had launched “Be a STAR,” an anti-bullying campaign. Ironic, don’t you think?
3 Making Trish Stratus Bark
Above you read about all the women Vince had on-screen "relationships" with, but nothing could compare to the relationship he had with Trish Stratus. In 2001, a storyline leading into WrestleMania saw Vince keeping his wife Linda sedated while he and his mistress, Trish Stratus, did their own thing on the side. At WrestleMania, Vince fought his son Shane and Trish turned on Vince in the middle of it all, but what was the last straw for her? Probably when Vince made her bark like a dog on live television.
Weeks before Trish kicked Vince to the curb, the two were involved in one of the most notoriously uncomfortable and offensive skits WWE has ever produced when Vince made Trish strip down to her underwear, get down on all fours and bark. It’s often cited as Vince’s most shameful moment and was brought up by opponents when Vince’s wife Linda ran for political office years later as evidence that the McMahons aren’t as wholesome as they claim.
2 Over the Edge 1999
If the Chris Benoit nightmare of 2007 was the darkest day in professional wrestling, then the night of Owen Hart’s death is the saddest. In the middle of the Over the Edge pay-per-view in 1999, long time WWE Superstar Owen Hart fell to his death during an elaborate entrance in front of the live audience. Though Hart fell from the scaffolding into the wrestling ring, the live cameras thankfully didn’t capture the incident as a prerecorded video package was playing at the time. Hart was rushed to a nearby hospital as the show went on.
Later in the night, announcer Jim Ross was tasked with the unfortunate responsibility of informing the viewers that Owen Hart had passed away. Vince McMahon made the decision that the show would continue to the very end. You can understand why that decision has been heavily criticized by fans and wrestlers alike, especially Owen’s family members. Critics say the show should have been called off instantly out of respect for Hart, although WWE did save a little face the following night with the Owen Hart tribute edition of Raw.
1 Steroid Scandal
Pro wrestling seems to have always been accompanied by the stigma of steroid abuse, probably more than any sport to ever exist. It’s easy to see how that got started, after all, it’s a business which, for a long time, focused heavily on the most muscular freaks of nature ever seen on television. That’s still true to some degree, though now WWE has a wellness policy which would seem to make it impossible for a performer to get by with using any sort of performance-enhancing medication.
Although this steroid issue has always seemed to be buzzing around the ears of the wrestling industry like a pesky mosquito, it really gathered momentum in 1993 when Vince McMahon was faced with a lawsuit that nearly took down his entire wrestling empire. The case got national coverage and Vince, his business and his employees were accused of illegal steroid use in front of the entire country. It was an embarrassing time for Vince and will go down as the lowest point in his career.