For some 35 years now, Vincent Kennedy McMahon has been the most powerful man in professional wrestling. Such is the extent of his authority that McMahon even managed to change the name of the business, transitioning his father’s mere wrestling company into a worldwide sports entertainment empire. The breadth of the WWE Universe that McMahon owns is a testament to his talents as a booker, promoter, and businessman, yet no matter how successful Vince has become, the man has nonetheless also made a shocking number of missteps on his path to glory.
All Vince should really need to do when confronted with criticism is take a peek at his bank account and let out a hearty belly laugh at his detractors. That said, the frequency with which people discuss his failures can still weigh heavily on his mind. Websites like this one constantly remind fans about each and every mistake McMahon has made in spite of his triumphs, and knowing how fragile his ego has been at times, there’s no doubt he would prefer we just shut up about it already.
On the other hand, it sure is fun to discuss, isn’t it? There’s a certain schadenfreude to be found in reminiscing about the biggest failures of wrestling’s most powerful CEO, especially considering how bizarre and bombastic some of them have been. That McMahon keeps making some of his worst mistakes to this day brings poignancy to the matter, as well, on the merit he could finally start slipping from the top if he can’t find out how to stop this trend. Not that he would want to hear about it, of course. Keep reading for 15 career regrets Vince McMahon wishes everyone would stop mentioning.
15 Fining And Suspending Titus O’Neil
Inside the wrestling ring, one of Vince McMahon’s greatest skills is his innate ability to react and overreact to news that frightens, displeases, infuriates or causes any other dark emotions within him. Unfortunately for his employees, it would appear this propensity for impulsively extreme action transcends to the real world, or at least it did on the night of Daniel Bryan’s retirement ceremony. Moments after the man of honor gave his farewell speech, Titus O’Neil grabbed McMahon in a hug from their respective places on the Raw entrance ramp, in what fans initially thought was a playful moment between the CEO and a lower-level talent. As it would turn out, McMahon wasn’t playing in the slightest, so upset over the embrace that he fined O’Neil around $5,000 and suspended him for 90 days. It’s hard to understand what the heck McMahon was thinking throughout the ordeal, and many fans told him as much, ultimately getting the suspension knocked down to 60 days, Vince’s way of telling his critics to shut up and be done with it.
14 Missing Out On A Decade Of AJ Styles
On the Raw after AJ Styles made his debut at the 2016 Royal Rumble, the Phenomenal One walked down a WWE aisle for the second time and proclaimed the company was where he belonged. Styles was far from alone in feeling this way, with his millions of fans around the world reacting accordingly with loud applause and smiles on their faces. The one strange thing about it was that Styles waited so long to sign with WWE in the first place, having already spent a solid 17 incredible years of his career wrestling for TNA, New Japan Pro Wrestling, Ring of Honor, and a variety of other companies that had nothing to do with Vince McMahon. AJ may not have been camera ready from day one, but he certainly could have made his way to WWE earlier than he did, and McMahon later called not giving AJ the opportunity to do so one of his biggest regrets. To make up for the mistake, Vince made Styles a WWE Champion seven months after his debut, which almost silenced his haters until AJ lost the gold to John Cena.
13 Losing His Cool With Bob Costas
Everyone has bad days, and Vince McMahon has certainly experienced more than his share of serious downers that put him in moods that made him unfit for television. Unfortunately for him, sometimes the very thing that turns McMahon into a sourpuss is being on TV, to begin with, at least when he’s interviewed by someone looking to get a rile out of him, that is. This was certainly the case during a 2001 interview for the HBO program On the Record with Bob Costas. The legendary sportscaster asked McMahon some hard-hitting questions about the failure of the XFL and some of his more notorious moments as a booker, clearly heating up McMahon as he shoved his finger in Costas’s face and angrily shot back. Anyone who's seen the interview knows McMahon lost his cool, and that’s why people still talk about it today. However, in McMahon’s defense, this is pretty much exactly what Costas wanted, and that’s why he manipulated the moment to become what it was.
12 Raw Is Benoit
Barring another extreme tragedy, the sports entertainment world will never experience a 24-hour period as emotionally devastating as what wrestling news sites were reporting between June 24th and June 25th, 2007. First, all fans knew was that something had happened to Chris Benoit and his family, soon learning the horrible news that he, his wife, Nancy, and their 7-year-old son, Daniel, were all dead. Immediately, WWE announced their condolences and set to work on an episode-long tribute to the former World Heavyweight Champion, which aired in lieu of that night’s scheduled episode of Raw.
The story would only get worse from there as reports started coming in with an explanation of how the family had all died—that Chris went mad and murdered Nancy and Daniel before taking his own life. Just as quickly as the company decided a tribute was necessary, they knew it was imperative to remove all traces of Benoit and especially the honorific Raw itself from history, never acknowledging the man or event again. Since McMahon had no way of knowing the truth at the time of the Benoit tribute and any other promoter would have reacted the same way, it would probably be fair if we stopped pointing out what a mistake it was.
11 Doing Business With Dr. George Zahorian
Although Vince McMahon was ultimately acquitted by federal courts of having any involvement in Dr. George Zahorian’s illegal steroid-distribution ring, it should go without saying he probably would've preferred to avoid the situation altogether. McMahon’s biggest mistake throughout the ordeal was hiring Zahorian in the first place, in the role of a mere ringside physician to assist with any medical troubles his performers might face on a given night. Eventually, Zahorian did indeed start selling steroids to select athletes, but McMahon was never, in any way, involved in that part of the deal. Because the federal government acknowledged McMahon didn’t do anything wrong, one might expect his critics would stop accusing him of doing so, and yet, plenty of wrestling detractors still cast aside WWE superstars as steroid-fueled monsters. In the very least, most of Vince’s fans are on his side on this one, rallying against any negative press that tries to mock his creation on a basis that was never true.
10 The Montreal Screwjob
Once Shawn Michaels and Bret Hart hugged it out on the January 4, 2010 episode of Monday Night Raw, the long book on the Montreal Screwjob should have been permanently closed. The two performers involved had finally put it all behind them, while Hart and McMahon had already done the same a few years earlier and resumed a business relationship. Despite all this, it's been hard for fans to forget that McMahon once conspired with HBK to trick Hart into losing the WWE Championship in the main event of Survivor Series 1997. Granted, a big reason why it's still discussed today is that WWE (and just about every other wrestling company around for that matter) has made a habit of constantly referencing the Screwjob in storylines, so McMahon is definitely at least a little bit complicit in the fact critics still castigate him for the way it went down.
9 Black Saturday
No one incident has cemented the fact Vince McMahon is on top of the sports entertainment world like the day he purchased his rivals of 13 years, World Championship Wrestling (WCW). Ironically, one of his earliest severe missteps would directly involve those same letters when he appeared on the NWA-affiliate George Championship Wrestling’s TV show, World Championship Wrestling, the same program that would later turn into WCW Saturday Night. Before that could happen, it almost became WWF Saturday Night, when McMahon purchased GCW and the time slot along with it. However, he didn’t understand the show’s audience at all, promoting his new sports entertainment in favor of the old-school wrestling they enjoyed. This caused audiences to turn away in droves, ultimately causing McMahon to sell the time slot back to the NWA. While this was indeed a huge failure on his part, McMahon obviously won the war in the end, making it irrelevant to criticize him for in the modern era.
8 Every Failed Champion He Tried Making A Star
Alright, so that header is probably just a little vague, but quite frankly, naming every wrestler Vince McMahon regrets pushing to the top of his company would take a couple lists in and of itself. For as often as it happens, McMahon’s ultimate reaction to the audience mocking, deriding, or otherwise criticizing him for it has always remained the same: get over it and stop complaining. Let’s clarify and point out we don’t mean the Diesels or Mizes of this world, who weren’t quite WWE Championship-ready when they won the gold but, nonetheless, do have some merits as performers. We’re talking about The Great Khalis and Jack Swaggers, superstars whom no one understands how McMahon could've seen as main event material at any point in time. No matter how bad any of these former top dogs were, though, McMahon can’t do anything to take back his choice to promote them as such and thus, simply wants everyone to forget he ever did.
7 Failing To Push Daniel Bryan
For as much as fans like discussing the various wrestlers Vince McMahon made champion and shouldn’t have, they probably take even greater stock in wondering how he missed the mark on countless much better athletes. Though Daniel Bryan did get a few short months in the sun as WWE Champion, the sports entertainment community at large had been begging for McMahon to make him a star for an exceptionally long time before he got that opportunity. Ultimately, it proved too little too late, as a serious of severe injuries led Bryan to retirement shortly after one botched comeback attempt after having been forced to vacate the gold. In hindsight, everyone who watches wrestling realizes one of McMahon’s biggest failings as a promoter was waiting on tapping into Bryan’s potential for so long. McMahon has kept Bryan around in a major role for exactly that reason, knowing full well he could be making far more money on the guy if he were still in the ring. As with everything on this list, though, there’s no way he can change what happened, so his audience should be happy Bryan gets to remain on their TVs at all.
6 The Time He Went Full Racist Live On Pay-Per-View
Countless critics have pointed out the inherent racism seen in a shocking number of WWE angles, yet no one moment better elaborates the wanton privilege Vince McMahon displayed at Survivor Series 2005. It should be stressed that McMahon wasn't a regular character at this time and quite openly showed up at the event for no reason other than to deliver one of the most controversial sentences of his career. After asking John Cena, “What’s good in the hood?” he told the WWE Champion to “keep it up, my n*****.” Cue Booker T and his wife, Sharmell, staring in shock and replying, “Tell me I did not just see that.”
While WWE played it off as a joke, many African American fans had pretty much the same reaction, shocked the company CEO would show up out of nowhere to sling a racial slur in jest in front of his most celebrated black star at the time. Years later, Hulk Hogan was released from the company due to racism allegations, causing the WWE Hall of Famer to point to this moment as a sign of hypocrisy. As he had done originally, McMahon doubled down on his defense it was a joke made by a character and not a hateful comment, basically telling fans he doesn’t care they were offended, so they should quit complaining.
5 The Time He Went Full Sexist On Live TV
As though it weren’t bad enough a billionaire CEO doesn’t realize the ramifications of mocking his African American audience with a bad joke, Vince McMahon has done far, far worse to the female portion of his WWE Universe. Women have been dragged through the mud on Raw and SmackDown figuratively and yes, literally, too many times for us to name, often getting McMahon and his company labeled misogynistic. This has largely died down in recent years, yet critics will never forget the early 2001 episode of Raw when McMahon himself forced Trish Stratus to strip to her underwear and crawl around his ring while barking like a dog. Many fans, including plenty of males in addition to almost all females, felt this was going way too far with the idea of a power-hungry boss, turning into blatant sexism that served no purpose but to degrade a future Hall of Famer on the basis of her gender. Believe it or not, though, Stratus herself has defended the angle on the grounds she later gave Vince his comeuppance at WrestleMania X7 and used it to spark her vanguard career. While this hardly sufficed for most, McMahon probably thinks it should.
4 Ignoring Women’s Wrestling For Decades
One single segment alone is hardly the reason WWE fans think Vince McMahon might have a problem with female wrestlers. In fact, the infamous Trish Stratus segment doesn’t even begin to describe McMahon’s real issue with his female employees, which is that until very recently, he hardly saw them as wrestlers at all. Instead, women were mere eye candy in the most literal sense, with several full years of WWE history featuring maybe one or two notable women’s matches at most, if any. This is a whole lot worse than mocking one single performer, no matter how harsh he was in doing so, as it prevented an entire gender from having any chance at pro-wrestling stardom. WWE hides behind excuses like the fact there weren’t as many female wrestlers around twenty years ago as there are today, but it only looks that way because the women trying to wrestle decades ago weren’t getting hired. Since the Women’s Revolution, though, McMahon has been unwilling to hear word one about his past foibles with female wrestling, feeling the situation is dealt with, and therefore, it’s time to forget about the past.
3 The XFL
What can be said about the failure of the XFL that doesn’t feel like rubbing salt in the $35 million wounds Vince McMahon earned through creating it? People said it was crazy to take on the National Football League in any way shape or form, and despite decent ratings on the debut broadcast, it turns out the XFL indeed didn’t stand anything close to a chance. As critics had feared, McMahon’s brand of football was more sensational and bombastic than traditionalist fans of the sport wanted to see, causing people to harshly reject the XFL in droves and soon make it the lowest-rated program on network television. McMahon and his partners in NBC accepted they made a huge mistake and called the whole thing off after one lousy season, but the press still likes making fun of him for it every time they get a chance. ESPN recently even made a documentary on the subject called This Was The XFL, and one can only assume McMahon’s appearance in that program will be his final word on the subject, so we critics should probably stop bothering him about it.
2 The World Bodybuilding Federation
On paper, it’s almost tempting to say Vince McMahon’s place to create an alternate football league had some merit. Competing with the NFL was a daunting and ambitious task, but McMahon’s experience with WCW proved competition creates cash and interest, and getting anywhere near the ratings football receives in America could have made him millions. That said, it’s almost impossible to figure out how McMahon thought he could compete with the International Federation of BodyBuilding & Fitness, nor why he would want to, considering professional bodybuilding was never exactly a money industry. However, being one of the few people who loved the sport, McMahon knew he had to try and make it big, creating the World Bodybuilding Federation. Adding wacky characters to the proceedings like Vince had done to make wrestling popular didn’t help popularize the sport, only making the tenuous posing-based sport look like more of a farce to those bored enough to watch it. If nothing else, the fact McMahon closed the company after a mere two years was an admission he knew it had failed, and thankfully, we almost never see anything bodybuilding-related in WWE today, so maybe it’s time to let this one go.
1 Whatever The Hell It Is He’s Doing Now
At this point, almost no one is able to defend, let alone understand, what exactly it is Vince McMahon is trying to accomplish with his booking of modern-day WWE. Ever since fans rejected his appointed face of the business in Roman Reigns, McMahon has been firing back by doing what some have called outright trolling his audience, presenting the worst show possible in every sense of the word for months on end now. Ratings are in a free fall, main events are getting booed out of the building and are only getting worse, and Jinder freaking Mahal has been WWE Champion for over two months now. Again, we can’t even begin to explain what the man is thinking in the way he’s presenting his company, but one thing we know for sure is that loudly telling him his product sucks on every Raw, SmackDown, Pay-Per-View, or special event simply isn’t working. Is Vince annoyed that people are complaining? Maybe. But is he going to do anything about it? No chance in hell. We guess anyone who realizes his product sucks these days has to sit back and accept it… or change the channel.
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