15 Career Mistakes Vince McMahon Probably Regrets

With the WWE Universe exponentially expanding with no end in sight, Vince McMahon spends every day reaffirming that he’s the most successful and powerful person in professional wrestling. Despite drop

With the WWE Universe exponentially expanding with no end in sight, Vince McMahon spends every day reaffirming that he’s the most successful and powerful person in professional wrestling. Despite dropping ratings, fans harshly rejecting the product, and criticism coming at him in every direction, McMahon continues to make a steady enough profit through his creation he’s more than set to remain a multimillionaire for life. Having said that, in the immortal words of CM Punk, Vince is “a millionaire who should be a billionaire.” His wealth fluctuates enough that Punk’s statement isn’t always entirely accurate, but there is some wisdom to be gleaned in what he meant when he said it.

The truth is, while Vince is responsible for thousands of brilliant ideas that changed wrestling into sports entertainment, he’s also the genesis for hundreds of complete and total duds. And that’s when you just consider wrestling—the failure is typically even worse when he attempts to leave the wrestling industry behind. For all of McMahon’s business acumen, nobody’s perfect, and the more bombastic one’s efforts at testing their limits are, the easier it is for onlookers to realize just how flawed they were when things fall apart.

Being the sort of person who goes big or goes home, Vince has taken a swing and missed in spectacular fashion more times than we can count. He’s also the sort of person who leaves the past behind him, though, especially when it doesn’t agree with him. Whether he tries to push these stories out of his own mind or not, the rest of the world should keep reading to discover 15 embarrassing career regrets Vince McMahon will never live down.

15 The World Bodybuilding Federation

On the surface, the similarities between professional wrestling and professional bodybuilding are abundant, to say the least. Both are performance-based displays of musclemen using their specifically toned bodies to entertain a niche crowd. The deeper you look at each industry, however, the more blatant it becomes that the types of performances the two sports adhere to are wildly different, and apparently Vince McMahon never got the memo. Attempting to turn bodybuilding into a new form of sports entertainment the same way he had with wrestling, McMahon created the World Bodybuilding Federation in late 1990, later creating two Pay-Per-View competitions that aired in 1991 and 1992. Gary Strydom won both competitions, but if you’ve never heard of him, you aren’t alone—neither show had a particularly large audience. Apparently, bodybuilding fans are staunch traditionalists, and didn’t appreciate that the competitors were all given garish cartoon characters like Vince’s wrestlers had—there was a surfboarder, an executioner, and a man in a red cape named the “Dark Angel.” With virtually no fan interest, the entire company folded shortly after the second Pay-Per-View aired.

14 How Things Went Down In Montreal

Coming up on the 20th anniversary of the Montreal Screwjob at Survivor Series 1997, there’s pretty much nothing left for wrestling fans, critics, or historians to add to the story. Bret Hart was the WWE Champion with a contract about to expire, and he couldn’t come to an agreement with Vince McMahon on extending that contract, mostly due to monetary reasons. Bret agreed to lose the belt before he left, but not to Shawn Michaels in Montreal, which naturally was where his last Pay-Per-View appearance had been scheduled to occur. Vince really wanted Bret to lose despite his wishes, so he told Mark Yeaton to ring the bell, ring the f***ing bell, and Bret was screwed into leaving for WCW a bitter, angry man. Pick the story apart however you see fit and wrestle as many shadows as necessarily while you do so, but there’s really only one sure thing about this whole scenario: it was a huge mess. Everybody involved obviously wishes it had gone down differently, and having had the most power to make that happen, Vince almost certainly has more regrets about how he handled things than anyone else.

13 Ignoring AJ Styles For Over A Decade

It may be true that Vince McMahon created more wrestling superstars than any other wrestling promoter, but this doesn’t mean he hasn’t missed out on his fair share of potential WrestleMania main event worthy talent along the way. The most recent example of this fact has been AJ Styles, who earned a worldwide reputation as arguably the greatest pro wrestler in the world while working for just about every wrestling company around except WWE. That finally changed in January of 2016, and the most surprising part about it was that Vince was apparently quick to admit he made a mistake in ignoring AJ for so long until then. It was pretty obvious Vince caught a shine to Styles when the Phenomenal One became WWE Champion within nine months of his debut. While there’s no way Vince was completely oblivious to AJ’s reigns as TNA and IWGP Champion, it was apparently his smaller stature that left McMahon weary about his star power. Once he saw the light, AJ’s career has been on an upswing ever since, and there’s no saying how far Styles, McMahon, or WWE as a whole could have gone if the relationship started years earlier.

12 Making Diesel A Babyface During His WWE Championship Run

There’s usually more than one person to blame if a wrestler’s main event run doesn’t pan out. The most integral player is obviously the wrestler in question, but their feuds, the bookers, the announcers, and especially Vince all play a pretty big role in how successful a sports entertainer is capable of becoming. In the case of Diesel’s year long World Championship run from November 1994 to November 1995, all of these factors came into play, and yet this time Vince was far and away more at fault than Kevin Nash or any of his opponents. While Nash hadn't possessed much in the way of technical wrestling prowess, he did have a great deal of charisma. The problem was that Vince wanted him to have goofy, smiley, white bread babyface charisma, cracking childish jokes and acting like a taller Hulk Hogan. Had he wanted the exact opposite, Diesel could have easily been a dominant jerk/monster, and then all Vince needs to do is take away Mabel from the equation and virtually the entire year could have been exactly the same with much better storylines. Though Vince rarely admits regrets, his bank account makes this one a guarantee, with 1995 allegedly the lowest drawing year in WWE history.

11 Black Saturday

While the second time Vince McMahon appeared on World Championship Wrestling was likely one of the best days of his life, the first time around was so embarrassing to him that newer fans might not even be aware it happened. The year was 1984, and he was purchasing every syndicated wrestling timeslot he could get his hands on, running territorial promotions out of business left and right. Back then, WCW wasn’t a company yet but rather a TV show, featuring the best and brightest stars of Georgia Championship Wrestling. As was his style at the time, Vince purchased GCW and the timeslot in one full swoop, keeping the WCW name for a special episode of WWE programming, retroactively dubbed by fans as Black Saturday. The negative sounding name relates to how harshly fans rejected the show, hating it even more than modern fans hate Roman Reigns. GCW viewers liked traditional studio wrestling, and Vince was presenting sports entertainment based on squash matches and outrageous characters. Viewers fast called TBS and voiced their anger, then stopped watching when WWE wouldn’t go away. Realizing he made a mistake, Vince sold the timeslot to remaining NWA affiliates. The NWA later took the WCW name and used it to rebrand their entire company, reverting the name of the show to simply Saturday Night.

10 Appearing On The Record With Bob Costas

2001 was a confusing year to be Vince McMahon. His wrestling empire achieved arguably its greatest triumph in forcing WCW out of business, allowing McMahon to pick up the scraps in March. At the same time, it was abundantly clear that his outside endeavor with the XFL (more on that later) was going to be a completely disaster. With both of these things swirling through his mind, McMahon appeared on the HBO series On The Record with Bob Costas. Rather than focus on the failing XFL, Costas grilled Vince on WWE producing risqué adult-oriented entertainment at the time. Feeling sandbagged and defensive, McMahon angrily got in Costas’s face during tough questions, acting unprofessional and yelling rather than answering honestly and acting respectful. It has generally been accepted that Costas “won” the moment, reacting calmly and dismissing McMahon’s angry attitude with a smile instead of responding to his provocation. Years later, McMahon and Costas would make up in a sense, with the sportscaster appearing in WWE a handful of times to promote and discuss important feuds.

9 The Chris Benoit Tribute Show

Before we go any further with this one, it should be pointed out that Vince McMahon had absolutely no connection to the tragedy that took place at Chris Benoit’s home on that horrible summer in 2007. For anyone who’s tried to block it out of their minds, it was June 24 of that year when Benoit murdered his wife and son before taking his own life. McMahon was obviously as heartbroken and shocked by the ordeal as anyone else, and this was before the whole story came out, and all anyone knew was that an entire family had died. Because the full circumstances were unknown, McMahon and dozens of WWE superstars held a tribute show colloquially known as Raw Is Benoit, celebrating the deceased athlete’s career while his friends and coworkers spoke fondly about his life. By the next night, it had been revealed Benoit was a murderer responsible for the other deaths, and what basically amounts to a retraction had to air the next night on ECW, with Benoit’s name seldom mentioned ever since.

8 Doing Business With Dr. George Zahorian

Few individual laws have affected the wrestling business more than the Anabolic Steroids Control Act of 1990. Until that point, it was pretty much fair game for pro wrestlers to use whatever performance enhancing drug they wanted, steroids high atop the list of their favorites. Hulk Hogan, Randy Savage, The Ultimate Warrior, and even Vince himself were all presumed to be on the juice at one point or another, and they found themselves forced into stopping immediately once it became illegal. Unless, of course, they found a doctor who would circumvent the law. That’s where George Zahorian comes in. Vince hired Zahorian a number of times throughout the 1980s into the early ‘90s as a ringside physician, a legitimate position required to ensure his wrestlers' safety. On the side, Zahorian also sold steroids, continuing to do so well after the practice became illegal. The government found out in 1991, and McMahon was implicated as an accessory in 1993. Ultimately, the jury decided McMahon had nothing to do with Zahorian’s illegal drug ring, acquitting him of all charges. While that’s probably the case, McMahon still never should have hired such a shady character in the first place.

7 The XFL

Everyone makes mistakes, and the more money they have to back up those mistakes, the faster they can spiral into downright catastrophes. When multiple billionaires get together and attempt to compete with other billionaires, catastrophe doesn’t even begin to cover it. In 1999, Vince McMahon teamed up with his old friend Dick Ebersol, longtime head of NBC Sports, forming the basis for what would turn into the XFL by 2001. The X Football League was riddled with problems from the start, most blatant of which being that the “X” didn’t mean anything, spotlighting how ill-formed and slapdash the entire organization seemed. On top of that, the football wasn’t particularly good, and ribald tactics like bringing a cameraman into the women’s locker room did more to hurt the league’s reputation than help. Ultimately, the XFL lasted all of two months, producing a single season, with ratings plummeting so fast other NBC programs were openly mocking it on air. By the time everything was said and done, McMahon and NBC both lost around $35 million, with absolutely nothing positive to show for it.

6 Tearing Both His Quadriceps At The 2005 Royal Rumble

The Royal Rumble has been around for over 30 years now, and it remains perhaps the second biggest spectacle in WWE, behind only WrestleMania. Every wrestler to win the match has gone on to varying degrees of fame, most usually well on their way to history before cementing their legacy by outlasting 29 other superstars. Unfortunately, not every win has been particularly historic, and at least once things went so wrong Vince himself had to run out to the ring and set it right. The year was 2005, and the ending was supposed to see Batista eliminate John Cena after an intense show off, no strings attached. Instead, Batista slipped, or tripped, or who knows exactly, but the point is he and Cena both toppled over the ropes and hit the ground at the exact same time. Making matters worse, when Vince came out to fix things via quick decision live on Pay-Per-View, he also slipped/tripped/etc. while sliding into the ring, tearing both quadriceps muscles. To his credit, he looked pretty tough withstanding the pain to lay down the law, but he also looked kind of ridiculous sitting in the ring with his hands on his hips like an angry child.

5 Wasting Millions On Linda’s Failed Senate Campaigns

There are a number of ways to look at Vince McMahon’s support of his wife Linda’s two failed US Senatorial campaigns in 2010 and 2012. On a personal level, it would be fair to say he was simply a supportive husband hoping his wife would get to make a political difference she/they thought was right. From a business standpoint, it was a great way to lose somewhere in the neighborhood of $97 million dollars. Granted, the money spent on the campaign was technically Linda’s and not his, and Vince himself has lost far more money on much less fruitless endeavors in the past. It still must have stung to look at their bank account in 2013 and realize nothing came of the fortune spent on Linda’s side career. All of that may have changed in 2017 when old friend and WWE Hall of Famer Donald Trump appointed Linda the new administrator of the Small Business Administration. In another manner of thinking, however, that may have only made the loss worse, because knowing how politics operate, Linda probably could’ve gotten her new position without wasting money on a failed campaign.

4 Co-Sponsoring A Pay-Per-View With Girls Gone Wild

For all the credit Vince receives in the wrestling world, one area that might go unnoticed is how he completely revolutionized Pay-Per-View in America. WCW might have pushed him to it, yet few industries have understood how to market standalone television events the audience had to pay for quite like he has—even boxing PPVs don’t come anywhere near wrestling’s frequency. With all of that in mind, take wrestling out of the equation, and it might turn out Vince has no idea what he’s doing. Some three weeks before WrestleMania XIX, WWE co-sponsored a Pay-Per-View called Girls Gone Wild: Spring Break, featuring a “Better Body Contest” between then-Playboy cover girl Torrie Wilson and stripper-turned-Tough Enough winner Nidia. The match barely happened, the real focus of the program an unannounced beauty pageant with unknown contestants. The judges were Jonathan Coachman, Stacy Keibler, Test, Snoop Dogg, GGW-owner Joe Francis, and supermodel Kylie Max, all of whom appeared to be various levels of drunk, and asked some seriously family unfriendly questions (the word “BJ” was uttered countless times). To call it a mess would be an understatement, and “embarrassing failure” comes pretty close.

3 Trying To Revive Saturday Night’s Main Event

In the era before Pay-Per-View was a staples of WWE programming, it was always a major deal when NBC produced Saturday Night’s Main Event. Big stars like Hulk Hogan and “Rowdy” Roddy Piper almost never wrestled on weekly shows like Prime Time Wrestling, so SNME was the show casual fans could watch and be assured their favorites would make an appearance. For a number of reasons, ratings started sagging by the early ‘90s, and switch from NBC to Fox wasted enough to save the show, leaving it on the backburner for over 14 years. It was revived in 2006 and produced five new shows, but at this point absolutely all of the magic was gone. SNME only worked when it was the biggest show around, and with anywhere from two to five weekly shows featuring top WWE superstars airing on cable plus a Pay-Per-View a month, there was absolutely nothing SNME could offer to casual or hardcore fans. The ratings harshly reflected this fact, never breaking more than a 2.9. By the end, it could barely pull a 1.0, worse than Raw or SmackDown has ever done, even to this day.

2 Partnering With Generation Rescue

There’s no way around the fact Vince McMahon loves celebrities getting involved with his product by any means necessary. Each year, the WWE Hall of Fame has a celebrity wing is a blatant attempt at mainstream exposure, and that The Rock and other movie stars get pushed ahead of regular talent pretty much speaks for itself. Accepting all of this as inevitable, Vince nonetheless needs to do some background checking into the celebrities and organizations he supports, lest he avoid another disaster like Generation Rescue. Throughout the summer of 2008, and culminating at the aforementioned lowest rated and final episode of Saturday Night’s Main Event, WWE superstars and celebrity supermodel Jenny McCarthy spread the scientifically false belief autism is reversible and caused by mercury based vaccines. McMahon and company are also understandably huge fans of supporting charities, which is usually a good thing, unless the charity happens to do more harm than good, like with GR. Amazingly, the partnership caused little controversy, and links to GR related information can still be found on, presumably due to how few people saw SNME.

1 Forcing Lord Alfred Hayes Into Retirement

All a wrestling fan needs to do to understand Vince McMahon’s appreciation for Lord Alfred Hayes is watch a single episode of Tuesday Night Titans. Hayes entered the WWE Universe in late 1982, impressing McMahon enough with his light humor and wrestling knowledge that he became his TNT sidekick, creating wrestling’s version of Johnny Carson and Ed McMahon. His Lordship popped up in countless comedy segments with every name wrestler from the ‘80s to the early ‘90s, forever endearing himself to Vince and his many fans. Times were getting tough in 1995, though, and Alfred’s pay was dramatically and repeatedly cut to the point he suddenly decided to leave WWE and retire. While he probably should’ve seen it coming, Vince was shocked to hear Hayes was done, not to mention extremely saddened by the decision. Lord Alfred passed away in 2005 and received the traditional 10-bell salute and tribute on the next Raw, but for some reason a WWE Hall of Fame induction has yet to happen. One can only assume Vince’s lingering guilt over Hayes retiring might have something to do with it.

Sources: WWE, Bloomberg

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15 Career Mistakes Vince McMahon Probably Regrets