Considering he’s made more money from professional wrestling than any other person, there’s a reasonable if misguided perception Vince McMahon always knows what he’s doing when it comes to the business of sports entertainment. While certain critics are probably too hard on the WWE CEO, there can be no denying he’s wasted countless opportunities over the years that could have greatly increased his already sizable bank account. Other times, he’s outright wasted millions on ideas that any rational person should have passed on in an instant, making some of the strangest financial decisions a certified billionaire could possible make and still retain that title.
In recent years, Vince has been leaving cash on the table due to stubbornness more than anything else, but most of his mistakes seem like just that. Nobody’s perfect, and that includes billionaire businessmen, who don’t always realize the opportunities they have in front of them. Endless employees all trying to influence him for selfish means don’t make it any easier, and McMahon’s notoriously strange interests have guided him in the wrong direction on more than one occasion.
Ultimately speaking, WWE’s continued success as the self-professed worldwide leader in sports entertainment means McMahon has gained far more through the industry than he’s lost. However, as CM Punk once so eloquently put it, there have been points when “Vince McMahon [was] a millionaire who should be a billionaire.” Though Vince has again become a billionaire since Punk made that statement, there’s as much wisdom in that statement today as there was back in 2011, and should the trend continue, it might become literal yet again in the near future. Keep reading to learn of 15 cases where Vince McMahon practically threw money away.
15 Misusing Daniel Bryan Until It Was Too Late
For as many popular superstars as there are in the wide-ranging WWE Universe, only a very select few have become crossover celebrities who truly define the sport. Hulk Hogan, Steve Austin, The Rock, and most recently John Cena have been more than wrestlers, they’re all pop culture sensations, and Daniel Bryan could well have been the same. No one has earned the unanimous, rabid approval of WWE crowds like Daniel Bryan in recent years, and that includes Cena. Outside of WWE, people were chanting “Yes! Yes! Yes!” at basketball, hockey, and football games, using Bryan’s hand gesture while they did it, making it clear just about everybody who watched sports knew who he was. Instead of capitalizing on this incredible acclaim, WWE did everything they could to push Bryan down the card until even they couldn’t ignore his popularity anymore and let him main event WrestleMania XXX. Unfortunately, by the time they made that decision, Bryan was so beaten down through injuries that he could barely celebrate his fame. That said, McMahon had no way of knowing Bryan would get injured, and there’s no saying things would have worked out the same if they forced the Yes Movement instead of letting it occur naturally. While there was certainly money lost here, the point is, it wasn’t entirely McMahon’s fault.
14 The Peak Of Hulkamania Needed More True Challenges
Pro wrestling has changed in countless ways since WWE was founded in the 1960s, which is why the epic 4+ year long championship reigns that defined the early years of the company would be virtually impossible today. CM Punk holds the record for being the longest running WWE Champion “of the modern era,” but that very distinction meant it was a long, long time since a truly lengthy reign had occurred. Prior to Punk, the last super champion was Hulk Hogan, at the time the most popular wrestler in WWE history. Hogan’s popularity more than justified him being in the main event for four years, but throughout it all, the threats against Hogan almost never escalated. Until he faced André The Giant, every match followed the exact same formula where he never really looked in trouble, and even with the André example that trouble didn’t last more than a few months. Without going too deep in the fantasy booking, the idea that has been floated the most as potentially increasing the millions made from Hulkamania was for “Macho Man” Randy Savage to unscrupulously retain the gold when the Mega Powers exploded at WrestleMania V. Even John Cena’s Superman act is better than Hogan’s because the odds escalate when he beats them, something Hogan never experienced.
13 Keeping Roman Reigns Face
Critics of Vince McMahon and WWE in general as of late have sounded like a broken record when it comes to one extremely important subject—the handling of WWE “top guy” Roman Reigns. Of course, McMahon is just about the only person alive who views Reigns as a “top guy,” and that serves the basis of our problem. Large, imposing, and excelling at naturally mean facial expressions, Reigns could be a landmark heel if given the right booking. For whatever bizarre reason, however, Vince McMahon sees Reigns as some sort of lovable scamp who won’t stand for sufferin’ succotash, and even stranger, he thinks that’s a good thing. The more Reigns gets pushed as a babyface, the more money McMahon is wasting, especially as he sacrifices every potential star in his company to make that dream come true. When fans thought it couldn’t possibly get any worse than Reigns winning the WWE Championship in the main event of WrestleMania 33, it appeared that McMahon set in motion plans for him to beat The Undertaker at this year’s event, showing this particular money pit may well be bottomless.
12 Killing Nexus In A Single Match
There have been a handful of moments in professional wrestling that truly shocked fans in the sense they never believed it could happen. Hulk Hogan and Steve Austin’s heel turns at their peak, the McMahon’s appearing on WCW television, and perhaps most recently, Nexus making their debut to attack John Cena, CM Punk, and various other WWE personnel. Not only did WWE manage to completely surprise their audience with the move, they potentially made no less than eight stars in a single segment, yet a mere two of them became anything close to the term. It all fell apart barely two months after Nexus made their first appearance, when John Cena and his Team WWE very definitively defeated the group in a 14-man tag team match, killing off their potential one by one all in a single night. The ending was the worst, when Cena eliminated both Wade Barrett and Justin Gabriel, winning the match singlehandedly. Immediately speaking, Vince was tossing out months of potentially exciting storylines that could have drawn in fans still intrigued by Nexus’s debut. In the longer term, Vince was ignoring whatever money all six forgotten Nexus members could have made, a total waste no matter what their individual star power may have been worth.
11 Funding Linda’s Two Failed Senate Campaigns
Everybody has dreams, and if we all had millions of dollars to spend on pursuing them, most people would probably lose tons of money on them. The McMahon family knows this problem all too well, thanks to matriarch Linda’s long running desire to enter the field of politics. It ultimately paid off for her when Linda became the Administrator of the Small Business Administration in February 2017, although this goal wasn’t met until she and her family spent somewhere around $100 million on the chase. Because that money was spent entirely on two Senatorial runs, and Linda has still never been a Senator, it would be fair to call the entire thing a loss. The more cynical one is about modern politics, it gets easy to compound that loss with the realization she probably could’ve been placed in charge of the SBA without any prior experience in government, the same way the man who appointed her to the position got his job. Had the McMahon’s simply waited for their friend to become President, millions could’ve been saved and they could’ve saved themselves the embarrassment of two highly publicized losses.
10 Investing Millions In Tout
Social media exploding has quite literally changed the entire world, from the technology industry where it was created all the way to pro wrestling. It makes sense that Vince McMahon, or any billionaire looking to add another zero to his net worth, would want to get whatever piece of the pie he could. Unfortunately for McMahon, not every networking web site is as popular as Facebook or even Friendster, with some smaller services like Tout almost irrelevant thanks to more popular platforms using the same basic concept. What set Tout apart was its use of 15-second videos, however it wasn’t long until Vine became more popular, plus Instagram added a similar feature that more or less made Tout irrelevant. Little of value was lost, unless you happen to be one of Tout’s key investors, which Vince McMahon and WWE were. Collectively, the company invested $5 million in Tout on July 11, 2012, starting a two-year partnership between the businesses. That partnership produced a bunch of videos that were, well, meaningless, and WWE ended the arrangement at the pre-determined time with little fanfare.
9 Everything About The Invasion
When it comes to sheer missed opportunities in the wrestling industry, no year was worse for WWE than 2001. Two of the three biggest companies in America collapsed, consumed by the sole survivor, and that meant somewhere around 80-90% of all reasonably famous wrestlers in the country were working for the same company. As the man in charge of all three enterprises, Vince McMahon had more to gain than any other individual, and yet there was one huge obstacle in him doing so. In order for the Invasion to truly work, WWE would need to look weaker than WCW and ECW, at least a little bit, and for prolonged portions of the show. McMahon absolutely never allowed this to happen, very quickly having Lance Storm, Booker T, “Diamond” Dallas Page, Chris Kanyon, and anyone else who could truly be considered a homegrown WCW star quickly lose to one of his own WWE talents. By the time they realized this made WCW look too weak to be a threat, they solved that issue by simply having WWE wrestlers join the fray for no reason. Everything about the Invasion was a bomb, completely whiffing dozens of dream matches and potential big money angles in the process.
8 Hiring Sting Just To Job Him Out To Triple H
As terrible as everything about the Invasion was, the one upside is that it was relatively quick, with WCW dead and buried on a literal sense in March, and kayfabe catching up with reality by November 2001. From that point forward, WWE pretty much dropped the subject, almost showing a certain degree of restraint when one considers how much boasting about the subject Vince McMahon could have gotten away with. Case in point, 13 years later, when he hired the then 55-year-old WCW icon Sting so they could relive the ordeal in bizarre and nonsensical fashion. Despite the Invasion’s failure, fans had nonetheless been dying for Sting to finally show in the WWE Universe all that time, and for him to do so solely to attack Triple H and hearken back to the Monday Night Wars was more confusing than anything else. While the audience made it clear they wanted to see Sting face The Undertaker, WWE instead went full steam ahead at a WWE vs. WCW battle at WrestleMania 31, the Dead Man distracted by a meaningless match with Bray Wyatt. The last true dream match was replaced with two messes, and Sting’s time in WWE was practically irrelevant as a result.
7 Keeping WWF New York Around And Stopping The Special Events
WWE wouldn’t be what it is were it not for televisions bringing the company into millions of homes, but to a fan, nothing beats the thrill of attending a wrestling event live. Because not everyone can keep up with the WWE travel schedule, it’s next to impossible to actually go to every Raw, SmackDown, and Pay-Per-View, so for a few short years, WWE created a solution by making a single place their fans could congregate and celebrate the sport. Called WWF New York and then The World, the theme restaurant/bar was filled with wrestling memorabilia and constantly aired WWE events on their televisions. Before it looks like we’re calling the idea brilliant or anything, let’s slow down and admit that it didn’t make much money, with the exception of Pay-Per-View nights, when the joint would understandably be packed. WWE could also get the club filled almost every Sunday night by having guest stars host Heat from the location, yet they suspiciously ended this practice with a year remaining on their lease. By deciding to no longer use WWF New York for the only thing it actually made money doing, McMahon was giving up on so much as cutting his losses, indicative of how little thought must have gone into the whole endeavor.
6 Completely Writing Off NXT
To many fans, the most exciting brand in WWE today is neither Raw nor SmackDown Live, but rather the little developmental promotion that could, NXT. Truth be told, that perception is rapidly changing for a number of reasons, most importantly being a lack of long-term storytelling, though that’s neither here nor there when discussing Vince McMahon’s mistake regarding his own training ground. According to insider reports, McMahon just doesn’t see the big deal with NXT, which explains why the majority of superstars who get called up are cast aside until they prove themselves all over again on the main roster. Each time Vince does this, he’s hitting the reset button on whatever money he could make, entirely defeating the purpose of having a system to feed him readymade stars. The good news is that the instant success of Fínn Balor would indicate this trend might finally be coming to an end. The bad news is that Balor injured himself in one of his first high profile matches, and McMahon might use that to embolden his stance and continue refusing to give NXT wrestlers the chance they deserve.
5 Trying To Take Bodybuilding National
Given Vince McMahon’s track record with taking territorial niche interests and turning them into global phenomena, it’s almost tempting to say his attempt at doing the same thing with bodybuilding was almost justified. On the other hand, anyone who’s watched more than five seconds of bodybuilding knows it’s a whole lot less interesting and spectacular than wrestling even at its worst, with the primary point being people who look like they’re on all the steroids in the world standing still. None of the World Bodybuilding Federation “BodyStars” were accused of using the drugs, but the point remained it was an incredibly boring pseudo-sport that not even McMahon could make interesting. Long before McMahon himself was accused of distributing steroids and could have started an entirely new mess, it was apparent that pretty much no one other than him had any interest in watching the WBF in the first place. The exact amount of money Vince lost has never been disclosed, yet it would be safe to say every penny spent on this endeavor was a penny wasted, if not openly discarded for fun.
4 Mark Henry’s Rookie Millions
Any discussion of an athlete’s monetary worth is bound to be a little crass, and worse, heavily biased based on the public’s perception of said athlete’s talent. Especially with WWE superstars, there can be far more to a wrestler’s value than his skills in the ring. In the case of Mark Henry, that includes unmatched legitimacy as the “World’s Strongest Man,” with endless legitimate world records in weightlifting. However, these credentials are nowhere near enough to justify a 10-year contract that gave him $1 million per year. Some 20 years later, only the absolute top stars in the company are breaking seven figures, and that Vince McMahon was willing to give that much money to a completely untested rookie simply because he could lift a lot of weight was shockingly short-sighted. There was no promise yet that Henry could even bump or cut a promo, and the first half of his career suggested he might never learn how. Although Henry finally came into his own as a top talent in 2011, it took over 15 years and millions of dollars, never coming close to earning his full paycheck.
3 Brock Lesnar’s Million-Dollar Contract
Contrary to everything that was stated in our earlier Mark Henry entry, the situation with Brock Lesnar has less to do with whether or not he’s worth the millions he makes and more to do with how WWE is using his character. As one of the highest paid wrestlers in the world today, one would expect Lesnar is either the best or highest profile employee in WWE, and at times it looks like he could be both. The downside is that he has an extremely limited schedule, and the few appearances he makes are almost entirely wasted on angles and matches that don’t get anyone over. Because of his unique crossover fame and legitimate credibility as a fighter, Lesnar could pay WWE back with huge dividends with a few well picked losses to rising stars. Instead, he wins, those new stars look weak, and nothing is gained. Not even Brock’s character benefits by being a destroyer of worlds, because he leaves for such a long time after each win that fans forget about it by the time he gets back. Much worse, nowadays, WWE is using Brock exclusively with other part-timers, meaning Vince McMahon is throwing money away each day he keeps Lesnar on the payroll.
2 Thinking He Could Compete With The NFL
It’s been claimed there’s no reason to become a wrestler if you don’t want to one day become World Champion, and on that credo, the sports entertainment industry has been filled with countless seriously ambitious individuals over the years. That said, in addition to being the most successful person in the biz, Vince McMahon is likely also without a doubt the most ambitious, as he is indeed one of the most ambitious businessmen on the planet. Who else would possibly believe they could compete with the NFL, not to mention doing so by deemphasizing the football aspect of the industry? Likely no one, including the American viewing audience, who turned away en masse after watching the X Football League’s first attempt at a game. Less and less people watched each passing game, McMahon losing more money every day the league continued to exist. Full documentaries have been released on the subject, and recently at that, so there may well be money to be made from the XFL yet. Unfortunately for Vince McMahon, he’ll probably never be able to personally profit, though, and certainly not to the tune of the $35 million creating the league cost him.
1 The New Generation Of Babyfaces Was A Complete Bust
While the majority of his life story is filled with unbridled success, there have actually been a few points in Vince McMahon’s career when he was flat out bleeding money. One of the worst eras in WWE history was the much promoted New Generation, from Hulk Hogan’s departure in 1993 to late 1996. The strange thing is that despite ratings being down and creativity hitting an all-time low, there was no lack of great wrestlers on the WWE roster, filled as always with incredibly talented superstars. Chief amongst them were Shawn Michaels and Bret Hart, with names like Razor Ramon, The 1-2-3 Kid, and Bam Bam Bigelow filling out the ranks. Given the right motivation, Diesel wasn’t too bad on the microphone, either, yet emblematic of the whole problem, he never found that stimulus during his year-long WWE Championship reign.
The same was true for Shawn Michaels, and though the others weren’t given any World title runs, they likewise were all better as slightly edgy heel type characters than as clear cut happy-go-lucky babyfaces. In fact, all of them would prove that much by turning heel in the next few years and making millions, more so in WCW than WWE. During the New Generation, though, they were all smiling do-gooders with no true personality, which was no longer enough to keep fans interested. Had Vince realized all along these wrestlers were natural bad guys, he could’ve been making money all along. On top of that, there would’ve been a huge readymade rouge’s gallery for when a true hero like Steve Austin or The Rock finally came and saved the day, showing that calling Vince a millionaire who should be a billionaire might not be going far enough.