With a net worth that usually gravitates around the certified billionaire mark, Vince McMahon has made significantly more money through professional wrestling than any other individual. Of course, this also opens the door for Vince to have lost more money on sports entertainment related endeavors, and that too is most definitely the case. That said, most of McMahon’s biggest losses have been generally unrelated to wrestling, with his fortunes plummeting every time he steps out of his comfort zone.
In rare cases, it’s almost understandable how and why McMahon made the moves that cost him millions. It makes sense for him to diversify his portfolio, trying outside investment opportunities to further flesh out his billions. The catch is that Vince refuses to take a backseat role in anything he does, always diving headfirst into things without doing all that much preparation. Because he’s doing it all by himself, no one can slow him down when the inevitable free fall happens soon into his new efforts.
Maybe one day Vince will come up with a secondary lucrative idea far away from the wrestling ring that works out perfectly for him and inches his family ever higher up the Forbes billionaires list. Then again, if that happened, he’d probably just waste it all on a whole new crop of ridiculous failures that never had a chance of taking off. There’s also the general issue that more money does indeed cause more problems, and the target on Vince’s back from lawsuits would only grow larger along with his bank account. Speaking of which, keep reading to learn how a single lawsuit cost Vince McMahon $10 million, along with 14 other costly mistakes from the WWE CEO.
15 Hiring Untrained Jobbers — $10 Million Lawsuit
Wrestling may be scripted, but sports entertainers really do bounce around the ring in dangerous fashion, and if they don’t know how to properly fall, the consequences could be truly horrible. Take it from Chuck Austin, a grappler who received barely a months worth of training before getting hired by WWE to lose in a match against The Rockers. Vince McMahon assumed Austin knew how to fall, as did Marty Jannetty, and chances are the poor jobber also believed he had the necessary skills to look like he was getting hurt without actually winding up in the hospital. Unfortunately, that wasn’t the case, as a botched Rocker Dropper left Austin paralyzed for the rest of his life. While Austin himself made some mistakes on the ring, McMahon and WWE were far more responsible for hiring someone clearly unfit for a job that can be deadly if performed poorly. Juries agreed, awarding Austin $26.7 million in damages, though McMahon somehow eventually talked him down to settling for $10 million.
14 Lying To Jesse Ventura About His Contract — $800,000 In Damages
In many respects, as the chief impresario of professional wrestling, Vince McMahon’s entire business is based on his ability to lie. With this in mind, perhaps it’s not that surprising he would bend the truth to his employees, even if it teetered on a legal grey area when he did so. It’s not illegal for Vince to tell someone who turns into a career jobber that they’ll be WWE Champion one day, because that’s more of a failed prediction than an outright fabrication. However, telling a talent they aren’t entitled to a certain form of payment they totally were entitled to is the sort of thing that landed him in court more than once. One of the few people who proved Vince lied to them in this way is future Governor of Minnesota Jesse Ventura. Apparently, Vince told Ventura that non-featured performers never received royalties on video releases, which was absolutely not the case. Juries were so shocked that McMahon would cheat his talent like this they awarded Ventura $801,333, plus $8,625 in back pay. Chances are Vince still lies to his talent to this day, but never when contracts are involved.
13 Mark Henry’s Original Contract — $1 Million Per Year For A Full Decade
By the time he officially retired, Mark Henry had etched out a pretty respectable place for himself in wrestling history. The so-called World’s Strongest Man’s last few years in particular were rather impressive, especially considering how long he had been in the game. It was a full 15 years into his career that Henry opened up the Hall of Pain and started winning World Championships, making fans care about him at long last after decades of mediocrity. So, why did Henry get so many chances and stick around so long until then? Because he was signed by Vince McMahon virtually sight unseen for a monstrous $10 million contract, to be paid out over the course of 10 years. Henry was almost entirely untrained in the ring at that point, and there was no way to tell if he’d ever figure the sport out. The fact it took him over to do so makes it pretty clear Vince wasted a whole bunch of money on this one, even if it did slightly pay off in the long run.
12 Buying And Selling The Debbie Reynolds Hotel And Casino — Broke Even
Oh, what could have been. Truth be told, this next entry very well could have worked out for Vince McMahon and WWE if things went differently. In the very least, they could have at least tried to enact their massive plan, rather than give up almost immediately for unclear reasons. Backing up a bit, the story begins in 1999, when McMahon purchased the Las Vegas Debbie Reynolds’ Hollywood Hotel for $10.65 million. Apparently, the plan was to build a pro wrestling casino/amusement park spectacular, with a giant rollercoaster called the PileDriver. After paying to strip the building and hiring contractors to prepare for demolition, Vince suddenly decided the location wasn’t big enough and sold it off a year after buying it. A Chicago realty group took it off his hands for $11.2 million, which was a slight gain that might make it seem undeserving of this list. However, factor in all the money Vince wasted on upkeep of a building he never used, and it was the sort of bizarre net loss only a billionaire could afford.
11 Trying To Make His Wife A Senator — Roughly $100 Million
Now that Linda McMahon has a seat in the United States Cabinet, it could be argued this next item on the list wasn’t a waste at all. Then again, her main qualification for the position as Administrator for the Small Business Administration was being friends with a certain amateur politician who happened to be in charge of selecting someone for the gig. This means Linda probably could have gotten the job without first spending $100 million dollars on two failed Senate campaigns in her native Connecticut. At the time, the McMahon family spent more of their personal fortune on her two bids in 2010 and 2012 than any other candidate in history, beating even Ross Perot’s self-funded attempt for the US Presidency in 1992. In both races, Linda just barely inched out the Republican nomination only to get blown out by her Democratic opponents in the general election, a predictable fate that should not have cost 9 figures over the course of 2 years.
10 Letting Jeff Jarrett’s Contract Lapse A Day Too Soon — $300,000
One of the oldest catchphrases in wrestling is that anything can happen in the WWE Universe, and recent years especially have shown Vince McMahon has an incredible capacity for forgiving those who once seemed like his worst enemies. That said, don’t expect former seven time Intercontinental Champion Jeff Jarrett to make a comeback any time soon. It doesn’t have anything to do with Jarrett’s status as the co-founder of Impact Wrestling, either, at least not directly. The whole reason Jarrett needed to start his rival company after WCW went under is that Vince would never let him back due to an incident at No Mercy 1999. That night, Jarrett was supposed to lose the Intercontinental belt to Chyna in a historic moment, but his contract technically expired the day before. Jarrett had no legal reason to participate in the match until Vince gave him one, to the tune of $300,000. If he had only made sure Jarrett was still under contract for the highly publicized match, though, things would have gone much smoother.
9 Trying To Turn Hockey Into Sports Entertainment — $15,000+
Long before he decided to dabble in football, and even prior to technically becoming the owner of WWE, Vince McMahon’s first solo endeavor in sports entertainment actually took place on a hockey rink. It began through a separate business venture that was actually quite successful, that being McMahon’s ownership of the Cape Cod Coliseum, a relatively popular venue for wrestling matches and rock concerts. In the early 1980s, the Atlantic Coast Hockey League formed and was looking for new teams, and Vince thought it would be perfect to have a homegrown group he could promote in his arena. In classic Vince McMahon fashion, rather than approach hockey experts for help, he just created his own team, called the Cape Cod Buccaneers, paying the dues to enter the new league out of pocket. As is generally the trend when Vince dives into a field he knows nothing about, the results were a huge mess, and the Buccaneers record was so bad Vince chose to fold the team rather than pay for a second year.
8 WWE Studios — A Continued Money Pit No One Understands
To Vince McMahon’s credit, he was eventually able to recognize most of the items on this list were misguided at best, cutting his losses and moving on before he lost billions rather than millions. What sets WWE Studios apart from all his other failures is that Vince just won’t give up on this one, continuing to pour millions of dollars into awful movies that no one wants to see each year. Granted, about halfway into it’s existence, the film division of McMahon’s empire did start turning an occasional minor profit. Movies starring John Cena make modest amounts in advertising, and anything directly marketed to children like their adventures with Scooby-Doo or The Jetsons are generally worth the investment. However, something like See No Evil 2 was destined to bomb from the day it was announced, and we’re not sure who exactly was begging for Dolph Ziggler to become a leading man. With more than half of the films McMahon produces being spectacular bombs, it’s hard to understand why he keeps trying to make a hit.
7 Forcing Owen Hart To Do A Deadly Stunt — $18 Million
Despite what some heartless corporations may try and suggest, there is absolutely no dollar sign that can be put on a human being’s life. While a tragic incident at the Over the Edge 1999 Pay-Per-View ultimately cost Vince McMahon $18 million in various legal fees, the real loss was one of his greatest and most beloved performers, Owen Hart. The plan was for Hart to fly off the rafters as comedy superhero The Blue Blazer, but a malfunction in his harness caused him to immediately fall to his death. Because this was a work place accident, Owen’s widow Martha was able to sue for wrongful death, and the evidence was pretty clearly against Vince. Not only did Vince demand the stunt happen when Owen asked him to reconsider, WWE also rushed the very necessary training that could have saved him. Given this evidence, juries awarded the Hart family the aforementioned millions, but it still wasn’t nearly enough to make up for the loss they suffered.
6 Guaranteeing Marc Mero’s Initial Contract — $500,000+
With all due respects to the talent of Marc Mero, his name doesn’t exactly come up that often when discussing wrestlers who genuinely changed the business. The former WCW Television and WWE Intercontinental Champion was a solid hand in the ring and had plenty of charisma on the microphone, especially as Johnny B. Badd, the character he played in WCW. That didn’t make him a main event talent, though, with his ceiling quite clearly somewhere in the mid-card. For this reason, Vince McMahon was pretty crazy to sign Mero to the first-ever guaranteed wrestler contract, which essentially gave him a yearly salary rather than an agreement based on how many matches he wrestled. For his inaugural year with WWE, this meant half a million dollars to appear in matches that didn’t set the crowd on fire, to say the least. Mero failed to catch on for another 3 full years, though his paycheque presumably got smaller as things went on.
5 WWF New York/The World — Roughly $19 Million
Believe it or not, there are actually a few dozen retired pro wrestlers out there who own restaurants, and quite a few of them are actually reasonably successful. As the industry’s number one businessman, it makes sense Vince McMahon would throw his hat into the ring with the full backing of his WWE Universe. Directly in the heart of New York City’s Times Square, McMahon purchased a property that later went by the names WWF New York and The World. The restaurant/bar was never all that popular, except for on WWE Pay-Per-View nights and in rare cases when a wrestler would stop by for an autograph signing. Unfortunately, that meant an empty house 6 nights out of the week, which is financial disaster for any restaurant. On the other hand, as an ad for WWE, it wasn’t that bad, as the organization earned about $16.3 million selling wrestling merchandise in it’s three year existence. However, the restaurant part of the business lost $35.5 million overall, pretty much canceling that minor success out and then some.
4 The World Bodybuilding Federation — Undisclosed Millions
The WWE Universe notwithstanding, it could be argued the athletic activity most ripe for a transformation into “sports entertainment” has always been bodybuilding. For the most part, bodybuilders don’t really do anything when actually competing, just posing and looking buff after having done all the real hard work for months prior to a competition. This can make the sport a little boring to outsiders, and if Vince McMahon had a way to try and spruce things up, it wouldn’t have been a bad idea for him to try. Unfortunately, his only real idea was to turn bodybuilding into pro wrestling with the World Bodybuilding Federation, even going so far as to hire wrestler Lex Luger as one of his top stars. Luger never quite made it to the competition, but the message was still pretty clear, leaving serious bodybuilding fans alienated from the start. As for wrestling fans, they largely believed bodybuilding segments in WWE were some of the most boring in history, so they likewise avoided the mess altogether. We don’t know exactly how much Vince lost on this one, but it’s very telling he abandoned the pet project after two short years.
3 The Original XFL — $35 Million
Even before the Monday Night War made it a priority, Vince McMahon has always thrived on competition. With the mind set of a championship wrestler, idea of beating a new opponent into submission and proving he’s the best is far better than just taking an easy victory lap with the accomplishments he already has. This is why when Vince achieved the peak of his success in wrestling, he decided it was time to take over football, as well. Unfortunately, he didn’t really plan about how he was going to do that, aside from investing $50 million into the franchise, alongside another $50 million on behalf of NBC. The stockpiles of money resulted in the XFL, an 8-team league that lasted only a single season of heavily maligned play. It was trashy, unsafe, and audiences unanimously found it second-rate to the NFL, leading to some of the lowest ratings in network television history. Both sides would lose 70 per cent of their initial investments, and yet it now looks like Vince wasn’t done there.
2 The Revived XFL — Potentially $100 Million+
Okay, so this one technically hasn’t happened yet, but give it a minute. The only thing crazier than Vince McMahon attempting to take over the world of football is Vince McMahon doing just that a second time, after it already cost him $35 million. Because Vince sees the word crazy as a challenge, he’s also decided to double and almost triple down on the surefire failed investment by putting up $100 million of his money this time rather than the paltry sum he wasted in 2001. In all fairness, the XFL revival has was only announced a few weeks before this article was written, so we can’t know for sure that it will be a total wash. However, given how bad things went the first time, coupled with the fact McMahon didn’t appear to learn a single lesson from the failure in his big announcement video about the revival, and it seems almost inevitable that history is about to repeat itself in a major way.
1 Signing A Bad TV Deal And Letting The Stock Market Go Wild — $340 Million In One Day
When a person has as much money as Vince McMahon, large amounts of it are tied up in stocks and bonds, meaning their entire fortune can skyrocket or plummet virtually overnight. This has actually happened to McMahon on multiple occasions, with the most jarring drop of all occurring in the 3-month period after WrestleMania XXX. On May 16, 2014 specifically, Vince lost $340 million in a single day after signing a bad contract with NBCUniversal. Vince didn’t really have any choice in the matter, needing to keep his agreement with the company that owns USA Network and broadcasts Raw at any costs, but it was still signing his name on the deal and making it official that caused his fortune to disappear. That wasn’t even the end of it, as some reports claim he lost up to $842 million in the span of a few months, all related to that same bad contract. Despite this massive loss, though, Vince has since bounced back in strong form as he always does, regaining a good chunk of his millions so he can waste it all over again some day soon.