10 Times Vince McMahon Was Not Boss Of The Year (And 10 Times He Was Better Than We Thought)

In order to earn recognition as a true professional wrestling legend, it’s basically a requirement for sports entertainers to spend at least a little bit of time working for Vince McMahon. Sure, plenty of other promoters and wrestling business owners exist, but none are nearly as successful as McMahon’s WWE Universe, which has been the top-ranked promotion in the industry for decades. Unfortunately, given McMahon’s track record as an employer, budding superstars may not be particularly pleased with this situation.

Despite the immense fame and fortune, or perhaps because of it, Vince McMahon is an extremely eccentric and particular individual, and he makes some strange and unreasonable demands from his employees. However, it’s these same peculiarities that lead to overwhelming displays of kindness and generosity, which seemingly come at completely random times. Obviously, Vince isn’t quite as crazy as he looked when fighting The Rock and Steve Austin during the Attitude Era, but the reason he was such a natural acting like an unbearable boss was that, well, sometimes he is one.

Of course, this information won’t stop anyone from trying to work for McMahon’s company, as it’s all been well known in the business for quite some time, and it hasn’t slowed him down yet. Nonetheless, fans might be a little surprised to learn about what WWE superstars go through when dealing with their employer. On the other hand, they might even be more shocked about the unspoken benefits that come with knowing a certified billionaire. For both sides of the coin, keep reading to learn about 10 times Vince McMahon was decidedly not the best boss of the year (and 10 times he was actually pretty great).

20 GREAT BOSS: Paying The Government For Alundra Blayze

Of all the people Vince McMahon has helped over the years, Alundra Blayze would appear to be the most surprising in retrospect. Then again, in a different world, Blayze could have kick started the women’s wrestling revolution a solid 25 years earlier than it actually began, so maybe she was worth the effort. Prior to signing with WWE, Blayze honed her skills wrestling around the world as Madusa, and the constant travel lead to mismanagement of her funds stateside, leaving her with a massive tax bill she had no idea how to pay. Luckily, McMahon asked if there was anything she wanted before officially signing, and she jokingly said he could take care of her debt. McMahon asked how much she owed, and despite the $35,000 price tag, he was happy to pay it for her in full. Nice as this was, the gesture didn’t take out the sting of firing Blayze while she was Women’s Champion barely two years later.

19 BAD BOSS: Spitefully Cutting People Out Of History

With most sports, it’s impossible for Hall of Fames or legitimate reporters to ignore the contributions of any legend who once made the game what it was. Not so with WWE, where history is written almost exclusively by Vince McMahon himself, and the man’s whims and changes of heart when it comes to this task are notoriously fickle. The mere fact Vince loves a superstar enough to make them WWE Champion one day hardly guarantees their spot in the record books on the next. Just ask Hulk Hogan or CM Punk how Vince feels about their contributions these days to see how far Vince can spin his past stars into irrelevance.

Of course, there are also counterexamples like the Ultimate Warrior, Randy Savage, or Bruno Sammartino, who fans thought would never be rightfully honored as vanguards of the sport, only for them to later show up in the WWE Hall of Fame after all. For more on that side of Vince’s personality, keep reading this list.

18 GREAT BOSS: Honoring Former Employees

Thanks to some of the stories on this list, Vince McMahon is occasionally painted as a ruthless and uncaring businessman who only ever forgives people if he thinks it will make him money. That definitely wasn’t the case in this situation, as making money off the deceased is pretty much impossible. Even so, when former WWE superstar Bam Bam Bigelow passed away with almost no savings or close family, McMahon stepped in and paid for his funeral.

While there’s no official word on Freddie Blassie’s final resting place, it’s also known that McMahon also helped that Hall of Famer pay his medical bills for many years prior to his passing. The same was true for Paul Bearer, as McMahon generously included a series of gastric bypass surgeries as a signing bonus in one of his final contracts. Of course, these are but three names in a group of countless others Vince didn’t pay for, but most bosses wouldn’t do this for anyone.

17 BAD BOSS: Claiming Cesaro Doesn’t Have “It”

With the sheer volume of talent Vince McMahon has to deal with at times, it’s almost a given that certain wrestlers will fall through the cracks. It’s also understandable that fans will be upset about this when their favorite WWE superstars don’t achieve the amount of success they deserve. However, there’s a difference between Vince McMahon not noticing someone and just not getting the picture whatsoever.

The latter scenario is what’s been happening with Cesaro recently, with many fans and reporters considering the Swiss Sensation perhaps the most underrated WWE employee in history.

Unfortunately, when confronted with Cesaro’s lack of a push by Steve Austin, McMahon plainly stated he believed Cesaro lacked the “it factor” that everyone else was screaming he had in spades. To his credit, Cesaro reacted calmly and simply said it’s made him work harder, but it must hurt knowing the boss refuses to accept what’s right in front of his face.

16 GREAT BOSS: He Never Gives Up

For all the negatives about Vince McMahon as a person, so long as a wrestler shows him respect and isn’t awful at their job, they pretty much become set for life by signing with WWE. At this point, there’s pretty much no chance in hell the company will ever go out of business, let alone fall from it’s spot as the highest rated wrestling organization in the world. Job security means a whole lot these days, and Vince is the sort of employer who ensures everyone close to him will always have it no matter what.

Even when WCW rose out of nowhere and attempted to take him down, bringing Vince near bankruptcy, he fought valiantly to keep his top stars paid at all times, never cutting costs unless it was absolutely necessary.

Knowing your boss will always fight for you and ensure you get a paycheck might just be worth a little weirdness in their booking.

15 BAD BOSS: Blatant Favoritism All Over The Map

Truth be told, many of the items on the other half of this list relate to specific moments where one wrestler had a particularly good time working with the WWE CEO. Unfortunately, far too many superstars have the exact opposite experience, unable to get along with Vince McMahon or any of his underlings from day one. The reason for this is that McMahon has long been known for picking favorites, immediately deciding whether he likes or dislikes a wrestler, and never changing his opinion on them after his first impression.

This has worked swimmingly for men like Shawn Michaels, Roman Reigns, and Triple H, who were all treated like McMahon’s best buddies as they were on top of WWE. The worst part is the favoritism continues regardless of how the crowd reacts, hence Reigns being a three time WWE Champion who remains in the main event despite receiving universally negative reactions.

14 GREAT BOSS: He Just Wants To Be One Of The Gang

When the unforgettable sounds of “No Chance In Hell” blare through the arena, the entire WWE Universe stops and stares in awe at the company’s CEO. After years of seeing this happen on television, most wrestling fans would probably assume McMahon is equally intimidating behind the scenes, but according to several of his coworkers past and present, the exact opposite of the case.

McMahon is the sort of boss with the reputation of always having his door open for any employee who wants to talk about their career. Granted, he doesn’t always agree with what they have to say, but he gives them an opportunity to speak to him directly, which is nonetheless a pretty big thing for a boss to do. Sasha Banks confirmed part of what makes the women’s revolution so natural for her is that Vince is easy to talk to, and even former employers like Matt Striker and Hornswoggle have claimed he’s a very approachable guy.

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13 BAD BOSS: Dealing With George Zahorian

Before we get into this next one, let’s be very clear about something: Vince McMahon was never officially convicted of muscle enhancer distribution, nor were there ever any rules stating WWE superstars needed to take them. That said, plenty of superstars used steroids in the past, and for McMahon to have been completely unaware of this is borderline impossible. This is obviously a problem because they are very illegal without a prescription, and possessing or selling them is a huge liability to all parties involved. Again, Vince himself didn’t ever sell them or promote them, be he did do business with a doctor named George Zahorian, who was much less innocent. Zahorian admitted as much after getting caught supplying a powerlifter, and then tried to flip on Vince when he was placed under investigation. Even though Vince himself didn’t do anything wrong, the owner of a billion-dollar industry getting involved with a character this sketchy is a danger to his whole company.

12 GREAT BOSS: He’s The World’s Biggest Wrestling Fan

In the business world, a large number of CEOs are motivated entirely by money, with the actual idea of passion for their work more or less irrelevant. That definitely isn’t the case with Vince McMahon, who was absolutely in love with sports entertainment from the moment his father brought him to Madison Square Garden at a very young age. For all the talk about how Vince hates his fans or is out of touch with the wrestling audience, there’s really no denying he still adores what he does to this day.

Most people with McMahon’s wealth would have retired long ago, but he keeps a firm grasp on WWE to this day mainly because he would rather keep performing his job than anything else in the world.

To his employees, this means every decision Vince makes is genuinely what he believes will be best for business, and even if he’s wrong about this sometimes, it’s the sort of quality a boss wants to possess.

11 BAD BOSS: Insulting Tiger Ali Singh’s Heritage

Bad as many of the items on this half of the list are, none of them border on illegal employment practices. Not so for this next one, which might have had the Equal Employment Opportunity Commission interested were there more concrete information. Truth be told, all there is to document this are repeat stories told by Patrice O’Neal, a legendary standup comedian who briefly wrote for WWE in the year 2000.

O’Neal did, however, tell this story to Triple H, who treated it like it was wholly believable. Backing up a bit, we’re talking about an incident O’Neal oversaw between Vince McMahon and Tiger Ali Singh, a wrestler/manager who worked for the company around the same time as Patrice. According to the comic, Singh was very upset about being forced to wear a turban as part of his gimmick, calling it offensive to his family and heritage. Coldly, McMahon ignores Singh’s heartfelt complaints and told him to “shut up and put on the turban.”

10 GREAT BOSS: Buying Bob Holly A Racecar

On very rare occasions, there can actually be an upside to a wrestler getting saddled with an outrageously stupid gimmick. Just ask Bob Holly, originally known as Thurman “Sparky” Plugg, wrestler/NASCAR wannabe. Initially, it looked like this was the sort of career killer that would make Holly hopeless, yet he somehow persevered for over a decade as a regular name in the WWE midcard. In addition to the job security, Vince McMahon gave Holly one heck of a bonus when he switched names. Up until that point, Holly had also been driving a WWE stock car at small time races, with McMahon paying for his car and team management.

Unfortunately, much like Sparky’s gimmick in general, this didn’t exactly bring in any money, and WWE was bleeding resources at the time, so the idea had to be scrapped. However, there was still a race car in the mix that the company now had nothing to do with, so McMahon gifted it to Holly.

9 BAD BOSS: Refusing To Pay For Health Insurance

With how outrageously physical their profession can be, one might expect professional wrestlers need health insurance more than anyone else. Unfortunately, this is one area where Vince McMahon and WWE have always been lacking. Using a legal loophole and qualifying wrestlers as “independent contractors” rather than full-time employees, the company has never once offered wrestlers health insurance. In fairness, it isn’t all bad, as they are covered during any in-ring accidents, and Vince has been rather generous when it comes to taking care of wrestlers who can no longer perform as a result of them.

However, if a wrestler gets sick or develops a chronic ailment, let alone just suffers a muscle strain while training for their next match, it’s up to them to pay for the medical costs involved. Several wrestlers have attempted taking McMahon to court for this practice in the past, always to no avail, so chances are the standard won’t be changing any time soon.

8 GREAT BOSS: Showing Face In The Ring

This list has said plenty of bad things about Vince McMahon, and some of them may inspire readers to think about how they would give the WWE CEO what he’s got coming to him if they ever became pro wrestlers. Unlikely as that may be, the reality is that quite a few WWE superstars have actually don’t just that, getting face to face with their boss and running down everything wrong with his management style, live and in front of millions of fans, all inside one of McMahon’s rings.

Some of them even literally beat the man into submission, leaving their boss a bloody mess for transgressions real and imaged. Not everyone is quite so violent, but most people have wanted to get some sort of revenge on their boss for one thing or another and never had any recourse. That fear isn’t there with McMahon, because if his workers have a problem, he might just ask them to slap him in the face.

7 BAD BOSS: The Montrealer That Took Out The Hitman

Ironically, the Montreal all began when Vince McMahon made a generous offer he couldn’t deliver. At the time, Bret Hart was the biggest WWE superstar around, so McMahon did whatever it took to keep the Hitman on his team. This lead to a massive bidding war when Hart’s contract was up in 1996, with McMahon digging deep into his pockets to find the money to pay Bret. Unfortunately, Vince couldn’t afford it, so he eventually told Bret he couldn’t pay him, letting the Hitman leave for the greener pastures of Ted Turner’s rising company. There was only one problem in that Bret was the WWE Champion by this point.

Vince wanted him to lose the gold this against Shawn Michaels at Survivor Series, but Bret refused, which was allowed due to Vince’s conceits in his last contract negotiations. In order to get his way, Vince broke the agreed upon ending, walking down to the ring and “screwing” Bret Hart into losing the title anyway.

6 GREAT BOSS: Giving Everyone A WrestleMania Payday

Thanks to who wins them, wrestling fans have a number of reasons to complain about the annual Andre the Giant Memorial Battle and recent female equivalents at WrestleMania. It doesn’t help that the matches are pretty much impossible to follow, with fans only able to notice slight flashes of action between random superstars at best. However, there’s a huge plus side for every wrestler in the matches, as they’re get their biggest payday of the year in front of larger crowds than most of them get to entertain.

Before coming up with a way to get 50 wrestlers on the card in two matches, McMahon would devise six-to-ten person tag team matches to ensure all of the talent he cared about would feature on the big show and reap the greatest rewards he can offer. Most bosses would only give bonuses like this to the biggest names on the card, but with Vince, the whole point is making sure everyone gets a shot to shine.

5 BAD BOSS: Ignoring The Audience

Technically speaking, this next issue doesn’t necessarily make Vince McMahon a terrible boss, but it does make him a questionable business owner. Obviously, his skills in this regard effect the ultimate fate of everyone in his company, so this is nonetheless an extremely important issue to the WWE superstars. When McMahon and his writers ignore a particular wrestler receiving a great deal of applause or the right kind of boos, every single wrestler is losing out on the money they could bring the company.

This problem has run especially rampant in recent years, with McMahon occasionally doing the exact opposite of what the crowd wants to see, on the Grandest Stages of Them All no less, just to prove he’s still in charge of his WWE Universe. It’s for this reason WWE fans are giving up on the promotion in droves, seen through dropping ticket sales, Pay-Per-View buy rates, and TV ratings, all of which is reflected in wrestler bank accounts.

4 GREAT BOSS: Forgiving Virtually Every Transgression

Depending on what a person does for a living, upsetting their boss in the smallest way could easily lead to getting blackballed from the entire industry. For this reason, people occasionally walk on eggshells around executives, and even watch their every action on social media, just in case the wrong person should happen to see it. The superstars of the WWE Universe definitely don’t have this problem, as Vince McMahon is surprisingly perhaps the most forgiving businessman on the planet.

Former wrestlers have openly attempted to drive WWE out of business, slandering McMahon and his company while supporting his rivals, only to later turn around and accept an induction to the WWE Hall of Fame with a big smile and a bigger hug. For examples, look no further than icons like Hulk Hogan, The Ultimate Warrior, and Bruno Sammartino. It seems there’s truly nothing a wrestler could do that McMahon would find unforgivable, with even his greatest enemies inevitably making comebacks in one way or another.

3 BAD BOSS: Forcing Owen Hart To Do Questionable Stunts

In all fairness, it’s a massive stretch to suggest that Vince McMahon killed Owen Hart. However, there’s also no denying Vince McMahon is the one who demanded Owen Hart do something that directly led to his untimely death. The event in question took place live on Pay-Per-View at Over the Edge 1999, when Hart, dressed as superhero The Blue Blazer, was supposed to “fly” to the ring from the rafters, only for the stunt to go horribly wrong. Owen’s release harness immediately malfunctioned, causing him to drop hundreds of feat to the ground, landing chest first into the turnbuckle.

Had it been up to Hart, the stunt never would have happened, as reports claimed he was extremely nervous about the idea, fearing this would happen.

Obviously, McMahon was aware his employee didn’t want to do something so risky, and he himself also knew there was a chance, no matter how small, it could backfire, and yet he forced Owen to do it anyway.

2 GREAT BOSS: Paying For Former Employees 

For far too long now, there has been a horrifying trend in the pro wrestling industry that sees former performers experience personal struggles that gradually destroys their lives. Obviously, Vince McMahon can’t be blamed for this in any way, but he could be deemed complicit if he didn’t do anything about it. Perhaps to deflect such criticism, or maybe just out of the kindness of his heart, Vince has made a practice of offering any past employee company sponsored rehab if they feel their problems are getting out of control. Some names like Road Dogg or X-Pac only take Vince up on this once or twice, while Scott Hall has gone through the program more times than any of his buddies combined to mixed results, and yet Vince is still completely willing to keep paying for his effort to get clean. Countless others have also gone down this same path, with Vince’s money legitimately saving their lives.

1 BAD BOSS: The Original Screwjob Was Worse Than Montreal

Ultimately, the Montreal Screwjob will always be the most famous of Vince McMahon’s double crosses for the names and talent involved, not to mention the far ranging effects it had. However, there was another similar incident about 12 years earlier that painted Vince McMahon in an even less flattering light. To this day, there’s some confusion about what exactly happened to make McMahon furious with Wendi Richter, by far the most popular female superstar of her day and WWE Women’s Champion at the point this incident took place.

Whatever the reason, McMahon decided Richter had to lose her title immediately, and rather than talk it out with the woman, he simply had The Fabulous Moolah wear a mask and legitimately attack her during a match. Richter was so furious she wouldn’t talk to Moolah for years, and she understandably left the company, which was McMahon’s intended result. Of course, he could’ve just fired her like a normal boss, and saved everyone the stress.

Sources: Vice, Sky Sports, Sports Illustrated, IW Nerd, Bleacher Report, Mandatory, Wrestling, Inc.

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