8 Times Vince McMahon Was A Jerk To His Employees (And 7 Times He Was Actually Nice)

For an athlete to become a success in the professional wrestling industry, it’s almost inevitable that Vince McMahon will be signing his or her paychecks for at least some portion of his or her career. As the owner of World Wrestling Entertainment, McMahon has been the top dog in wrestling, a status he has held since purchasing the company from his father. Depending on which employees one asks, McMahon has either been a great boss or an absolute nightmare to work for, and it seems like both of these perceptions are at times accurate.

When cameras are rolling, it’s hard to imagine anyone actually wanting to work for the insane madman, giving no chance in hell to those who cross him. While real life isn’t quite the same as what happens inside the ring, the best performers tend to base their characters on their true personalities, and McMahon truly is one of the finest in his own business. That isn’t to say he’s entirely bad, though, or incapable of basic human compassion. On many occasions, McMahon has spent his millions to help his current or past employees during hardships in their lives, and sometimes, he could even be considered generous for almost no reason whatsoever.

How exactly wrestlers make their way toward McMahon’s good side or bad side remains unclear. Unless one plans of becoming a wrestler, they’ll probably never know for sure, let alone completely understand the pros and cons of each side. All we can say for certain is at least two Vince McMahons exist, and only one of them sounds like someone we would ever want to work for. Keep reading to learn about 8 times Vince McMahon was a huge jerk to his employees, and 7 times he actually did something nice.

15 JERK BOSS: Creating The Kiss My Ass Club

For the most part, this list is going to ignore the many horrible things Vince McMahon has done to his employees inside the square circle. The truth is, no matter how offensive or inhumane some of his scripted actions have been, McMahon’s employees always consented to performing them. Sure, they could have lost their jobs should they've refused, but most of the time, merely working with McMahon directly is enough to convince wrestlers to do anything. That said, there are certain things absolutely no wants to see or be a part of under any circumstances, high amongst them joining the infamous Vince McMahon “Kiss My Ass” Club. Thus far, six unfortunate souls have become members by literally placing their lips on McMahon’s backside during the course of a WWE event -- William Regal, Jim Ross, Shawn Michaels, Shane McMahon, Mick Foley, and Hornswoggle. It doesn’t matter how loyal these employees were, if the ass kissing helped their careers, or what the specific technical details were; there’s no doubting none of these WWE personalities actually wanted to perform the deed their boss forced them to.

14 NICE BOSS: Paying For Surgeries, Med Bills, And Funerals

Legally speaking, any time a wrestler gets injured while working for WWE, the McMahon family is at least partially responsible financially for whatever medical costs result from said accident. However, issues related to former wrestlers experiencing pains and other bodily problems years after their retirement is more of a gray area. There’s no reason McMahon needs to pay the medical bills of people who haven’t worked for him in decades, and yet he’s done just that on more than one occasion. “Classy” Freddie Blassie, for example, was covered pretty much for life, with McMahon keeping him hospitalized and healthy long past retirement. Paul Bearer also received a similar gift when McMahon paid for his gastric bypass surgery, which may have extended his life several years. Then there are wrestlers like Bam Bam Bigelow, who passed away years after leaving WWE and on less than perfect terms, and this didn’t stop McMahon from paying for his funeral in full. As nice as this practice is, who exactly McMahon helps seems a little random, likely leaving the wrestlers he didn’t or doesn’t send aide to wondering what they did wrong.

13 JERK BOSS: Telling Debra To Keep Quiet

Very few WWE superstars have so much as come anywhere near the levels reached by “Stone Cold” Steve Austin. Austin was the biggest star of the Attitude Era, and Austin’s looming presence was responsible for WWE consistently defeating WCW in the ratings. With all this pressure on Austin’s back, his boss, Vince McMahon, did whatever it took to keep Stone Cold happy. If this entry is starting to look like it’s on the wrong half of the list, keep in mind Austin was a pretty horrible person behind the scenes, at this point, and allegedly beat his wife and fellow WWE superstar Debra on no less than three occasions. According to Mrs. Stone Cold in various interviews, Austin’s employers were fully aware of these incidents and asked her to wear makeup and hide the abuse whatever way possible in order to keep their cash cow safe. This is more than McMahon being a bad boss -- it’s him outright being a horrible human being, helping an abuser get away with his crimes for financial gain.

12 NICE BOSS: Taking Care Of The Guerrero Family

When Eddie Guerrero suddenly died in late 2005, the entire wrestling world was in a state of shock, including Vince McMahon. While certain members of the McMahon family have a tendency of thinking about tragedies solely in personal terms, Vince was able to think about the true victims in Guerrero’s shock demise, that being the family he left behind. Most glaringly, there was Eddie’s widow Vickie, along with two young girls who had to grow up without a father. Immediately after Guerrero passed away, McMahon reached out to his surviving family and offered a Hall of Fame induction, but that was hardly the end of this story. Knowing Eddie’s family would struggle financially without him around, McMahon also offered Vickie a long-term role in the company, one which quickly made her a pretty big star in her own right. Even if fans were booing the hell out of Vickie, she was making good money and celebrating Eddie’s history in a subtle way, something that probably never could have happened without McMahon giving her the idea.

11 JERK BOSS: Firing Dawn Marie While She Was Pregnant

Chances are, any of the employees who've taken Vince McMahon to court over the years would agree he wasn’t always a pleasure to call boss. Some of these bitter former superstars might not have the best reasons when sending him subpoenas, although a few of them most definitely had a case, including former ECW starlet Dawn Marie. Quite frankly, Marie was never that big a deal in the WWE Universe, almost entirely unable to revive the success she once had in ECW. Outside of a few strange feuds with Torrie Wilson and Jackie Gayda, it could be said Dawn didn’t really do much at all, which made it fairly routine when she was fired in 2005. That is, it would have been a relatively routine dismissal had she not been pregnant at the time, which made it totally illegal. Even looking beyond the fact that firing women for being pregnant has been against the law for a long time now, it kind of makes McMahon a huge jerk as he was taking away a woman’s livelihood right when she needed money the most.

10 NICE BOSS: Giving Bob Holly A Racecar

Upon first glance, Vince McMahon turning a man with a perfectly acceptable name like Bob Holly into the ridiculous Thurman “Sparky” Plugg was enough to land on the jerk half of this list. Holly himself probably knew this, and that’s why he requested the name eventually get changed to his real one. There was an upside, however, in the fact Holly had always been a fan of racecars, so the gimmick itself was never a problem to him. In fact, he loved getting to compete in actual racing events, not to mention simply riding around in the extremely fast WWE-sponsored car. Unfortunately for Holly, and McMahon, for that matter, WWE wasn’t as successful back in the mid-'90s as it is today, and the idea of a WWE racecar wasn’t one meant to last. McMahon still bought a racecar for the idea, though, and he didn’t exactly have anything to do with it when the idea died, so he simply let Holly have it. There’s no way to exactly quantify how much McMahon was giving Holly in this offer, but racecars don’t exactly come cheap, and it definitely beats the heck out of a low-level wrestler’s salary.

9 JERK BOSS: Pranking Jonathan Coachman

Pretty much since wrestling was invented, sports entertainers have been passing their spare time by playing pranks on one another. The trend has become so prevalent, the industry made its own word for it: ribbing, meaning to play some sort of painful practical joke on a coworker, or in Vince McMahon’s case, employee. Perhaps the meanest rib in history was enacted against Jonathan Coachman, and the highest branches of the WWE infrastructure were directly involved. Apparently, at McMahon’s order, top stooge Gerald Brisco first instructed Coach to start a small gambling pool, taking bets on football games. Mere weeks into the practice, real police came and arrested Coach for his illegal operation, and McMahon initially refused to bail him out despite being behind the ordeal. Shortly before arriving at the police station, the jig was up, as the cops brought Coach back to the arena, where McMahon and various wrestlers were all sharing a big laugh at his expense. While this might sound a little bit funny on paper, remember that Coach did absolutely nothing wrong, except listen to his boss, and wound up a crying mess afraid he was going to jail because of it.

8 NICE BOSS: Paying Alundra Blayze’s Tax Debts

Given the terms under which Alundra Blayze left the WWE Universe, many fans thought she would never be welcomed back. That theory was thrown out the window in 2015, however, when Blayze was surprisingly inducted into the WWE Hall of Fame. Perhaps, part of what made Vince McMahon so forgiving is that their relationship started with the two discovering a strong similarity in their problems with the IRS. While McMahon’s various tax problems always went away when it was revealed he actually was paying his taxes all along, Blayze wasn’t quite so lucky and managed to rack up a genuine $80,000 debt she had little chance of paying without years of hard work. Once she informed McMahon of this fact, plus the additional detail that her problem led to living out of a car, he was so sympathetic that he paid the bill in full without question. This story in mind, one really wonders how Blayze could ever double-cross him the way she did by tossing the WWE Women’s Championship into the trash on an episode of WCW Monday Nitro.

7 JERK BOSS: Getting In A Fight With Kofi Kingston

Fighting is fairly commonplace in professional wrestling, and that holds true behind the scenes almost as much as it does in the ring. Alright, maybe that’s a mild exaggeration, considering a good majority of wrestlers have managed to get by without experiencing any backstage tussles throughout their careers. It remains true, however, that plenty of wrestlers have taken things a little too seriously and gotten into real “shoot” fights when the cameras weren’t rolling, and that includes Vince McMahon against a fairly unlikely personality. According to Chris Jericho, McMahon randomly insulted Kofi Kingston one night, intentionally trying to goad him into a fight. Once Kingston took the bait and started arguing, McMahon tackled him to the ground, starting a legitimate contest. In most industries, a person’s boss going for a single leg takedown would be the basis for a lawsuit, even if single leg takedowns were what their business was all about. Presumably, it’s only because Kingston has few other places he could go work that he brushed this incident off so easily.

6 NICE BOSS: Partying With The Wrestlers

The flipside to Vince McMahon occasionally getting down and dirty with his wrestlers by tackling them to the ground is that on even rarer occasions, he’ll get down and dirty with the boys by painting the town red. According to Bret Hart and several others, back in the 1980s, when the golden age of wrestling was at its peak, McMahon once joined his employees at an after-hours strip club and toasted his loyal employees to one hell of a night. Not only did McMahon get as wild as the rest of them, he eventually started demanding they all perform their finishing maneuvers on him, ending with a bombastic Hart Attack care of Hart and Jim Neidhart that nearly knocked him out. To some people, this might not sound like McMahon being a nice boss so much as a party animal with eccentric tendencies, and maybe that’s the case. However, enough people have experienced a horrible boss with no sense of fun that stories like this humanize McMahon and make him seem more relatable, and that probably went tenfold for all of the wrestlers in attendance that fateful night.

5 JERK BOSS: Mocking Tiger Ali Singh

There’s no behavior more deserving of the “jerk” moniker than unadulterated racism, and unfortunately, the wrestling industry is loaded with this sort of behavior. Part of the problem is that gimmicks have existed for decades mocking wrestlers for having anything unique in their personality, which for Tiger Ali Singh was his Indian heritage. Of course, Vince McMahon didn’t understand much about the Indian heritage, and thus, the turban Singh wore as part of his gimmick turned into a source of mockery rather than one of pride. According to comedian Patrice O'Neal, who briefly worked for WWE in the late ‘90s, Singh would regularly beg McMahon to either stop making fun of the turban or remove it from his character entirely, which McMahon always replied to with cold looks and angry statements, such as “Wear the f---ing turban.” In all fairness, Tiger Ali Singh was never exactly an important wrestler, and his industry reputation isn’t the best, regardless of this story. That said, Oneal was hardly Singh’s friend; he was simply a person in the room at the time this happened, and thus, it can be reasonably assumed he was telling the truth about this incident.

4 NICE BOSS: Letting Mick Foley (And Others) Retire Gracefully

Considering the things certain pro wrestlers do in order to entertain the public, some people have questioned whether or not Vince McMahon should feel responsible when they retire early or wind up hurt. This list already covered the fact McMahon often pays for these problems, but we also mentioned he sometimes has to, making it less noble and more of a legal issue. In certain cases, though, McMahon had the law entirely on his side to force wrestlers into hurting themselves further, and he never took that option. Take for example Mick Foley, who decided at 33 that he had put his body through enough and needed to leave WWE behind. McMahon could have pointed to Foley’s contract and made him keep wrestling or convinced him to work though the pain, but instead, he respectfully told Foley he had wrestled his last match the first time he so much as complained about maybe needing to retire early. In addition to Foley’s story, there have no doubt been countless other wrestlers who walked away from WWE gracefully because they felt they could no longer compete, and McMahon never did anything to force them into staying, so long as he truly felt they deserved to step away.

3 JERK BOSS: Firing CM Punk On His Wedding Day

They say a person’s wedding should be one of the best moments in one's life, and that’s no different for professional wrestlers. Male or female, no matter how tough a WWE superstar is in the ring, there’s always a softer side he or she can exhibit around friends and loved ones, and no one day is more filled with friendly love than an individual’s wedding -- unless, of course, some bitter vindictive soul does something to take the joy out of the experience, which is what Vince McMahon did to CM Punk and AJ Lee the morning of their betrothal. Granted, Punk had recently walked out on WWE under pretty negative terms, but he still had a contract with the company that he fully planned on renewing after recharging his batteries and taking time off to be with his bride. However, instead of giving Punk this opportunity, McMahon waited until the day of his nuptials and faxed over termination papers, doing his best to ruin the happiest moment of Punk’s life, or so it seems. Although McMahon himself later claimed it was an unfortunate coincidence, Punk rejects that possibility, and we find ourselves siding with the Voice of the Voiceless on this one.

2 NICE BOSS: Offering To Pay For Everyone’s Rehab

One element of the wrestling industry Vince McMahon doesn’t necessarily deserve the blame for is the high mortality rate that has been increasing at a terrifying rate. For whatever reason, pro wrestlers have proven more prone to drug and alcohol abuse than nearly any other industry, not to mention the constant toil the sport puts on their bodies, leading to a mortality rate significantly above the national average. As the top name in sports entertainment, Vince McMahon needed to make a statement about this trend, and he finally did shortly after the death of Andrew “Test” Martin in 2009. In an open letter to more than 500 former WWE employees, McMahon presented a free offer to pay for any drug and alcohol rehab services retired or struggling wrestlers might need help with. Fans will probably never know exactly how many wrestlers took him up on this offer, let alone which ones, and yet it’s almost a certainty that letter saved some lives. McMahon can thus probably be considered to be a true lifesaver, so long as his old employees are willing to ask for his assistance.

1 JERK BOSS: Everything He’s Ever Done To Jim Ross

Ultimately, whether a WWE superstar views Vince McMahon as a good boss or not is probably a personal decision. Even the wrestlers who find themselves hating McMahon’s guts on their own death bed probably profited from him in some way, and their families and fans might feel that was enough to make it all worthwhile. After all, if a person as talented and respected as Jim Ross was able to put up with the worst treatment of any WWE employee in history and keep coming back to the company in his 60s, working for McMahon can’t be that bad. Think about the things McMahon has done to him over the years. In addition to joining the aforementioned Kiss My Ass club, JR has been mocked and insulted at every opportunity possible, including whenever he experiences real-life medical problems, and he almost never gets a genuine onscreen comeuppance. The only thing JR did to deserve this behavior is being better at his announcing job than McMahon ever was, not to mention how he managed to earn a fonder place in the average fan’s heart than anyone in Vince’s family.

Sources: WWE

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