There is nobody who has been as consistently interesting, irritating and maddeningly unapologetic for the last 30 years in wrestling than Vince McMahon. You can point to The Undertaker or Hulk Hogan, but for anybody who has grown up on WWE programming, Vince McMahon has been the glue that holds the WWE Universe together. He’s always been there. Despite sometimes drawing our ire, he’s a constant and one of few we can count on.
McMahon is a proud man. It’s easy to see why he gets along so well with Donald Trump in that aspect. Neither like to look stupid and in instances that they should, they will somehow sell that they are fine with the situation or it isn’t as bad as presented. Psychologists would called this a defense mechanism and when discussing WWE publicly, McMahon uses them as deftly as anybody we’ve seen. He also knows how to use them when talking about things that are out of his hands, presenting himself as a victim.
It’s hard to point to very much WWE programming Vince doesn’t stand proudly behind, no matter how crass and innapproriate the audience or society at large would judge it. He has done more demeaning things to people and had them done to him as the Mr. McMahon character than we can count and while many were stupid, few crossed the imaginary line Vince has drawn for himself.
Vince McMahon doesn’t want you to know about his mistakes. He doesn’t want you to know when he made the obviously wrong call. He’s not always at fault and sometimes he is a victim of circumstance, but he’s also made bad choices on his own, sometimes even doubling down to make them worse. Whatever the situation, there are plenty of things he’d like us to forget. Thankfully, we have photographic proof to the contrary. Here are 15 photos Vince McMahon wished didn't exist.
18 Gridiron Goof
A major press conference announcement that would change the face of sports forever was announced on WWE programming leaving most thinking it was just another Vince McMahon stunt. It was, but it was on a level nobody could imagine. McMahon decided to create a football league, the XFL, to compete with the NFL during their off-season. In typical WWE fashion, there were some modifications to the presentation. Players could put whatever name they wanted on the back of their jersey, with “He Hate Me” probably the most notable. A larger emphasis was placed on the cheerleaders because it was the “Sex Sells” Attitude Era. Coaches on the sidelines were harassed and almost needled by sideline reporters during the games. Jesse Ventura and Jim Ross were your main announce crew while guys like Brian Bosworth and Matt Vasgersian made up the other commentator teams. McMahon knew he’d lose money, but he simply lost too much in year one, with estimates between $35 and $50 million. Ratings were also abysmal. In fairness, the league gave many fringe players another look by the NFL. Tommy Maddox led the Pittsburgh Steelers into the playoffs one year after regular quarterback Kordell Stewart went down with injury. That never would have happened without the XFL.
17 First Diva, Second Adult star
Tammy “Sunny” Sytch changed the landscape for women in the WWE in ways that only The Fabulous Moolah and the Four Horsewomen could claim. She ushered in the era of the diva. Wrestling valets had been around for decades, but they had never been hard sold on their sex appeal. In the early days of the Internet, Sytch’s bikini photos were the most downloaded on the America Online service. Ironically, she turned down an offer to pose in Playboy that went to Sable. Then it all went bad. Sytch got into the painkillers and her life has been an ever downward slope since. Rock bottom may be the contract she signed with adult film producer Vivid to appear as herself in multiple movies. She also has been reported to do one-on-one sessions via Skype. She is the only person who WWE stopped sending to rehab again and again after both bad-mouthing the company and being arrest a half dozen times. Sytch has also done dirty website videos with Missy Hyatt, has spent some time in jail and her name is one that is rarely mentioned by WWE. And if you're scoring at home, Chyna was the first mainstream adult star.
16 His Failed New York Restaurant
Let’s start with the things Vince McMahon isn’t good at, which appears to be just anything he puts his hands on that doesn’t take place in a 20-foot by 20-foot ring. In the late ‘80s and early ‘90s, Times Square in New York City went from a seedy place with adult theater after adult theater to a corporate marketer’s Valhalla. Hoping to get in on the action, McMahon took over a corner for his WWE-themed restaurant, The World. Like Hard Rock Cafe or Planet Hollywood, you went for the name and the stuff on the wall, not the overpriced food. Despite its prime location, non-stop promotion on WWE’s Sunday Night Heat show on USA Network and near constant autograph signings, the restaurant simply couldn’t make money and the losses in trade for the visibility weren’t a fair trade-off. Ironically, Hard Rock Cafe took over the location when The World went under.
15 That Whole Katie Vick Thing
You can tell when Vince McMahon recognizes he’s gone too far with a storyline because it disappears and is never mentioned again. While he loves crass and over-the-top storylines, the Katie Vick one is taboo to talk about in the halls of Titan Tower. In a nutshell, Triple H and Kane were feuding and to make Kane feel bad, Triple H told the world the story of Katie Vick, the girl Kane murdered in a drunk driving accident. Technically manslaughter, but whatever. Kane tried to tell his side of the story, but the next week, in the one of the most darkly strange vignettes ever, Triple H - wearing a Kane mask at the time - was in a funeral parlor, standing over an open casket. Inside was a mannequin, meant to represent Katie Vick. Triple H climbed on top of the casket and started dry-humping it, as if to say Kane liked to have sex with dead people. Somebody pulled the plug the following week and we never heard of Katie Vick again.
14 Bad Guy at a Sad Time
We’ve all said and done things that were not intentionally our fault and technically aren’t even that bad. You leave a plant outside overnight and then it snows, you go through a carwash with your sunroof cracked open or you walk into somebody in a public bathroom who forgot to lock their stall. You forget about it until you’re reminded and when you’re reminded, you look back with more regret it happened than you did at the time. This photo was taken just a couple of minutes after Owen Hart’s funeral. We’ll assume McMahon is trying to be consoling here, but it turns out he’s being consoling to a guy who not too long after would commit double murder and suicide. Chris Benoit was a close friend of Hart and we’re guessing this was probably a tender moment between two men who rarely are/were. Unfortunately all of these years later, it’s not a photograph of a candid moment of emotion. It’s Vince McMahon and a murderer.
13 Linda is a Loser
Vince McMahon always talks about how he only wants to surround himself with winners, yet his wife is a two-time loser for a U.S. Senate seat in Congress, having wasted millions of dollars of their own money on a pair of failed campaigns. In political circles her name popped up again as someone who might be considered for the Department of Commerce Secretary position in Donald Trump’s cabinet, but that went nowhere. Vince McMahon is a smart businessman who keeps out of politics. Despite Trump being a Hall-of-Famer, that was never mentioned on television during the presidential campaign. Business and politics not mixing seems to be one of McMahon’s rules. Linda broke it in a big way and ended up with nothing to show for it. During one of her concession speeches, at a time when the family is usually standing directly behind the losing candidate, you can see Shane and Stephanie, but missing is Vince, who is on the far end of the stage and has a pained look on his face when Linda mentions him. Mr. WWE is a loser by association.
12 It’s Only Degrading If It’s Real... Right?
We’ve already mentioned Linda McMahon’s failed bid for a U.S. Senate seat. During her face race, the dirt opponents always dig up was centered around the WWE and it’s Attitude Era storylines. The one that kept coming up again and again was when Vince McMahon forced Trish Stratus to strip down to her thong and panties in the middle of the ring and walking around like a dog on her hands and knees barking for Vince McMahon. Now, as bad as this is within the context of an episode of Monday Night Raw, imagine how it looks as an isolated five second clip in a campaign commercial. Since Linda was the CEO of the company at the time, the argument made was if she’d allow her company to present something like this, what might she do when she was one of the most powerful people in the country? The WWE-bashing eased in her second race since WWE returned to its family friendly roots.
11 No Quads For You
Vince McMahon is often referred to as a man who wouldn’t ask anybody to do anything he wouldn’t do himself. It’s an honorable trait for a boss to have and when Vince started wrestling in his late 40s and early 50s, it was not surprising he put on some decently physical matches, including street fights and even a Hell in a Cell. Ironically enough, despite the beating he'd get, he never came out with any serious injuries, but he did manage to tear both of his quads during the 2005 Royal Rumble. How? Walking to the ring. Everybody loves the Vince strut, but it was what did him in at the end. He was supposed to come to the ring and lay down the law, but he crawled into the ring gingerly and was forced to sit, supported by the ropes while he made his ruling. Sitting down to chide people loses a lot of its intended drama.
9 Happy Moment, Bad Memories
Vince McMahon is obviously joyful in this photo, having just won his heavily-covered by the media trial on accusation of supplying his wrestlers and requiring them to take anabolic steroids. There really wasn’t much to the allegations. The defense didn’t even put up a defense since the prosecution presented witness after witness who were either bitter ex-employees like the guy who played “Nailz” a character who was a convict and little more than a foil for the Big Boss Man or ex-employees who didn’t have an axe to grind. The highest profile of the latter group was Hulk Hogan, who testified McMahon never gave nor forced him to take steroids. It was a big deal because Hogan had gone on The Arsenio Hall Show and said he never was on the juice. Some people don’t know behind the scenes, Vince had a backup plan where Jerry Jarrett would have played a big role in running the then-WWF had McMahon been forced into a prison sentence. Yes, it’s a good thing he was acquitted of all charges and this photo proves it, but it’s from a dark time in McMahon’s life that he never goes on record about.
8 Losing His Cool For No Reason
The day Daniel Bryan retired was well documented and seems like a generally maudlin day for not only WWE fans but also everybody who worked backstage with WWE. Bryan gave a slightly rambling, but very heartfelt speech at the end of that night’s episode of Monday Night Raw, even if he didn’t want to. As is customary when a giant event like that happens, the entire crew of wrestlers came out to the entrance era to show their respect and applaud along with the crowd. McMahon usually enters the ring and raises the hand of whomever is being recognized. Everything was going according to plan, but on his way back to the dressing room, Vince McMahon was grabbed on the arm by Titus O’Neill. Why? It’s not clear, although it looks like he’s just trying to get McMahon’s attention so he could say something. McMahon was incensed and backstage talk was that O’Neill was going to see a lengthy suspension for assaulting the boss. Cooler heads prevailed and maybe it was just the emotion of the moment, but we can’t think McMahon is proud of this moment.
6 Money Doesn’t Solve Problems
Somebody must have said, “Vince this is a bad idea. Nobody is going to care and things can go horribly wrong on live TV.” McMahon likely shot back, “This is the greatest idea since we gave away a house at In Your House!” That person said, “Yes, and an 11-year-old won it and we looked stupid giving a house in Florida to a kid from New York.” Vince said, “Yeah, it’ll be different this time!” That person, knowing Vince McMahon knew they couldn’t win. “Whatever Vince, it’s your money.” And there began the fiasco known as million-dollar mania by which Vince McMahon would call a WWE fan on live today and give away money, culminating with a big million-dollar giveaway. The gimmick never changed the ratings, but more embarassingly, it first showed Vince McMahon couldn’t dial a phone on live TV and when he could, people weren’t often home. Bad ideas on the drawing board and generally bad ideas in practice.
5 McMahon’s First Big Disaster
It’s not a secret Vince McMahon loves bodybuilding as much if not more than wrestling. Triple H has told stories of going into the gym at Titan Tower after midnight to find McMahon pumping iron and for a guy who is now 70, he still has the body of a man half his age. With Hulkamania allowing McMahon to almost print money, the then-WWF head honcho was looking to expand his reach and enter other industries. He thought bodybuilding was the next step because like wrestling, it was popular but had not reached the heights he believed it could. If he reinvented wrestling, why couldn’t he do the same with bodybuilding competitions? Mostly because they’re boring, but he didn’t know the rest of us thought that. He paid big money contracts for stars to leave the only major bodybuilding company at the time to join him. He gave them all gimmicks and introduced them in vignettes on WWE programming. One notable name fans recognized was Lex Luger, who was coming off his motorcycle accident injury. It didn’t help and all of the Ico-Pro in the world wasn’t going to save it.
3 Stand Back
You know, this may be something Vince McMahon is very proud of and we’re just hoping he has enough good sense to realize this was a big, big mistake he should burn the video footage. The then-WWF produced two albums in the 1980s that saw modest successes on the charts. Some wrestlers, like Koko B Ware had great voices. Others were little more than professional karaoke, but people ate it up. In one of his first times not playing strictly commentator, McMahon had a song on the second album called Stand Back. It was a ditty about a man overcoming the odds and not letting people hold him down - essentially his story. The big mistake came when the WWE hosted one of its first “Slammy” shows to promote the albums and WWE. Vince performed his song to a live crowd, complete with dancers. He danced too. Not silly, drawing heat dancing. Choreographed dancing meant to entertain. It didn’t help he was dressed like it was 1974. This was so bad it was awesome.
2 The Show Must Go On
It’s happened a few times and nothing is more tragic than when a professional wrestler dies in the ring. The most dramatic ever was Owen Hart. Playing his Blue Blazer character, Hart was supposed to be descended from the rafters in a goofy superhero entrance. His harness got detatched and he fell 30 feet, smacking a turnbuckle and dieing in front of a pay-per-view crowd and a visibly shaken Jim Ross and Jerry Lawler. Instead of cancelling the show then and there, McMahon made the call to continue. Considering the PPV audience and the logistics of refunds, not to mention the live crowd who still didn’t know Hart had died, most feel McMahon made the right call, but there will always be those people who say the boss made the wrong move. Whichever is right doesn’t matter. Wrestling lost one of its great entertainers that way in a tragedy McMahon probably doesn’t want to remember.
1 A Tribute to Evil
Chris Benoit was an amazing wrestler. We said it, now the Internet trolls can go away. After missing a PPV show, word started leaking into the WWE that Chris Benoit had been found dead at home along with his wife, best known as Woman or Nancy Sullivan to wrestling audiences, and his little boy. Details were sketchy the next day and during the afternoon on Monday, McMahon made the call to cancel Monday Night Raw - an episode ironically dealing with the fact he was probably dead after being blown up - and tell the live crowd to stay home. That episode opened with McMahon in the ring saying that a tribute would be held. It was interspersed with wrestlers paying personal tributes. Later that night and into Tuesday morning, the reality Benoit killed his wife and son and then committed suicide was apparent. McMahon appeared at the beginning of the live ECW TV show that night and mentioned Chris Benoit’s name for the last time on WWE programming. This isn’t embarrassing and with the knowledge he had of the situation at the time, McMahon probably did the right thing. He just doesn’t want to be reminded.
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