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15 Shameful WWE Moments Vince McMahon Probably Regrets

The reality of making a list about how many shameful moments have come from the tenure of Vince McMahon as owner and chairman of the WWE is that there simply aren't enough spots to list how many despicable things McMahon has done. It didn't take long to find 15 underhanded things that "Mr. McMahon" did to either his family, his employees or to society in general. The fact that we left off items like wrestling his own daughter, potentially covering up a murder for one of his employees, falsely claiming he offers a fair opportunity to every individual in his company or having his staff do some of his dirty work is a testament to how shameful the items that did make this list are.

Vince has screwed over so many people on his way to the top that some might believe there is a special place in hell waiting for him. Others believe that nothing Vince has done is outside the bounds of business or the drive to make his company the most successful sports entertainment company on the planet. Those people would likely argue that all is fair in love, war and television ratings. No matter what side of the fence you sit on in this debate, what can't be denied is that Vince McMahon has lived a very interesting life. You can't possibly call him boring or a procrastinator. He'll try anything if he thinks it will work.

Here is a list of 15 Shameful WWE Moments Vince Probably Regrets.

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17 Faxing CM Punk His Termination On Punk's Wedding Day

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When CM Punk left the WWE, it was kind of a jerk move on behalf of Punk who literally just grabbed his ball and went home. He was unhappy with the direction his character was headed and claimed the WWE was forcing him to work in conditions that were unhealthy for him due to injury. Because of this he decided to basically leave the company without notice.

Unhappy that Punk had abandoned his job, Vince decided to terminate Punk's contract. Fair enough. But, it was still pretty low that Vince decided to facsimile the termination papers to Punk on his wedding day. Punk was marrying AJ Lee the day he got his official release from the WWE. McMahon claims it was all a lack of communication, but that seems too big a coincidence not to be intentional. There are 364 other days in a year and Vince just happened to choose Punk's wedding day. Vince said on Steve Austin's podcast he regrets doing it, but does he?

16 Screwing Over Bret Hart

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Some will suggest Bret Hart got what he had coming to him. Refusing to do a job you're paid quite well to do simply because you believe losing your title in Canada before you leave for the competition isn't classy is a good way to upset the boss. Bret Hart did just that when his big ego and sense of pride clashed with The Chairman's authority. That said, two wrongs don't make a right.

After Vince saw that Bret wasn't willing to do "business", Vince and Shawn Michaels would force him to do business and cheated him out of the WWE Title by changing the match finish in a scandal now known as the "Montreal Screw-job". They lied to Bret about the ending of the match and on a live pay-per-view sent him packing to WCW looking like a fool. Bret then went on to flounder in WCW until he took an errant Goldberg kick to the head which ended his career. That Bret's career ended so poorly probably makes Vince feel at least a little guilty.

15 Starting the XFL

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Vince determined that the NFL needed some competition and that the United States was sorely missing a football league that would offer what the NFL didn't. In an effort to take over the sporting world, McMahon teamed with NBC to create the XFL. The XFL was probably the worst idea in sporting history. While the initial weekend of football action actually found itself some viewers, the talent was second-rate, the rules were wonky and Vince couldn't help but inject his WWE Superstars into the football broadcasts. It failed miserably and likely cost McMahon millions of dollars. Nobody can lose ten of millions of dollars and not regret it. His foray into football made him the laughing stock of the sporting world for quite some time and in the end he only proved that nothing can compete with the NFL, not even Vince McMahon.

14 Starting His Exclusive Club

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In an effort to continually get him over as the top heel in the company, Vince decided the most disturbing and abusive show of power a boss could use on an employee would be to make them literally kiss his backside. Thinking this idea was hilarious, Mr. McMahon had people do it over and over again on WWE programming.

Vince did everything in his power to make people grovel on their knees and if he wanted to really punish them, he made them not just kiss his buttocks, but he would pull his pants down to expose his skin and have them do it the hard way. He did this to his enemies, his friends and just regular employees looking to not lose their jobs. Perhaps as a one time segment it would have been tolerable, but to do it as often as they did, it came across as power-hungry and pathetic. It was like Vince was living out a real life fantasy of people having to kiss his butt and it was pretty low to ask your employees (let alone anyone) to do that.

13 Making Out In Front of His Wife

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There was a time in the WWE when Vince McMahon used any excuse he could think of to make-out with or fondle the Divas of the roster. In other interviews, Vince actually admitted to his infidelity to his wife Linda McMahon, and it shouldn't come as a shock if it were ever revealed he'd been cheating on Linda with the current talent at the time.

The lowest of the low was an angle in which Linda was to play an emotionally scarred wife and recent victim of a stroke that had confined her to a wheelchair. While she was unable to do anything but sit there and watch, Vince started to make-out with Trish Stratus.  It was pointless and likely a low point in the lives of both Linda and Trish. But, Vince being Vince, found a way to work the disgusting tonsil hockey into a storyline. If Vince had any conscience, he'd feel bad for making his wife sit through that.

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11 Approving the Katie Vick Storyline

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The WWE has moved ahead on some pretty classless storylines in their day. Among the worst is the angle that saw Triple H molest a corpse by the name of Katie Vick. Whatever would have possessed Vince to approve an idea where he lets Kane and Triple H (two of the WWE's biggest stars) sink so low in their background story is still baffling. While the terrorist story of Muhammed Hassan and the idea of Mae Young giving birth to a hand were both tasteless, this idea was the worst.

At the time, WWE was in the midst of the Attitude Era and pretty much anything was fair game in the name of shocking television. There were just too many good people involved for this idea to have made it as far as it did. The minute someone suggested it Vince should have shut it down but he didn't. In fact, he probably loved the idea!

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10 Threatening Bob Costas

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During Vince's struggle to make the XFL a legitimate alternative to the NFL brand, McMahon took on an interview with Bob Costas on his show On the Record. Costas was always a wrestling fan, but he wasn't fond of how Vince was trying to dabble into football with a low-brow product in much the same way that Vince's WWE product had gone after shock value and low-brow antics.

After being called out on the show about the WWE's level of class and the colossal failures of the XFL, Vince became angry. So much so, he leaned forward in his chair, poked Costas in the chest and began berating Costas to which he didn't budge or bend. It was a terrible look for Vince who came across as a bully and Costas got the better of him that day in many ways. Vince surely regrets letting someone make him look foolish on national television.

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8 Creating the Death Storyline

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Not only was it probably in bad taste to create a storyline that revolved around Vince McMahon exploding in a limousine, his timing couldn't have been worse. The idea was that Vince was depressed and after a Raw Appreciation Night that did more to show he was disliked than appreciated, he entered a limo, closed the door and it exploded. The crazy part was, WWE played it off like a legit newsworthy item.

Some news outlets reported it as real, stock values fell and WWE Headquarters were inundated with calls and letters. Where it went off the rails was when WWE held a tribute show to Vince, much like they'd done for actually deceased wrestlers. They went so far as to give a ten-bell salute, which was completely inappropriate. When Chris Benoit actually died in the middle of the storyline, it was immediately dropped and everyone felt like this was a "you should have known better" situation.

7 Heavily Involved In The Steroid Scandal

via fightnetwork.com

During the late 80's and early 90's, Vince was in the middle of a nasty steroid allegation that almost brought him down from his pedestal as king of the wrestling world. McMahon was charged by a U.S. Attorney for routinely obtaining anabolic steroids for employees and wrestlers, even going so far as to hire a doctor out of Pennsylvania who would prescribe shipments of steroids to be delivered to the WWE Headquarters in Stamford, Connecticut.

The only thing that saved McMahon from serving time in Federal Prison was a series of sloppy legal mistakes and shady witness testimonies. McMahon was acquitted of all charges but it seemed pretty clear he was guilty after guys like Hulk Hogan lost a ton of size immediately following the scandal. Most are certain the WWE covered up evidence that would have put McMahon away for a long time. There's no way he regrets getting away with it, but do you think he regrets getting involved?

6 Approving Undertaker's Loss At WrestleMania

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You'd probably be hard-pressed to get Vince McMahon to admit it, and he may never, but to approve the Undertaker losing at WrestleMania was a mistake. In one of the most shocking moments in WWE history, a then undefeated Undertaker took on Brock Lesnar and lost. Up to that point, Taker had never lost at WrestleMania and he was set to be remembered as the greatest WrestleMania icon, setting a record no one would ever touch.

Instead of letting The Undertaker hold that record and leave it as part of his legacy, McMahon decided to promote Brock Lesnar, a UFC fighter who didn't need the win to be considered tough, and who is a part-time employee that really couldn't and wouldn't give back to the WWE in a way The Undertaker did.

5 Becoming WWE Champion

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The one thing that the WWE should never do is give a title to a character or talent who takes away from its prestige. WCW did it with David Arquette and although the WWE swore it would never stoop that low, they eventually put the title around the waist of The Chairman. In a smart reversal, Vince took the title off of himself the next week.

By giving the title to a manager, owner, GM or announcer, you're basically saying all the hard work the wrestlers do is meaningless. The belt is merely a means to entertain the crowd and if the WWE thinks that giving a non-wrestler the belt is entertaining, they'll do it. Because the WWE is all about entertainment, there is value in this logic, but it's probably an uncomfortable position to be in for wrestlers who work their entire careers to hold the WWE Title.

4 Chris Benoit Tribute Show

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When Chris Benoit died, he took a wife and son with him. It was a mess and to this day is still considered one of the lowest and saddest points in WWE history. The issue here was that before McMahon realized what had happened or how the Benoit family perished (Benoit killed everyone including himself), the WWE held a tribute show for Benoit to recognize his legacy and fondly remember him as a part of the WWE family.

Once McMahon realized what had actually occurred there was no going back. The closest thing he could do was erase all references to Benoit from all videos, marketing material and library footage and try to distance the company from the disaster that was the circumstances surrounding three deaths. It was a quick decision to hold a tribute show before they'd learned about what the investigation would have uncovered. They moved much too soon, and haven't been able to fully recover since.

3 Dropping the N-Word

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In what was meant to be a moment of comic relief between John Cena and Vince McMahon, McMahon was trying desperately to be a part of the "cool" C-Nation and talk like a thug might (this was at a time Cena was known as the Doctor of Thuganomics). Vince actually decided to say, on air mind you, "what's up my n****?" to which Cena gave him a crazy look and a shocked Booker-T (who overheard the conversation) responded with "tell me he just didn't say that".

Vince will defend his actions calling it television and acting and no worse than someone who might say something in a movie. The reality however is that it wasn't appropriate, it wasn't funny and the WWE ended up firing Hulk Hogan for a similar use of the word many years later. In retrospect, it's not something Vince would probably do again.

2 Fighting God

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Vince decided in his infinite wisdom that after bringing back Shawn Michaels (who in his time away had become a born-again Christian), Vince would get some cheap heat as the heel and poke fun at Michael's new religious beliefs. Wanting to prove that Michaels faith had nothing to do with his success, McMahon challenged Michaels and his tag partner "God" to face Vince and Shane McMahon at Backlash in 2006.

You don't have to be religious to feel like this storyline was merely brought about as a way to gain easy media attention and provide shock value to the product at the time. They went to churches to shoot footage and likely alienated much of the WWE audience who were religious. Michaels had to have been slightly uncomfortable despite knowing McMahon was not being serious.

1 Owen Hart Tragedy

via whatculture.com

There is some debate as to why and how Owen Hart got into a position where he was going to rappel from the ceiling in his Blue Blazer costume, but it was a last minute decision and by most accounts, Owen wasn't completely comfortable with the stunt. They were using a quick release harness and Owen accidentally released the trigger sending him falling to his death in the middle of a pay per view.

It was tragic, but it left the WWE and Vince McMahon with a difficult decision. Do they continue on with the show or cancel it due to Owen's passing? After a brief pause, they chose to venture on even though the crowd was stunned, the wrestlers were clearly distracted and in hindsight, it was probably the wrong decision to make. Owen's family didn't appreciate what they felt was a total lack of respect.

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