Vince McMahon's Bloodiest and Most Outrageous Moments in WWE Career

The Doctor Chris Mueller@@BR_DoctorFeatured ColumnistSeptember 16, 2017

Vince McMahon's Bloodiest and Most Outrageous Moments in WWE Career

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    Kevin Owens made the crucial mistake of attacking the boss.
    Kevin Owens made the crucial mistake of attacking the boss.Credit:

    People can say whatever they want about WWE chairman Vince McMahon's business practices and ethics, but nobody can deny how dedicated he is to his craft.

    This is a man who set out to be a promoter, not a wrestler. His job was to book the show, hire the talent and make sure the arena was full.

    The Montreal Screwjob changed everything for the McMahon family patriarch. He instantly turned himself into the biggest villain in the wrestling world by orchestrating the plan to force Bret Hart to drop the WWE title to Shawn Michaels before The Hitman departed for WCW in 1997.

    Instead of trying to hide backstage and hope everyone would forget about it, McMahon embraced his new status as a heel and became one of the most entertaining characters in the company.

    His trademark strut, gravelly voice, "you're fired" catchphrase and willingness to make a fool out of himself slowly turned his haters into fans. You don't let D-Generation X shove your face into Big Show's backside unless you are passionate about what you do, and the WWE Universe appreciates passion.

    McMahon has been involved in some of the most outrageous moments in WWE history, and some of them involved him leaving the arena covered in blood, like he did on Tuesday's SmackDown Live after Kevin Owens headbutted him.

    Let's take a trip down memory lane with McMahon's bloodiest and most outrageous moments.

Honorable Mentions

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    Trying to narrow down McMahon's top 10 bloodiest and wildest moments was difficult, and once the picks were made, there were still a few items deserving of inclusion.

    One thing McMahon has done plenty of in WWE is objectify women, but it was never worse than when he humiliated Trish Stratus by forcing her to do demeaning things as a way of getting back at his storyline ex-wife, Linda.

    She was made to bark like a dog and crawl around the ring in one of the more cringeworthy segments from this period, but she might not have minded that as much as having to kiss him on camera.

    Mr. McMahon didn't let his male employees off the hook, either. He has a club for people he forced to kiss his backside, and it's made up entirely of men.

    As far as bloody moments are concerned, Unforgiven 2006 has to be mentioned. By the end of the match, Vince, Shane McMahon, Big Show, Triple H and Shawn Michaels were all bleeding from cuts on their heads. It was gruesome.

The Montreal Screwjob

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    Screwing Hart out of the WWE Championship at Survivor Series 1997 forever changed the course of McMahon's company, his on-screen persona and the world of wrestling.

    Even 20 years later, this is still one of the most talked-about moments in the history of the industry. People who weren't even alive at the time know the tale.

    Hart was leaving WWE for rival promotion WCW, and he wanted to go without losing the title to Shawn Michaels. While McMahon may have agreed to these terms, he decided to make a different call.

    When Hart was locked in his own Sharpshooter by The Heartbreak Kid, McMahon set his plan in motion. The Hitman was in the process of reversing the hold when the chairman called for the bell.

    Hart quickly figured out what had happened and proceeded to spit in his former boss' face. From that point forward, McMahon was the company's most reviled heel, and he took the opportunity and ran with it.

    It's too bad nobody ever talks about how great the match was leading up to the end. It was, as Jim Ross would say, a slobberknocker.

    Since that fateful night, McMahon, Hart and Michaels have buried the hatchet and worked together on several occasions. Maybe time does heal all wounds. Emotional wounds, anyway.

WrestleMania 22

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    The Heartbreak Kid and Mr. McMahon have crossed paths as opponents several times, but their most brutal encounter took place at WrestleMania 22.

    The two had been embroiled in a personal feud for months. Vince used Triple H, Shane and The Spirit Squad to make HBK's life miserable.

    However, Michaels was able to get revenge. This was before the PG era and WWE's strict concussion-testing guidelines, so there was no shortage of shots to the head with various weapons.

    By the end of the encounter, McMahon was bleeding profusely and had been put through a table. HBK stood him up and told him to watch as he superkicked McMahon's teeth down his throat. It was awesome.

    Because of the violent nature of this bout, WWE has kept it off YouTube, but anyone with a WWE Network subscription can relive this bloody encounter anytime they want.

Faking His Own Death

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    When it comes to outrageous stunts, faking your own death is right up there with staging a Bigfoot sighting, but that didn't top Vinnie Mac from doing it.

    On June 11, 2007, McMahon was shown entering a limo a second before it exploded. even went as far as posting an update immediately following the show stating he was "presumed dead."

    The storyline only lasted two weeks because he was forced to make a statement on June 25 about the Benoit family tragedy in an empty arena, acknowledging the story of his own death as a hoax in the process. 

    The limo explosion looked somewhat convincing because you could see him lifting his foot into the car and shutting the door right before it blew up.

    However, a few small signs indicated the stunt was nothing more than Hollywood trickery, so it was surprising when some people thought it might be true.

    The company even had to give a statement to Darren Rovell of stating it was just a storyline and that McMahon was alive and well.

    Had this been a storyline from the territory era, nobody would have broken kayfabe and the company would have let the fans believe he was dead. Ah, the good old days.

Vince Sacrifices Stephanie

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    Vince and daughter Stephanie McMahon have had a roller coaster of a relationship on WWE television, and one of the most bizarre moments came when Steph was going to be forced to marry The Undertaker.

    The Billion Dollar Princess was strapped to a giant symbol by Taker's Ministry of Darkness, and Paul Bearer officiated the mock wedding while a robed Deadman taunted the McMahon family.

    Stephanie wound up being saved by the most unlikely person in the world: "Stone Cold" Steve Austin. He had always been enemies with the McMahons, but his code of honor wouldn't allow him to sit by and watch a woman be given away against her will.

    Vince appeared thankful to The Rattlesnake, but he was eventually revealed to be the higher power behind the Ministry of Darkness, which means he helped orchestrate her abduction while appearing to be a father frantically looking for his missing daughter.

    WWE has indulged in wacky segments countless times over the years, but this is easily one of the most memorable for its weirdness.

Survivor Series 2005

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    Booker T is probably still wondering why Vince McMahon said what he said.
    Booker T is probably still wondering why Vince McMahon said what he said.Credit:

    Mr. McMahon has done outlandish things during his career as an on-screen persona, but one moment people still bring up is the time he used a racial slur at Survivor Series 2005.

    He was hanging out backstage and speaking with Eric Bischoff and John Cena, and he was trying to sound hip because the latter was still in his rapper phase, which is somehow the least offensive thing about this ordeal.

    Then it happened. A white billionaire from Connecticut who has rarely booked an African American to win the World Championship said "Keep it up, my n---er" to Cena.

    It is inappropriate to use that word in any context, but Vinnie Mac let it fly while he was standing a few feet away from Booker T.

    To make the whole situation even more politically incorrect, it happened moments after Cena made a joke about Bischoff's desire to have sex with him.

    Granted, with Booker involved in the segment, it was obviously done so he could mutter his "Tell me he didn't just say that" catchphrase, but it still shocked the world and caused an uproar.

    Obviously, WWE would never put this clip on YouTube, but the moment remains uncensored on the WWE Network replay of the PPV.

No Mercy 2003

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    Stephanie prepares to hit Vince with a lead pipe.
    Stephanie prepares to hit Vince with a lead pipe.Credit:

    It takes a special kind of scumbag to want to physically fight his own daughter, and Vince was more than willing to play the part when he faced Stephanie at No Mercy 2003.

    This was one of many McMahon family feuds we have seen over the years, but it's usually Shane and Vince duking it out in the ring, not father and daughter.

    Most people probably forgot about this match because it was overshadowed by Brock Lesnar vs. The Undertaker in the main event, but it's still one of Vince's wilder moments.

    And keep in mind, this wasn't a standard one-on-one encounter. It was an "I Quit" match, which means there were no disqualifications or count-outs.

    Beating up your own daughter is disgusting enough, but Vince had to make matters even worse by attacking her from behind as soon as the bell rang.

    To top everything off, he won by choking her out with a lead pipe and forcing Linda to throw in the towel for her daughter. It was one of the most despicable things Vince has done in the ring.

St. Valentine's Day Massacre 1999

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    Back when WWE still used the In Your House pay-per-view name, it would often attach a second title to it so there was a theme.

    One of these events was subtitled St. Valentine's Day Massacre in 1999. It took place on February 14, so WWE naturally decided to connect it to a violent incident in Chicago instead of the holiday devoted to love.

    This event saw McMahon and Austin compete inside a steel cage. Keep in mind, this was the old style of cage. It was made entirely of hard bars instead of the flexible chain link fencing WWE uses today.

    Toward the end of the match, Austin rammed McMahon's head into the middle of the cage wall a few times, busting him wide open.

    While it's possible McMahon did a good job blading without anyone noticing, it looked like he had cut his forehead by smashing it into the bars as hard as he could.

    Stone Cold had several chances to escape the cage, but he kept going back to inflict more damage. Again, this would never be allowed in light of today's wellness policy and concussion awareness.

Vengeance 2003

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    Zach Gowen made headlines this year with an impressive showing on American Ninja Warrior, but he will always be known for his time with WWE.

    During his run, the one-legged wrestler made an enemy out of Mr. McMahon, and the two met for a singles match at Vengeance 2003.

    The Chairman toyed with Gowen at first, but the underdog managed to make a comeback by capitalizing on McMahon's overconfidence.

    Gowen thwarted an attempted chair shot from his opponent with a dropkick. It sent the chair into McMahon's head and busted him open in a way we have rarely seen, even during the Attitude Era.

    He wasn't just losing a few drops from a cut. He was pouring blood as if the massive gash on his forehead were a faucet. It's hard to remember a more gruesome moment in WWE history that didn't involve barbed wire. There were puddles of crimson on the mat.

    This is another one of those moments WWE scrubbed from its YouTube channel because simply changing it from color to black and white wasn't enough to mask the level of violence, so check out Gowen's run on ANW instead.

WrestleMania XIX

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    When you talk about the people who have had the biggest impact on the world of wrestling, McMahon and Hulk Hogan will always be in the conversation.

    Neither one of them could have made pro wrestling into a worldwide phenomenon on his own, but together, they were able to take WWE and make it into the biggest game in town.

    When they finally met for a singles match at WrestleMania XIX, both men were approaching the age when most people start thinking about retirement, so expectations weren't high.

    This same show boasted The Rock vs. Austin, Brock Lesnar vs. Kurt Angle and Michaels vs. Chris Jericho. The card was stacked with great matches. The only way Hogan and McMahon were going to make their encounter memorable was to make it the most personal feud of them all.

    McMahon brought up real things from their past like Hogan testifying against him in federal court and going to WCW after he invested so much time into making The Hulkster into a household name. When they signed their contract for the match, McMahon attacked Hogan and used his blood to sign on the dotted line.

    Hogan made McMahon bleed about halfway through the bout, so he spent several minutes gushing from his head down to his chest and arms. The canvas in the ring and the pads at ringside were covered in little spots of red, and by the end, Hogan's bleached hair had turned red from his own wounds.

Vince McMahon Brings God to the Ring

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    WWE has done a lot of controversial things, but few moments can compare to the night McMahon brought God to the ring for a match.

    This debacle happened at Backlash 2006. Michaels had returned to the company a couple of years earlier as a changed man. He had shed his hard-partying ways by embracing his religion, and he brought those beliefs into his character.

    Considering how many people were watching WWE at the time, it's surprising McMahon would have risked alienating anyone who is religious by using God as part of a storyline.

    It was all a joke. McMahon wasn't pretending God was in the ring with him. He was simply using Michaels' faith as a way to get under his skin. He even went as far as threatening to "send God and Michaels straight to hell."

    This moment had to top the list for its ridiculousness. In today's PG environment, WWE would never consider running an angle like this, and that's probably for the best.