Cross the Boss: Mr. McMahon's Biggest Foes

RiZESenior Writer INovember 27, 2010

Cross the Boss: Mr. McMahon's Biggest Foes

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    Don't cross the boss. One of the most significant warnings in the workplace. One man epitomizes those words. Vincent Kennedy McMahon.

    The Chairman of WWE has amassed multiple feuds over the years. From being a humble announcer to a power hungry boss, McMahon has become one of the most popular figures in sports entertainment.

    Have you ever seen employees treat the guy that signs their checks this way?

    Absolutely not.

    Can you blame them? Vince McMahon is one the most cruel figures in WWE. The majority of the feuds he is involved in were in some way caused by his own actions. Funny thing is Vince always ends up on the receiving end of a beat down.

    If not that, some sort of misfortune.

    Enough small talk. The following are some of Vince's biggest foes.

    Remember this is an all "wrestler" slideshow. Nothing outside of it like Ted Turner and Paul Heyman.

Degeneration X

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    Shawn Michaels and Triple H. Two men who have made Vince McMahon's life a living hell. Aside from the brief feud in the 90s, the McMahon's and DX have taken part in some of the most memorable and humorous segments in RAW history.

    The feud began when HBK informed McMahon that he should move on. Basically saying McMahon should let go of the Montreal Screwjob.

    Vince became infuriated by Michaels' words and told HBK that he would never let it go. From VKM's demeanor, we knew bad things were to come for HBK.

    Even threatening HBK not to force Vince to "screw" him.

    Despite the warning, Vince placed multiple obstacles options in Shawn's way. At the time, HBK was attempting to regain the WWE Title.

    Vince's antics became more and more violent as the weeks passed. Bringing HBK's former Tag Team Partner, Marty Jannetty in the mix. After a match with Chris Masters, Jannetty was strapped in the Master Lock. HBK ran out to save him only to be laid out by Shane McMahon.

    McMahon then shoved Michaels face in Vince's bottom, and HBK officially joined the Kiss My Ass club. After numerous screw overs by Shane and Vince, Michaels vs. Vince was announced for Wrestlemania 21. At the event, Michaels beat McMahon to a bloody pulp, dropping an elbow onto a trash can cover on Vince for the win.

    However, Vince continued to pursue HBK. In a tag match where Shawn's partner was "God," The Spirit Squad assisted Shane and Vince in the win. Around the same time, Triple H was becoming more and more frustrated by his chase for the WWE Title.

    McMahon was the center of The Game's frustration. McMahon enlisted Triple H's help against HBK. In an attempt to get rid of Shawn, The Game inadvertently nailed Shane McMahon. Vince later announced HHH would join the Kiss My Ass club.

    Learning from HBK's problem's with McMahon, Hunter thwarted an attempt by Shane at drugging him. Switching the water bottles causing Shane to drink the drug.

    In the ring, Triple H faked passing out and Vince instructed Shane to shove his face in his bottom. Shane succumbed to the drug, and Triple H Pedigreed McMahon, cementing his face status.

    Vince used his lackeys The Spirit Squad as an attempt at revenge. It failed horribly when HBK returned and saved Triple H from a beat down. Reuniting DX.

    Quickly disposing of the Spirit Squad, DX brought back their humorous promos and antics building up to a SummerSlam match against the McMahons. Despite interference from multiple RAW and Smackdown! Superstars, DX defeated the McMahons.

    Vince McMahon then enlisted the help of ECW Champion, Big Show.

    In a two-on-three Hell in a Cell handicap match at Unforgiven, DX defeated Big Show and the McMahons. One of the most memorable spots came when DX shoved Vince's head in Big Show's ass.

Bobby Lashley

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    One of the only men to bring Vince's wrath upon himself. When Vince McMahon challenged Donald Trump to a match at Wrestlemania 22, Vince chose Umaga as his representative.

    After a long wait, Lashley was announced as Trump's representative. At Wrestlemania, Lashley defeated Umaga, and Vince was shaved afterwards.

    Lashley, like HBK, soon had Vince on his back, defending his ECW Championship against Umaga, Vince, and Shane in a three-on-one handicap match. After brutal offense from Shane and Umaga, Vince pinned Lashley. In the process, Lashley severely damaged his rotator cuff during the match and was absent for a few weeks.

    When he returned, he received his rematch at Judgment Day. In the same three-on-one handicap match, Lashley defeated them after pinning Shane. Because he didn't pin McMahon himself, he did not win the ECW Title.

    In a street fight against McMahon at One Night Stand, Lashley destroyed Vince and regained the ECW Title, thus ending their feud.

Randy Orton

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    While Orton may not be Vince's biggest foe, what he did to McMahon stands out for itself. Vince McMahon had been out of WWE after an accident during the quarter of a million giveaway. Without a GM, Stephanie ran RAW. Because of her handling of a No. 1's contender match, Stephanie made enemies out of Y2J and Orton.

    Y2J requested Vince's return to WWE to handle Stephanie. Vince sided with Stephanie and threatened to fire Jericho if he had not apologized to her. Jericho quickly complied, and Orton made his entrance. Orton argued his point to Vince and trashed Stephanie.

    Vince demanded an apology from Randy and he refused. Vince threatened to fire Orton but to no avail as Orton insisted that Vince would not want to do that. Right before Vince said his famous catchphrase, Orton slapped him in the face.

    Orton then kicked Vince in the face. Then Orton shocked us all by punting Vince in the head. Putting Vince out of action once again.

    In Vince's absence, Orton injured Stephanie and Shane before falling to Triple H at Wrestlemania. Vince returned to challenge Orton to a match on RAW.

    The Chairman was dominated by Orton only for Batista to return. Two weeks later, Orton put Triple H on the shelf after a punt.

Hulk Hogan

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    Hogan and Vince's feud began when Hogan left the WWF in 90s. Hogan joined WCW and almost put WWE out of business. When Hogan returned to WWE in 2002, there was no tension between him and McMahon. When Hogan turned babyface and left the NWO, he won the Undisputed Title.

    McMahon still showed a strong dislike for Hogan, costing him the Title in a match with The Undertaker. Afterwards, Hogan had small feuds with Brock Lesnar and Kurt Angle before leaving on hiatus. When he returned, Vince still tried to kill Hulkamania, placing Hogan in a Wrestlemania rematch against The Rock.

    At No Way Out, The Rock defeated Hogan after an assist by McMahon and a paid ref, setting up a match for Wrestlemania 19.

    In the weeks building up, McMahon had left Hogan a bloody mess and insisted that he created Hulkamania. At Wrestlemania, after a back-and-forth battle by the two, Hogan defeated McMahon after the Leg Drop.

    Their feud continued as McMahon had Hogan removed from WWE Programming. Hogan briefly returned as Mr. America. Vince attempted to prove that this was Hogan and after a Smackdown! went off air, Hogan revealed himself to be Mr. America.

    The next week, Vince showed the footage and fired Hogan, ending their feud.

Shane McMahon

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    One of Vince's biggest rivals has been his own son, Shane O'Mac. Shane and Vince had many confrontations in the late 90s but always ended up siding with one another. After Shane lost his Hardcore Championship, he disappeared from WWE Programming.

    When Vince began an affair with Trish Stratus, Shane McMahon returned to defend his mother. Shane challenged Vince to a match at Wrestlemania. The feud intensified when Shane announced he purchased WCW under his father's nose.

    At Wrestlemania, Shane defeated Vince after a coast to coast. As Shane went on to feud with Big Show and Kurt Angle, Vince was helping the Two Man Power Trip rise to the top, helping Austin win the WWF Title at Wrestlemania, then suspending The Rock the next night.

    Shane returned to WWF with his WCW Wrestlers and waged war on WWF. Claiming his father had black balled WCW. Not allowing to gain television access. Shane soon turned heel after attacking Undertaker and as did the rest of WCW.

    ECW later joined WCW to from the Alliance. In a WCW vs. WWF match, Alliance gained the victory after Steve Austin turned on the WWF team. As months progressed, the WCW and WWF titles changed sides multiple times before Shane proposed another five on five match, but this time the loser would go out of business.

    Vince accepted and The Rock-led Team WWF against Austin's Team Alliance. After Angle turned on the Alliance, The Rock gained the pinfall over Austin ending the Alliance, effectively ending their feud.

The Rock

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    While maybe not as heated as the others, Vince McMahon and The Rock have crossed paths on numerous occasions. More than anyone else, Vince has screwed The Rock out of the WWE Title.

    When Rock became more popular with WWF fans because of his numerous promos, Vince believed Rock was a problem.

    Vince didn't like the people and the Rock was the People's Champion. Their feud halted before it began with Rock and Vince parodied the Montreal screw job in a match with Mankind. Rock turned heel and led Vince's stable, The Corporation.

    Soon afterwards, The Rock lost his WWF Title to Steve Austin. Once again due to his huge popularity among WWF Fans, he was turned face. After Shane McMahon betrayed him and kicked him out of the Corporate Ministry. The Rock then feuded with Undertaker and Triple H.

    The Rock and Vince would come across one another again. After The Rock controversially won the 2000 Royal Rumble. Big Show had eliminated The Rock, but the Rock seemingly won after he held onto the ropes and reentered the ring.

    In the coming weeks, he lost and re-won his Wrestlemania title match in matches with The Big Show. At Wrestlemania, The Rock would face Triple H, Mick Foley and Big Show in a four-way elimination match. Rock had Vince, Triple H had Stephanie, Mick had Linda and Show had Shane.

    In the end, Triple H pinned Rock after Vince turned on him and hit him with a chair. Vince attempted to cost Rock a WWF Title match with Triple H but failed when Stone Cold returned. The feud between the two died down until Wrestlemania 17.

    In a match where Rock was close to defeating Austin for the first time, Vince gave Austin a chair and cost Rock his WWF Title. The next night on RAW, McMahon gave Rock a rematch after The Rock applied the Sharpshooter on him.

    Later in the night, Vince and Triple H cost Rock the title in a Steel Cage. The next week, Rock was suspended by McMahon. When the WWF was in dire straits due to the Alliance, Vince announced Rock's return.

    The Rock sided with the WWF but gave Vince a Rock Bottom in the process.

    After the Alliance lost the five-on-five match, Ric Flair bought Shane and Stephanie's remaining stock. Flair and McMahon decided to unify the World and WWF Titles, crowning the first Undisputed Champion.

    Vince and Rock's feud had already reignited when Rock forced Vince to kiss Rikishi's ass.

    When Rock faced Y2J in a match for the World Title, McMahon interfered allowing Jericho to win.

    This would be the last time these men crossed paths as enemies.

Stone Cold Steve Austin

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    This historic rivalry began in the midst of Austin's and Owen Hart's feud. While giving a speech to the audience, Austin attacked Hart and was about to attack police officers. McMahon quickly ran to the ring and stopped Austin. After a brief lecture, Austin stunned McMahon to the shock of the audience and McMahon himself.

    Austin was then arrested. Their feud continued in a segment with Mike Tyson. McMahon declared Tyson the Baddest Man on the Planet much to the disliking of Austin.

    Austin and Tyson shoved one another, and Vince feared if Austin had become WWF Champion at Wrestlemania. He had already won that year's Royal Rumble.

    With Tyson's help, Austin defeated Michaels at Wrestlemania, ushering in the Attitude Era.

    The next night, Austin was presented with the new WWF Title and was informed by McMahon to change his rebellious ways. Austin stunned McMahon. After numerous weeks of taunting by Austin, McMahon began to use his power to make sure Austin would lose the title, even involving Dude Love, but to no avail as Austin would retain against Love twice.

    McMahon finally got his wish when Kane defeated Austin in a first blood match at King of the Ring. Undertaker had inadvertently hit Austin with a chair, causing Kane to win.

    It was short-lived as Austin won the WWF Title back the next night. Austin retained in a match with The Undertaker at Summerslam. McMahon set up a triple threat between Austin, Taker and Kane. Austin lost the title after a double chokeslam allowing both brothers to pin him.

    McMahon fired Austin only to be kidnapped by him later. In this famous segment, Austin taunted McMahon with a gun that only shot out "Bang 3:16" but caused McMahon to urinate on himself. Austin was later re-signed by Shane McMahon.

    McMahon and Austin's feud intensified afterwards. McMahon had Austin enter the 1999 Royal Rumble at No. 1 while McMahon entered at No. 2, thanks to HBK. At the Rumble, Austin was attacked by the corporation and was injured.

    Austin re-entered the match in a ambulance. Austin made it to the end, but Vince had snuck out of the ring, allowing WWF Champion The Rock to blindside Austin so McMahon could win. McMahon gave up his WM Title match, and Austin was rewarded it by Commissioner HBK.

    In a cage match which featured the debut of Big Show, Austin won the WM Title match after Show threw Austin through the cage. 

    Austin won the WWF Title from The Rock only to lose it to Undertaker at Over the Edge due to interference from Shane McMahon. Austin became the CEO of the WWF and put his new position on the line in a match against Shane and Vince.

    Vince and Shane won, but Austin already made a WWF Title match with him and The Undertaker. Austin won the WWF Title and was challenged to a match by Vince McMahon. If Austin lost, he could never challenge for the WWF Title again. If he won, Vince would leave WWE.

    Austin won the match and gave Vince a stunner on the way out.

    The feud died down until Wrestlemania 17, where Vince helped Austin regain the title in a match with The Rock. Austin and Vince joined forces and with Triple H formed the Two Man Power Trip. After Triple H went down with an injury, Austin feuded with the Alliance before turning on the WWF.

    In their last confrontation, Vince McMahon helped Y2J win the WWF Title from Austin after a shot by Booker T.