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6 WWE megastars Vince McMahon has pinned

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Vince has pinned both these men
Vince has pinned both these men

Over two decades after Vince McMahon turned heel, it's still amazing how this calm and composed babyface announcer turned into possibly the evilest villain in the history of this business. Bret Hart bashing Vince on an episode of Raw in 1997 kicked off this slow heel turn, and in a matter of months, Vince had become a full-fledged heel. He went on to compete in the squared circle, going on to actually win the Royal Rumble Match in 1999 by eliminating his arch-rival Stone Cold Steve Austin.

Over the past 20 years, Vince McMahon has competed in a string of matches, and has mostly been used as a villain who would get pinned by the hero in the end, to send the fans home happy. But there have been instances where Vince actually won matches against top Superstars. Here are six megastars Vince McMahon has pinned.


#6 Randy Orton

Randy Orton
Randy Orton

Back in 2009, Shawn Michaels and Triple H arranged a birthday party for Vince McMahon on the August 24 episode of Raw. The same episode saw DX and Vince take on The Legacy (Randy Orton, Ted Dibiase, and Cody Rhodes) in a 6-man tag-team match.


The bout ended when John Cena came out and threw Orton inside the ring, hitting him with an Attitude Adjustment. Vince McMahon then pinned Orton to end the night on a high note.

Also read: CM Punk reacts to Seth Rollins and Becky Lynch attending NFL game


#5 Ric Flair

Ric and Charlotte Flair
Ric and Charlotte Flair

On the June 10, 2002 episode of Raw, Mr. McMahon faced Ric Flair in a No Holds Barred Match, for 100% ownership of Monday Night Raw. Flair got busted open during the match. During the closing moments, Flair locked in the Figure Four, as Arn Anderson watched Vince McMahon writhing in pain.

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Suddenly, Brock Lesnar hit the ring, prompting Anderson to flee. He hit Flair with an F-5 and helped Vince defeat the Nature Boy.

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