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#4 Shawn Michaels
Heading towards WrestleMania 22, Vince McMahon and his son Shane McMahon got into a feud with Shawn Michaels. The duo cost Michaels a shot at the top title at WrestleMania 22 during the Royal Rumble Match.
At WrestleMania 22, Shawn Michaels defeated Vince McMahon in a bloody brawl, but this wasn't the end of the feud. Soon after, Vince and Shane met Michaels and "God" in a Tag Team Match at the upcoming PPV, Backlash. The match saw interference from The Spirit Squad, and the group helped Vince steal a victory against The Heart Break Kid.
The ending to the match saw The Spirit Squad throw Michaels on a table, followed by McMahon comfortably pinning him to win the match for his team.
Also read: 10 oldest pro-wrestlers who are still wrestling in 2019
#3 Triple H
Back in 1999, Triple H met Vince McMahon on an episode of SmackDown, and put his WWE title on the line. McMahon was out to fight for the honor of his family, and did everything in his power to put down The Game, but to no avail.
Suddenly, Stone Cold Steve Austin came out and chaos ensued. Austin hit Chyna and Triple H with Stunners and put Vince's body on an unconscious Triple H. Shane McMahon made the three count and Vince became WWE Champion in shocking fashion!
