1. Booking Himself Against Shawn Michaels In 2006

When it came time for WrestleMania 22, Vince McMahon elected to book arguably the best in-ring performer at WWE’s disposal in a No Holds Bar Match against himself.
It’s questionable if McMahon was the right opponent for Shawn Michaels, but The Chairman did have some credibility as a top level heel at the time, and this was a first time pairing in the ring. The resulting match was fun—surely not Michaels’s best performance in a WrestleMania match, but a worthy chapter to add to his distinguished resume at the Showcase of the Immortals.
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The program went on with McMahon using his authority to bully Michaels. That included booking a tag match. McMahon and his son would team against Michaels and “God,” in an effort to ostensibly poke fun at 'The Showstopper’s' religion. The angle may have been in poor taste, but it led to Michaels finding backup in the form of old ally Triple H.
A reunited DX was white hot at the time and would become a team WWE would revisit time and again in the years to follow. While the tandem arguably eventually wore out its welcome after too many angles of coming back together, the Michaels vs. McMahon feud was brilliant in the way it told a one of a kind comeback story.
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