20 Most Memorable Humiliations In WWE History

2. Battle Of The Billionaires (WrestleMania 23)

Vince McMahon has and will always live by the credo that the boss should never ask his employees to do something that he, himself, would not do. He has proved that countless times in the past, including at WrestleMania 23. In a match dubbed the Battle of the Billionaires, McMahon led representative Umaga to the ring for a match against Bobby Lashley, who represented Donald Trump. The billionaire whose Superstar lost would have his head shaved in the ultimate blow to their ego. It was a wild stipulation but one that made the match that much more must-see. Lashley would secure the victory for Trump, who would then join the ECW champion and guest referee "Stone Cold" Steve Austin in shaving McMahon bald. Coverage of the boss' humiliation played on all of the morning newscasts and helped make the show the biggest in history, at least to that point. McMahon's chrome dome helped add a new element to a character that was growing staler by the minute. https://www.youtube.com/watch?v=UZ1L013k5Hw So, unlike some of the Superstars elsewhere on the list, the humiliation did more good than harm.
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Erik Beaston is a freelance pro wrestling writer who likes long walks in the park, dandelions and has not quite figured out that this introduction is not for Match.com. He resides in Parts Unknown, where he hosts weekly cookouts with Kane, The Ultimate Warrior, Papa Shango and The Boogeyman. Be jealous.