#3 1st Bad Guy to Win Main Event of WrestleMania
Triple H was the first "bad guy" to win the main event of WrestleMania. By the main event of WrestleMania, we mean the final match of the show, not WWE's version of the main event which sometimes means three or four different matches on the show all being declared the main event.
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It was WrestleMania 2000 and the final match of the night was a 4-Way elimination match featuring Triple H, the Rock, "Stone Cold" Steve Austin, and Mick Foley. The McMahon family was heavily involved in helping Triple H keep his title that night but it was the first time a bad guy walked into the main event of WrestleMania and got his hand raised. Others have done it since but Triple H was the first.
For 15 straight years, stars like Hulk Hogan, Ultimate Warrior, Randy Savage, Shawn Michaels, and Bret Hart defeated bad guys to close the biggest show of the year. Triple H would be the first bad guy to buck the trend.