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#1 Vince McMahon won the WWE Championship (WWE SmackDown 14/9/1999)
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Though he's not a wrestler, Vince McMahon has booked himself to win multiple Championships in WWE. He won the ECW Championship from Bobby Lashley a few weeks after the champion and Donald Trump shaved McMahon's head at WrestleMania 23, but seeing the chairman win the WWE Championship was even more shocking.
At the height of the Attitude Era, McMahon gave himself the company's top title. Having won the Royal Rumble Match in January 1999, the chairman of WWE won the gold in September. He did so with a lot of help, particularly from "Stone Cold" Steve Austin.
McMahon's nemesis stunned Triple H and allowed him to pin "The Game," with special guest referee Shane McMahon counting the three. This moment was stunning and controversial, even with McMahon being a babyface at the time.
His reign did not last very long at all, which may explain why it isn't frequently remembered. The belt was vacated on the following episode of WWE RAW. However, it will always be in the record books: McMahon defeated Triple H to win the WWE Championship right at the peak of the Attitude Era.
