If you're a villain as maniacal and over-the-top as Mr. McMahon, where do you go next to draw the ire of the crowd? The logical conclusion of course, you crown yourself champion. McMahon's first title came on September 16th, 1999 and he was actually the babyface defending his honour against the diabolical Triple H. Thanks to interference from his long-time rival Stone Cold, McMahon actually defeated The Game and won the title. He would later vacate the championship a few days later due to a clause in his contract. It wouldn't be the last time McMahon would taste gold, however. https://www.youtube.com/watch?v=Fa2lUwwTa8U Mention WWE's incarnation ECW to the right people and you'll hear all you need to know about why Vince McMahon winning their title was a disgrace, but as a heel it was the perfect move. It took Vince, Shane McMahon, and Umaga to take down rising star Bobby Lashley, and Vince looked ridiculous with his bald head under an oversized hat, carrying around the ECW Championship. Vince would hold into the belt for over a month, until Lashley finally defeated the Boss.