#4: He out-wrestled Kurt Angle
Kurt Angle is one of the greatest wrestlers of all time. Before hanging up his boots and singlet at WrestleMania 35 earlier this year, Angle was a phenomenal athlete in WWE, as well as IMPACT Wrestling, and various other promotions around the world. As good as Angle was in the ring, there was one instance where he fell to the Chairman of the Board.
In Angle's autobiography It's True! It's True! the former WWE World Champion talks about a time backstage where McMahon jumped him from behind and took him down by surprise. Being the competitor that he is, McMahon rubbed it in Angle's face every time he could. After a while, Angle couldn't take it anymore and decided that revenge was in order.
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While on a plane ride, the only Olympic gold medalist in WWE history was able to pin the chairman down in the aisle. During the ensuing scuffle, the one and only Undertaker awoke from his sleep and choked Angle out thinking it was a legitimate fight. I suppose Angle won the "match" via disqualification, but it's a great McMahon tale nonetheless.