#1 Vince McMahon - 54 years
Vince McMahon is primarily known for being the CEO and the evil heel during the Attitude Era, but many may not know that he also held the WWE Championship, briefly.
The Chairman of the WWE won the Championship on the SmackDown that aired on September 16th in a match against Triple H. McMahon won thanks to an interference from Stone Cold, but he vacated the title on the next week's RAW.
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Edited by Rohit Nath