Chris Jericho worked for Vince McMahon in WWE between 1999-2005 and 2007-2018. The WWE Chairman competed sporadically in WWE matches during that period of time. One of McMahon’s most surprising match outcomes came in July 2006 when he and Shane McMahon lost to Eugene on RAW.
Speaking on Chris Jericho’s Talk Is Jericho podcast, Nick Dinsmore (aka Eugene) recalled how he pinned his boss with a schoolboy to win the match. Jericho joked that WWE’s top decision-maker did not impress him as an in-ring competitor.
“Vince, the worst wrestler ever. He probably even screwed up the schoolboy.”
Chris Jericho only faced Vince McMahon on one occasion in an official WWE match. The match took place on a June 2001 episode of WWE SmackDown when he joined forces with Chris Benoit to defeat McMahon and Steve Austin.
Eugene told Chris Jericho why he defeated Vince McMahon
Eugene explained how Vince McMahon and Shane McMahon tormented him by pouring paint on him and shoving his head down a toilet. Another on-screen rival of the McMahons at the time, Shawn Michaels, suggested that Eugene should win the handicap match.
“I think it was Vince and Shane against Eugene. They were just gonna beat him up and they were gonna beat him. It was Shawn Michaels who went, ‘Eugene should win if you’re doing all that stuff to him.’ ‘Okay, yeah.’ So at the very end, I just rolled up Vince, one, two, three.”
The finish to the match saw Michaels and Triple H cause a distraction on the stage area. Eugene then rolled Vince McMahon up with a schoolboy to record the victory.
Please credit Talk Is Jericho and give a H/T to SK Wrestling for the transcription if you use quotes from this article.