Although Chris Jericho boasts notable victories over wrestling greats such as Steve Austin, Triple H, and John Cena, he finds himself down 0-1 in a unique rivalry with his former boss, Vince McMahon. This competition didn't take place inside a wrestling ring but rather originated during their previous work association. The incident occurred on a return flight from the production of "Tough Enough," a program where Jericho held the role of host, showcasing McMahon's unyielding drive for competition outside of the squared circle. Jericho explained on Busted Open Radio:

"Vince and I just stayed up drinking listening to AC/DC and The Stones. We landed at 4AM and he goes, 'Let's go to the gym.' I said, 'I can't go to the gym, I've got press at 7AM,' so he goes, 'Well, I've got to be at the office at 6:30, let's go to the gym,'" Jericho recounted on "Busted Open Radio." Given the late hour and their inebriated state during the flight from Orlando to White Plains, Jericho assumed McMahon was merely jesting.

That assumption turned out to be a mistake for Jericho, "I go back to the hotel, I go to sleep, I wake up literally two and a half hours later and I've got a message on my phone and a picture of Vince in the gym and he wrote, 'Vince 1 – 0 Jericho,'" he revealed.

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