#1 When he fired Vince McMahon
Back in 2011, John Cena faced off against CM Punk in the Money In The Bank PPV for the WWE title. Cena lost the title after Punk managed to hit a thunderous GTS on the former champion. This didn't sit well with Vince, who decided to fire John Cena on Raw. As Vince was about to fire Cena, Triple H's music hit and The Game came down to the ring.
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Vince McMahon looked ecstatic on seeing his son-in-law, but his joy soon turned into grief, as Triple H informed him that the Board of Directors had fired him. An incredibly emotional moment followed, as Triple H embraced Vince McMahon amidst a sea of roaring fans. Although Triple H managed to control himself after shedding a few tears, Vince McMahon was an emotional mess on that night.