3: Shawn Michaels
The Heartbreak Kid would become the third member of The Kiss My Ass Club during the February 27, 2006 edition of Monday Night Raw, live from the Nations capital, Washington DC.
The Spirit Squad came out first, introducing a special cheer they had created specifically for the boss man. Vince praised the Squad, mentioning how The Squad reminded him of another former team...The Rockers. Marty Jannetty came to the ring next, as McMahon stood there smiling, with his muscle for the evening, Chris Masters. Marty pleaded with McMahon to give him a job. Vince ordered Jannetty to his knees and as he began to drop his drawers, Marty begged for an alternate method of obtaining a job, to which McMahon answered by having Masters apply the Master lock on Jannetty.
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As Jannetty was subdued by the Master lock, Vince barked for Chris to "break his neck," until finally, Shawn Michaels raced down the ramp to save his friend. Unfortunately, HBK was nailed by a steel chair, compliments of Shane-O-Mac. Vince then once again revealed his bottom for the world to see, as Shane McMahon lifted Michaels' lifeless body up and forced his lips onto his dad's rear-end, resulting in Shawn forcibly joining the Mr.McMahon Kiss My Ass Club.