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#2 Mr. Kennedy
Not many would remember that Mr. Kennedy won the third Money in the Bank ladder match at WrestleMania 23. The WrestleMania 23 Money in the Bank ladder match had a few future WWE legends and Mr. Kennedy.
The match featured Edge, Jeff Hardy, CM Punk, King Booker, Finlay, Matt Hardy, and Randy Orton, as well as Kennedy, and the then mid-card talent went on to win the match.
But the win didn't help him. He faced off against Edge for the contract, and lost the match, following which he had to give it up. Edge moved to SmackDown after winning the contract on RAW, and the very next day defeated The Undertaker to win the title.
It was later revealed that Kennedy had to give up the contract because he had suffered an injury. Quite unfortunate for Mr. Kennedy.
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