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#4 CM Punk
Before his exceptionally long reign as WWE Champion, CM Punk was fighting to get to the top of the roster. Punk managed to win the Money in the Bank contract twice back-to-back in 2008 and 2009.
His first cash-in was successful, but the ensuing title run was mediocre. The next year, Punk decided to cash-in on Jeff Hardy who had just overcome Edge in a Ladder match. Hardy managed to kick out of Punk’s GTS, but couldn’t withstand a second one.
This, of course, led to Punk’s major heel run and a pretty good feud with Hardy, which in turn helped Punk grow into one of the biggest stars in the WWE.
#3 Edge
Edge was the 1st superstar ever to cash-in the briefcase against John Cena at New Year’s Revolution 2006. This time nobody really knew how the cash-in process worked. Many thought it was a match that would be set up beforehand like any other.
After Cena overcame five other men in the Elimination Chamber to retain his title, he lay bloody and exhausted in the ring.
Vince McMahon appeared and announced that Edge was cashing in at that very moment. Soon after, Edge would hit Cena with two spears to win his first World Championship.
