#2 CM Punk

Edge may have cashed in twice, but only one person has ever won the Money in the Bank ladder match twice, and to top it off he did it back to back.
CM Punk won Money in the Bank at WrestleMania 24 and then again at WrestleMania 25. The first briefcase he cashed in on Edge, marking the ultimate karma for Edge, to finally taste his own medicine, while the second time he cashed in Jeff Hardy, who had just won the title from Edge.
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His second run with the contract set the stage for the hottest feud of 2009 against Jeff Hardy. The cash in on Hardy who won a hard fought ladder match against Edge was perfect. It set the scene up for a series of very personal matches that culminated in a TLC match at SummerSlam.
CM Punk was never supposed to be the top dog, just a placeholder, but his showings in these ladder matches help him become a big name in WWE, something he would hold on to until he left the company.
CM Punk has become synonymous with Money in the Bank, making it fitting he won the WWE Championship at the PPV of the same name. No one will ever do what Punk did, and for that Punk takes the number one spot on this list.