#3 Two time MITB winner
CM Punk became the first and only superstar to win the Money in the Bank ladder match two times. At WrestleMania 24, CM Punk won the MITB ladder match and went on to successfully cash-in his contract against the World Heavyweight Champion Edge in June 2008 on an episode of Raw.
CM Punk had a decent run as the World Champion, and defended his title against the likes of Batista and JBL.
CM Punk was scheduled to defend his championship in a 5 way championship scramble against Batista, JBL, Kane and Rey Mysterio at Unforgiven 2008, but he was attacked by Randy Orton and his Legacy stablemates before the match. Causing CM Punk to vacate the title and be pulled out of the match. He was replaced by the eventual winner, Chris Jericho.
The following year at WrestleMania 25, CM Punk again won the Money in the Bank ladder match, and this time he cashed-in his contract on Jeff Hardy, who had just won the World Title in a ladder match against Edge.
CM Punk defeated Jeff Hardy in a minute to become the World Heavyweight Champion for the 2nd time, turning heel in the process - for the first time ever in WWE. CM Punk then feuded with the likes of Jeff Hardy and The Undertaker for the World Title in the following months.