Every WWE Money In The Bank Winner Ranked Worst to Best

At WrestleMania 25, CM Punk became the first and only person to win consecutive Money in the Bank matches. After moving to the SmackDown roster, Punk took his opportunity to win his second World Heavyweight Championship, defeating Jeff Hardy at Extreme Rules and beginning his heel turn.

Combining Punk’s new preachy, straight edge disciple gimmick with Jeff’s overwhelming popularity, the Hardy/Punk feud was the hottest thing of the summer. Jeff would regain the title in the main event of Night of Champions, but in what would be his last match with the company for nearly eight years, he lost it back to Punk in an acclaimed TLC main event at SummerSlam. Punk would then defend against the Undertaker in the main event of Breaking Point (albeit in a very screwy fashion, i.e. they just redid the Montreal Screwjob) before dropping it to the Deadman at Hell in a Cell.

While not one of the most memorable reigns, Punk’s second run as Mr. Money in the Bank was a major turning point for his career. It allowed him to break the chains of his babyface persona and show off how good of a talker he was. Plus, he got to main event against big stars like Jeff Hardy and The Undertaker. True, he would be remembered more for what he did in 2011 onward, but give credit where credit is due when it comes to 2009.