Ranking Every WWE Money In The Bank Winner’s Run With The Briefcase

The following year, CM Punk was at it again when he once again won Money in the Bank at WrestleMania and cashed it in successfully.

This time around, he didn’t hold the briefcase for quite as long and though his booking was once again patchy, he did score some wins over the likes of Edge, Chris Jericho and finally Umaga in a Samoan Strap match at the Extreme Rules PPV.

After a match like that, you’d be forgiven for thinking Punk’s night was over. Oh contraire. Instead, he’d emerge in the aftermath of Jeff Hardy’s win over Edge, in a ladder match no less, to see off Hardy and successfully cash-in for the second year in a row.

The timing of the cash-in was particularly cruel as it had been Hardy’s first taste of a world championship after a protracted rise the company ranks. Plus, it allowed Punk to finally let loose that awesome heel persona that gave us the Straightedge Society. Granted, the official turn came in the following weeks, but the seeds were certainly sown in his blindsiding of Hardy.