#1 CM Punk
CM Punk is the only WWE Superstar to win the Money in the Bank Ladder match on 2 occasions. He won the briefcase for the first time at WrestleMania 24, and cashed it in on Edge months later, to become World Champion. The next year at WrestleMania 25, Punk won the briefcase again, cashing it in on Jeff Hardy and effectively turning heel. Over the next few years, Punk turned into one of the biggest Superstars in WWE history. He won the World title on 5 occasions. Punk left WWE in early 2014 and hasn't stepped foot inside a wrestling ring as a competitor ever since.
He is currently working for FOX and occasionally appears on its weekly show named WWE Backstage. As an analyst, Punk shares his views on WWE's current product and storylines. He is scheduled to appear on the show next week. Punk's FOX gig led to many believing that a WWE return was on the horizon, but he seems to be content with not being a professional wrestler, and it's hard to predict whether we will ever see him back in WWE again.