CM Punk-4 appearances, 2 wins
If somebody can boast two back to back straight Money In The Bank wins in WrestleMania history, it’s the Straight Edge Society leader. He did the unthinkable and most importantly, cashed it in successfully to become a world champion on two separate occasions. The first cash-in came against Edge in 2008 whereas the second one happened against Jeff Hardy at Extreme Rules 2009 PPV.
WWE Not Interested To Sign CM Punk Or Alberto Del Rio, At All