#2 Edge – 3 appearances, 1 victory... or 2 victories
Number two on our list is the winner of the inaugural Money in the Bank Ladder match twelve years ago at Wrestlemania 21, Edge. The Rated R Superstar became The Ultimate Opportunist when he won the briefcase and then cashed it in to some thunderous applause.
Edge has participated in the match three times in his career and while he may not have won the other two Money in the Bank Ladder matches, he has carried the briefcase two times as he defeated Mr Kennedy to win contract off him.
Is this man the funniest man in wrestling?
It’s not just his great record that earns the WWE Hall of Famer a place on this list, however, as he always gave 110% during these matches, as expected from someone who made a name for himself in ladder matches.