Edge-3 appearances, 1 or 2 wins
Edge is undoubtedly the greatest performer ever in the history of ladder matches and no wonder he tops this list. The significance of his Money In The Bank wins is how he solidified his legacy as the Ultimate Opportunist as well as made the MITB briefcase mean something to the WWE Universe. He won the first-ever MITB ladder match at WrestleMania 21. Two years later, Mr. Kennedy won the briefcase but he baited Kennedy in a match with the briefcase on the line and captured it. Thus, he is the only one history to win the opportunistic briefcase even after not winning the ladder match.
Hall Of Famer Edge On How AEW’s Offer Made WWE Return Possible
The first time Edge cashed in Money In The Bank was at 2006 New Year’s Revolution pay-per-view to pin John Cena and win the WWE Championship. The next time, he pinned The Undertaker to win the World Heavyweight Championship on SmackDown. Both these moments have become cult in the history of WWE.