#1.) WrestleMania 21
It’s only suitable that we go to the very first MITB match. It was a great match that involved a good mix of veterans and young guns. In a night of coronations, Edge would have the first major step towards his own, as he overcame five other incredible superstars to win the Money In The Bank ladder match.
It was an overall great contest and Edge was the perfect person to pull the trigger on. While WWE often doesn’t get credit for timing, this one was perfect and Edge was a deserving first MITB winner.