#2 (tie) - Christian (6)
Christian is one of the most criminally under-appreciated wrestlers in WWE history. His tag team work with Edge was stellar, before playing a dastardly heel. He was part of the WrestleMania 21 ladder match as well, before leaving WWE for a few years. Upon returning in 2009, he played the valiant babyface on the revived ECW brand.
He also competed in the last two Money in the Bank ladder matches at WrestleMania, before wrestling his second MITB match in the same year when he took part in the Smackdown briefcase match at the first ever pay-per-view named after the match. He would also play a part in two other ladder matches, in 2012 and 2013.
The MITB briefcase would have been perfect for somebody like Christian, who needed that extra something to win their first world title. He could have been turned into a main event player through Money in the Bank, like his best friend Edge. Fortunately though, he did win the World Heavyweight Championship twice in his career.