#9 Tito Santana
Tito Santana is a two-time Intercontinental Champion and a two-time tag champ from the WWF days, and he also held various titles in other promotions and territories. More importantly, nearly all his matches on big stages were entertaining and technically sound.
Both of those things would be great assets for a Money in the Bank match, but his energy level would be an even bigger positive. His high-octane style in the ring would have helped get the fans out of their seats for a false finish or real victory.