#1 Christian
A man synonymous with ladder matches, it is somewhat of a crime that Christian has not won a single Money in the Bank Ladder Match. He has taken part in six of them, making him the joint-most experienced competitor to not win the briefcase, along with Kofi Kingston.
Christian absolutely should have won one of them, possibly in 2010. That would have delivered him his first WWE world title much sooner. He was a consistent figure in every such bout he was a part of, putting the shine on all competitors in the match.
A top AEW star just called one of his colleagues 'spoiled' and 'narcissistic' HERE.
Much like Edge, Christian could have done with a little boost to send him over to the main event scene. The Money in the Bank contract would have been perfect for him.
Christian's time should have come at WrestleMania 26, especially with two of his former tag team partners fighting for the World Heavyweight Championship on the show. Adding Christian to the Chris Jericho vs Edge storyline would have been an excellent touch, but WWE decided to go with Jack Swagger.
And while Christian's eventual world title win in 2011 (in a ladder match, no less) was emotional, WWE missed a huge opportunity a year prior.