Six WWE superstars with the highest number of Money in the Bank ladder match appearances

#5 (tie) - Shelton Benjamin (5)

Shelton Benjamin was the MITB MVP in its early days.

Shelton Benjamin was the highlight of the first portion of Money in the Bank matches when they were held at WrestleMania. In fact, he was part of five out of the first six matches of this kind. Pretty much every year, Benjamin would come up with more and more dangerous spots.

He never failed to deliver in a Money in the Bank ladder match, shocking the WWE universe with his bruising leaps and bumps. His quick sprint up a leaning ladder was the biggest spot of the first ever MITB ladder match at WrestleMania 21. Since then, he has been trying to better himself every time.

At WrestleMania 24, Shelton took a terrifying fall through a horizontal ladder. The ladder he was on got tipped over and he took a front flip before crashing through the ladder. It remains one of the biggest crashes in the history of this match. It's a shame that WWE failed to utilize his massive potential and push him above the mid-card. He deserved to win the briefcase at least once in his career.