#3 Mr. Kennedy
By the time 2007 came around, Mr. Kennedy had become a big name and a hated heel on SmackDown. He had engaged in feuds with the likes of Batista and The Undertaker and was a favorite to win the Money in the Bank match at WrestleMania 23. The match featured major names like Edge, Randy Orton, CM Punk, King Booker, The Hardy Boyz, and Finlay as well, but Kennedy managed to bag the briefcase in the end.
He lost the briefcase to Edge mere days later, after being hit with a monitor moments before the match began. Edge successfully cashed in the briefcase on The Undertaker on SmackDown, winning the World title in the process. Kennedy never won the World title during his WWE stint. He was released by WWE in 2009. Kennedy later stated that his release came after WWE veteran Randy Orton complained backstage that he was reckless in the ring.