#3 Wade Barrett
Wade Barrett is one of the unluckiest WWE Superstars in recent history. The number of stops and starts he's had during his time with the company is frustrating. Some of those stops and starts involved the Money in the Bank Ladder Match.
Barrett was seemingly set to win the SmackDown Ladder Match in 2011 before plans changed and Daniel Bryan won it instead; not a bad decision in hindsight. Anyway, the former leader of the Nexus looked to redeem himself grandly in 2012.
WWE was apparently planning a Money in the Bank Ladder Match for WrestleMania 28, with Wade Barrett winning the briefcase. Unfortunately, Barrett got injured and missed the show, scrapping any plans they may have had for the ladder match.
He was always very close to breaking out into the main event scene, but it never materialized. If not for his rotten luck, Barrett may have won Money in the Bank and become a main eventer in WWE. He had all the tools to do so.