#5 Jack Swagger
The Real American Jack Swagger shocked the WWE Universe by winning the Money in the Bank ladder match at WrestleMania XXVI. This was the final time that the traditional ladder match took place at the Show of Shows as WWE initiated a pay-per-view with the same name in the same year.
Hence, Swagger never got the right amount of spotlight and ultimately, his cash-in took place in a rushed manner. Just 5 days after winning the contract, Swagger cashed it in and won the title from Chris Jericho.
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Also Read: 4 Worst WWE Money in The Bank winners
Jack Swagger is no longer a WWE superstar but the superstar has moved to Mixed Martial Arts now. He even had a victorious debut as he crushed JW Kiser in just 2 minutes and 9 seconds. It seems like he may emerge more successful in the MMA field.