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#5 Damien Sandow
The 2013 Money in the Bank PPV saw Damien Sandow winning the contract. In October that year, he cashed in the briefcase on John Cena, moments after attacking him and targeting his arm.
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Cena somehow managed to pick up the win and Sandow became the 2nd Superstar to cash in the briefcase and fail, with Cena himself being the first one. He was released in 2016 and is currently working for NWA, as well as in the indies.
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#4 Jack Swagger
Jack Swagger won the last Money in the Bank contest that was held at WrestleMania, in 2010. The match got a PPV of its own, months later. Mere days after winning the match, Swagger cashed in the briefcase on Chris Jericho, who was attacked by Edge on SmackDown moments ago.
Swagger pinned Jericho to become World Heavyweight Champion but didn't carry the belt for long. He is currently signed to All Elite Wrestling, where he is a part of Chris Jericho's "The Inner Circle" stable, in an interesting turn of events.
