5 Worst WWE Money in the Bank Winners of All Time

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Credit: WWE.com

3. Damien Sandow

Damien Sandow has the dishonor of being the only Superstar in the Money in the Bank’s history to lose his match for the World Championship where he cashed in. So, it may be surprising that he is only number 3 on this list.

Damien Sandow’s run with the briefcase started out with so much promise. His intellectual character was getting over as a heel and had a good run as Cody Rhodes’ partner. Also, his betrayal of Rhodes to win the Money in the Bank briefcase should have sparked his triumphant singles run.

Instead, Sandow was treated as a joke. Up until his cash in, he won one match and lost 12. His only PPV appearances were on the kickoff show and would lose to the likes of R-Truth, Santino, and Ziggler.

By this point, everyone, WWE creative and the fans, had given up on Sandow as a credible main event level talent. So, this resulted in Damien Sandow losing his cash in match to John Cena.

Sandow attempted to re-injure Cena’s arm with various shots with the briefcase, but Super Cena was able to overcome the pain and send Sandow straight to jobberville.

After an extended losing streak asa lower tier jobber, Sandow finally hit his stride with the Mizdow character. He was able to get over and gain fan support as The Miz’s stunt double, but WWE was unable to capitalize on Sandow’s popularity. Eventually, Sandow was released from the company.

It is a shame that Sandow’s Money in the Bank push came a couple years too early. Otherwise, we could have been seeing Sandow as a current main eventer. Instead, he will go down in history as the only Money in the Bank winner to lose his cash in attempt.