7 WWE Money In The Bank Winners That Flopped

3. Damien Sandow

This one makes me sad just to think about it because they botched it so bad. Sandow won the blue briefcase for the World Heavyweight Title in 2013, which was something of a surprise because he wasn't booked that strongly going into it. When he won, the assumption was that he would be elevated to a main event level. They even did a great job of making Sandow's briefcase reign entertaining because he lost the briefcase thanks to Cody Rhodes tossing it into a river and then he had a new one made. It was funny. After John Cena won the World Title in October 2013, the thinking was they could have Sandow cash in on him and it would help Sandow tremendously. Makes sense right? Midcarder beats top guy, then midcarder becomes a bigger deal. That's wrestling. Instead of the successful cash in, Sandow failed in his initial attack. Cena had a full match with Sandow where Cena was selling his arm injury the whole match and fighting back from everything Sandow could offer. Cena won clean with the Attitude Adjustment in a very competitive match as a lot of internet fans complained about an opportunity lost. Look at where Sandow is now. He's in a much worse spot than he was when he was holding the MITB. It's a shame.
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John wrote at WhatCulture from December 2013 to December 2015. It was fun, but it's over for now. Follow him on Twitter @johnreport. You can also send an email to mrjohncanton@gmail.com with any questions or comments as well.