10 Biggest Ever Heel Vs. Heel WWE Matches

5. Damien Sandow Wins Money In The Bank - MITB 2013

This is one of the more unique heel matchups ever because WWE decided to have one of their Money in the Bank briefcases be contested only among heels. There were seven guys in the match: Damien Sandow, Wade Barrett, Cody Rhodes, Dean Ambrose, Fandango, Jack Swagger and Antonio Cesaro. A lot of us had no idea who was going to win. Ambrose was still fairly new with The Shield, Barrett was a guy that always seemed like a favorite in these kinds of matches, the same can be said about Cody Rhodes and then there was Damien Sandow, who ended up as the victor. The match was memorable for the finish. It looked like Cody Rhodes was going to win after he cleared everybody else out of the ring. It sounded like Cody was the favorite of the crowd too. Then his best friend Damien Sandow showed up, knocked Rhodes down and then Sandow climbed up to take the win. It was played up as a cheap move by Sandow against his buddy with Rhodes turning face as a result of the finish. It was a cool way of telling a story within the context of the match. We really didn't know how it was going to play out, yet by the end of it the reaction was more like "damn that was great" because it was.
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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.