#2. Damien Sandow - 2013
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There is no reason that the 2013 Money in the Bank winner Damien Sandow shouldn't still be in WWE right now. He's been given plenty of opportunities, nailed those opportunities, and still found himself floundering. It's not fair.
Sandow won Money in the Bank and turned on his tag team partner
Case in point, the aforementioned Money in the Bank of 2013. Sandow not only won the briefcase, but he did it while turning against his Team Rhodes Scholars teammate Cody Rhodes (and his epic mustache at the time). So, he was working an important and entertaining midcard angle while also ready to jump into the main event at any moment.
Sandow would hold on to his Money in the Bank contract until October of that year, when he finally cashed in at the World Heavyweight Champion at the time, John Cena. In fact, Sandow had the bright idea (no sarcasm) of attacking Cena with the briefcase continuously before cashing in. Unfortunately, he made the mistake of cashing in against John Cena. So, that clearly wasn't going to work.
Damien would go on to make the best of what he was given, including an amazing run as The Miz's "stunt double" - a joke gimmick he turned into pure gold - but eventually left the company shortly thereafter.