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#2 Damien Sandow
Damien Sandow was once considered to be the most interesting character on the main roster. His 'intellectual' gimmick was really starting to get over with the WWE Universe, but the main problem was that his Money in the Bank win felt like it was happening way, way too soon. It's not like he didn't deserve it, but it just didn't feel like something he'd earned yet.
The cash-in itself was even more embarrassing, as John Cena kickstarted a chain of events that eventually wound up leading to his exit from WWE. In an alternate universe, we would've enjoyed seeing Cesaro win the briefcase, before immediately getting on the mic and stating that he isn't interested in any sneak attacks - before declaring that he was going to cash in at SummerSlam.
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