WWE Money in the Bank: All 16 Winners, Ranked

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5. Daniel Bryan – Money in the Bank 2011

Much like Ambrose’s win in 2016, the Smackdown MITB  match was an absolute classic.  Bryan, a budding star, overcame the advances of Cody Rhodes, Heath Slater, Justin Gabriel, Wade Barrett, Kane, Sin Cara, and Sheamus to climb the mountain, but he went through the ringer to do it.  Bryan, constantly the smallest guy in the room, withstood a barrage of punishment in a fascinating MITB that seemed more like a car wreck than a wrestling match.  Heck, Sin Cara didn’t even make it to the final bell.

During his run with the briefcase, Bryan, ever the perfect baby face, slowly began to show his heel side.  He showed signs of smugness and arrogance, and actually went back on his guarantee to cash in the case at the following WrestleMania when he did just that on a prone Big Show at TLC 2011, 5 months after first earning it.  Bryan would then hold the belt for 105 days, impressive considering he was battling giants like Mark Henry, The Great Khali, Barrett, and the aforementioned Big Show.  It was a really fun reign but ended in ridiculous fashion when he lost it to Sheamus at WrestleMania 28 in just 18 seconds.

Bryan’s first title win came on the feels of his MITB win but it did a lot more than just give him a chance at a title belt.  His title reign proved that all the hype about him was very real and he had the goods to be a main event type star.  2 years after his WrestleMania 28 debacle, Bryan headlined WrestleMania 30 after months and months of having the WWE Universe eating out of the palm of his hand.  MITB 2011 was the beginning of the story that lasts to this very day.  The modern day David won the briefcase and not too long after became one of the most popular superstars in WWE history.