When Ken Kennedy won the Money in the Bank contract at WrestleMania 23 it was a big deal because it showed that WWE was going to use it to make a new star. Previous winners like Edge & RVD were long term WWE guys by that point while Kennedy was pretty new. Unfortunately for Kennedy, he wasn't able to cash in due to injury. It's an interesting story because when they had him drop the briefcase to Edge in a match on Raw (the only time somebody lost a briefcase they won) they thought that Kennedy tore his triceps and would need surgery that would put him on the shelf for about six months. Did WWE panic by taking the briefcase off him? That's what I always thought because they said Money in the Bank winners could cash in for a year, so it was odd that they would just strip him of it so quickly. It definitely helped Edge move to Smackdown to become a main guy over there, but it really hurt Kennedy. It ended up that he didn't need the surgery and he missed a lot less time, so WWE probably could have kept the briefcase on him. Two years later after other injuries and a suspension due to performance enhancing drugs, Kennedy was gone from WWE. It might be harsh to list Kennedy in this spot because he was injured legitimately, but he's the only Money in the Bank winner that never tried to cash in his briefcase so he is the biggest flop.
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.
