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#4. Mr. Kennedy (Kennedy) - 2007
Did you know that the Money in the Bank briefcase doesn't have to be won in a ladder match? Mr. Kennedy certainly does.
The story of Ken Kennedy (aka Ken Anderson) in WWE is probably the ultimate "What If?" tale in pro wrestling, just maybe outside "What if Magnum TA didn't crash his car?" Every time the guy seemed to be making serious traction, he'd either get hurt or tick off Randy Orton, both of which might as well be the same thing.
Money in the Bank should have led to big things for Kennedy
Take, for example, his victory in 2007, back when the Money in the Bank match was held at WrestleMania. Following his victory, the Man Who Likes To Say His Last Name Twice proclaimed that he was going to cash his contract in at the following WrestleMania (which would have been 24, for those keeping count) and securing himself a Main Event.
Then came the episode of Raw in May of that year, where Edge challenged him to put up his Money in the Bank briefcase in a match against him. Which... why would you do that? Well, Kennedy did, and Edge not only became the first Mr. Money in the Bank to not win the briefcase in the ladder match, but the first to win it twice.
Edge would go on to cash in the Money in the Bank contract on The Undertaker on an episode of SmackDown later that year. Mr. Kennedy would be out with an injury (the legit reason he gave up the contract), only to return and almost be Vince McMahon's illigitimate child. That honor, of course, eventually went to Hornswoggle. As most things do.
