WWE Money in the Bank: All 16 Winners, Ranked

credit: wwe.com

16. Mr. Kennedy – WrestleMania 23

For the majority of the superstars who capture the briefcase, it turns out to be the best thing that happened to their careers.  For Mr. Kennedy, it seemed more like a curse.  Kennedy won the MITB match at WrestleMania 23 and shortly after announced that he would wait until WrestleMania 24 to cash it in.  And that’s where the trouble began.  Just over a month later, Kennedy was forced to defend the case against Edge in a match that he lost.  However, during the match, he sustained what first appeared to be a torn triceps that would’ve put him out for several months.  This injury took him completely out of the title picture only for it to be found out a few weeks later that the injury was only a severe hematoma.

Four months after losing the biggest shot of his career, Kennedy was caught violating the WWE’s Talent Wellness Policy and received a 30-day suspension.  He did wrestle at WrestleMania 24 like he said he would, but it was in that years MITB match, he was unsuccessful.  Then in June 2008, he was drafted to Smackdown but was injured again shortly after.  Kennedy’s fall from grace eventually hit rock bottom when he was released from the company in May of 2009 after dropping one of Vince McMahon’s golden boys, Randy Orton, awkwardly on a suplex.

From the day Kennedy won the case his career was a roller-coaster, albeit one that only went down.  And it’s a shame.  Kennedy was a solid talent and put in a terrific performance during his case-winning match which also turned out to be one of the better MITB matches of all time.  But just for the sake that he’s the only guy to win the case yet never even attempt a cash-in, Kennedy has to be #16.