Every WWE Money In The Bank Winner Ranked Worst to Best

17. Mr. Kennedy (2007)

It’s only appropriate to have someone who didn’t even get to attempt a cash-in.

In the mid-2000s, WWE were primed to push one Ken Anderson, known then as Ken Kennedy, or Mr. Kennedy, or MISTEERRRRRRRR KENNNNNEEDDYYYYYYYY (whichever you prefer). With a solid heel gimmick and a high-profile feud with The Undertaker under his belt, 2007 looked to be Kennedy’s year as he won the Money in the Bank match at WrestleMania 23. Supposedly, the plan was for Kennedy to become WWE champion, and then be revealed as Vince McMahon’s illegitimate son, which would lead to a feud with Triple H that would culminate at the following ‘Mania.

Unfortunately, we saw none of that. Kennedy suffered a legitimate injury and ended up losing his briefcase to Edge on an episode of SmackDown. From there, injuries, brand switches, a wellness policy violation, and massive heat with company golden boy Randy Orton would keep Kennedy mired in midcard limbo until his release in May of 2009.

It’s unclear how successful Kennedy would have been had the plans for him come to fruition. However, this is not a list of “what ifs,” and what Kennedy is is the answer to the trivia question “Who is the only Money in the Bank winner to lose their briefcase without cashing in?”