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Top 5 Worst Money In The Bank Winners


In honor of Money in the Bank tonight, we should be prepared for the worst. Expectations are too high and we should temper them down a bit, just in case WWE decides to book it like WWE does. So let’s look back at the 5 worst Money in the Bank winners of all time.

Mr Kennedy

Mr Kennedy…or Anderson…or Ken Kennedy. A big “what if” in the annals of WWE history. Kennedy was on fire during his ascent to the main event scene in WWE, and his WWE career peaked at Wrestlemania 23 where he captured the Money in the Bank briefcase. Everything seemed fine. Kennedy was on his way, he was hot and it made sense. And then it all came crashing down…Kennedy would get hurt, lose the briefcase to Edge and would never be the same again.

Jack Swagger

I don’t think there has been any more of a dud Money in the Bank winner than Jack Swagger. The dude is a legit athlete, looks good, and is a solid worker. But boy did he fall short of expectations. He could never get past that lisp, or his Marijuana bust. I was actually in attendance at Wrestlemania 26 when Swagger won the briefcase, and I was stoked at the time…but was quickly let down.

John Cena

I was also in attendance win John Cena won the briefcase for the RAW brand in 2012. There are definitely worse men they could give the briefcase too, but Cena kind of surpasses Money in the Bank. The whole point of the match is to give someone a chance to instantly get into the main event scene. He didn’t win the title off his cash in and only held the briefcase for 8 days…it felt like a useless way to get CM Punk vs John Cena on the 1000th RAW.

Alberto Del Rio

I am a Del Rio mark, but his MITB win and subsequent cash in only 28 days later in 2011 was pretty much underwhelming. Del Rio was already past the briefcase point when he won and was already established in the main event scene. He also went over a super hot CM Punk who was champion at the time. What a waste.


The most recent Money in the Bank winner, Sheamus. Another case of “we got nothing for ya, so here’s the briefcase.” Sheamus was already a multi time world champ by the time he won the Money in the Bank. There were better guys on the roster and in the match, that could have used the win. His cash in was underwhelming…and I don’t even remember the subsequent reign.

Will the 2016 winner end up on this list next year? With the list of participants this year, I somehow doubt it, but we shall see.



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