Eight Worst Money In The Bank Winners In WWE History

Money in the Bank is a great star-making tool WWE has in its arsenal, but the company has failed to capitalize on the concept in recent years.

The match was such a feature attraction at WrestleMania that it became its own premium live event. It’s a marquee match that has created main-event stars, but the gimmick combined with a rigid world title scene has created a sense of malaise for Money in the Bank.

And it sure wasn’t helped by these eight superstars damaging the concept as the worst winners in Money in the Bank history.

8. John Cena (2012)
The goal of Money in the Bank should be to create new stars, so it was baffling when Cena won the match. He announced his cash-in the night after on “RAW” to challenge then-WWE champion CM Punk at “RAW 1000” a week later on July 23. The match ended in a disqualification after Big Show interfered, which served to set up a triple-threat match for SummerSlam. Cena became the first person to fail his cash-in, and the only reason was to continue the Cena-Punk feud, when there were multiple other ways to accomplish that.

7. Jack Swagger (2010)
This simply was WWE pushing a person that wasn’t ready for the role. Swagger won the briefcase at WrestleMania 26 and cashed in on the following “SmackDown” on world heavyweight champion Chris Jericho after Jericho was attacked by Edge. It was a classic heel that cashes in on the babyface after the latter gets attacked, but Swagger’s stern reaction didn’t fit the bill. Swagger just wasn’t world-champion material and needed more time to develop.

6. Damian Sandow (2013)
Sandow had a unique gimmick that had the potential to be a solid heel in the upper mid card. But the Massachusetts native simply lost a lot on his road to his cash-in. His character was an old-school intellectual, but he failed his cash-in when Cena, who he thought was injured, still beat him even after Sandow worked on the world heavyweight champion’s arm. Sandow became the second person to fail their cash-in.

5. Alberto Del Rio (2011)
The “Summer of Punk” had the potential to give WWE another boom period. Punk was the hottest star in pro wrestling after he cut his infamous “Pipebomb” promo and beat Cena to win the world title. The pair had a unification match at SummerSlam, and Punk won, which was the right call. And then Kevin Nash made his return and gave Punk a jackknife powerbomb, which opened the door for Del Rio to cash in and become the new champion. It simply was the worst timing for Del Rio, and WWE’s attempt at using him to boost their Latin American audience withered away like Nash’s knees.

4. Mr. Kennedy (2007)
Mr. Kennedy had a lot of what WWE looks for in its stars. He talked loudly and had a decent physique. But a misdiagnosed injury and a need to take the title off the Undertaker caused WWE to have Mr. Kennedy gamble his briefcase against Edge, who won it and cashed in a second time. The angle made Mr. Kennedy look really foolish and killed any momentum he could have had.

3. Baron Corbin (2017)
People in WWE really like Corbin, and they also seemingly love to make him look like the biggest idiot on the planet, which is what happened when he tried to cash in during Jinder Mahal and Cena’s world title match. (WWE also, for some reason, loves to involve Cena in disastrous Money in the Bank moments.) Corbin ate the pin and lost to Cena at SummerSlam, which marked a steep fall for Corbin.

2. Otis (2020)
When you have someone win Money in the Bank because the briefcase just landed in their general direction, there’s no recovering from that. The briefcase simply was a tool for Otis’ comedy gimmick, but there was no shot he was ever going to win the world title. He also was made to look like an idiot and put up his briefcase in a match against The Miz. Otis lost and remains a walking gag machine.

1. Austin Theory (2022)
For all the failed cash-ins and the foolish attempts at staking the briefcase, at least those misadventures were for the world title. Theory, like Sandow and other Money in the Bank winners, lost a lot of his matches. His primary gimmick when he had the briefcase was to take selfies with it. But he was a young talent who WWE could push as its next star. Instead, he challenged for the United States championship and failed after interference from Bobby Lashley. The loss was meant to give him more of an edge, but he still remains mediocre at best, which was not helped by his failed Money in the Bank run.

An honorable mention should go to WWE’s consistency with having most of its women’s stars cash in on the night of the event. Four of the six winners cashed in on the same night they won it, and when Asuka won in 2020, she didn’t cash in and simply was rewarded the title when Becky Lynch announced her pregnancy and relinquished her belt. The cash-in has become akin to winning the world title, which is the problem with how WWE books the concept. The briefcase should be the tool to build a star and not the grand prize to be won.