Easier Said Than Done: Every WWE Money In The Bank Winner Who Cashed In And Failed

Ah, to be the owner of the Money in the Bank briefcase. Life must be pretty swell.

Not only did you risk life and limb by competing in a hellacious ladder match along with some of WWE’s absolute best, but you actually won the thing. When you climbed to the top of that ladder, pulled down that briefcase, and raised it high above your head, you staked your claim as a future champion of your respective brand, whether it be RAW or SmackDown.

As your music played throughout the arena, the WWE Universe showered praise — or a chorus of boos — towards you, the future champion.

Life must be pretty good at that moment, right?

Not so fast.

The statistics don’t lie: As it turns out, winning the briefcase in the first place isn’t even the hardest part of the whole process of becoming a champion. Sure, winning Money in the Bank is a stepping stone to greatness, but in the end, you have to beat the champion at some point. Simply claiming ownership of the briefcase does not guarantee a championship — it simply guarantees a title opportunity.

And sometimes things don’t go according to plan.

Here are the only men who won their Money in the Bank match, took ownership of the briefcase, and officially cashed in their Money in the Bank contract only to fail to bring home the gold.

John Cena – 2012

When Edge became the first Superstar to cash in their Money in the Bank contract in 2006, he used the element of surprise: He didn’t schedule a championship match, he cashed in after a grueling one had just finished! In doing so, he set an example for future Money in the Bank winners: be the ultimate opportunist and strike when the champion least expects it. Oh, and who was the champion that Edge beat to become WWE Champion? John Cena, who makes this list for ironically being the first Superstar in history to fail during his own cash-in opportunity.

John Cena became the first man to “call his shot” ahead of time when he announced to the world that he would be challenging WWE Champion CM Punk in a match set for the 1000th episode of Monday Night RAW.

While it was an exciting back-and-forth match, after the referee was accidentally knocked out, both Big Show and The Rock got involved in an absolutely chaotic moment. While Cena was declared the winner by disqualification, that unfortunately meant that CM Punk would retain the WWE Championship. And just like that, Cena became the first person ever to fail to parlay their Money in the Bank contract into an official championship reign.

Of course, John Cena went on to win so many more titles in the years ahead that most fans forget about this wild moment in WWE history!

Damien Sandow – 2013

The year was 2013, and John Cena (man, we’re mentioning him a lot already) was the WWE Champion. Damien Sandow was the up-and-coming Superstar whose skills in the ring — and on the microphone — were championship-caliber.

As one of the self-professed smartest Superstars of all time, Sandow utilized an interesting strategy when he cashed in his Money in the Bank contract. After blindsiding Cena during an in-ring interview segment with a cheapshot to Cena’s injured shoulder, Sandow proceeded to lay down an immensely physical beating, literally adding insult to injury. When it became clear that Cena’s shoulder was sufficiently hurt, Sandow cashed in his contract right then and there.

After an incredible back-and-forth match, Cena fought through the pain of his shoulder injury and managed to hit an Attitude Adjustment on Sandow — with only one good arm — and retain his WWE Championship, effectively dashing Sandow’s hopes of ascending to the top of WWE. It was the closest Damien Sandow would ever come to being WWE Champion, as he faded into obscurity as a result of this disappointing loss.

Baron Corbin – 2017

Long before he became Happy Corbin, Baron Corbin was just a lone wolf. A dangerous, capable wolf — but a lone wolf nonetheless. And on one fateful night in 2017, he made the wrestling world stand up and notice him, as he interfered in a match between John Cena and WWE Champion Jinder Mahal and cashed in his Money in the Bank contract right then and there on SmackDown.

It wasn’t the worst strategy in the world. But what did Corbin think Cena would do? Stand idly by as Corbin stole the WWE Title? All it took was a very timely distraction for Corbin to squander one of his best chances to become king of the mountain, as the lengthy title reign of Jinder Mahal continued unabated.

In the end, Baron Corbin failed to realize his dream of becoming WWE Champion. But on the other hand, the WWE Universe narrowly avoided Baron Corbin realizing his dream of becoming WWE Champion. So we like to think it all worked out in the end.

Braun Strowman – 2018

When Braun Strowman announced his intention to cash in his contract against Roman Reigns at Hell in a Cell, it made perfect sense for the Monster Among Men. Locked inside the confines of the Cell, there’d be nowhere for Reigns to run. Common sense says Strowman would use brute force to capture the WWE Universal Championship and start a new reign of terror.

During the match, everything turned into bedlam as Drew McIntyre and Dolph Ziggler attempted to interfere on Strowman’s behalf, which in turn brought out the rest of the members of the Shield to help even the odds.

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Both Strowman and Reigns had contingency plans in case their opponent decided to play dirty, but neither Superstar had a plan for what happened at the end of the match. Brock Lesnar made his shocking return to WWE and he was not in the greatest of moods. Lesnar arrived in the arena, kicked the door of Hell in a Cell completely off its hinges, and proceeded to lay waste to both competitors in the match. The beating that Lesnar gave both men was so severe that the referee had to rule the match a no-contest, meaning Strowman gained the unflattering distinction of being yet another Superstar who managed to win the Money in the Bank ladder match but failed to take home a championship.

Austin Theory – 2022

We’ll be honest, Theory’s failed cash-in this past Monday night against Seth Rollins was the inspiration for this list because we’re still flabbergasted that he didn’t walk away as the United States Champion. Theory checked all the boxes for a successful cash-in: He seized the perfect opportunity (Seth Rollins just became incapacitated by Bobby Lashley sending him through a table, rendering him helpless), he stayed aggressive, and he kept Seth Rollins down. On paper, this is the perfect equation that usually equals a championship. Except he didn’t account for one huge, imposing variable: Bobby Lashley.

By end of the title match, both Austin Theory and Seth Rollins were reduced to rubble — but Rollins still held on to his coveted championship.

Don’t get us wrong, we love Theory — he’s a great interviewee — but if we had the chance to interview him again, our first question would be the question that is on everybody’s minds: Austin Theory, why didn’t you cash in on Roman Reigns for the Undisputed WWE Universal Title, the biggest championship in all of WWE?

Maybe one day the WWE Universe will get an answer to that question, but for now, Theory is forever in the record books as one of only five men to ever cash in their Money in the Bank contract — and fail.