The Money in the Bank ladder match might be the most important match in WWE, with the power to change careers and make stars. The winner gets a guaranteed title match against the champion of their choosing.
Winning Money in the Bank should be a highlight in anyone’s career, and to WWE’s credit, it usually is. But, any gimmick that’s gone on as long as Money in the Bank has (15 years) will have its misfires, whether it’s bad booking or unfortunate circumstances. Here are five of the most egregious examples of WWE wasting one of its most valuable prizes.
Ken Kennedy is one of the biggest “what could have been” stories in WWE history. Kennedy felt like a star in the making when he first arrived in WWE. After competitive feuds with Batista and the Undertaker, Kennedy was the obvious choice to win the Money in the Bank Ladder Match at WrestleMania 23, in a match filled with future main eventers like Edge, Randy Orton, CM Punk, Booker T. and the Hardy Boyz.
After winning the briefcase, Kennedy vowed to cash it in at WrestleMania 24, but he wouldn’t be able to live up to that promise. After suffering a triceps injury, Kennedy would be the first (and only) winner of the Money in the Bank contract to lose it in a singles defense. Edge defeated Kennedy to win his second briefcase and went on to cash it in on an injured Undertaker days later.
The cruel irony of Kennedy’s triceps injury is that it wasn’t as bad as it seemed. Instead of tearing it off the bone, as it was originally diagnosed, it turned out he’d only suffered a hematoma. He was originally scheduled to be out for 5-7 months but wound up returning to WWE TV in a matter of weeks. His missed opportunity was the beginning of a string of missed connections that defined the rest of his WWE career. His WWE run would end in 2009 with Kennedy never holding a world championship.
The Miz’s career has been defined by overachieving, but he’s never punched above his weight class more than when he cashed in the Money in the Bank briefcase to win the WWE Championship. He went on to defend the title against John Cena at WrestleMania 27. Unfortunately for him, he wound up being the third most important person in the biggest match of his career.
The Miz was completely overshadowed by Cena and the Rock, who returned to a prominent role in WWE after a long absence in the build-up to WrestleMania. Despite holding the top title in WWE, Miz was a footnote in the burgeoning Cena/Rock rivalry. Even the fact that the Miz retained the WWE Championship is tainted by the fact that he suffered a concussion during the match, a fitting ending to one of the least consequential WrestleMania main events ever.
Sandow, whose “intellectual savior of the masses” gimmick made him a cult favorite, was a surprising choice to win what turned out to be the final World Heavyweight Championship Money in the Bank match. His run began well, when he betrayed tag team partner Cody Rhodes to win the ladder match to massive crowd heat. That set up a feud between the two which Rhodes dominated. In fact, Sandow was dominated by everyone he wrestled while he held the briefcase, having a 1-12 record during his time as Mr. Money in the Bank.
Despite a total lack of momentum, Sandow still had an opportunity to elevate himself to the main event by cashing in his briefcase. He picked the traditional spot of going after a wounded champion following a grueling title match. Unfortunately for him, he picked the wrong champion.
Sandow would attempt to cash in on John Cena at the height of the “Cena wins LOL” era. Sandow targeted Cena’s arm, which had been softened up by Alberto Del Rio, battering it with everything from his briefcase to a steel chair before the match. Cena wound up overcoming the odds in true LOL fashion, defeating Sandow with a one armed Attitude Adjustment.
Baron Corbin’s 2017 Money in the Bank victory was the first attempt to make him a main event player, and it got off to a promising start. Corbin dumped A.J. Styles and Shinsuke Nakamura off the ladder, dashing the crowd’s hope that one of their favorites would win. Corbin seemed poised for a long run with briefcase where he could eventually threaten a fan favorite like Styles or Nakamura with a cash in. His lone wolf gimmick and bullying tendencies could have made him a good choice to menace a babyface with the looming threat of a cash in.
Instead, he chose to target heel champ Jinder Mahal a few months after winning the briefcase. It was a surprising move, but one that seemed like it could bring some welcome chaos to SmackDown’s main event scene. That is, until Corbin lost seconds later due to his greatest weakness, a roll up. That match set the standard for Corbin’s losses for years to come. In spite of makeovers and gimmick changes, Corbin’s never really overcome his moment of Money in the Bank infamy.
Braun Strowman’s recent Universal Championship win at WrestleMania 36 was definitely a case of being in the right place at the right time, but it’s hard to say it was unearned. He’s lost so many championship matches that he became synonymous with failed title shots.
It looked like he would finally break through and win the Universal Championship in 2018, when he won the Money in the Bank ladder match. Strowman having a title shot at the time and place of his choosing should have been unstoppable. But, beatings at the hands of Brock Lesnar and a reunited Shield after he tried to announce his cash ins ahead of time proved otherwise. A frustrated Strowman announced in advance that he’d be cashing in his briefcase for a Hell in a Cell match with Reigns, which should have guaranteed Strowman a match with a winner and without interference. He didn’t count on Lesnar breaking the cell door down and WWE booking the first no contest in the history of the match, an intersection of low points for two venerable WWE gimmick matches.
While winning the Money in the Bank briefcase is usually a highlight in a superstar's career, sometimes it doesn't work out so well.