23. Baron Corbin – SmackDown (August 15, 2017)
This wasn’t the first time someone failed to cash in Money in the Bank, but it was by far the worst. Baron Corbin had been in possession of the briefcase for less than a month when he decided to cash in on then-WWE Champion Jinder Mahal.
Corbin was immediately distracted by John Cena and rolled up for the win in just seconds. Literally nothing came from this as Corbin lost to Cena at SummerSlam and never came close to the title again. Reports said he had substantial backstage heat prior to this, which resulted in him losing.
22. Damien Sandow – Raw (October 28, 2013)
It is shocking to look back and think of Damien Sandow as a Money in the Bank holder. Sandow was a rising star with a shot at the World Heavyweight Championship at the time, but circumstance stood in the way of him becoming champion.
After John Cena won the title from Alberto Del Rio, Sandow attacked him on Raw and had a short match. Cena was able to overcome the beating and fight back to retain. As far as someone doing a surprise cash-in, Sandow was the first person to fail. Ultimately, timing was the problem here as WWE had plans to merge the World Heavyweight title and the WWE title in December and they weren’t going to involve Sandow in those plans. In another year, he may have become World Champion.
21. Braun Strowman – Hell in a Cell 2018
In my heart, this should be last place. Braun Strowman cashed in Money in the Bank for a scheduled Hell in a Cell match with Roman Reigns for the Universal Championship. The problem with this is how the match ended. If they had just had a good match and Strowman lost, so be it, it still would have been near the bottom but oh boy did this suck.
At the climax of their Hell in a Cell match, Brock Lesnar made his return. He beat both Strowman and Reigns, leaving them laying but this is where things got bad. A referee ran in and waved off the match, something unheard of at the time. A Hell in a Cell match being a no contest? Blasphemy. And a total waste of the Money in the Bank contract.
20. John Cena – Raw 1000 (July 23, 2012)
You hear that? It is the sound of Big Show coming to ruin everything. John Cena won the Money in the Bank contract in 2012 and cashed in for a scheduled match at Raw 1000 just weeks later. He was taking on CM Punk who was in the middle of his WWE Championship run and this was looking like a possible moment when Punk’s reign could end.
When Cena looked like he had the match won, Big Show ran down for the disqualification. This made Cena the first person to cash-in Money in the Bank and fail.
19. Jack Swagger – SmackDown (April 2, 2010)
At the time, Jack Swagger was the worst person to hold the Money in the Bank briefcase. He had never been pushed as anything close to a main event star and he was not given a chance to prepare for his cash-in.
On the first SmackDown after WrestleMania XXVI, Swagger took advantage of a downed Chris Jericho and hit the Gutwrench Powerbomb to become the champion. In doing so he lost every ounce of personality he had. He didn’t even react. They may have been going for him being confident or something but it just made the moment feel even more flat. It also doesn’t help that Swagger went on to be one of the worst champions in WWE history.