#2 Damien Sandow cashes in against John Cena
Damien Sandow was a very entertaining Superstar during his time with the company in 2014-2015. His impersonations were so spot on and fun-filled that the WWE Universe loved to see him and were disappointed whenever he didn't show up for an episode. His most entertaining bit was when he portrayed the character of Damien Mizdow.
Before his run of impersonations, Sandow's run could be easily forgotten. In the Money In The Bank PPV of 2013, Sandow won the MITB briefcase by pushing his then Tag Team partner, Cody Rhodes off the ladder and claiming the briefcase himself. The following night on Raw, Rhodes turned face and attacked Sandow finally breaking their alliance.
Rhodes and Sandow went on to feud for quite some time with Rhodes getting the better of Sandow in the end. Rhodes also dumped the briefcase into the Gulf of Mexico which led to Sandow bringing in his custom-made briefcase. Rhodes even thwarted Sandow's attempt of cashing in the briefcase against Alberto Del Rio.
After losing many matches to the likes of Santino Marella, R-Truth, and Dolph Ziggler, Sandow confronted the then World Heavyweight Champion, John Cena on an episode of Raw, attacked him and cashed in his briefcase for a match for the Title. Even though Sandow dominated the majority of the match by focusing on John Cena's injured arm, Cena fought back with resilience and single-handedly beat him in the center of the ring.
Hence Sandow became the second Superstar to fail to capture the title after a cash in and the first Superstar to outright lose a cash-in match. All thanks to John Cena.