WWE Money in the Bank Winners Who Didn't Become the Stars Everyone Expected

Winning the Money in the Bank Ladder Match may be a fast-track to a main event push and a world title reign, but it does not guarantee success for every WWE Superstar who emerges from it victoriously.

CM Punk, Edge, Seth Rollins, Liv Morgan, and Iyo Sky are among the best to win the annual high-stakes matchup; not everyone can achieve the success they did.

Ahead of the October 10 return of the Money in the Bank premium live event, emanating from New Orleans, these are the competitors for whom acquiring the most coveted briefcase in professional wrestling did not net the expected stardom.

Mr. Kennedy

It appeared as though the stars had aligned and one of the most intriguing new faces in WWE in the mid-2000s was on his way to superstardom when Mr. Kennedy scaled the ladder and retrieved the Money in the Bank briefcase at WrestleMania 23.

Cocky, confident, and a great talker, he had captured the attention of the fans and had some thinking he was the next big thing in professional wrestling.

He may have been, but a perceived injury forced him to the sidelines, and WWE called an audible, with Kennedy dropping the briefcase to Edge, who would become the first Superstar to ever successfully cash in two of them.

During an interview with NBC Boston's Steve Fall, Kennedy noted that the triceps injury that kept him out was a misdiagnosis, one that altered the course of his wrestling career.

Damien Sandow

Realistically, there was probably a window on Sandow and how far he was going to go in WWE.

He was incredibly popular with the audience under his "Damien Mizdow" persona and his willingness to mimic WWE's past and present Superstars each week. Still, there was only so far that was going to take him, regardless of how warmly accepted his 2013 Money in the Bank victory was.

Booking never really gave him much of a chance, either.

Shortly after John Cena returned from injury in October 2013, Sandow cashed in his title opportunity by telling the babyface he would, then lost a competitive match in which the champion put him over as a threat, but little more.

What should have been a bigger moment for Sandow, one that would have better justified his loss, was instead a forgettable loss that would doom him to midcard status the remainder of his WWE run.

Otis

The year 2020 was a fever dream for most, especially in WWE, where the global pandemic forced significant changes, including the format of that year's Money in the Bank premium live event.

Not held in the Thunderdome where the rest of the shows were, the event's namesake matches took place in WWE Headquarters, where the Superstars involved fought up several stories before grabbing the briefcase on the roof of the iconic building.

Not only was Otis' title shot doomed to failure because he was nowhere near ready at that point, but he was also not a believable main-event star despite his popularity among fans.

The finish did not help matters, either.

Otis did not so much as climb the ladder to win the match as he simply lucked into it, catching the briefcase as AJ Styles fumbled it directly into his arms.

By the time October rolled around, it had become evident that Otis was not the guy the company needed at that point and he lost the briefcase to The Miz at the October Hell in a Cell PLE.

He has been a midcard mainstay since, but is one of the most beloved stars on the roster, if the audience's reaction to him is any indication.

Austin Theory

If there was ever a Superstar whose run with the Money in the Bank briefcase felt sabotaged, it was Austin Theory's.

The winner of the 2022 match, he was in the midst of a big push and very much felt like a Superstar ready to have the rocket strapped to his back and to be pushed to the moon.

Then creative regimes changed, and so did Theory's trajectory.

On the November 7, 2022, episode of Raw, the young Atlantean cashed in his guaranteed championship opportunity...on the United States Championship.

And lost.

A young star who had previously shared the same ring with "Stone Cold" Steve Austin, Vince McMahon, and Pat McAfee at WrestleMania 38 had just lost his opportunity to become a main event star in a match for a secondary title.

It was a massive letdown for Theory, but not for the fans who believed he was not ready for that position in the first place.

He would bounce back and beat John Cena at WrestleMania the following year, but he never returned to the heights he was at when he first captured the briefcase. Within a year, he would be tagging with Grayson Waller and losing more than he won.

His arrival in The Vision was a nice step up, but he is still clearly not valued as a main event star, fairly or not.