Best and Worst Winners of WWE Money in the Bank Ladder Matches

The Money in the Bank ladder match is a great concept that has helped to elevate several WWE superstars. For example, Shelton Benjamin astonished viewers in the early iteration with stunts that will appear on highlight reels for years. However, the winners of the stipulation match live on in the annals of history, for better or worse.

Winning the Money in the Bank briefcase has been instrumental to some wrestlers’ success. Meanwhile, others were unable to use the opportunity to develop into bigger stars and remain in the title picture.

This Saturday, the titular pay-per-view will emanate from MGM Grand Garden Arena in Las Vegas, Nevada. Admittedly, the fallout from the event has grown a little stale due to recent uninspiring winners and disappointing cash-ins. However, it’s still an exciting time of year that will potentially have lasting ramifications on WWE programming ahead of SummerSlam.

While you attempt to predict this year’s victors, let’s take a look at the best winners of the WWE Money in the Bank ladder match, with an accompanying worst selection on each slide.

Worst: Braun Strowman

Braun Strowman’s run with WWE can be described best as a series of missed opportunities. At one point, The Monster Among Men was one of the hottest acts in the company, but the powers that be waited a bit too long to make him a world champion.

Strowman dominated in the finishing stretch of the 2018 men’s Money in the Bank to secure the briefcase. It was an impressive win, but his time with the contract and his eventual cash-in were underwhelming. In the end, he anticlimactically used it to challenge Roman Reigns to a Hell in a Cell match, which resulted in a no-contest due to interference from Brock Lesnar.

Best: Bayley

It is often difficult for a babyface to effectively use the Money in the Bank briefcase to create a convincing title win. It’s a plot device better suited for heels because it allows them to steal a victory and create a memorable moment in the process.

Nevertheless, Bayley is probably the best Ms. Money in the Bank thanks to her feel-good win in 2019. After Lacey Evans emerged to help Charlotte Flair defeat Becky Lynch for SmackDown women’s title, the two attacked the former double champion until Bayley came to her aid. Then, The Hugger used the opportunity to cash in and become the first women’s grand slam champion.

Worst: Baron Corbin

Baron Corbin is such a divisive character. One could argue that he is a potent villain because he elicits such a strong reaction. Still, it’s also hard to buy into his hackneyed character moments and repetitive feuds at times.

There were so many better options in the 2017 men’s Money in the Bank ladder match, but The Lone Wolf prevailed. Corbin went on to hold the briefcase for 58 days before he failed to cash it in on Jinder Mahal after John Cena distracted him on the Aug. 15 episode of SmackDown.

Best: Dolph Ziggler

Dolph Ziggler’s run in 2012 was legendary. The Showoff made a believer out of even his biggest skeptics when he won the men’s Money in the Bank ladder and executed one of the greatest cash-ins of all time.

Ziggler held the contract for 267 days, and the building anticipation made his crowning moment so much sweeter. The thunderous ovation as he stormed down the ramp to confront Alberto Del Rio on the April 8, 2013 episode of Raw shortly gave way to an even louder reaction as he pinned him to become the world heavyweight champion.

Worst: Mr. Kennedy

Mr. Kennedy was a forgettable winner whose time with the briefcase was unfortunately cut short. The Green Bay, Wisconsin, native won the third men’s Money in the Bank ladder match at WrestleMania 23.

Thirty-six days later, Edge goaded him into a match and unceremoniously defeated him for his Money in the Bank contract. WWE made this decision after Kennedy sustained a tricep injury that would seemingly put him on the shelf for a while. However, it turned out to be a minor injury that wouldn’t have affected his run as much as expected.

Best: Seth Rollins

Seth Rollins is one of the most accomplished wrestlers on the WWE roster. To that end, The Heist of the Century will always be one of the highlights of his career.

Becoming the first person to cash in his briefcase on the Grandest Stage of Them All granted him his first WrestleMania moment. It also propelled his heel persona following the implosion of The Shield to another level. For many of us, it’s the best Money in the Bank cash-in to date.

Could The Visionary become the second two-time winner this weekend and attempt to seek revenge on Roman Reigns?

Worst: Damian Sandow

Damian Sandow was a great comedic character with loads of potential. He was similar to Rusev, a wrestler who grew in popularity despite WWE booking decisions.

Unfortunately, the 2013 Money in the Bank winner holds the distinction of the first wrestler to fail to cash in their briefcase. On Oct. 28, Sandow attacked John Cena, who suffered an arm injury, and attempted to challenge for the WWE World Heavyweight Championship. The Leader of the Cenation surprisingly beat him outright and doomed him to months languishing in obscurity.

For those counting at home, Cena was involved in three failed cash-in attempts, including his own.

Best: CM Punk

CM Punk is arguably the best Money in the Bank winner because he’s the only wrestler to win the contract two years in a row. The Second City Saint won it for the first time in 2008 at WrestleMania 24 and went on to defeat Edge for the World Heavyweight Championship.

A year later, he returned to the event and secured the briefcase for a second time. This time he used it to cash in on Jeff Hardy at Extreme Rules 2009 and laid the groundwork for their iconic feud. Punk’s second world heavyweight title win was also significant because it set up his heel turn, which eventually led to the creation of the Straight Edge Society.

Worst: Otis

In 2020, Heavy Machinery was a hot new tag team. Even more, Otis was riding the wave following his popular storyline with Mandy Rose, which culminated at WrestleMania 36.

Yes, this romantic pairing was unconventional, but it worked. It was one of few times that one of WWE’s running gags paid off well in the end.

A month later, Otis qualified for the men’s Money in the Bank ladder match. Then he won a bizarre but entertaining edition of the match that took place at WWE's global headquarters in Stamford, Connecticut, during the COVID-19 pandemic.

In theory, this wasn’t a bad decision because the 30-year-old was such a likable character. However, WWE never presented him as someone who could become a world champion, and he didn’t show any interest in using his contact to capture the tag titles.

Instead, Otis introduced a Money in the Bank lunchbox to keep it in and eventually lost it to The Miz at Hell in a Cell.

Best: Edge

Edge earned the top spot on this list because he is truly synonymous with the highly sought-after briefcase. The first Money in the Bank winner set the tone for the concept for years to come.

As The Rated R Superstar, he made a name for himself as a conniving opportunist. His cash-in at New Year's Revolution 2006 may not be as memorable as Ziggler’s or Rollins'. Nevertheless, it set the precedent for every heel who attempted to follow in his footsteps and use the Money in the Bank contract to become the new world champion.

Edge is also technically the first two-time winner because he beat Kennedy for his briefcase on the May 7, 2007 episode of Raw.