WWE Money in the Bank Credit: WWE.com | Bayley is among the 28 MITB winners, but where do she and the others rank?

On July 1, WWE will host its annual Money in the Bank event. The company will make history when they do, as the premium live event emanates from London, England, which marks the first time that WWE will hold a Premium Live Event in London since SummerSlam 1992.

Annually, Money in the Bank creates a lot of excitement. The men’s and women’s Money in the Bank Ladder Matches have a big prize for the winner: a guaranteed title shot for them to use any time within 365 days.

Money in the Bank has been a WWE staple since WrestleMania 21. Who is the best? Who made the best use of the case? Who changed their career?

Here, we’ll aim to find out.

Since 2005, there have been 28 Money in the Bank briefcase winners. Only one man, CM Punk, has been a two-time winner. Technically speaking, Carmella is a two-time winner, but only because former wrestler James Ellsworth “won it” for her the first time.

Immediately, to get down to 10, we’ll wipe out the wrestlers who failed their cash-in. So, gone are John Cena, Damien Sandow, Baron Corbin, Braun Strowman, and Otis. Additionally, considering that Asuka’s MITB prize was immediately the Raw Women’s Championship (because Becky Lynch left WWE in May 2020 after announcing her pregnancy), Asuka will not make it to the Top 10 either. Neither will Mr. Kennedy, who infamously lost his case to Edge, who went on to cash in. That sequence nor Kennedy will make it.

As far as criteria go here, I’ll be thinking about the following things:

The Cash-In: How memorable was your cash-in? All of them are exciting, but was yours much more than the others?
The Surprise Element: Could everyone see it coming? Or did you catch people by surprise?
The Follow-Up: What happened after the title win? Did you go on a marathon? Or were you hanging out in the interim? None of these are necessarily their faults, but they’re things looked into when making a list.
#CaseEffect: Did winning the case really “change your life?” For some, it did. For others, it was maybe gratuitous. Maybe some fall in the middle. But this is what we’re here to find out.

And so, here are the Top 10 Money in the Bank winners.

10. Daniel Bryan

Daniel Bryan made his first significant imprint on a show best known for one of his wrestling peers. Money in the Bank 2011 emanated from the Allstate Arena in the Chicago suburbs. The event is most known for a WWE Championship collision between John Cena and CM Punk, but the night started in a big way too. Bryan, rising steadily in popularity, won the World Heavyweight Championship Money in the Bank match that night. By winning, he could cash in on his brand’s champion, the World Heavyweight Champion, anytime he wanted.

Bryan would eventually do that at TLC in December. He became the World Heavyweight Champion at a time when Punk was the WWE Champion, which made for a seminal moment for each of their careers.

Bryan’s title reign didn’t last very long. When he wrestled Sheamus to begin WrestleMania 28, Sheamus booted him with the Brogue Kick to start the match and won it three seconds later. However, after that match, Bryan’s upshot in his career was for the better. He was never lower than that point for the rest of his WWE career amid some up-and-down storylines. It’s fair to say that cashing in for the World Heavyweight Title spearheaded his run to the top, and by that measure, is one of the best winners. Ultimately, he can’t be placed high due to his short reign as champion, but he can make the Top 10.

9. The Miz

Miz is polarizing among WWE fans and wrestling fans alike. But at the time of Miz’s cash-in in 2010, the hate was sky-high. Many discredited the former Real World star’s credentials and abilities, leading many to pan his title reign and cash-in. Things got worse when The Miz main-evented WrestleMania against John Cena.

Miz’s career was never the same after he could call himself a WrestleMania main-eventer. He went around the bases again and got another Grand Slam later in his career. He’s one of his era’s most accomplished superstars; love or hate him.

The time period Miz was champion was a down period for WWE. Miz held onto the WWE Championship for several months, had several defenses, and also main-event WrestleMania. His career was never the same after he “changed his life” one night in 2010, so he ranks as the ninth-best winner ever.

8. Liv Morgan

Six women have won the Money in the Bank briefcase, two of which are in this Top 10, and the first is rising star Liv Morgan.

Morgan’s rise to the top in WWE is a classic case of what happens when you take the kid gloves off them. Liv began her WWE main roster career in The Riott Squad, a faction that lasted roughly 15 months before it dissolved. Morgan’s 2019 was mainly lost due to shuffling and direction. 2020 sprang off a new opportunity for Liv to reunite with Ruby Riott, but WWE eventually released Riott in Spring 2021.

So, Liv was left with no one but herself. Fans began to rally around her as the company returned to touring after the COVID-19 pandemic shut them down. Her reactions started getting more visible, and she got more opportunities. She wrestled Becky Lynch twice in the Winter of 2021 and at WWE Day 1 in 2022. After a brief run with mega-star Rhea Ripley in a tag team, Liv again entered the MITB field in 2022. This time, though, she won miraculously after pushing her boot off the top rope to propel herself and the ladder back into a standing position. She knocked Lynch off her ladder, grabbed the case, and later cashed in on Ronda Rousey to win the title.

Morgan is the most real-time example in the Top 10 because her story is unfinished. But what’s true is that since her victory and title run, she’s enjoyed a very comfortable and enviable spot on the card. Before her unfortunate injury, she was on TV weekly, wrestling in big matches against name-brand opponents and, most importantly, keeping viewers’ attention. She’s a fast-rising star who keeps getting better and has stayed afloat, so her #CaseEffect is high and keeps getting higher. Next year, maybe if we do this again, she’ll be higher on

7. Rob Van Dam

Two wrestlers from the mid- or late-2000s are featured on this list, and the first is Rob Van Dam.

RVD’s Money in the Bank victory and cash-in is very fondly remembered. Van Dam became a cult favorite and an innovator in ECW in the early years of his wrestling career. Upon joining WWE (then the World Wrestling Federation) in 2001, “The Whole Damn Show” got reactions that would make even Stone Cold and The Rock blush. Van Dam quickly became a favorite of many WWE fans, and as his career continued, many wanted him to be World Champion.

An injury sidelined Van Dam for much of 2005, which was unfortunate since the company ran an ECW homecoming event – ECW One Night Stand – that summer. RVD appeared at that event and excited the crowd, but his presence needed to be added. Sorely. Flash-forward to 2006, and RVD was back on the scene. He competed in the first inter-promotional Money in the Bank match and the second-ever edition of it at WrestleMania that April. He unhooked the case and took it down to many cheers in Chicago that night, and that was just the beginning. Two months later, Van Dam cashed in his briefcase against the great John Cena at One Night Stand II.

The atmosphere in which Van Dam fought Cena – and later won the WWE Championship – is among the hottest and most memorable in company history. RVD’s victory for the championship was very fitting since it happened at Hammerstein Ballroom under the ECW guise.

Unfortunately, as wrestling fans know, this is where the story takes an unfortunate turn. Just a few weeks later, Van Dam was arrested for marijuana charges. And then, on July 3, less than a month after winning the title, he lost the title to Edge in a Triple Threat Match that featured Cena on Raw. WWE then issued him a suspension, and the rest was history.

RVD did enough to cement his status in the Top 10 with the win, the cash-in, and the story. But of the MITB winners, he holds the shortest title reign. His career in WWE only lasted about another year, as he’d depart the company in 2007. Nevertheless, Mr. Monday Night deserves recognition, especially as he still stands today as one of the only winners to “honorably” cash his MITB contract ahead of time.

6. Dolph Ziggler

Dolph Ziggler has the distinction of having one of the most memorable cash-ins ever.

Ziggler cashed in the contract the night after WrestleMania 29. A rowdy crowd at the Continental Airlines Arena provided an incredible soundtrack for Dolph as he marched to the ring to go after World Heavyweight Champion Alberto Del Rio. Although Ziggler wrestled as a bad guy at the time, the New Jersey crowd didn’t care. They sensed a title change, and they got one!

Ziggler went on to hold the title for about three months after. He lost it back to Del Rio in a memorable bout that included a double-turn, where the bad guy in Ziggler turned good, while Del Rio earned too many boos to call himself a good guy by the end of the match.

Still, while he only held the title temporarily, the cash-in helped his cause in this case. It’s one of the biggest pops of the 2010s and one of WWE’s best moments from that decade. Dolph probably would have been propelled into the next tier if the reign had gone on longer.

5. Dean Ambrose

Dean Ambrose finishes outside the Top 5 for Money in the Bank winners. He may, however, hold one of the most significant victories of them all though.

Ambrose began the night in Las Vegas in 2016 with a victory in the Money in the Bank Ladder Match. A few hours later, Seth Rollins challenged Roman Reigns for the WWE Championship. Rollins defeated Reigns in a lengthy match, and then afterward, Ambrose turned up and cashed in on Rollins to win the WWE Title.

He made history in doing so. All of The Shield, one of WWE’s most popular and dominant factions of all time, held the WWE Championship on the same night. And it was Ambrose who held up the title to end the night.

A month later, he won the one and only Shield Triple Threat Match ever to occur as he went into Smackdown as WWE Champion on the new live edition of the show. He ultimately lost the championship to AJ Styles at Backlash that September, but Ambrose made a lot of memories that night in Las Vegas.

4. Randy Orton

Randy Orton might not have the most “beloved” cash-in, but The Viper built up a strong case after he won the WWE Title at SummerSlam 2013.

Orton won the briefcase the month before at the MITB event. Then, John Cena defended the title against Daniel Bryan at The Biggest Party of the Summer. Triple H worked as the Special Guest Referee in what became an instant classic. Bryan defeated the legendary Cena, but the fun stopped for him moments later.

Orton helped orchestrate a reversal of fortune for the new champion. With help from Triple H, The Viper cashed in successfully and won the championship.

Randy’s reign then went up to WrestleMania 30 (161 days). It remains one of the longest reigns anyone’s had with their championship after cashing in. Much of the reigns end up being short. Whilehile Orton won the briefcase long after he established himself, reign length and the cash-in boosted his cause to just outside the Top 5.

3. Seth Rollins

Seth Rollins holds one prominent edge over every Money in the Bank winner.

After Rollins pulled “The Heist of the Century” at WrestleMania 31, he took that moment and ran with it. Rollins held the WWE Championship for 221 days, the longest continuous reign for any previous MITB holder after they cashed in.

Rollins’ cash-in is arguably the most famous of them all. He took control of the main event of WrestleMania 31 between Roman Reigns and Brock Lesnar. Sliding into the match late, he charged the crowd at Levi’s Stadium and thrillingly won the WWE Title. It’s still the only time someone has attempted a cash-in at WrestleMania, and given the enormity of the moment, it’s hard to suggest it ever being replicated.

You could easily make the case for Rollins to be #1. While he’s #3 on this list, there’s no doubt he ranks in the elite echelon of MITB winners.

2. Edge

It’s tough to top the original. As far as the men’s winners go, none have been better than Edge.

Edge’s story going into winning MITB was that he felt he had long earned a shot at the top of the mountain. So when he won the first-ever MITB Ladder Match, it felt like he was fulfilling his prophecy.

Fans had to play the long game for the first reign with the contract. Edge fought once over it with Matt Hardy in a Ladder Match at Raw Homecoming in October 2005. Other than that, however, his case wasn’t the subject of pursuit. So he held onto it and bided his time and waited.

Then came January 8, 2006. At New Year’s Revolution, Edge cashed the contract in on WWE Champion John Cena following an Elimination Chamber Match. After several Spears, Edge shocked everyone and finally became WWE Champion.

The original cash-in is still one of the best pieces of business of that era and this century. Nobody expected it, and fans wanted it to happen desperately for Edge, even while he played the villain role.

Edge’s championship reign wouldn’t last very long. He’d drop the title back to Cena a few weeks later. So he has one of the shortest reigns after cashing it in.

So, why’s he ahead of Seth Rollins? It’s pretty much a pick them at this point. But considering he was the original, how well done it was, and how it sent Edge up into the stratosphere after over seven years with the company, it magnified the moment more. So, he ranks as the top men’s MITB winner.

1. Bayley

No Money in the Bank Ladder Match winner underwent as significant of a shift in one night like Bayley did.

Entering the 2019 MITB event, the previously-known ‘Hugger’ was in limbo. Sasha Banks disappeared after WrestleMania 35, an event where she and Bayley lost their Women’s Tag Team Championships. After making so much history early on in her career, it seemed like she would end up lost.

But that all changed in Hartford, Connecticut. The XL Center played host to MITB that year, and Bayley entered the Ladder Match and was part of a strong field that led off the night. Bayley eventually rose to the top of the ladder and retrieved the briefcase, sending her fans into a tizzy. But she wasn’t done.

Later at night, Charlotte Flair and Lacey Evans picked apart Becky Lynch. Lynch had won the Raw and Smackdown Women’s Titles in the first-ever women’s main event of WrestleMania that April. She defended her title successfully against Evans, but Flair won the Smackdown title.

Hartford fans responded to the two-on-one attack on Lynch by chanting for Bayley to appear. Bayley appeared, blew the roof off the building, and decided to go all in after taking Flair out. She cashed in the briefcase, hit an Elbow Drop on Flair, and won the Smackdown Women’s Title.

Bayley was Smackdown Women’s Champion for 520 of the next 525 days. She lost the title at Hell in a Cell that October but sprang up four days later with a new look and won it back. Bayley wouldn’t relinquish it until falling to longtime rival Sasha Banks in a HIAC Match.

No other wrestlers who cashed in their contracts held the title for as long as Bayley. She had it for 140 days before losing to Charlotte. Rollins went 221 in a row with the WWE Championship.

#CaseEffect also helps Bayley because despite losses on TV, her star power is unrivaled, and she hasn’t fallen out of the top picture since. It’s hard to believe that until the time of the cash-in, she went a full two years without a one-on-one title shot at a big event.

By many measures, Bayley is the greatest MITB winner in WWE history.

About Chris Novak

Chris Novak has been talking and writing about sports ever since he can remember. Previously, Novak wrote for and managed sites in the SB Nation network for nearly a decade from 2013-2022