TheMoney In the Bank PLEis where dreams are made, and potential future champions get their roadmap planned out for them. Win the briefcase, and you’re guaranteed a shot at any championship in the WWE, with up to a year to cash in the contract.
The most exciting thing about a cash-in is the spontaneous factor, as it can happen any time within the year. During a match, in the middle of a promo segment, you name it; if the champion is vulnerable, you best be sure the holder of the briefcase is about to run out.
7 Terrible WWE Wrestlers That Are Great On The Mic
In the ring, he’s average at best, boring at worst, but a lot of the time, his feuds are still incredibly compelling because of his ability on the mic
This doesn’t mean every cash-in is successful, mind you, as the champion can still pull a quick one and ruin the Money in the Bank winner’s opportunity. This list will cover every winner of Money in the Bank, the reaction to their cash-in attempt, and whether it was memorable or a complete failure.
26John Cena
Money in the Bank (2012)
Cashed In On
CM Punk (Failed)
Cagematch Rating
Meltzer Rating
At a time when two Money in the Bank ladder matches took place in one night on the men’s side, the Raw version of the 2012 PLE left a lot to be desired. Compared to the eight participants on the SmackDown side, Raw’s match only had five, and nobody wanted to see John Cena win.
Looking back at the participants involved, there wasn’t much to get the fans excited about this one. Chris Jericho, The Miz, Big Show, and Kane were the other participants, so even though Cena’s win was met with a collective groan, realistically, there wasn’t really anyone else who stood a chance.
The only memorable thing about this match was how Cena won, as it appeared to be a total mistake when the briefcase was dislodged from the chain as Cena used it to bash Big Show in the skull.Cena’s cash-in attemptwas a failure, too, as the very same Big Show caused a DQ during Cena’s match against CM Punk.
Money in the Bank (2015)
Roman Reigns (Successful)
Sheamus' win in 2015 wasn’t a terrible decision for the most part, but fans weren’t thrilled about it either. The match included popular names like Dolph Ziggler, Kofi Kingston, and Neville, giving the WWE plenty of opportunity to shock the Columbus crowd that night.
Considering Sheamus was already a two-time WWE Champion by this point, it would have been nice to see someone else get their shot at glory. KofiMania may not have felt as special in 2019 if he had won the championship earlier, but you have to feel for him after a disgruntled Orton stunted his previous push.
Ironically, Sheamus ended up cashing in on Roman Reigns, who was also involved in this Money in the Bank ladder match. The Big Dog had won the WWE Championship at Survivor Series, but his first reign was cut short when Sheamus came down to cash in, and put Reigns down for the three count.
24Jack Swagger
WrestleMania XXVI (2010)
Chris Jericho (Successful)
WrestleMania 26 was the last time the Money in the Bank ladder match was held on the grandest stage, and it couldn’t have went out with a bigger dud. Jack Swagger captured the briefcase in a year that had three briefcases passed out, and fans to this day forget about his run as World Heavyweight Champion.
In 2010, credit has to be given to Vince McMahon and the creative team for trying out new things to shake up the rosters, but Swagger becoming one of your world champions turned out to be a major flop. Particularly because nobody cared, but Swagger was also painfully average on the microphone and in the ring.
Even his cash-in on Chris Jericho, a major heel at the time, was met with disinterest from the WWE universe. There was a mix of booing and groaning from the crowd that night, and even his celebration lacked any enthusiasm, which you could say is synonymous with his entire WWE career.
Money in the Bank (2020)
N/A - Lost contract to The Miz
If you don’t remember Otis winning Money in the Bank and holding the briefcase, or his cash-in attempt, I don’t blame you. That’s because a cash-in never happened, as Otis lost the briefcase in a match to The Miz after holding it for 193 days.
While the briefcase isn’t something that is defended very often, it has happened occasionally to create drama and uncertainty for the WWE universe. Unfortunately for Otis, he never got his opportunity to become a World Champion, likely due to the fact that the WWE lost any interest in seeing him do so.
One man’s loss is another man’s gain, and The Miz joined CM Punk as a two-time Money in the Bank winner to also successfully cash in. The Miz would defeat Drew McIntyre at Elimination Chamber but lost the title two weeks later to Bobby Lashley, missing out on annoying fans with anotherWrestleManiamain event appearance.
22Austin Theory
Money in the Bank (2022)
Seth Rollins (Failed)
Austin Theory is a great example, then and to this day, of a superstar that has all the tools to make it as a main eventer, yet never gets that opportunity. That all changed in 2022, when he won the briefcase and defeated big names like Seth Rollins, Sami Zayn, and Drew McIntyre.
WWE Attitude Era Moments That Defined The Era
To really get into what the Attitude Era was all about, we’re going to check out some of the most iconic moments that began the best era.
You would be led to believe that this was finallythe opportunity Theory had been waiting for, that chance to jump into the main event picture and become a World Champion. If naivety could be profitable, fans who believed in Theory would all be rich right about now.
Not only was Theory’s cash-in attempt unsuccessful, he didn’t even try to challenge one of the two world champions. Instead, he targeted Rollins, who was the United States Champion, and was ultimately humiliated in front of the WWE universe, something that continues to happen in 2025.
21Dolph Ziggler
Alberto Del Rio (Successful)
While the match itself falls a little higher on this list than I thought it would be, the reaction to Dolph Ziggler’s cash-in could be one of the biggest pops I’ve heard in the modern era. Ziggler’s Money in the Bank win was the moment fans had been waiting a long time for.
Like Theory,Ziggler was one of those wrestlersthat fans were calling out to get pushed more and be given a chance to succeed. After years of getting behind him, fans couldn’t be happier to see Ziggler win the briefcase and have that chance to become a world champion.
When he came out to cash in on Alberto Del Rio, the entire stadium was shaking. The WWE did their best to suspend the belief that he would win after a nearfall left the crowd stunned, but every Ziggler fan in the world got their wish when he hit the Zig-Zag and pinned Del Rio, finally making it to the top of the WWE.
20Drew McIntyre
Money in the Bank (2024)
Damian Priest (Failed)
The 2024 Money in the Bank ladder match had one of the most stacked line-ups you could ask for as a fan. Even though Drew McIntyre ended up winning the briefcase, you could have realistically made a case for any of the participants involved, and it would make sense.
Where the wheels fell off with this briefcase run was the cash-in, which ended up happening on the same night that McIntyre won it. That’s not to say a same-night cash-in is a bad thing, there are a few examples higher up on this list, butDrew’s felt like a wasted opportunity.
You can’t argue that he picked his spot poorly, as Seth Rollins and Damian Priest were both feeling the exhaustion of their match, but CM Punk made sure Drew would fail. He attacked him, even hitting him in the head with the title, allowing Damian Priest to retain and put an immediate end to McIntyre’s championship aspirations (again).
19Seth Rollins
Money in the Bank (2025)
Currently holding
Seth Rollins did what many thought would be impossible by winning his second Money in the Bank briefcase. Only CM Punk had that honor up until this point, and I’m sure Rollins will be taking every opportunity to rub it in his face.
Fans were a little less thrilled this time around, as the favorite to capture the briefcase in 2025 was LA Knight. Many felt he was in need of a significant push into the main event after dropping the United States Championship, and this was yet another missed chance.
Be that as it may, Rollins new role as the leader of a faction including Bron Breakker, Bronson Reed, and Paul Heyman needed some extra heat. There’s no better way than to give Rollins a similar run akin to Triple H’s time in Evolution, so his inevitable cash-in could top his previous moment 11 years ago.
18Braun Strowman
Money in the Bank (2018)
Roman Reigns (Failed)
Let it be known that, regardless of the year, everybody is a fan of Braun Strowman. He’s big, he’s mean, and he’s lovable, but his Money in the Bank felt like a horrible decision at the time, and still feels that way knowing what we know now.
It’s another one of those cases where you look at whodidn’twin and wonder why they went the Strowman route. Names like Kevin Owens, Rusev, Samoa Joe, and even Bobby Roode would have been a better choice, but we got the monster of all men instead.
Strowman’s cash-in attempt was about as memorable as his win for the briefcase; The only difference was that he failed to capture the championship. Brock Lesnar intervened during his attempt on Roman Reigns at Hell in a Cell, leading to a no contest decision, and subsequently throwing the briefcase up the ramp like a lawn dart.
17Alberto Del Rio
Money in the Bank (2011)
CM Punk (Successful)
Alberto Del Rio may go down as one of the most underwhelming Money in the Bank winners of all time, but at least the match itself entertained the crowd. Despite their efforts, names like Rey Mysterio, Kofi Kingston, and Evan Bourne gave us thrilling moments, but couldn’t get to the briefcase before Del Rio.
It was a weird time in this era, as the WWE did everything to get the machine behind Del Rio, from providing him with a personal ring announcer, a fabulous entrance presentation, and main event push. The only thing missing was the crowd reception, which, more often than not, just wasn’t there.
A successful cash-in saw Del Rio dethrone CM Punk to become the new WWE Champion, but this wasn’t Punk’s historic 434-day reign. That came three months later, at Survivor Series, when Punk got his revenge on Del Rio, effectively bringing his last reign as champion to an abrupt but satisfying end.
