It’s that time of year again, when opportunity is hung high above the ring and the only way to seize it is to climb every rung up that ladder of success – no matter how many times someone hits you with a chair. Or another ladder.

Of course I’m talking about Money In The Bank – a multi-person train wreck where the winner has a guaranteed shot at the world championship at any time of their choosing. With the Money In The Bank Ladder Match stretching back to 2005, several men (and a few women) have had the disctinction of calling themselves Mr. or Ms. Money In The Bank.

With a couple of new briefcase holders about to take their place in line, it seemed like a perfect time to rank every person who had held the contract in the past.

#26 – OTIS

While there have been a bunch of great Money In The Bank briefcase holders you could call the best, it’s not hard to narrow down the worst. Only two men have lost their MITB briefcases without ever cashing it in. Most recently was the former Hard Workin’ Blue Collar man himself and one half of Heavy Machinery – Otis.

Otis won a fairly competitive and innovative Money In The Bank Ladder Match. Held in 2020 during the pandemic, 6 men and 6 women would compete simultaneously. The group would start on the ground floor of WWE’s headquarters in Stamford, CT and fight their way to the roof, where the briefcases were hung above a ring.

Otis won without even climbing the ladder – King Corbin & AJ Styles accidentally dropped the briefcase into his hands. He’d hold on to the briefcase for nearly half a year before Otis’s tag team partner Tucker turned on him and caused Otis to lose the contract to The Miz.

#25 – MR. KENNEDY

Oh, Mr. Kennedy. We hardly knew ye.

Ken Kennedy was on a hot streak in WWE in 2007, coming close to winning major championships a couple of times. At Wrestlemania 23, Kennedy found himself as part of a huge 8-man MITB Ladder Match that also included Edge, Randy Orton, Booker T, and others. Kennedy got in one of the most notable MITB spots ever when he hit the Green Bay Plunge on Finlay’s tiny manager Hornswoggle from the top of the ladder. He’d go on to knock fan favorite CM Punk from the top of the ladder before ascending to nab the briefcase.

After winning, Kennedy announced that he’d hold the briefcase all the way until Wrestlemania 24, where he’d main event and win the World Title. Unfortunately, that plan was written in pencil at best. On a May episode of Smackdown, Kennedy would lose his briefcase in a match with Edge. Worse still, he’d end up on the injured list for a few months.

#24 – JOHN CENA

No one would argue that John Cena’s not an all time great, but as Mr. MITB, he was an all-time worst.

Cena was part of the MITB Ladder Match at Money In The Bank 2012. It was a stacked 5-man match also featuring Chris Jericho, Kane, The Big Show, and The Miz. During the match, Cena found himself on top of the ladder with The Big Show. Show was trying to land a Knockout Punch on Cena to get him off of the ladder, but Cena grabbed the briefcase to block the blow. Shockingly, the punch also broke the handle of the briefcase – surprise! Cena is your winner.

Cena announced that he would cash-in the briefcase for a match against WWE Champion CM Punk, just a week later on the 1000th episode of Raw. Just a quick side note – announcing you’re cashing in the briefcase in advance rarely works out.

Unfortunately for Cena, Big Show interfered in his WWE Title match, forcing a disqualification. Since the title doesn’t change hands on a DQ, Cena found himself both lacking a title and his briefcase.

#23 – BRAUN STROWMAN

Braun Strowman put on a dominant performance in the 8-man MITB Ladder Match at Money In The Bank 2018. As you may expect, he looked like a total monster. In the end, Strowman tossed Finn Balor off of the ladder and Kofi Kingston off of his back to reach up and grab the briefcase.

Braun would go on to successfully defend his briefcase against Kevin Owens at Summerslam in another dominant showing.

So why is Braun ranked so low? Well, here’s what The Monster Among Men did wrong – he announced his cash-in ahead of time. On Raw, Braun committed to a Hell In A Cell match with Universal Champion Roman Reigns at the Hell In A Cell PPV. During the match, Brock Lesnar made his shocking return, smashing in the Cell door and taking out both competitors. The match would end in a No Contest, and Braun’s MITB briefcase would find itself wasted.

#22 – DAMIEN SANDOW

Damien Sandow was certainly a dark horse pick when he entered the 2013 Money In The Bank PPV for a shot at the World Heavyweight Title MITB contract. In a hot opening match that featured more interference than any other MITB Ladder Match in history, Sandow shocked his tag partner Cody Rhodes and the world when he pushed Cody off of the ladder and reached up to fulfill his destiny.

Sandow – working his “Better Than You” gimmick – would hold on to the briefcase for months, but it was unfortunately months of bad luck. Sandow racked up several losses, his ex-partner Rhodes would dog him at every corner, and he even had his original briefcase destroyed.

Finally in October, Sandow interrupted World Champion John Cena during a promo to cash-in. Like so many of his other matches, Sandow would go out on his back, becoming to the first man to lose a MITB cash-in.

#21 – BARON CORBIN

When Baron Corbin beat down Shinsuke Nakamura before Nakamura could enter the MITB Ladder Match at the 2017 Money In The Bank PPV, it drew a lot of boos. But not nearly as many boos as when Corbin pushed Nakamura and AJ Styles off of the ladder and actually won.

Corbin held on to the briefcase for nearly two months. On an episode of Smackdown, during a match between John Cena and WWE Champion Jinder Mahal, Corbin made his play.

Unfortunately for Corbin, a distraction by Cena led to Mahal scoring the victory.

#20 – DOLPH ZIGGLER

Dolph Ziggler – what a prick, huh? Ziggler was in the middle of a good heel run when he entered the MITB Ladder Match at the 2012 Money In The Bank PPV. The 8-man field was somewhat underwhelming with the likes of Sin Cara, Santino Marella, and Tensai in the match, but the contract was good nonetheless. Dolph Ziggler siezed the opportunity.

Ziggler’s reign as Mr. Money In the Bank was filled with drama. Multiple non-start cash-ins, plus Ziggler had matches against both Chris Jericho and John Cena where his briefcase was on the line.

Somehow, Dolph survived all of this and successfully cashed in against an injured Alberto Del Rio on the Raw after Wrestlemania 29. Ziggler scored his second World Heavyweight Title, but the feud with Del Rio would ultimately turn Dolph face and lead to maybe the hottest run of his career.

#19 – DANIEL BRYAN

Daniel Bryan’s career was somewhat directionless when he ended up winning the MITB briefcase at the 2011 Money In The Bank PPV. Luckily, a contract for a World Heavyweight Title shot was just what he needed.

Bryan announced the next week that he planned on holding the briefcase all the way until Wrestlemania, a fact that he reminded the audience about multiple times over the next few months. That is, until The Big Show and Mark Henry came into the picture.

Big Show began urging Bryan to cash-in against The World’s Strongest Man for the title. Bryan did on a November episode of Smackdown, pinning Henry, but Smackdown GM Teddy Long said Mark had been unable to compete and reversed the decision.

Bryan justified his decision by saying that Mark Henry was going to keep attacking him until Bryan couldn’t even make it to Wrestlemania. At the TLC PPV, the Big Show defeated Henry for the title, but was then attacked by Mark after the match. Seeing an opening, Bryan stepped in and cashed in for his first World title.

#18 – ASUKA

Asuka was the female winner in the 2020 “Corporate Ladder” version of the MITB Ladder Match. Asuka started things out with a bang, taking out all of her other competitors with a jump from above the Titan Towers elevators.

The match ended when Asuka tossed Nia Jax and Lacey Evans (and King Corbin) off of the rooftop ladder and nabbed the women’s briefcase.

The next night on Raw, Women’s Champion Becky Lynch announced that she was taking a leave of absence from WWE because she was pregnant. Because of this, Lynch revealed that the women’s MITB Ladder Match had never been for a contract. Asuka opened the case and inside was the Raw Women’s Championship.

I’m of the opinion that gifting someone a title is never a good idea, so it kind of threw cold water on the excitement of Asuka holding the MITB contract.

#17 – NIKKI A.S.H.

Nikki A.S.H. is the latest women’s MITB winner, taking home the briefcase after the 2021 Money In The Bank PPV. Nikki was a dark horse going into the match, and her victory was both surprising and anti-climatic.

With 6 of her other competitors fighting atop three ladders, Nikki came in from the outside to climb over them and snag the briefcase. The other ladies were none too happy.

The next night on Raw, a match between Rhea Ripley and Women’s Champion Charlotte Flair devolved into a wild brawl. After Rhea took Charlotte out, Nikki appeared and cashed in, scoring the victory and her first title.

#16 – JACK SWAGGER

Trivia question – who was the last person to win the Money In The Bank Ladder Match at a Wrestlemania? If you don’t know, put your hand over your heart, and in a loud clear voice say, the Real American American (American) Jack Swagger!

Swagger won a massive 10-man MITB ladder match at WMXXVI. Swagger was a big hoss during his time with WWE, but no one was really losing their mind when he knocked Christian off the ladder and unhooked the briefcase.

Jack didn’t hold on to his briefcase too long. At the Smackdown after Wrestlemania, Edge took out his frustrations on the reigning World Heavyweight Champion Chris Jericho. This gave Swagger the chance to come out and pick the bones.

With Swagger only appearing twice with the briefcase, and the fact that WWE made Money In The Bank its own PPV just a few months later, the Real American American had a fairly forgettable time as Mr. Money In The Bank.

#15 – BAYLEY

Bayley was part of the 8-woman MITB Ladder Match at the 2018 Money In The Bank PPV. Bayley scored the victory by playing spoiler to Fire & Desire, pushing both Mandy Rose and Sonya DeVille from the ladder to score the victory and the contract.

Elsewhere, Becky Lynch was enjoying her run as Becky Two-Belts. Well, enjoying may not be the right word. Becky was booked in two matches on the PPV to defend the Raw & Smackdown Women’s Titles. Becky defeated Lacey Evans to retain the Raw title in the first match, but was forced to defend the Smackdown title against Charlotte Flair directly after.

During the match, Evans returned to the ring to get even with Becky. The interference led to Charlotte scoring the title and the pinfall. Charlotte and Lacey continued their assault on Becky after the match, and Bayley ran out to even the odds. During the brawl, Charlotte ended up posting her shoulder. Bayley saw the opening and cashed-in her briefcase. One elbow drop later and Bayley was Smackdown Women’s Champion.

The win made Bayley the first ever women’s Grand Slam champion.

#14 – BIG E

Big E won a massive 8-man MITB Ladder Match at the 2021 Money In The Bank PPV. Nearly a decade after he helped protect Dolph Ziggler while DZ was Mr. Money In The Bank, Big E finally seemed poised to take the last step into immortality as a WWE champion.

Big E didn’t take the easy route though. After nearly 2 months holding the briefcase (and some shenanigans with Baron Corbin), E announced on Twitter that he would be coming to Raw and cashing in. WWE Champion Bobby Lashley was scheduled to defend against Randy Orton that night, and E called his shot, saying he was cashing in on the winner.

Lashley retained against Orton that night, but was unable to handle Big E afterwards, leading to a memorable and emotional title victory.

#13 – CARMELLA

Carmella holds the distinction of being the first woman to win a MITB Ladder Match AND the only woman to win the briefcase twice.

As a perceived underdog, Carmella shocked the world when she won at the Money In The Bank 2017 PPV. The win was not without controversy. Carmella’s manager James Ellsworth climbed the ladder for Carmella and dropped the briefcase into her hands to give her the win.

On the next episode of Smackdown Live, GM Daniel Bryan announced that Carmella’s method of winning probably shouldn’t be allowed, and stripped her of the briefcase – the first and only time that has happened.

A rematch was held on Smackdown, and to everyone’s surprise, Carmella won again. Did James Ellsworth help? Sure, but he didn’t climb the ladder for her, so it counted.

Mella spent a record 287 days as Ms. Money In The Bank. After a few false starts for cash-ins, Carmella saw her opportunity on the Smackdown Live after Wrestlemania 34. When Smackdown Women’s Champion was beaten down by The IIconics, Carmella showed up to fulfill her destiny and win the title for the first time.

#12 – ALBERTO DEL RIO

Alberto Del Rio is probably tied with Carmella for most dastardly MITB Ladder Match win. At the Money In The Bank 2011 PPV, Del Rio competed in the Raw MITB Ladder Match. Late in the match, he found himself battling on top of the ladder with Rey Mysterio. Running out of options Del Rio unmasked Rey to try and gain an advantage. The gamble paid off and Del Rio walked out with the briefcase.

But wait – there are more dastardly deeds. At Summerslam 2011, John Cena and a returning CM Punk faced off in a hugely anticipated rematch to determine the Undisputed WWE Champion. Punk won, drawing a big pop from the crowd. That is until Del Rio’s music hit. Oh, mierda.

Not only did Del Rio rain on Punk’s parade, it took help from Kevin Nash of all people. If this was a list of most hated briefcase holders, it’d be hard to beat Alberto Del Rio.

#11 – KANE

Hey, do you remember when Kane was Mr. Money In The Bank? No? Well, it’s understandable.

Kane was the first man to win a MITB Ladder Match at the first Money In The Bank PPV in 2010. The Big Red Machine won a grueling 8-man match featuring some of Smackdown’s biggest stars at the time, chokeslamming Drew McIntyre off the ladder to grab the briefcase.

47 minutes and 3 matches later, Rey Mysterio won the World Heavyweight Title by defeating Jack Swagger. Swagger was none too pleased at losing the belt, and attacked Rey post-match. Kane had barely finished taking his promo pictures with the briefcase when he made his way back out to cash-in. It was the first time someone had won and cashed-in the briefcase on the same night, and it paid off.

#10 – BROCK LESNAR

Brock Lesnar made one of many shocking returns to WWE at Money In The Bank 2019. The MITB Ladder Match found itself down one competitor after Sami Zayn was attacked by Braun Strowman earlier in the night. No replacement was announced – that is until Ali attempted to pull down the briefcase during the main event and “The Next Big Thing” hit.

The win put Lesnar on a collision course with Universal Champion Seth Rollins. Lesnar managed to tease cashing in for 2 months – a time period that also gave us the bizarre “Fun Brock” persona with his boombox Brock Parties.

At the Extreme Rules PPV, Rollins and Raw Women’s Champion Becky Lynch were set to face Lacey Evans & Baron Corbin in a Last Chance Winners Take All Extreme Rules Mixed Tag Match. Becky and Rollins were able to come out of the match with their titles, but Seth didn’t fair so well after the bell. “Next Big Thing”, F-5, new champ.

#9 – DEAN AMBROSE

What if on one night, everyone in The Shield held the WWE Title?

That’s what happened at Money In The Bank 2016. Seth Rollins had recently made his return to the WWE after a long injury, and he wanted to also make his return to the top of the roster by winning the WWE Title. The only problem was the man standing in his way – Roman Reigns.

Reigns and Rollins went at it during the main event of the evening, but it might have been hard for either man to focus, seeing as how their other former Shield-brethren – Dean Ambrose – won a certain gold briefcase just an hour before.

In the end, Rollins nailed a couple of pedigrees to take the title from Reigns. Ambrose’s music hit, but Rollins was ready. As The Architect watched the entranceway, Ambrose used the briefcase for a sneak attack from behind. A Dirty Deeds later and Ambrose was the ex-Shield member walking out of the PPV with the WWE Title.

#8 – RANDY ORTON

Randy Orton won a hotly contested 6-Man MITB Ladder Match main event at Money In The Bank 2013. Former MITB winner Rob Van Dam was making his WWE return in this match, and it looked like RVD had the match won, but it would be The Viper that played spoiler.

If spoiling RVD’s big moment wasn’t enough, Orton’s cash-in was even nastier. At Summerslam 2013, John Cena defended the WWE Title against fan favorite Daniel Bryan. Bryan was somehow able to best the veteran Cena and won his first WWE Title to a huge ovation from the crowd. Special referee Triple H was even cheering for Bryan’s big moment – that is until he hit Bryan with a pedigree.

With DBry left dazed and confused, Orton made his appearance to cash-in and ruin the moment. It still makes me mad.

#7 – SHEAMUS

After being thwarted in his WWE Title quest at Wrestlemania 31, everyone thought Roman Reigns had the 2015 MITB Ladder Match in the bag. It’d be the perfect way to fulfill his destiny and win his first WWE championship.

But fate was against Roman at Money In The Bank 2015. More specifically, Bray Wyatt was against Roman. Thanks to interference from the Eater of Worlds, Reigns was knocked out of the match, and none other than the Celtic Warrior Sheamus was able to capitalize.

Sheamus held the briefcase for several months. By Survivor Series, the WWE Title was vacant, and a tournament was held to crown a new champion. Reigns and Dean Ambrose went at it in the finals match, with Roman coming out on top and finally taking that next step to hold the WWE Title.

But wait, fella. Triple H appeared after the match, attempting to squash the long beef with Roman Reigns via handshake. Reigns refused and, wouldn’t you know it, Plan B. Sheamus’s music hit. 5 minutes and 15 seconds later, we had another new WWE Champion.

Sheamus even had his own “Sheamus 5:15” shirt to gloat about the victory. What a dick.

#6 – ALEXA BLISS

The Goddess was able to stand tall with the briefcase at Money In The Bank 2018. In an 8-woman match that also included Becky Lynch, Charlotte Flair, and Sasha Banks, Alexa was the one who came out on top.

Later that night, UFC legend Ronda Rousey was set to have her first singles match in WWE – taking on Raw Women’s Champion Nia Jax for the title. With so much invested in new signee Rousey, it seemed a foregone conclusion that Rowdy Ronda would walk out of Chicago with the championship. Not so fast.

During the match, with Nia looking ready to submit to a Ronda armbar, Alexa Bliss hit the ring and attacked Ronda with the briefcase. This drew a DQ and left Nia Jax with the title. With the match over, Bliss continued her assault on both Rousey and Nia. Playing spoiler to what was supposed to be Rousey’s big moment, Alexa cashed in and became the new women’s champ.

#5 – ROB VAN DAM

Even thought Rob Van Dam wasn’t the first winner of the MITB Ladder Match, it can be argued that the match was made for guys just like RVD.

RVD won a classic MITB Ladder Match at Wrestlemania 22. First order of business – airbrush that briefcase. Second order of business, feud with Shelton Benjamin and win the Intercontinental Title.

With that done, RVD made the risky decision to call his shot – announcing he would cash-in for a WWE Championship Match with John Cena in the main event of ECW One Night Stand 2006.

If you haven’t seen Cena/RVD from One Night Stand, go right now and watch that historic match. If you don’t understand the term “rabid fanbase”, you will after seeing the pro-ECW and RVD crowd from that night.

With a little help from Paul Heyman and Edge, RVD was able to reach the highest of highs, pinning Cena to win the WWE Championship.

#4 – CM PUNK

CM Punk holds the distinction of being the only man to win two MITB Ladder Matches. Punk won the briefcase in a huge 7-man inter-promotional match at Wrestlemania XXIV. Punk’s cash-in was highly memorable, too. When World Heavyweight Champion Edge announced he had been drafted to Smackdown, Punk came out to a huge pop. It only took a GTS to ensure that the title stayed on Raw.

Punk would win the briefcase again the very next year at the 25th Anniversary of Wrestlemania. Punk’s cash-in would see him turn heel, taking out new World Heavyweight Champion Jeff Hardy after a punishing ladder match. The heel turn would lead to Punk’s most memorable run in the company.

#3 – EDGE

Only one person can do something for the first time. When it comes to Money In The Bank, that man is Edge.

Edge won the first MITB Ladder Match at Wrestlemania 21 and pretty much set the standard for how to hold a MITB contract. In spite of challenges from Matt Hardy, Edge held the briefcase for 280 days – still the longest time for any male superstar.

At the 2006 New Year’s Revolution PPV, a bloody WWE Champion John Cena raised his hand in victory after competing in a punishing elimination chamber match. But not so fast John – Mr. McMahon himself made his way to the entrance to announce that Edge would be cashing in. That first cash-in scored Edge his first WWE Title reign, as well as the nickname The Ultimate Opportunist.

#2 – SETH ROLLINS

Seth Rollins won the briefcase at the 2014 Money In The Bank PPV with a little help from Corporate Kane. Briefcase holders in the past talked a lot about waiting and cashing in at Wrestlemania – well, Seth Rollins actually did that.

At Wrestlemania 31, all indications were that Roman Reigns would step up and take his place at the top of WWE by defeating Brock Lesnar for the WWE Title. It wouldn’t be an easy feat – Lesnar spent most of the match beating Reigns to a bloody pulp. Reigns looked poised to make a comeback late in the match, laughing maniacally at Lesnar’s continued punches.

The crowd was finally starting to get on Roman’s side when a certain two-toned hair prick hit the ring. Rollins became not only the first person to cash-in at Wrestlemania, but the first to cash-in during a championship match. This effectively made the match a triple threat. Lesnar went down to a curb stomp and a spear, and then a final shocking curb stomp to Reigns sent Rollins home with the WWE Title. Perhaps the most surprising moment in Wrestlemania and Money In The Bank history!

#1 – THE MIZ

Few people fit the Money In The Bank briefcase holder prototype like The Miz. A smarmy guy who probably couldn’t win the belt in a fair fight but can strike from the shadows when the enemy is vulnerable? Check, check, and check.

The Miz won the briefcase at the first Money In The Bank PPV, to the collective groan of fans everywhere. At that point, every MITB cash-in had led to a title change, and the thought of Miz as WWE Champion turned everyone’s stomach. Even having to listen to him brag about holding the briefcase was annoying.

Miz picked his spot on an episode of Raw after WWE Champion Randy Orton was beaten down by The Nexus. A skull crushing finale later, we had a new champ to hate.

But hey, that’s not all. The Miz won the MITB briefcase a second time in 2021 when he defeated the lovable Otis to take the contract. After several false starts, Miz may have come up with the most despicable cash-in ever. Wait for WWE Champion Drew McIntyre to go through a grueling Elimination Chamber match, then pay Bobby Lashley to beat him up afterwards. That made The Miz a 2x Champ and 100x prick.