The Last 10 Money in the Bank Winners Ranked and Tiered
- May 16, 2025
- 12 min read
Updated: Nov 28, 2025
Qualifying matches are underway in late May. That can only mean one thing- it's Money in the Bank season. For 2 decades the Money in the Bank has been an acclaimed concept. Annually, (except in 2010 and 2017) WWE would pair up to 8 superstars, men and women, to clash against one another in a ladder match for a guaranteed World Championship match respectively. This year, the event falls on June 7 and two qualifying matches have been scheduled for tonight's edition of Friday Night Smackdown. With that, on this post by PINACL Wrestling we will look over the last ten Money in the Bank Winners, women and men, and rank them.
*Disclaimer: Rankings are based on primarily on remarkability and significance to the legacy of the Money in the Bank. (Was the winner deserving? did they properly represent a good holder?). Also, cash-ins will be acknowledged and be a large part in the ranking (Was it memorable? On the right person and right time?).
*Disclaimer 2: Last ten Money in the Bank winners include the years between 2014-2024
#19 Otis (2020)
Come on...do I have to even explain. Hell, they could've at least had the man climb up to get the briefcase if we're crying out loud, btw he wasn't even the one that unhooked the contract. Aside from the ridiculous result, Otis and heavy machinery made the Money in the Bank a complete joke. They quite literally turned the briefcase into a lunchbox... And I know what you're thinking. How good was the cash-in? -Well, I'm going to leave that out to the room. Why? Because he didn't even cash in the briefcase. Otis lost the briefcase in a one-on-one match months later to the Miz, and while he proceeded to have a successful cash-in, he would hold the belt for two weeks. Yes. Two weeks before losing it in a squash match against Bobby Lashley on a random episode of Monday Night Raw. Otis (and the Miz) managed to not only have the worst MITB run in the past decade, but perhaps the worst in its 20-year history.
Cash-In: - -
Legacy: 0 stars
Memorability: 0 Stars
Rating: 0 out of 5 stars
#18 Asuka (2020)
Isn't it ironic 2020 fell to the bottom of this list? but hear me out. This was bit of an awkward ranking. Was Asuka the wrong winner? No. Did she cash-in? yes? It wasn't the most tradition way of a cash-in, but it happened. Asuka won her third world champion as she was awarded the vacant Raw Women's Championship.
Cash-In: - -
Legacy: 2 stars
Memorability: 0.5 Stars
Rating: .75 stars
#17 Brock Lesnar (2019)
Now take everything I said about Asuka and flip it. In the worse year of WWE, WWE would book the MITB winner to someone who was in the match for 20 seconds. In a very stacked MITB match consisting of Drew McIntyre, Ricochet, Andrade etc. Brock Lesnar- perhaps the most undeserving and senseless choice on the roster- would unhook the briefcase making himself the 2019 Men's MITB winner. The longer I write, the more I believe that Vince gave the briefcase to Brock just for the sake of Brock having a MITB on his resume. We should've known. At the very least he was able to cash-in the briefcase. Which is a first on this list.
Cash-In: 2.5 stars
Legacy: 2 stars
Memorability: 1.5 stars
Rating: 1 star
#16 Baron Corbin (2017)
In theory, the purpose of the MITB is to elevate a superstar's career. However, this was not the case for Corbin. Corbin was a fast-rising star in 2016 getting over with the WWE Universe in addition. Just not over enough to be a MITB holder. Corbin was a terrible decision to win the match, with fans favorites like Dolph Zigler and A.J. Styles in the same ring, fans were appalled to witness the briefcase go to Baron Corbin. Weeks later Corbin would fail to cash in on...Jinder Mahal. Baron Corbin have not recovered since this moment in his career. Which is truly underwhelming considering how great the talent is.
Cash-In: Failed
Legacy: 1.5 stars
Memorability: .5 stars
Rating: 1 star
#15 Austin Theory (2022)
Not about to get too deep into this. This run was plagued from the beginning. Austin Theory was not only the most unfavorable opponent in this match, but with Vince announcing his entry last minute also didn't do him any justice. Months later, following numerous teases, Theory would unsuccessfully cash-in the briefcase... For the United States Championship. This run was even worse knowing that Theory won the MITB during the peak of the Bloodline saga. So, fans instantly knew it was going to be a failed cash-in. another reason why this was a terrible decision. At least Theory run will be remembered. In the sense that he's the only superstar in MITB history to cash-in and unsuccessfully cash-in on a non-world champion.
Cash-In: Failed
Legacy: 1 star
Memorability: 2 stars
Rating: 1.5 stars
#14 Braun Strowman (2018)
Man, the late 2010s can't catch a break. In this case, Braun wasn't the absolute worst choice, but you can argue that he should've been the winner last year which he very much should've considering the actual winner. Nevertheless, Braun would go as a solid holder, until he wasn't. It all began when Braun went up to the former Universal Champion- Roman Reigns, and blatantly told him the time of the cash in. Which was at the upcoming PPV, Hell in a Cell. Whilst this made sense for the character of the former Universal Champion, this really did take away on of the most loved, and anticipated aspects of the MITB concept. that is the surprising cash-in. With that, Roman and Strowman would have a disappointing match, which was a real letdown following their acclaimed rivalry the year prior. WWE would fail to pull the trigger on Braun following a terrible TKO finish involving a returning Brock Lesnar. Lesnar needs to stay away from anything involving the MITB.
Cash-In: Failed
Legacy: 2 stars
Memorability: 2.25 stars
Rating: 1.75 stars
#13 Drew McIntyre (2024)
The semi-most recent winner on this list, Drew McIntyre won the briefcase defeating superstars like L.A. Knight and Jey Uso. This is the range in this ranking where we are getting at least tolerable winners and/or runs as Drew McIntyre was a favorite for some alongside the previous listed. What's dropping his run back so far down this list is the awful decision to book a same day cash-in. Generally speaking, same day cash-ins are hit-or-miss. In Drew's case it was a miss. Look, McIntyre is one of the most versatile superstars in the world, and keeping Drew with the briefcase for even a couple weeks would've been a great thing to witness. Subsequently, The Scottish Psychopath would fail to cash-in the briefcase and while doing this to enhance the amazing feud of the year between McIntyre and Punk, they did not need to essentially waste the Money in the Bank to enhance a rivalry that was already at its peak. Especially when other favorites like Knight and Uso were great options.
Cash-In: Failed
Legacy: 2.25 stars
Memorability: 2 stars
Rating: 1.75 stars
#12 Liv Morgan (2022)
Very simple explanation Besides it being a same-day cash-in, they proceed to make Liv like an incredibly weak superstar during her cash-in. Morgan despite getting an amazing pop following her win and announcement, WWE gave Liv the win of a roll-up pin after almost losing to Ronda Rousey in record time. Which would become a theme in her title defenses. It was an incredible decision to have Liv win, and even the same-day cash-in was a good decision, just terrible delivery.
Cash-In: 2.5 stars
Legacy: 2.25 stars
Memorability: 2.5 stars
Rating: 2.5 stars
#11 Sheamus (2015)
Long story short, Sheamus winning the 2015 MITB was a terrible and widely hated booking decision by the WWE. Despite this Sheamus would have an ok/slightly forgettable run with the briefcase. And after 6 months, he would one of the best and memorable cash-ins on this list. Crashing the celebration of the recently crowned World Champion Roman Reigns. In genius fashion, Sheamus would Brogue kick Reigns out of nowhere and away he cashes in the MITB. The four-minute bout was an exciting rollercoaster but, in the end, Sheamus would win his second World Championship ending Roman's 5-and-a-half-minute reign.
Cash-In: 3 stars
Legacy: 2 stars
Memorability: 2 stars
Rating: 2.5 stars
#10 Bayley (2019)
Once again, with these same-day cash-ins, it's hit-or-miss. Bayley's cash in was amongst one of the best. Bayley was the perfect winner for this year's MITB, and her cash-in was even better. Other stories involving this cash: Becky Lynch unified the Raw and Smackdown Women's Champions in the first ever Women contested WrestleMania main event. While her reign with one championship was acclaimed, the other last only until its first defense. Charlotte Flair was granted her rematch for the Smackdown Women's Championship immediately following Becky's Raw Women's Championship match. In a solid match for what it was Charlotte would pick up the victory to obtain her 10th Women's Championship. After short-lived victory, Bayley entered the arena just minutes after her MITB victory, cashing in on the Queen. Bayley would receive an incredible pop from the crowd after winning the MITB and capturing her third Women's Championship.
Cash-In: 3.5 stars
Legacy: 2.75 stars
Memorability: 2.25 Stars
Rating: 2.75 stars
#9 Alexa Bliss (2018)
Mirroring everything stated about Bayley can be applied to Alexa Bliss' MITB run. The perfect winner, with the right atmosphere, and a cash-in at the right time. What gives Alexa's cash-in the edge over Bayley's that I feel like her cash in was slightly better. After costing Ronda Rousey the championship in just her second match ever in the WWE, Bliss would put the MITB to Rousey's back once more, then to the champion Nia Jax. Before winning her most recent championship to date.
Cash-In: 3.75 stars
Legacy: 3 stars
Memorability: 3 stars
Rating: 3 stars
#8 Nikki A.S.H. (2021)
I get it, Nikki A.S.H. may have not been the most favorable winner but she has had a great run with the briefcase and had an even better cash-in. Against Charlotte Flair, Nikki would get perhaps the biggest pop on this list. Pinning the champ clean to pick up her first world title.
Cash-In: 3.75 stars
Legacy: 2.5 stars
Memorability: 2.75 stars
Rating: 3 stars
#7 Iyo Sky (2023)
Apart of perhaps the best Women's MITB match so far, Iyo Sky would take the MITB as London erupts. Iyo was as over as anyone could possibly be, and Iyo was by far the odds-on favorite to win the match. Iyo would be an incredible MITB holder. And as good as her run was, the cash in was even better. taking advantage of a recently crowned and injured Bianca Belair. Iyo would cash-in and win her first Women's Championship.
Cash-In: 4 stars
Legacy: 3 stars
Memorability: 3 stars
Rating: 3.5 stars
#6 Damian Priest (2023)
Damian Priest received the push of a lifetime in 2023. Taking the role of co-leader of the judgement day and following match of the year candidate at that years Backlash in Puerto Rico. Priest big payday would come at the very next PPV as he would win the MITB briefcase. Whilst many were pushing for this to be L.A. Knight's big moment, Priest would go on a remarkable run with the briefcase. He would even personalize the briefcase itself, giving it an all-new look, and renaming; Senor Money in the Bank. Priest would hold the briefcase for months, until finally cashing in at the Showcase of Immortals. Becoming only the second to do so.
Cash-In: 4 stars
Legacy: 3.25 stars
Memorability: 3.25 stars
Rating: 3.5 stars
#5 Big E (2021)
Big E has been a part of the WWE roster for almost two decades. beginning in NXT and becoming amongst one of the first ever NXT champions, to being a third of the greatest tag team of this generation, and now a former WWE Champion. Big E was the right superstar for WWE to pull the trigger on in 2021. And after an emotional year for the 6-time tag champ, winning the MITB was his big break. Big E always made that element of surprise present during his reign, constantly teasing his cash-in. In a few months it would actually happen. Big E successfully cash in against Bobby Lashley in Fall 2021. He would receive an incredible reaction from the fans despite his announcement of the cash-in which did not take away from the feel-good moment all together. Big E would become the second and most recent member of the New Day to win a world championship.
Cash-In: 4 stars
Legacy: 3.5 stars
Memorability: 3.25 stars
Rating: 3.5 stars
#4 Tiffany Stratton (2024)
Completely contrasting everything I said about Austin Theory, Tiffany Stratton was bound to be a top star in the WWE. Stratton debuted on the main roster in February 2024 following a very successful 2023 NXT year. She managed to get instantly over with the fans after her Elimination Chamber performance and in just six months she was booked to win the MITB. Tifany Stratton won the briefcase just 4 months after main roster debut -which is the fastest ever. Tiffany would further elevate her run as Ms. Money in the Bank with her yearlong story/alliance with Nia Jax. Giving the briefcase a redesign, various teases, and a few conflicts and drama between her tag partner, Nia Jax. As the year went on Stratton, realized week-after-week that Nia would mistreat her around in various ways and this created a sense of surprise for the fans. As she could either betray her best friend or cash-in on Liv Morgan, meaning that the team would have both world champions. In January the next year, Stratton would finally cash-in on Nia and successfully take the championship. Stratton would become just the fifth woman in history to win the championship in her first year on the main roster. Joining Charlotte Flair, Becky Lynch, Alexa Bliss, and Paige. While subsequently being the only superstar in history (men and women) to win the briefcase and world championship respectively, in their first year of main roster status.
Cash-In: 4.25 stars
Legacy: 3.75 stars
Memorability: 3.5 stars
Rating: 3.75 stars
#3 Carmella (2017)
For the best Ms. Money in the Bank, we have Carmella. Whether you hated her, or loved her as MITB holder, Carmella set the standard high for the Women's MITB. Not only was she the first ever, but she managed to win the briefcase on two occasions and being the only MITB holder to successfully defend the briefcase. Aside from her victory, the former Women's Champion was able to represent the briefcase for a hot minute as she would successfully cash-in almost a year later on Charlotte Flair. Carmella gave the briefcase high hopes for future years, and whilst the Women's MITB continued to have great holders and very little bad moments, Carmella began it all. Putting her at the three spot.
Cash-In: 3.5 stars
Legacy: 3.5 stars
Memorability: 3.75 stars
Rating: 3.75 stars
#2 Dean Ambrose
Dean Ambrose did exactly what he said he was going to do. Aside from 2016 being one of the most well-built MITB matches in its history, it added more drama as Dean Ambrose invited Seth Rollins and World Heavyweight Champion, Roman Reigns -who would fight for the championship at the MITB event. Dean blatantly told the two superstars aside him that he was going to win MITB and cash in following their match that same night. Despite the warning, Seth just couldn't get out quick enough. Following an incredible match against Reigns' and picking up the title he never lost, Dean Ambrose would smash Rollins in the head with his recently crowned MITB briefcase. After cashing-in, Ambrose would pin Rollins, and after a 6-second bout, Ambrose would win his first World Championship.
Cash-In: 4.25 stars
Legacy: 3.25 stars
Memorability: 3.25 stars
Rating: 4 stars
#1 Seth Rollins (2014)
In my opinion the most influential and significant MITB run in its history. When you think of MITB runs the first that comes to mind is Seth Rollins 2014 run. Not only does he have the best run, but he also had the best cash-in undoubtably as the Heist of the Century is one of the greatest moments in the history of the WWE. With the briefcase, Rollins had numerous feuds that elevated his character in the likes of Dean Ambrose, John Cena, and Brock Lesnar. And in-ring classics like vs. Ambrose at HIAC 2014 and vs. Lesnar and Cena. In the same way, Seth with the briefcase was the driving factor of the Authority in its peak. Back to the Heist of Century, In the middle of the acclaimed WrestleMania 31 main event contested between Brock Lesnar and Roman Reigns, Rollins music hits. And in the most shocking fashion, Rollins rushes down to the ring and cashes in the MITB, making it a triple threat. The exciting, yet intense three-minute match came to an end when Rollins gives a curb stomp to Reigns to win the World Heavyweight Championship. In doing so, Rollins set multiple records giving it the name The Heist of the Century:
-Only superstar in history to cash-in the MITB briefcase in the Main Event of WrestleMania
-First Superstar to cash-in the MITB briefcase at WrestleMania
-First superstar to successfully cash-in the MITB briefcase after forcing a triple threat match
Cash-In: 5 stars
Legacy: 5 stars
Memorability: 5 Stars
Rating: 5 Stars
Tiering
A+ | Seth Rollins |
A | Dean Ambrose |
A- | Tiffany Stratton, Carmella |
B+ | Damian Priest, Big E |
B | Iyo Sky, |
B- | Bayley, Alexa Bliss, Nikki A.S.H. |
C+ | |
C | Liv Morgan, Sheamus |
C- | Drew McIntyre |
D+ | Braun Strowman |
D | Austin Theory |
D- | Asuka, Brock Lesnar, Baron Corbin |
F | Otis |
Summary
Altogether, The Money in the Bank is an amazing concept created by former WWE Superstar, Chris Jericho, in 2005. and since then turned into its own PLE event. With the event seeing soaring ups, and terrible downs, the next holder is the most anticipated moment on the WWE calendar. With the event continuing to elevate itself one year at a time, the MITB legacy will live on forever. Thank you for viewing today's edition of PINACL Wrestling.
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