The Money in the Bank Ladder Match stands as one of the most transformative concepts in modern professional wrestling history. First conceived in 2005, the high-stakes match grants its victor a contract for a world championship match at any time and place of their choosing within a one-year window. Over the past two decades, this signature briefcase has served as the ultimate launching pad for rising talent, a narrative tool for dramatic heel turns, and the catalyst for some of the most unforgettable pop-culture moments in WWE history.
However, winning the briefcase does not automatically guarantee a legendary run. While some contract holders struggled under the weight of creative missteps, an elite group of performers mastered the art of the briefcase—delivering match-of-the-night ladder performances, orchestrating heart-stopping cash-ins, and leveraging the contract to permanently alter the trajectory of their careers.
Evaluating the overall quality of the ladder match, the career impact of the victory, the legacy left on the concept itself, and the dramatic execution of the cash-in, here is the definitive ranking of the ten greatest WWE Money in the Bank winners of all time.
10. Rob Van Dam (2006)
At WrestleMania 22 in Chicago, Rob Van Dam captured the second-annual Money in the Bank Ladder Match, overcoming a star-studded field that included Bobby Lashley, Finlay, Matt Hardy, Ric Flair, and Lashley. “The Whole F’N Show” utilized his signature high-flying, martial-arts-infused style to dominate the contest, securing his place as the rightful holder of the briefcase.
Unlike the sneaky, opportunist archetype that would come to define the stipulation, Van Dam redefined the concept by becoming the first performer in WWE history to announce his cash-in well in advance. Challenging John Cena for the WWE Championship at ECW One Night Stand 2006, Van Dam engineered one of the most electric, hostile atmospheres ever captured on pay-per-view. Inside the iconic Hammerstein Ballroom in New York City, surrounded by an unyielding ECW faithful who famously threatened to riot if Cena won, Van Dam defeated Cena following a Five-Star Frog Splash and outside interference from Edge.
Van Dam’s cash-in delivered his first world championship victory, simultaneously reviving the ECW brand and proving that the Money in the Bank contract could be used for an honorable, high-stakes duel rather than just a surprise ambush.
9. The Miz (2010)
By 2010, the Money in the Bank concept had grown so popular that WWE established it as a standalone, self-titled pay-per-view featuring dedicated ladder matches for both the RAW and SmackDown brands. In the RAW brand ladder match, The Miz outlasted Edge, Randy Orton, Chris Jericho, Mark Henry, Ted DiBiase, Evan Bourne, and John Morrison to secure the briefcase.
For four months, The Miz carried the briefcase while sharpening his promos and solidifying his position as the top villain on the red brand. On the November 22, 2010 edition of Monday Night RAW, following a grueling title defense by Randy Orton against Wade Barrett, The Miz pounced. He cashed in his contract, targeting Orton’s injured leg and hitting the Skull-Crushing Finale to capture his first WWE Championship.
The cash-in produced one of the most famous audience reactions in wrestling history—the viral “Miz Girl” meme, featuring a young fan glaring in disbelief and disgust. That iconic moment signaled a changing of the guard. The Miz carried the championship into WrestleMania 27, where he successfully defended the WWE Championship against John Cena in the main event, cementing his status as a permanent fixture in WWE’s main-event landscape.
8. Big E (2021)
Heading into 2021, Big E was widely viewed by fans and analysts as a powerhouse singles star destined for world championship glory. Having achieved immense success alongside Kofi Kingston and Xavier Woods in The New Day—accumulating historic tag team title reigns and Intercontinental Championship runs—Big E entered the 2021 Men’s Money in the Bank Ladder Match looking to break through the glass ceiling.
The match itself is widely regarded as one of the finest in the history of the stipulation. Competing against Seth Rollins, Drew McIntyre, Ricochet, Shinsuke Nakamura, Kevin Owens, Riddle, and John Morrison, Big E delivered an incredible performance. The match featured breathtaking high-risk spots, culminating in Big E delivering a devastating Big Ending to Seth Rollins off the ladder to retrieve the briefcase.
On the September 13, 2021 episode of Monday Night RAW, Big E pre-announced his intention to cash in on social media earlier that afternoon. Following Bobby Lashley’s successful WWE Championship defense against Randy Orton, Big E marched down to the ring, cashed in his contract, and hit the Big Ending to capture his first WWE Championship. Though his in-ring career was tragically cut short by a severe neck injury just a year later, Big E’s Money in the Bank victory remains a crowning achievement that proved he belonged at the absolute summit of the industry.
7. Damian Priest (2023)
The 2023 Money in the Bank event in London, England, served as a star-making night for Damian Priest. Competing in a brutal, physical ladder match against LA Knight, Logan Paul, Ricochet, Shinsuke Nakamura, Santos Escobar, and Butch, Priest utilized his size and striking power to outlast the field. His victory kicked off a compelling, year-long narrative arc that elevated him from a midcard faction member to a legitimate main-event presence.
As a core member of The Judgment Day, Priest carried the briefcase through months of internal faction drama and high-stakes rivalries. His patience paid off in unforgettable fashion at WrestleMania 40 (Night Two) at Lincoln Financial Field in Philadelphia. Immediately following Drew McIntyre’s victory over Seth Rollins for the World Heavyweight Championship, an enraged CM Punk ambushed McIntyre at ringside.
Recognizing the moment, Priest sprinted to the ring, cashed in his contract, and struck McIntyre with the South of Heaven chokeslam to capture the World Heavyweight Championship. Becoming only the second wrestler in history to successfully cash in at WrestleMania, Priest achieved a career-defining triumph on “The Grandest Stage of Them All,” launching his reign as the leader of RAW’s upper echelon.
6. Daniel Bryan (2011)
When Daniel Bryan first arrived in WWE, traditionalists doubted whether his technical, indy-wrestling style would ever translate into a world championship run on sports-entertainment’s biggest stage. Those doubts began to evaporate at the 2011 Money in the Bank pay-per-view, where Bryan won the SmackDown ladder match by defeating Cody Rhodes, Wade Barrett, Sheamus, Kane, Sin Cara, Justin Gabriel, and Heath Slater.
Initially, Bryan declared his honorable intention to hold the contract until WrestleMania 28 for a scheduled world title match. However, opportunistic instincts intervened at TLC 2011. After Big Show defeated Mark Henry in a grueling Chair Match for the World Heavyweight Championship, Henry brutally attacked Big Show post-match. Bryan sprinted to the ring, cashed in his briefcase, and pinned Big Show to capture his first World Heavyweight Championship.
The victory served as the critical catalyst for Bryan’s evolution. Celebrating his win with unbridled, arrogant joy, Bryan began chanting “YES! YES! YES!” repeatedly. That heel turn laid the organic foundation for the historic “Yes Movement” that swept through WWE over the next three years, culminating in his iconic main-event victory at WrestleMania 30. Without the initial spark of his 2011 Money in the Bank victory, one of the most beloved underdog runs in wrestling history may have never materialized.
5. IYO SKY (2023)
Since WWE introduced the Women’s Money in the Bank match in 2017, the stipulation has produced numerous memorable moments, but IYO SKY’s performance in 2023 stands as the gold standard for the women’s division. At the O2 Arena in London, “The Genius of the Sky” competed against Damage CTRL teammate Bayley, Becky Lynch, Trish Stratus, Zoey Stark, and Zelina Vega in a masterpiece of creative match layout and athletic spectacle.
In the climax of the bout, SKY executed one of the most innovative finishes in ladder match history: she handcuffed Becky Lynch and Bayley to each other through the rungs of the ladder, stepping over their trapped bodies to climb uncaught and retrieve the briefcase.
SKY did not hold the briefcase for long. Just one month later at SummerSlam 2023, following a grueling Triple Threat match where Bianca Belair defeated Asuka and Charlotte Flair to win the WWE Women’s Championship, Belair suffered a injured knee. SKY rushed the ring alongside Bayley, cashed in her contract, and hit her signature Over-the-Top-Rope Moonsault to capture her first WWE Women’s Championship. The win transformed SKY from a revered NXT workhorse into an elite main-roster headliner.
4. Dolph Ziggler (2012)
Dolph Ziggler’s Money in the Bank journey represents the absolute pinnacle of fan anticipation and pop-culture explosive payoff. At the 2012 Money in the Bank event, Ziggler won the SmackDown contract in a grueling contest featuring Christian, Cody Rhodes, Damien Sandow, Santino Marella, Sin Cara, Tyson Kidd, and Tensai.
For 267 days, Ziggler defended his briefcase in multiple high-stakes matches while fans eagerly awaited his inevitable crowning moment. That moment arrived on April 8, 2013, on the legendary “RAW After Mania” at the IZOD Center in East Rutherford, New Jersey. World Heavyweight Champion Alberto Del Rio emerged to address the crowd despite suffering a legitimate leg injury during his match the night before.
When Ziggler’s music hit, the arena erupted into one of the loudest, most deafening sustained pops ever recorded in WWE history. After a tense two-minute encounter where Del Rio desperately attempted to lock in the Cross Armbreaker, Ziggler targeted the damaged leg and hit the Zig Zag to win the World Heavyweight Championship. The sheer emotional volume of the crowd reaction cemented Ziggler’s cash-in as the undisputed gold standard for post-WrestleMania surprises.
3. CM Punk (2008 & 2009)
CM Punk’s rise to the top of WWE is fundamentally tied to his back-to-back victories in the Money in the Bank Ladder Match—a feat that remains unprecedented in the history of the stipulation.
At WrestleMania 24 in 2008, Punk defeated Chris Jericho, MVP, Shelton Benjamin, John Morrison, Carlito, and Mr. Kennedy to win his first briefcase. Months later, on the June 30, 2008 episode of RAW, Batista laid out World Heavyweight Champion Edge. Punk rushed to the ring, cashed in the contract, and hit the GTS to claim his first world title in WWE.
One year later, at WrestleMania 25, Punk made history by winning the briefcase for a second consecutive year, outlasting Kane, Mark Henry, MVP, Shelton Benjamin, Christian, Finlay, and Kofi Kingston. At Extreme Rules 2009, after Jeff Hardy defeated Edge in a brutal Ladder Match to win the World Heavyweight Championship, Punk’s music hit. Punk cashed in on a battered Hardy, hitting two Go To Sleeps to take the title.
This second cash-in served as the catalyst for Punk’s legendary 2009 heel turn, launching his iconic “Straight Edge Savior” persona and setting off a deeply personal rivalry with Hardy that dominated WWE television for the rest of the year. The dual Money in the Bank wins provided the structural backbone of Punk’s transformation into a true main-event attraction.
2. Edge (2005)
Edge is the spiritual father of the Money in the Bank concept. At WrestleMania 21 in 2005, “The Rated-R Superstar” won the inaugural Money in the Bank Ladder Match, defeating Chris Jericho, Chris Benoit, Christian, Kane, and Shelton Benjamin in a genre-defining match that established the high-flying, brutal template for all future ladder bouts.
Edge held the briefcase for an astounding 280 days, earning the nickname “The Ultimate Opportunist.” At New Year’s Revolution 2006, after John Cena survived a bloody, exhausting Elimination Chamber match to retain the WWE Championship, Vince McMahon appeared on the stage to announce that Edge was cashing in his contract. Edge marched out, hit two Spears on a bloodied Cena, and captured his first WWE Championship.
That night established the template for what the Money in the Bank contract could truly be: a sudden, ruthless strike that turns the world champion into prey.
Edge would duplicate this magic in 2007. After winning the briefcase from Mr. Kennedy on an episode of RAW, Edge capitalized on a battered Undertaker following a Steel Cage match and a post-match assault by Mark Henry on SmackDown. Edge cashed in, hit the Spear, and captured the World Heavyweight Championship once again. Edge’s masterclasses with the briefcase shaped the identity of the contract forever.
1. Seth Rollins (2014 & 2025)
While Edge laid the foundation for the concept, Seth Rollins elevated the Money in the Bank stipulation to its absolute artistic and historical peak.
At the 2014 Money in the Bank pay-per-view, just one month after betraying The Shield to align with The Authority, Rollins won the briefcase by defeating Dean Ambrose, Dolph Ziggler, Rob Van Dam, Kofi Kingston, and Jack Swagger. Rollins carried the briefcase for 273 days, establishing himself as the premier villain in the company.
At WrestleMania 31 at Levi’s Stadium in Santa Clara, California, Rollins produced “The Heist of the Century.” During the grueling main event between Roman Reigns and Brock Lesnar, with both men lying battered in the center of the ring, Rollins’ music hit. For the first time in history, a wrestler cashed in during an ongoing match, transforming the main event into a Triple Threat. Rollins executed a Stomp on Reigns, pinned his former Shield brother, and sprinted up the ramp with the WWE World Heavyweight Championship as fireworks erupted—creating the greatest, most dramatic ending in WrestleMania history.
Rollins added a historic second chapter to his Money in the Bank legacy at SummerSlam 2025 (Night One). After winning his second briefcase earlier that summer over LA Knight, Solo Sikoa, Andrade, and Penta, Rollins suffered a legitimate-looking knee injury that appeared to sideline him from action. However, after CM Punk defeated Seth’s bitter rival to win the World Heavyweight Championship at SummerSlam, Rollins shocked the world by sprinting down the aisle, shedding his knee brace, and cashing in on a stunned Punk. Executing “The Ruse of the Century,” Rollins captured the world title once again.
Through two era-defining cash-ins separated by a decade, Seth Rollins proved that no superstar in WWE history has ever commanded the Money in the Bank briefcase with greater tactical brilliance, narrative shock value, or main-event legacy.
Honorable Mentions
While they narrowly missed the top ten, several other superstars left an indelible mark on the Money in the Bank concept:
- Dean Ambrose (2016): On the same night he won the 2016 Money in the Bank contract, Ambrose cashed in on his former Shield brother Seth Rollins just minutes after Rollins defeated Roman Reigns. The victory meant all three members of The Shield held the WWE World Heavyweight Championship on the exact same evening.
- Carmella (2017): As the winner of the inaugural Women’s Money in the Bank Ladder Match, Carmella held the briefcase for a record-setting 287 days—the longest reign for any briefcase holder in WWE history—before successfully cashing in on Charlotte Flair.
- Bayley (2019): After winning the Women’s Ladder Match at Money in the Bank 2019, Bayley cashed in her contract on Charlotte Flair later that same night to win the SmackDown Women’s Championship, kickstarting her critically acclaimed transformation into a dominant heel champion.
- Liv Morgan (2022): Morgan’s emotional victory in the 2022 Women’s Ladder Match culminated in a same-night cash-in on Ronda Rousey, providing one of the most heartwarming underdog title victories in modern WWE history.
- Naomi (2025): Naomi captured the 2025 Women’s Money in the Bank contract in a grueling match, using the briefcase to embark on a career-redefining singles push that culminated in a spectacular world championship victory.
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