Money in the Bank is a game of patience and payoff. The Superstar who holds the contract — a free ticket to a World Title Match for up to one year after they win it — doesn’t just have the opportunity to win a championship, but to create a moment. Even the contract-holders who didn’t get the job done when they cashed in succeeded in making an impact, but which cash-ins were the most historically significant? WWE.com ranked every Money in the Bank cash-in, taking into account the victor, who they beat and the surrounding context. Who’s the most Money? Read and find out.

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Baron Corbin (WWE Championship; 2017)

Baron Corbin is one of the most capable Superstars on the roster today, and between his Andre the Giant Memorial Battle Royal win and impressive run as United States Champion, he’s proven that he can deliver in big moments. Unfortunately, what should have been the easiest — and most significant — putt of his career ended up being a hard shank right: The Lone Wolf cashed in his contract in the middle of such a brouhaha that he was immediately rolled up by Jinder Mahal to lose his title match. To his credit, Corbin shook it off and plowed forward as he always does, rebounding to win the U.S. Title. His cash-in brings up the rear of this list, but in the grander context, it’s an anomalous smudge on an otherwise promising career, and this moment may well end up being more exception than rule.

John Cena (WWE Championship; 2012)

Is it the height of irony that John Cena — John Cena! — became the first man to unsuccessfully cash in the Money in the Bank contract? It’s definitely up there, especially given that Cena was near the peak of his dominance in 2012, and he’d picked the perfect time (Raw’s 1,000th episode) and champion (CM Punk) to call his shot. But Big Show’s interference cut the match short, handing Cena a disqualification win while keeping the title on Punk due to champion’s advantage. Historical significance keeps this cash-in from the bottom, but it can only be ranked so high for the same reason.

Damien Sandow (World Heavyweight Championship; 2013)

Hold the Hallelujahs, folks. Damien Sandow was a surprise World Heavyweight Championship contract-carrier in 2013 (doubly so since he betrayed Cody Rhodes by shoving him off a ladder to win it), though The Intellectual Savior of the Masses' tenure as a briefcase-bearer ended in disappointment when he became the first Superstar to flat-out lose his cash-in match — in this case, to John Cena. (He’ll pop up a lot on this list). Points awarded, however, because their match was among the finest of both Superstars’ careers.

Jack Swagger (World Heavyweight Championship; 2010)

Between 2007 and 2010, the Money in the Bank Ladder Match became the go-to conquest for a crop of blue-chip talent who used the briefcase to jump the line and win a World Title. Jack Swagger’s World Heavyweight Championship cash-in on Chris Jericho seemed to be the most potent sign of a sea change at the time, but despite a three-month reign for the Oklahoma big man, the trend that led to his rise would prove somewhat untenable: Most of the contract holders after Swagger were industry veterans who had either yet to win the big one or hadn’t won it in a while. Though, given that we’re circling back around with recent winners like Corbin and Carmella, the final verdict on The All-American American’s win may well be that it happened 10 years too soon.

CM Punk (World Heavyweight Championship; 2009)

The only reason CM Punk’s two Money in the Bank cash-ins are on the low end of this list is that they are so wildly overshadowed by his achievements in the back end of his WWE career. This cash-in, his second, was remarkable both for who he beat (Jeff Hardy) and what it led to (a title defense against The Undertaker where Punk is said to have earned the respect of a reticent Deadman). But at that point, such a thing was just confirmation of what the WWE Universe already knew: Punk was championship-caliber material, and he would not be told otherwise.

Alberto Del Rio (WWE Championship; 2011)

Alberto Del Rio used his contract to take out CM Punk at the height of his man-of-the-people popularity to cash in his contract just moments after The Second City Saint defeated John Cena in a dramatic Undisputed Championship Match. So, points awarded for brazen timing. But this cash-in takes a hit because Del Rio quickly found it was harder to keep the crown than win it: The Essence of Excellence played hot potato with the title over the ensuing months and ultimately lost it back to Punk, who kicked off his record-setting reign as a result. 

CM Punk (World Heavyweight Championship; 2008)

Despite the resounding endorsement of Paul Heyman, CM Punk was something of a question mark during the beginning of his WWE career. Even after he won his first Money in the Bank contract, nobody was ever truly sure what the ceiling was for the scrappy, tattooed Chicagoan. That he ultimately cashed in on a red-hot Edge to win the World Heavyweight Championship was both a validation of The Straight Edge Superstar’s talents and a sigh of relief to his supporters. Punk would attain greater glory down the line, but it was refreshing to know there was a place at the top for him after all. 

Edge (World Heavyweight Championship; 2007)

Stealing The Undertaker’s thunder was a lot like tugging on Superman’s cape in 2007. So, Edge’s second contract cash-in, where he pounced on The Phenom to steal the legendary Superstar’s “holy grail,” earns special consideration for both its boldness and its efficiency. Much like Punk’s second cash-in, this was more affirmation than coronation for The Rated-R Superstar, but Edge gets extra points for his opponent of choice; it had been a long time since anybody had make The Deadman look mortal.

TIE: Randy Orton (WWE Championship; 2013) and Sheamus (WWE World Heavyweight Championship; 2015)

They say history doesn’t repeat itself, but it rhymes. In that case, the near-identical cash-ins of Randy Orton and Sheamus were a lovely bit of in-ring verse. Both were former champions years removed from their previous World Titles. Both cashed in on a vulnerable champion at the end of a grueling battle (Daniel Bryan had just beaten John Cena when Orton came calling, while Sheamus pounced on Roman Reigns after a tournament final). And both experienced a nice bump in business as a result (Orton joined The Authority; Sheamus got a sweet T-shirt). Even the final chapters of these respective stories were mirror images of each other, with the wronged champions winning their titles back in a WrestleMania comeback that involved a win over Triple H. 

Carmella (SmackDown Women's Championship; 2018)

Carmella started out as the token girl of a boys’ club in NXT. She only had one championship opportunity at Full Sail University before becoming the very last pick of the 2016 WWE Draft. She won the Women’s Money in the Bank contract with help. Everybody with a smartphone and an egg avatar was calling her cash-in a disaster waiting to happen, but lo and behold, she took out Charlotte Flair, who had all the momentum in the world after snapping Asuka’s 500 some-odd day undefeated streak two days prior. Everything about Money Mella’s cash-in speaks to the power of perseverance and patience, to say nothing of making good on whatever opportunities are thrown your way. While the verdict is still out on The Princess of Staten Island’s very young championship reign, this was a tough one to beat as far as statements go.

Daniel Bryan (World Heavyweight Championship; 2011)

The Daniel Bryan who won the Money in the Bank contract was far closer to the “American Dragon” of the indies than the grand marshal of The “Yes!” Movement, which made it a particularly cool moment when the buzz-cut grappler cashed in on a vulnerable Big Show to win the World Heavyweight Title in 2011. But the real significance of the victory was what came after; this is one of the few times the ripples of a cash-in have legitimately changed WWE history. Bryan’s reign as World Heavyweight Champion led to a match with Sheamus at WrestleMania 28. That led to a humiliating 18-second defeat, which paved the way for… well, everything else.

Kane (World Heavyweight Championship; 2010)

By 2010, Kane’s sole reign as a top WWE titleholder had been 10 years earlier and lasted all of one day, but his World Heavyweight Championship contract cash-in carried all the historical significance that his earlier stint had been denied. Not only was Kane the first man to cash in the contract the same night he won it, he set a speed record for doing so that remains unbroken to this day. You can’t blame the WWE Universe for applauding in the moment, even though Kane downed the beloved Rey Mysterio to win the title: They knew The Devil’s Favorite Demon had finally gotten his due.

Rob Van Dam (WWE Championship; 2006)

Imagine for a moment you’re sitting on your parents’ couch watching ECW in 1997 and someone hops out of a time machine to inform you that, in nine years, Rob Van Dam will defeat WWE’s standard-bearer on an ECW show to win the WWE Championship. Your first reaction, probably, would be, “what’s WWE?” Your second, after a brief explanation, would be to laugh in this wayward traveler’s face. But come ECW One Night Stand 2006, you would see the impossible come true, as Rob Van Dam used his Money in the Bank contract to challenge John Cena at ECW’s raucous revival show and claim the ultimate prize, with Paul Heyman himself counting the three. RVD’s time as champion was short-lived, so points must be deducted here. But this was a capital-M moment for both RVD as a competitor and ECW as a whole: The bingo hall promotion had finally hit the jackpot.

Edge (WWE Championship; 2006)

The OG contract cash-in still ranks among the best because right up until the ref counted three on Edge’s pinfall against John Cena, nobody knew if the Money in the Bank experiment would work. A million things could have gone wrong, be it a miscalculated cash-in or The Ultimate Opportunist simply losing the Halliburton at the airport. But it went off like a charm. Spurred on by a command from Mr. McMahon — rumored to be “prove me right” — Edge toppled Cena to win his first WWE Title. The rest, from Edge’s WWE Hall of Fame career to the legacy of the contract itself, is history.

The Miz (WWE Championship; 2010)

“Anything can happen in WWE.” Sure, it’s a catchphrase, but it’s also unbelievably true. How else to explain a Cleveland loudmouth going from fanboy reality show veteran to a Money in the Bank contract holder who got one over on Randy Orton — Randy Orton! — to become WWE Champion, a title he would successfully defend in the main event of WrestleMania against John Cena. Not only did The Miz’s cash-in give us the eternal gift of Angry Miz Girl, but there’s a nice under-the-radar moment that sums up The Awesome One’s path to the title: After winning the title, before perching on the turnbuckle, Miz looked directly into the camera and sneered, “I told you. I told you all.”

Dean Ambrose (WWE World Heavyweight Championship; 2016)

Between Seth Rollins stealing whatever thunder he could find and Roman Reigns’ march to the top, Dean Ambrose seemed destined to bang his head against the glass ceiling his brothers had powered through in the wake of The Shield’s breakup. That was a horribly unworthy fate for the most grassroots-popular Hound of Justice, but his narrow losses to Reigns and Rollins in 2014 and 2015 made his same-night contract victory and cash-in — on Rollins, no less — all the sweeter. Here was a guy who had quietly, diligently toiled during the two years since The Shield imploded, and when his moment came, he proved himself just as worthy of the spotlight as the two supermen he upstaged to get it — a statement that carried over into the 2016 WWE Draft, when The Lunatic Fringe was selected by Shane McMahon and Daniel Bryan as the first pick of the new-look SmackDown LIVE.

Dolph Ziggler (World Heavyweight Championship; 2013)

Some of the cash-ins on this list suffer in hindsight because of their aftermath. Dolph Ziggler’s has a particularly bittersweet one, as injuries cut his World Heavyweight Championship reign short before it could really get going. But The Showoff’s cash-in on Alberto Del Rio maintains its status because it still holds up as a moment of joy for both Ziggler and the New Jersey faithful (Bruce Springsteen could have cashed in a Money in the Bank contract and gotten less of a reaction) so visceral that it makes you forget what’s coming down the pike. You think we’re kidding? Cue it up on WWE Network and tell us this guy isn’t about to rule the world.

Seth Rollins (WWE World Heavyweight Championship; 2015)

First cash-in to happen at WrestleMania. First cash-in to happen in the main event of WrestleMania. First cash-in to happen in the middle of any match, ever. Seth Rollins’ “Heist of the Century” against Brock Lesnar — and, to a lesser extent, Roman Reigns — carries all the historical hallmarks worthy of a No. 1 selection, but it’s the top moment because, in the simplest possible terms, nobody saw it coming. Not only did it defy the conventional wisdom surrounding that particular WrestleMania main event, it challenged the norms of Money in the Bank itself. The contract was an institution by then, and had been thought of as one thing for 10 years: A tool you use to pounce on a weakened champion after a match. By making his move in the middle of a match — the match — Rollins didn’t just burn that norm down. He rebuilt it in his image.