The 7 Most Jaw-Dropping Money In The Bank Cash-Ins

The ingredients for a standard MITB cash-in are simple: the current champion lays beaten and battered in the ring, and the briefcase holder seizes the opportunity to collect their prize.

We can thank Edge for pioneering the recipe. At New Year’s Revolution, WWE Champion John Cena competed in a grueling Elimination Chamber match in which Kurt Angle took him to Suplex City (no, Lesnar wasn’t the first!), and Chris Masters DDT’d his head onto the steel outside the ring. A bloodied Super Cena miraculously survived the onslaught and emerged victorious because, well, that’s what Super Cena did.

Before Big Match John could rise to his feet, Vince McMahon announced that Edge would be cashing in right then and there. Could he do that? Was that even allowed? To quote a future MITB winner, “YES!”

Edge speared what was left of Cena, and Cena kicked out because, well, did I mention the Super Cena thing? He then speared him a second time and captured his first WWE title.

We’re desensitized to this type of MITB moment now because it’s the norm, but at the time, the WWE Universe hadn’t experienced anything like it. It broke their collective brain.

From 2003 – early 2025, John Cena was the consummate good guy… save for one night in 2006.

Rob Van Dam elected to cash in his MITB briefcase at ECW One Night Stand and had the ultimate home court advantage. The hostile crowd at the Hammerstein Ballroom hated Cena with a passion, hurling toilet paper at him; repeatedly tossing his shirt back at him as if it was an opposing team’s home run baseball; and showering him with brutal NSFW chants. They threatened to riot if Cena won.

At first, visibly shaken by the vitriol, Cena started to embrace it as the match went on, wrestling as a villain. He beat down the underdog RVD for a majority of the contest (a role reversal for Cena) and nailed him in the head with steel steps. He even knocked out the referee.

This wasn’t Super Cena. This was Lex Luther. Edge slid out from under the ring and speared Big Match John through a table. As fans chanted “Thank you, Edge,” RVD frog-splashed Cena, and Paul Heyman counted the pinfall.

Plankton had a better shot of stealing the Krabby Patty secret formula than John Cena did of losing in 2006. Rob Van Dam had never really reached main event status. On this night, everything we thought we knew changed

The Miz’s Money in the Bank cash-in is criminally underrated, just like his wrestling career.

It began with John Cena (notice a pattern here?) getting fired from the WWE on Raw due to his failure to secure a title victory for Wade Barrett against champion Randy Orton the night before. Barrett was granted a rematch, and as “The Viper” made his way to the ring, the Nexus jumped him, badly injuring his knee.

Still, the match went on as scheduled, and as Barrett closed in on a win, Cena returned to interfere, and a hobbled Orton hit Barrett with an RKO to retain.

Night over. All is good in the world. Right? Wrong.

Shortly after commentator Jerry “The King” Lawler remarked, “Awesome, awesome,” on Randy Orton’s heroic title defense, The Awesome One’s music hit and he cashed in his briefcase, much to the chagrin of the WWE Universe. Miz targeted Randy’s knee and pulled off one of the smoothest finisher reversals you’ll ever see, countering an attempted RKO into a silky Skull-Crushing Finale.

The storytelling beats in just one evening amounted to an electrifying, heat-generating cash-in. The look on “Angry Miz Girl’s” face said it all.

By 2012, 11 superstars had grabbed the Money in the Bank briefcase. All of them successfully cashed in to win the title. John Cena—the most unbeatable, winningest champion in history—looked to extend that streak to 12, which was about as inevitable as The Undertaker notching a victory at WrestleMania. Except, things didn’t go as expected.

Cena challenged fellow babyface CM Punk on the 1,000th episode of Monday Night Raw, giving The Best in the World advance notice of his cash-in; an unusual tactic, but not surprising given Cena’s good guy persona.

As the match reached its climax, the Big Show stormed the ring to take out Cena, disqualifying Punk. A DQ finish meant the champion retained, cementing the first instance that a MITB winner was unsuccessful in their cash-in attempt. Punk’s actions afterwards made the moment even more stunning.

As Show attacked Cena, the champ slinked into the corner and watched, agonizing over whether he should help. Amid the hesitation, The Rock’s music hit, and he made the save. Before he could hit the People’s Elbow on Show, Punk clotheslined and then GTS’d The Great One.

Punk turned heel, something he hadn’t been since his infamous pipe bomb promo.

Nelson Mandela. Betty White. 2013 Daniel Bryan. What do these three have in common? Untouchable approval ratings.

John Cena (after this slide, I promise you won’t see him again) hand-picked the leader of the YES! Movement to be his SummerSlam opponent for the WWE title. After an entertaining contest, Bryan won! Vanquishing Cena clean—sans shenanigans—is no easy feat, but the real shocker came post-match.

The MITB briefcase holder Randy Orton walked down the ramp, teasing a cash-in. Before he could make a move, special guest referee Triple H shockingly pedigreed Bryan, turning heel and allowing Orton to pin an incapacitated Bryan to steal the WWE Championship minutes after he’d won it.

The Game’s actions led to the formation of The Authority. Of course, the group’s relentless mission to prevent Bryan from ever becoming champion culminated in a WrestleMania 30 payoff for the ages, and it all started from one MITB cash-in.

WWE fans can smell a forced babyface push from a mile away. That’s why they couldn’t bear the stench of a Roman Reigns victory at WrestleMania 31. The not-yet Tribal Chief would challenge his toughest opponent yet; Brock Lesnar, a man who ended The Undertaker’s undefeated streak at WrestleMania a year prior and six months earlier squashed John Cena to win the WWE Championship.

Given Roman’s recent Royal Rumble triumph, awkward co-sign from The Rock, and defeat of mega face Daniel Bryan at FastLane, it was a foregone conclusion that this was Roman’s time. He was WWE brass’s chosen one.

Seth Rollins had other plans.

About 15 minutes into Lesnar and Reigns’ slugfest, Rollins ran to the ring and cashed in, turning the main event bout into a Triple Threat match. Seth curb stomped his former Shield brother, pinned him, and ran away with the title—the first of his career—in jaw-dropping fashion. The “heist” denied Reigns the same accomplishment, much to the delight of the WWE Universe.

It’s not a coincidence that we’re fast-forwarding 10 years into the future to reach our next moment on the list. Before it was Tiffy’s time to cash in her Money In The Bank briefcase, 37 other superstars had done the same. There are only so many new ways to shock the WWE Universe, but Tiffany Stratton did just that.

On the January 3 episode of Smackdown, Tiffy’s friend Nia Jax defended her WWE Women’s Championship in a match against Naomi. As the contest was coming to a head, Stratton’s music hit, and she ran down to the ring holding her briefcase in one hand and the ref’s hand in another.

Despite the telltale signs of a cash-in, Tiffy instead hit Naomi in the head with her briefcase, aiding Jax to victory as she’d done several times previously.

We were swerved. And then, we were swerved again. As Bianca Belair went to check on Naomi, Jax attacked Belair and set her up for The Annihilator. Before she could execute it, Stratton whacked Jax with the briefcase, Belair followed up with a massive Kiss of Death and Tiffy took advantage, landing the Prettiest Moonsault Ever on Jax for the 1-2-3.

Betraying a friend—who was also the champion—with a cash-in is something we’d never seen. The soft face turn and exuberant crowd reaction helped solidify the moment in MITB lore.