Top 5 WWE Money In The Bank Cash-Ins

In the words of the Atlanta based rapper Lil Scrappy, "I got money in the bank, shawty what you drank?" That's right, it's that time of year once again where a whole host of WWE stars look to climb the ladder of success and retrieve the coveted Money in the Bank briefcase and earn themselves a shot at either of WWE's top champions at any time within the next year.

While the 2025 Money in the Bank Premium Live Event will be the show's 15th anniversary, the match itself has been around for two decades. Debuting in 2005 at WrestleMania 21, the Money in the Bank ladder match has become a staple in the WWE calendar each year, and its early success has led to the PLE named after the match to be perceived as the biggest event WWE has to offer outside of the annual "Big Four."

Once the high octane action of the ladder match is over, fans then get to look forward to the eventual cash-in by the winner. Questions like when and where they will cash-in their contract run through the minds of fans, as well the inevitable question of will they actually be successful in their attempt to cash-in their contract? Since the match was created, a total of 32 cash-in attempts have been made, with 26 of them resulting in a new champion being crowned, including a 100% hit rate for whoever becomes Miss Money in the Bank. But as far as the actual cash-ins are concerned, which are the ones that stand out the most?

So sit back, relax, and climb a 12-foot ladder with us to see what are the five best Money in the Bank cash-ins in WWE history, in chronological order (not rank-ordered). Mind your step.

It's almost cliché to say something like "you never forget your first" in a list like this, but it would be very hard to run down the five best Money in the Bank cash-ins and not start off with the one that started it all.

By the time 2006 rolled around, John Cena had cemented himself as the new face of WWE, defeating every big name that "WWE Raw" had to offer at the time. Chris Jericho, Christian, Shawn Michaels, Kurt Angle, even upcoming stars like Carlito and Chris Masters were no match for "The Doctor of Thuganomics." However, the ultimate opportunist was lurking in the shadows. Edge had held the inaugural Money in the Bank briefcase for as long as Cena had held the WWE Championship, and after feuding with the likes of Kane and Matt Hardy throughout the year, many people had almost become accustomed to the visual of Edge holding the briefcase when he started feuding with Ric Flair at the end of the year.

However, at the end of New Year's Revolution 2006, a show Edge had already competed on, Vince McMahon strolled out following Cena's victory in a violent and bloody Elimination Chamber match to announce that Edge was cashing in his Money in the Bank briefcase. No one really knew what was happening as this was the first time anything like this had taken place, but after two spears, "The Rated-R Superstar" won his first of 11 WWE World Championships. The reign that followed might have only lasted until the end of the month when Cena won his title back at the 2006 Royal Rumble pay-per-view, but it did include the infamous "live sex celebration" the night after New Year's Revolution, and a wild TLC match against Ric Flair.

Staying in 2006 for the second-ever Money in the Bank cash-in, one that couldn't have been more different to Edge's triumph at New Year's Revolution if it tried.

After Rob Van Dam missed almost an entire year of action due to a serious knee injury, he returned to WWE at the 2006 Royal Rumble and was as, if not more, beloved by the fans than he was before he got hurt. RVD was often considered to be one of the greatest WWE talents at the time to have never won a WWE World Championship and everyone knew that had to change in the immediate future. Fans got very excited when Van Dam qualified for the Money in the Bank ladder match at WrestleMania 22, and "Mr. Monday Night" would be the one to leave that year's "showcase of the immortals" with the briefcase in hand.

RVD would go on to win the WWE Intercontinental Championship during a short feud with Shelton Benjamin following WrestleMania 22, but in the lead-up to second-ever ECW One Night Stand pay-per-view that June, Van Dam became the first man to cash-in his Money in the Bank contract ahead of time. He announced that his WWE Championship match against John Cena would take place at One Night Stand as the environment worked "extremely" well in his favor (pun very much intended), and that he would re-christen the belt as the ECW World Championship when he won it.

The match itself has been heralded as one of the best WWE main events of the 2000s, with the crowd itself being remembered as arguably the most hostile set of fans of all time, but they all aided Van Dam during the match as he left the Hammerstein Ballroom as the WWE Champion.

By the time he won the Money in the Bank ladder match for a shot at the World Heavyweight Championship in July 2012, Dolph Ziggler had become one of WWE's most reliable hands. His days as a member of the Spirit Squad were long forgotten, and reigns with both the WWE Intercontinental and WWE United States Championships had established the "Show Off" as someone fans could always rely on for a great showing whenever he was on the card. He even had a cup of coffee with the World Heavyweight Championship in 2011, being awarded the title by Vickie Guerrero during her own feud with Edge, making him a Grand Slam Champion by the time he became Mr. Money in the Bank.

However, nine months after winning the briefcase, with feuds against the likes of John Cena, Chris Jericho, and Randy Orton to fill the time, Ziggler finally picked his moment on the April 8, 2013, episode of "WWE Raw," the night after WrestleMania 29. The fans in attendance on the night are largely responsible for the "Raw" after 'Mania being seen as a marquee episode of WWE television each year as they regularly hijacked the show with beachballs and renditions of Fandango's entrance music, but there was one thing they all wanted when Ziggler charged to the ring; a new champion.

With electricity in the air, Ziggler and wounded champion Alberto Del Rio engaged in a short back-and-forth, with the champion trying everything he could to wrestle on one good leg, but it was no use. Ziggler hit the Zig-Zag for the victory and finally won the World Heavyweight Championship in a proper manner for the first time. His reign as champion might have been short-lived, but Ziggler's cash-in has gone down in history.

If this list was ordered by what is objectively the best Money in the Bank cash-in as opposed to going in chronological order, this would take No. 1 by a considerable margin for a variety of reasons.

To put it bluntly, there weren't many people who wanted to see either Roman Reigns or Brock Lesnar leave WrestleMania 31 with the WWE World Championship. Reigns was being pushed as the face of the company, much to the disdain of the fans who had turned on the "Big Dog," while there were multiple reports at the time that Lesnar was on his way out of WWE in favor of a return to the UFC. There seemed to be no way out for the WWE Universe. That was until the last minute when the decision was made to insert a third man into the match.

Having held the briefcase since the summer of 2014, Seth Rollins had reportedly pitched the idea of cashing-in at WrestleMania to Vince McMahon, as it had never been done before. However, the decision to make the main event an impromptu triple threat match wasn't actually made until the day of the event, with Rollins only learning of the decision after his scheduled match against Randy Orton during the show.

With both Lesnar and Reigns down in the ring, Rollins sprinted to the ring to make history, becoming the first man to cash-in his Money in the Bank contract while a match was taking place, not to mention he was the first man to cash-in at WWE's biggest event of the year. The plan went off without a hitch, and the closing visual of WrestleMania 31 was Rollins holding the WWE World Championship above his head having pulled off the "Heist of the Century." 

Truth be told, the WWE women's division hasn't exactly had a lot of luck when it comes Money in the Bank. The first match was technically won by a man, four of the first five winners cashed in their contracts within 24 hours of winning it, and at times it seemed like WWE didn't necessarily have a real plan for whichever woman won the match outside of knowing they would eventually become champion. However, that all changed when Iyo Sky became Miss Money in the Bank in July 2023.

WWE was still in the honeymoon phase of Triple H's time in charge of the creative direction of the company, meaning that a lot of people were very excited to see what was in store when Sky opted not to be the fifth woman in a row to cash in her contract within a day of winning it. Sky had long been seen as one of the best wrestlers in the world, regardless of gender, but had never been able to get close to the top of the WWE women's division, a division that was already getting very cramped at the top of it.

However, Sky made room for herself at the top of the division at the SummerSlam Premium Live Event in August 2023, charging to the ring after Bianca Belair defeated both Charlotte Flair and Asuka in a triple threat match. "The EST" thought she was going to enjoy a lengthy reign as the WWE Women's Champion, but it was Sky who left Ford Field in Detroit with the title around her waist, defeating Belair in 10 seconds to begin a reign as champion that would last until WrestleMania 40 the following April, when she was defeated by her former Damage CTRL stablemate Bayley.