The 10 Most Memorable Cash-ins in WWE Money in the Bank History

When Money in the Bank was first announced, no one could have truly understood what it would become. This No. 1 contendership did not just promise a title match. It delivered a true moment.

While everyone was able to capitalize on this opportunity, some of the greatest moments in WWE have been executed thanks to the Money in the Bank briefcase.

In these last 20 years, stars have been made. Hearts have been broken. New eras have been built, all off this concept.

The moments have been spectacular over the year. Just to name a few:

• The very first cash-in by Edge on John Cena at New Year's Resolution.
• Rob Van Dam's big win for the ECW faithful at One Night Stand.
• Seth Rollins' shocking mid-match addition to the main event of WrestleMania 31.
• Bayley realizing on the night she won the Money in the Bank briefcase that she was about to be SmackDown Women's Championship by cashing in on Charlotte Flair.
• Liv Morgan's first title win at Money in the Bank 2022.

These are just the tip of the iceberg when looking back at the most memorable cash-ins in WWE history ahead of WWE Money in the Bank 2023.

10. Carmella (SmackDown April 10, 2018)

The first-ever Mrs. Money in the Bank, Carmella, remains the best to hold the briefcase. Some of this is because the women to come after her would rarely hold the briefcase more than a couple days.

However, this does not take away from the work that she did to elevate herself with the briefcase. Carmella was a compelling heel, constantly seeking her opportunity to capture her first women's championship.

She finally found her opening on the SmackDown after WrestleMania. Moments often come on the shows after The Show of Shows, but they rarely have come for the women of WWE.

That change when The IIconics attacked current SmackDown women's champion Charlotte Flair, setting the stage for The Princess of Staten Island to cash in and take the gold.

Even if her title reign is better known for how it ended, beginning the rise of Becky Lynch, the build-up and moment at the end of WrestleMania week made a unique impression rarely matched by other cash-ins.

9. CM Punk (Extreme Rules 2009)

WWE may not like to mention CM Punk these days, but his back-to-back Money in the Bank victories remain unmatched. No other man has ever won the ladder match twice, certainly not twice in a row.

The first cash-in was a special moment as it began the rise of The Best in the World. However, it was the second that made a lasting impression.

In both cases, Punk took advantage of a vulnerable champion. He almost cashed in on the same man as Edge was the WWE world heavyweight champion going into both nights.

However, the second time, at WWE Extreme Rules 2009, Jeff Hardy defeated The Rated-R Superstar to capture his first WWE World Heavyweight Championship. Punk arrived and stole the moment from Punk.

What makes this moment so spectacular is the juxtaposition. Because of who Punk cashed in on, the crowd's reaction was drastically different. This would lead to a heel turn that would forever define Punk as one of WWE's best until his departure.

8. Randy Orton (SummerSlam 2013)

In 2013, the WWE Universe had Daniel Bryan fever. The most popular act in the company was not the company's choice. He was a relatively small independent star that should not have been able to succeed.

However, consistently great in-ring work combined with a charismatic ability to connect with the fans through humor made him popular. Fans wanted to see him succeed.

Finally, he got the biggest opportunity of his career, challenging John Cena for the WWE Championship at WWE SummerSlam 2013.

This is where Randy Orton came into the picture. He had won the Money in the Bank briefcase just one month prior and loomed over this world title match.

After an unforgettable main event, Bryan won the battle, only to find himself in a new losing war. The "Yes" Man defeated The Champ, seemingly crowned as the new top babyface in WWE.

The Viper walked to the ring and waited for special guest referee Triple H to Pedigree Bryan. Orton waltzed in to ruin the crowd's fun and take the WWE Championship.

While it was a tough moment for the fans, it was intensely memorable, beginning the rise of The Authority and Bryan's long journey to his grandest triumph at WWE WrestleMania XXX.

7. Bayley (Money in the Bank 2019)

WWE started an unfortunate tradition of immediately booking women to cash in at WWE Money in the Bank after winning the briefcase on the same night. It has worked better for some over others.

Bayley was the last member of the Four Horsewomen to arrive on the main roster, following a successful NXT Women's Championship reign.

WWE rewarded her patience with much success right off the bat. However, not everything was clicking. Her gimmick was not connecting with a tougher audience. This pushed a change for Bayley that has followed her to this day.

At WWE Money in the Bank 2019, The Hugger won the Money in the Bank briefcase. Up until that point, Bayley has always been the naive hero, trying to win the day.

On this night though, after Charlotte Flair won the SmackDown Women's Championship with the help of Lacey Evans, Bayley came out to even the odds with Becky Lynch. In the ensuing brawl, The Queen went down.

The Hugger saw an unexpected opportunity to cash-in, defeating The Queen to become champion. In the following months, Bayley would slowly turn heel, beginning a transformation that redefined her career trajectory to this day.

6. Dean Ambrose (Money in the Bank 2016)

No group has more completely defined the past decade than The Shield. Three men took over the wrestling industry: Roman Reigns, Seth Rollins and Dean Ambrose.

After a completely dominant run as a trio, the only wrestler that could break The Shield was someone within the group. The Architect blasted his own friends with a steel chair to join The Authority and find his lasting success.

Along the way, Ambrose and Reigns never quite got their revenge until WWE Money in the Bank 2016. The Lunatic Fringe overcame the field to capture the Money in the Bank briefcase.

Less than an hour later, Rollins defeated Reigns in a main event classic to capture the WWE Championship. Finally avenging years of suffering at the hands of Rollins, Ambrose cashed in to win the WWE Championship.

On that night, every member of The Shield had been world champion, and they would go onto deliver the long anticipated Shield triple threat match that solidified Ambrose's reign as WWE champion.

While it would take The Lunatic Fringe leaving WWE for All Elite Wrestling to make him a lasting main event stars, this moment will forever live as the last great act of The Shield rivalry, allowing Ambrose a brief time at the top that fans had awaited.

5. Liv Morgan (Money in the Bank 2022)

Liv Morgan is one of the most beloved wrestlers in WWE. She has always been a hard worker, overachieving despite never being the favored star.

Both of her closest friends were fired by WWE, leaving her without direction. When she got to perform, time was often cut from her work. Still, she kept a positive attitude.

It all paid off at WWE Money in the Bank 2022. First, Morgan overcame the best strategies of Becky Lynch to capture the Money in the Bank briefcase.

Then when she saw an opportunity, following a physical match between Ronda Rousey and Natalya, she cashed in her shot. She defeated The Baddest Woman on the Planet with a cleverly timed roll-up to become SmackDown women's champion.

It was the culmination of near-decade-long journey to reach the top. It was the prize that Morgan deserved, and WWE can never take away this important victory from her.

While it is easy to look down upon the aftermath of Morgan's title reign, it is rare to see such a crowd-pleasing moment delivered in such shocking fashion.

4. Rob Van Dam (ECW One Night Stand 2006)

The Money in the Bank briefcase offers a guaranteed title match any time, anywhere. However, too often, Money in the Bank winners will just use it to get a cheap win when an opportunity outside of their control gives them an opening.

The second-ever Money in the Bank cash-in remains one of the most unique. Instead of cheating to capture gold, Rob Van Dam simply wanted his fair shot in his ideal environment.

He challenged John Cena to a WWE Championship match at ECW One Night Stand 2006. In the Hammerstein Ballroom, The Champ was reviled. He was as clear a heel to the crowd on this night as he would ever be.

Easily the longest cash-in match in WWE's history, Cena and RVD went 20 minutes before Edge in disguise ran in to Spear The Champ. He set up The Whole Dam Show to hit a Five Star Frog Splash and win the world title.

While RVD's only reign as WWE champion would last just 22 days before Edge took the gold, this remains a truly unique moment that few have tried to replicate with future cash-ins.

Until more babyface heroes decide to embrace a fair fight with the Money in the Bank briefcase, RVD will stand as the most noble Mr. Money in the Bank in history.

3. Dolph Ziggler (Monday Night Raw April 8, 2013)

The Raw after WrestleMania holds a special aura as the night that brings even more surprises than The Show of Shows. It is the chance to capitalize on a massive crowd from all over the world to deliver moments that are never forgotten.

There may not be a single moment more well remembered than the night Dolph Ziggler cashed in his briefcase on an injured Alberto Del Rio to a raucous ovation.

The Showoff is often praised as one of the modern workhorses of WWE. He was almost too good at putting other wrestlers over, leaving himself behind.

His first reign as WWE world heavyweight champion was so messy that it barely counted. When he won Money in the Bank, few believed he would even capitalized on it.

That is what made this simple cash-in so impactful. The crowd at his back made Ziggler a bigger star in one night than he ever had been or ever would be again.

An untimely concussion would lead to a short title reign, but he would turn face for the first time in his WWE career. If WWE was not so stubborn, The Showoff would have carried this forward for a long time to come.

However, the unfortunate failure to follow up almost makes this more special. It is a moment in time that the crowd got exactly what it wanted, and no future Raw after WrestleMania has been able to live up to this moment.

2. Seth Rollins (WrestleMania 31)

The dream is always to win at WrestleMania, even better still to walk out as WWE champion. It is shocking that between 28 Money in the Bank winners, only one chose to cash in at The Show of Shows.

This is what makes Seth Rollins' cash-in so distinct. He walked into 'Mania, only set for a fight with Randy Orton. After losing that match with The Viper, his night was far from over.

He fully embraced the opportunity of a cash-in at any time, using the briefcase to insert himself into Brock Lesnar vs. Roman Reigns once both men had exhausted each other.

He made sure The Beast Incarnate was out of the way before Curb Stomping The Big Do to capture the WWE Championship. He ended the night standing tall in front of a reported 76,976 fans in Levi's Stadium.

No cash-in has happened in front of a larger crowd. No cash-in since this time has created a bigger star than The Architect.

This cash-in set a new standard that WWE has not remotely met in the eight years since.

1. Edge (New Year's Revolution 2006)

Everyone has been chasing Edge's first cash-in. In 27 attempts, few have created quite the same impact. Even The Rated-R Superstar himself could not pull it off in his second try.

No one quite understood the potential of Money in the Bank when it was first introduced. It was a No. 1 contendership that could be used at any time.

Most thought it would lead to a conventional match. No one expected that Edge would cash in after John Cena won an Elimination Chamber match, barely able to stand and bleeding from his forehead.

The Rated-R Superstar showed that Money in the Bank could give someone their ideal odds to become champion. Not everyone would be able to take advantage of the opportunity, but it was something truly unique.

Edge would carry this first world title win forward into 11 world championship reigns and a WWE Hall of Fame induction.

To this day, no one has truly escaped the shadow of this first cash-in. Many have creative cash-ins, but not one has been imitated more than this.