WWE Money in the Bank: Power Ranking the 8 Money in the Bank Cash-Ins

With the second annual Money in the Bank pay-per-view less than a week away, many WWE fans have been reminiscing about the best Money in the Bank ladder matches of all time. Perhaps more entertaining and compelling than the match itself, however, is how the winner chooses to cash in his contract.

Including the inaugural bout at WrestleMania XXI, there have been eight Money in the Bank ladder matches. The winner of each of those matches (or at least the holder of the briefcase) successfully cashed in their contract and became a world champion. With two more ladder matches on the docket Sunday, we could witness the coronation of two future world champions.

The way Money in the Bank contracts have been cashed in have run the gamut from cashing in that very night (Kane) to waiting nine months (Edge). With that in mind, there are many means of cashing in the contract that the WWE Universe has never seen, much less thought of. This includes an unsuccessful attempt which is bound to happen at some point.

Here are the eight Money in the Bank cash-ins ranked from worst to best.

8. Jack Swagger

In the final Money in the Bank ladder match to take place at WrestleMania, Jack Swagger unlatched the briefcase at WrestleMania XXVI in 2010. More surprising than Swagger’s eventual cash-in was the fact that he won the match at all. Christian was a heavy favorite heading into the match, and considering Swagger had been jobbing to Santino, he was nothing more than an afterthought.

Swagger certainly had an itchy finger when it came to cashing in his contract. He made a feeble attempt to cash-in on WWE Champion John Cena the night after WrestleMania on Raw. He called it off, however, when Cena looked like he was about to get the upper hand. Swagger did cash in his contract the following night on SmackDown, although it wasn’t officially recognized until three days later.

Due to the fact that SmackDown is taped on Tuesdays and broadcast on Fridays, Swagger’s cash-in was widely known by most internet wrestling fans. This took some of the luster away. For those that saw it live, though, I’m sure they were surprised.

After World Heavyweight Champion Chris Jericho was laid out by Edge, Swagger came down and delivered a gutwrench powerbomb to Jericho and became the new World Heavyweight Champion. Swagger will have another chance to fast-track himself to championship gold on Sunday.

7. Kane

Kane won the first SmackDown-exclusive Money in the Bank ladder match at last year’s Money in the Bank pay-per-view. Although Kane was viewed as a possible contender in the match, both Christian and Drew McIntyre were considered to be favorites. Kane secured the briefcase, though, triggering a major change in his character and demeanor.

Later in the card, after Rey Mysterio defended the World Heavyweight Championship against Jack Swagger, Kane came to the ring in order to cash in his contract. Swagger assaulted Mysterio after the match and put him in the ankle lock. The Big Red Machine first scared Swagger off to the locker room, but then came back to capitalize on the vulnerable Mysterio. Kane chokeslammed and tombstoned Mysterio to pick up the victory.

This cash-in was particularly shocking since a Money in the Bank winner had never cashed in on the same night they won the briefcase. The win led to a Kane heel turn that saw him feud with Mysterio, The Undertaker and Edge throughout the summer and early fall.

Kane did well as a transitional champion, although his reign was considered a bit boring. He’ll be in the SmackDown Money in the Bank match once again on Sunday, but another win seems unlikely.

6. Edge (Second Time)

To this point, Edge is the only man to successfully cash in a Money in the Bank contract without actually winning the contract in a Money in the Bank ladder match. While Edge won the inaugural Money in the Bank ladder match at WrestleMania XXI, he earned the briefcase in a much different way two years later.

Mr. Kennedy won the Money in the Bank ladder match at WrestleMania XXIII and eventually announced that he would hang onto the briefcase until WrestleMania XXIV. He was goaded into a match against Edge in which he put the contract on the line, however. Edge beat Kennedy for the briefcase on the May 7, 2007 edition of Raw. Edge went on to cash in his contract the next night on SmackDown against The Undertaker.

The Undertaker, who was the holder of the World Heavyweight Championship, was beaten and bloodied by Mark Henry. After Henry finally left the ring, Edge came out with the briefcase. He immediately went for a cover, but The Undertaker kicked out. He eventually hit The Undertaker with a spear and scored the win. Although this particular cash-in may not have been as shocking as his original one, it was a great moment nonetheless.

5. CM Punk (First Time)

To date, CM Punk is one of only two superstars to cash in their Money in the Bank contract as a face and remain one throughout their title reign. Punk won his first of two Money in the Bank ladder matches at WrestleMania XXIV. When Punk won the briefcase, he was a member of the SmackDown roster. He was drafted to Raw three months later, however, which is where he went on to cash in his contract.

Punk made his Raw debut on June 30, 2008, which was the night after the Night of Champions pay-per-view. The World Heavyweight Champion Edge defended his title against Batista the night before, but Batista felt as though he was screwed out of the title. Because of that, Batista proceeded to batter Edge. Once Batista was done, Punk shockingly came out with his Money in the Bank briefcase.

Once Punk got to the ring, Edge staggered to his feet. Punk then hit Edge with the Go to Sleep and earned the three-count to become the new champion. This marked the first of Punk’s three World Heavyweight Championship reigns.

As surprising as this particular cash-in was, it was no match for what he would do one year later.

4. The Miz

The Miz won the second ever Raw-only Money in the Bank ladder match at last year’s Money in the Bank pay-per-view. Heading into the match, The Miz was red-hot and it was very apparent that he was on the verge of becoming a main-eventer. In a match with the likes of Randy Orton, Chris Jericho and Edge, however, The Miz wasn’t exactly expected to win.

The Miz teased cashing in against Sheamus on consecutive episodes of Raw following Money in the Bank, but due to interference he was unable to. The Miz then embarked on an entertaining four-month run with the briefcase. He was built up well during has time with the briefcase and was undoubtedly ready to make the leap when he finally cashed in on the Nov. 22, 2010 edition of Raw.

WWE Champion Randy Orton had a title match against Wade Barrett, who was the leader of Nexus at the time. Nexus attacked Orton prior to the match, weakening him for Barrett. Although Orton ultimately came out on top, he could barely stand. The Miz then came out, and in a fairly lengthy match for a cash-in, he picked up the victory after a Skull Crushing Finale.

The Miz went on to have a prosperous five-month title reign and cemented himself as one of the WWE’s top heels.

3. Rob Van Dam

Rob Van Dam won the second-ever Money in the Bank ladder match at WrestleMania XXII. While many considered his win to be predictable, there was nothing predictable about the way he decided to cash in his Money in the Bank contract. Traditionally, Money in the Bank winners choose to ambush fallen champions when cashing in their contracts, but RVD took a much different approach.

To this day, RVD is the only Money in the Bank winner to actually set up a match ahead of time. Van Dam challenged John Cena for his WWE Championship at the One Night Stand pay-per-view on June 11, 2006 in an extreme rules match. Edge came out in a disguise and speared Cena through a table. He then incapacitated the referee.

With the referee still knocked out, Paul Heyman ran down the aisle as RVD hit Cena with a Five Star Frog Splash. Heyman made the count and RVD became the new WWE Champion. When you consider the fact that seven of the eight Money in the Bank winners have exploited the vulnerability of the respective champions they defeated, RVD’s cash-in is among the most surprising.

If a face is able to win one of the ladder matches on Sunday, we might see a reprisal of RVD’s strategy at some point.

2. CM Punk (Second Time)

As good as CM Punk’s first Money in the Bank cash-in was, it was his second one that helped elevate him to the stardom he enjoys today. Punk became the first and only wrestler to win back-to-back Money in the Bank ladder matches when he took the briefcase at WrestleMania XXV.

Things were much different for Punk the second time around, however.

After holding the briefcase for two months, Punk struck following a match between Jeff Hardy and Edge at Extreme Rules. Hardy defeated Edge in a grueling ladder match to become the new World Heavyweight Champion. After the match, Hardy began to celebrate, only for Punk to come to the ring wielding his Money in the Bank briefcase. Hardy could barely get to his feet and Punk made sure to take advantage.

Punk hit Hardy with his patented Go to Sleep, but Hardy shockingly kicked out. Hardy then scored a near fall on a small package. Punk was able to execute another Go to Sleep, though, and win the World Heavyweight Championship for the second time. The win essentially made Punk a heel as Hardy may have been the most over face in the company at the time.

This allowed Punk to develop his straight-edge character and become one of the biggest heels in the WWE. If it weren’t for that cash-in, Punk may not be the hottest thing in the wrestling world right now.

1. Edge (First Time)

As is the case with most movies, the sequel is never as good as the original. The same can be said for the original Money in the Bank cash-in by Edge. Edge won the first-ever Money in the Bank ladder match (exclusive to Raw Superstars) at WrestleMania XXI in 2005. While most Money in the Bank winners since have only held the briefcase for a few months, Edge kept his for over nine months.

Due to the fact that Edge was in possession of the briefcase for so long, it came as a complete shock when he cashed in his contract at New Year’s Revolution on Jan. 8, 2006. After retaining the WWE Championship in a hellacious Elimination Chamber match, John Cena laid in the middle of the ring with his face covered in blood. At that moment, Vince McMahon came to the ramp and announced that Edge was cashing in his title opportunity.

Edge immediately hit Cena with a spear, but Cena kicked out. After a second spear, however, Cena couldn’t muster enough strength to do it again as Edge became WWE Champion for the first time. Since this cash-in, no superstar has been replicated the drama that went along with it.

Since storylines are cyclical when it comes to wrestling, I would expect somebody to have an Edge-like run with the briefcase in the near future. Perhaps that superstar will be determined on Sunday.