The Money in the Bank match started in 2005 at WrestleMania 21. Ever since then, WWE has done at least one Money in the Bank match every year and the event has become arguably the most popular “gimmick match” in WWE history.

A big reason why it’s become so popular is the prize that the winner receives. There’s a briefcase that hangs above the ring while the competitors in the match (at least six people, sometimes more) battle it out to see who can climb a ladder to retrieve it. It’s a concept that legendary WWE performer Chris Jericho devised with former writer Brian Gewirtz (as noted by Jericho on Twitter).

Once a wrestler has the briefcase, they are allowed to challenge the WWE or World Champion any time and any place they want, as long as they have a referee with them to start the match. It’s an exciting match that has fans guessing from the get-go as they try to figure out who might win. Then once the briefcase is in play, fans wonder when that individual may cash it in.

The cash-in attempts work so well because you might see somebody try to cash in after the champion had a grueling match and the person with the briefcase ends up having second thoughts right before the attempt. There have been cash-in moments after the champion was beat up by somebody else. It’s even happened at a WrestleMania.

As a sign that the Money in the Bank idea worked so well, WWE changed it from being just a WrestleMania match to giving it a PPV of its own in 2010. In 2010, there were three different briefcase winners since they had the match at WrestleMania and two separate winners for the brands in 2010. From 2010 to 2013, WWE also had two MITB briefcases in play (red for Raw and blue for Smackdown) for the separate brands.

Even though there’s a brand extension starting on July 19, it appears as though one Money in the Bank briefcase will be won on June 19. It could be the launching pad for somebody like Dean Ambrose, Kevin Owens, Sami Zayn or Cesaro to be a World Champion for the first time, or perhaps Chris Jericho and Alberto Del Rio can win it to get back to that level again. There are plenty of ways it can go.

With Money in the Bank on our minds, here’s a ranking of all 16 Money in the Bank cash-in attempts from worst to best. In each case I’ll mention if the person won the only briefcase that year or if they won it for a specific title.

16. Damien Sandow (2013 World Title winner)

Poor Damien Sandow. That’s all I can think of when remembering this one. Sandow was a rising star as a heel on the Smackdown brand. It was either going to be him or Cody Rhodes as the winner of the match. They went with Sandow, while also having him turn on Cody towards the end of the match to set up a feud. Their feud was okay, but we wanted to see Sandow cash in that briefcase.

On the Oct. 28, 2013 episode of Raw, Sandow attacked World Champion John Cena with the briefcase and it led to a match. Cena had just returned from biceps surgery, so he was selling the arm injury a lot. There were several times in the match where Sandow almost won. The match was really competitive, but in the end, it was the same old Cena match with Cena getting the victory with the Attitude Adjustment.

It’s fair to say that Sandow never really recovered from that loss while a win could have propelled him to that next level. Sandow’s place in Money in the Bank history is as the first and only man to get pinned while he was doing a cash-in attempt. So sad.

15. John Cena (2012 WWE Title winner)

Cena won the smallest Money in the Bank match in 2012 with only five competitors in the match. Then he told current WWE Champion CM Punk that he would face him for the WWE Title on the July 23, 2012 episode of Raw. They had a good match like they always do, but then Big Show attacked Cena and it ended in a disqualification.

The booking of the whole thing was weird. He won by disqualification, meaning that there was no title change, so shouldn’t he have received another singles title match? It would have made sense. They just moved on from it.

Those are the only two cash-in attempts that didn’t result in a title change.

14. Sheamus (2015 Winner)

Putting the briefcase on Sheamus in 2015 was met with a lot of groans. He’s a former WWE and World Champion who didn’t have much momentum at all, but WWE always wants to push him because he’s got the look that Vince McMahon loves.

They went the predictable route with his cash-in by doing it against Roman Reigns after he won his first WWE Title at last year’s Survivor Series. A month later, Reigns won it back. Sheamus has been struggling in the midcard ever since. It’s fair to say they picked the wrong guy to win it last year.

13. Jack Swagger (2010 Winner)

Swagger’s the name on the list that gets people to say “huh?” because his career has been stuck in the midcard ever since. WWE wanted to elevate him, so he surprisingly won the briefcase in 2010. He had one of the quickest cash-ins in WWE history.

Two days after he won the briefcase at WrestleMania 26, Edge attacked the World Champion Chris Jericho and Swagger capitalized on the situation by leaving with the gold. It was a pretty forgettable World Title run for Swagger after that, but this was definitely the highlight of his career.

12. Alberto Del Rio (2011 Winner WWE Title)

It was clear that WWE had high hopes for Del Rio in 2011 since he won the Royal Rumble earlier in the year. His MITB win was obvious too. They didn’t wait long to have him cash in to get the WWE Title either.

Following CM Punk’s win over John Cena at SummerSlam 2011, there was a random attack by Kevin Nash. It was so odd to see that, but it was part of a bigger story that ended up not making a lot of sense. Nash “stuck” Punk with a Powerbomb. Del Rio capitalized on the situation and left with the WWE Title. He ended up dropping it back to Punk a few months later.

11. Edge via Ken Kennedy (2007 Winner)

When WWE talks about 14 of 16 MITB winners leaving with a title, there’s an asterisk on this one. Ken Kennedy won the briefcase at WrestleMania 23. Then he suffered an arm injury, so they made him defend the title in a match against Edge. That led to Edge winning the briefcase from him about five weeks after Kennedy won it. It’s the only time that the winner lost the briefcase. I’ve always felt like it was dumb to have the winner defend the briefcase because it’s not a title, but that’s how WWE operates.

Edge ended up cashing in the briefcase the next day at a Smackdown taping that aired on May 8, 2007. The Undertaker was hurting from a cage match with Batista and then he was attacked by Mark Henry. It was a cheap win for Edge, but it fit his character well. Kennedy ended up fired by WWE in 2009. He will probably never be back.

10. Daniel Bryan (2011 Winner World Title)

Big Show had just defeated Mark Henry to win the World Title in a Chairs match at the December 2011 TLC event. It was a physical match between two big men. Henry took out his frustration after the match by attacking Show. The attack left Show down on a pile of chairs. Bryan ran down to the ring, covered the fallen giant and left with the World Title. Bryan was a heel at the time, but he would go on to become a huge face over the next couple of years.

Bryan told a funny story in his book about this because he wasn’t actually scheduled to be at this show. He was just in town for a contract signing. Then he found out that afternoon that WWE wanted him to win the title and that was it. It just shows how sometimes plans can change in an instant.

9. The Miz (2010 Winner WWE Title)

Randy Orton was the babyface WWE Champion that had a grueling match with Wade Barrett on Raw on Nov. 22, 2010. Orton also had to deal with the Nexus group. Barret took him to the limit as Orton did a great job of selling a knee injury during the match. After his win, the music of The Miz hit for a cash-in attempt.

What I liked about this one is that they had a bit of a match before the title change. If Miz just pinned Orton right away it would have been fine. Instead, they wrestled for about three minutes with Miz going after the knee and then eventually hitting the Skull Crushing Finale for the win.

8. CM Punk (2008 Winner World Title)

They went with the popular formula for this one. Edge was the champion that got destroyed by Batista on the June 30, 2008 episode of Raw. Punk swooped in as a babyface wrestler that was on the rise as the crowd went wild. Punk hit the GTS, covered Edge and suddenly became a much bigger deal than he was before.

It was a bit different from what Edge did on Smackdown a year earlier because in this case it was a babyface Punk that cashed in on a heel champion instead of the other way around. It was a star making moment for Punk while showing that WWE was starting to believe in him.

7. Randy Orton (2013 Winner WWE Title)

Daniel Bryan winning the WWE Title against John Cena at SummerSlam 2013 was a huge deal. Bryan was the most popular guy in WWE at the time, so to see him holding that title at one of the biggest shows of the year was really cool. However, it was also obvious that there was something else that was going to go down.

Triple H, who at that point was a face authority figure, was the referee of that match. Randy Orton, also a face at that time, walked out with the briefcase. Triple H attacked Bryan from behind, hit the Pedigree and Orton won the WWE Title from Bryan. It was an obvious setup that we could see coming, but it still worked really well. Bryan went on to have a really long feud with Orton culminating in his WWE Title win at WrestleMania 30 in 2014.

6. Kane (2010 Winner World Title)

This is one of my favorite cash-ins because it makes the most sense. Kane was getting pushed as a dominant heel on the Smackdown brand. He won the Money in the Bank match in impressive fashion at the 2010 Money in the Bank event.

Later that same night, Rey Mysterio defeated Swagger to retain the World Title. Kane is a much bigger man than Rey, so he took advantage of that by dominating the smallest World Champion ever and beating him for the gold.

From a storyline perspective, it makes so much sense. If you just won the briefcase, you should want to win it that same night. It’s the only time somebody successfully cashed in on the same night they won it.

5. CM Punk (2009 World Title Winner)

https://www.youtube.com/watch?v=jjG-zZclHLU

The storyline was so key for this one. Punk won for the second year in a row. He was a face when he won it. Jeff Hardy beat Edge to win the World Title in a great match at Extreme Rules 2009. It looked like it finally ended the long Hardy/Edge feud. Instead, Punk was there to cash in while Hardy had this look of despair on his face because he was exhausted from a tough match. Punk hit him with the GTS two times to leave with the gold. Hardy was the most liked guy on the roster at this point, so to see the title snatched away from him hurt a lot of fans.

Shortly after the win, Punk had one of the most brilliant heel turns, as he made life tough for Hardy by becoming the biggest jerk in WWE. It was great storytelling, all thanks in part to how he won the briefcase in the first place by ending Jeff Hardy’s dream. That’s the beauty of Money in the Bank.

4. Rob Van Dam (2006 Winner)

RVD won the second Money in the Bank match at WrestleMania 22 in 2006. Instead of a cash-in during a show, he told WWE Champion John Cena he wanted his title match at the ECW One Night Stand 2006 event because RVD was the face of ECW. It was the first time they had a guy set up a match beforehand like that and they’ve only done it one other time, with Cena in 2012.

The match had an incredible atmosphere. Cena was hated by the NYC crowd in ECW territory while RVD received the biggest ovations of his career. They had a competitive match. Then Edge showed up dressed as a biker, took off his helmet and hit a Spear on Cena through a table. RVD hit the Five Star Frog Splash, Paul Heyman went into the ring to count the pin and RVD was awarded the WWE Title. It was a great moment.

3. Dolph Ziggler (2012 Winner World Title)

This was a favorite for a lot of people because Ziggler was seen as a hard-working guy that was talented enough to be a main eventer, but he never got a chance to show it. After he won in 2012, there was a lot of excitement about when he might cash in. WWE chose the perfect day in front of the perfect crowd because it was April 8, 2013 on the Raw after WrestleMania. They are known as being one of the loudest crowds of the year.

The World Champion Del Rio had just beaten Jack Swagger and Zeb Colter in a handicap match. Del Rio was selling a knee injury. Ziggler, who was a heel at the time, took advantage of the situation. They had a match for over two minutes. Ziggler ended up hitting the Zig Zag and covered Del Rio to win the World Heavyweight Championship.

The crowd reaction for Ziggler’s win was one of the loudest in the history of WWE. They turned him face soon after, but his title reign didn’t last long due to a concussion and Del Rio got the title back. This is the highlight of Ziggler’s career. While I hope he can top it one day, it may be difficult considering how WWE uses him these days.

2. Edge (2005 Winner)

Edge was the first Money in the Bank winner after winning it at WrestleMania 21. He was the right choice at that time because he wasn’t a main eventer, even though he had been in the company for seven years and shown a lot of potential.

The WWE Champion John Cena won an Elimination Chamber match to retain the gold at New Year’s Revolution on Jan. 8, 2006. Cena was a bloody mess and looked exhausted. It was weird setup because Vince McMahon did a promo saying the MITB winner Edge was cashing in right now and that’s when Edge came out. They really don’t need the promo beforehand, but since it was the first time, they can be forgiven.

Edge walked out there with the briefcase, gave it to McMahon, and then went into the ring to attack a staggered Cena. Edge hit a Spear. Cena kicked out. Edge hit another Spear. That was enough and Edge won his first WWE Title.

In a historical note, Edge held the briefcase for 280 days, which is still the most amount of days somebody has held the briefcase before cashing in.

1. Seth Rollins (2014 Winner)

Seth Rollins turned heel on his Shield brothers two years ago on June 2, 2014. Then he won the Money in the Bank briefcase a month later. We didn’t know when he was going to cash in, but as a heel with a bright future, it was obvious WWE had high hopes for him. To their credit, they waited for the biggest night of the year to give Rollins his historic moment.

Brock Lesnar and Roman Reigns had an awesome match for the WWE Title in the main event of WrestleMania 31. Most people thought that Reigns would win the title because he was the future star of the company. After nearly 20 minutes of a physical match, the music of Seth Rollins hit, he ran down to the ring with the briefcase, nearly took a F5 from Lesnar, avoided it, Reigns hit a Spear on Lesnar and Rollins hit a Curb Stomp on Reigns.

What’s interesting about that finish is when WWE showed replays of it over the next year, they edited out the Curb Stomp since they banned the move.

It’s the best Money in the Bank cash-in moment because it happened at WrestleMania, Rollins was the true superstar of the future and nobody had ever done anything like that before where it took place during a title match that ended up being a triple threat match. History making indeed.

In Closing

Who will win the briefcase this year and how will he cash in? We don’t know yet. Here’s a scenario that might work. Reigns is WWE Champion, Rollins wins the 2017 Royal Rumble and Ambrose has the briefcase. A month before WrestleMania, Ambrose says he’s cashing in at WM to make it a triple threat. All of a sudden you have a Shield triple threat match for the first time. It’s new and different. That’s what Money in the Bank should be all the time. Don’t repeat what we’ve seen before. Give us something different.

About John Canton

John has been writing about WWE online since the late 1990s. He joined The Comeback/Awful Announcing team in 2015. Follow John Canton on Twitter @johnreport or email him at mrjohncanton@gmail.com with any comments or questions. He's written for UPROXX, WhatCulture, Bleacher Report, Layfield Report, Rajah and many other places. Cheap pop! For more of his wrestling opinions, visit his website at TJRWrestling.net.