The Five Count: Top WWE Money in the Bank Winners


In 2005 at WrestleMania 21, the Money in the Bank Ladder match made its debut, with Chris Jericho, Kane, Chris Benoit, Edge, Christian and Shelton Benjamin competing to grab a briefcase containing within it a contract enabling the right to challenge for either the WWE or World title at a time of the holder’s choosing for up to a calendar year. Per Jericho’s second autobiography, “Undisputed,” the concept for the match came from a brainstorming session between he and writer Brian Gewirtz, albeit with the competitors and prize being tweaked along the way (prior to his injury a couple months earlier, Rob Van Dam had been penciled in as winner with his reward being not a title shot, but the opportunity to bring back ECW; both occurrences would be deferred a year).

Watching the first MitB from my tiny apartment in Highland Falls, New York, I enjoyed the chaos of the ladder match taken to the next step in its evolution—Razor Ramon battling Shawn Michaels to TLC to now this—but didn’t necessarily peg it as a fixture on the WWE landscape. Not only would the contest itself gain enough of a following to become a WrestleMania institution for several before earning its own self-titled pay-per-view, holding the briefcase and choosing to cash in at the right time has becomes one of WWE’s de facto formulas for creating new stars and memorable moments over the past near decade.

In this Five Count, myself and the distinguished panelists joining me whittle down the 12 Money in the Bank winners—or 13 depending on how you score 2007—to our personal top five lists. Criteria can vary greatly on this one, with some perhaps choosing to focus on the quality of the match a competitor won while others may zero in on the cash-in process.

For my personal mileage, I will be judging mostly on the effectiveness of the winner’s time holding the briefcase and their eventual cash-in in regards to making them a star in the long run, but certainly other factors will creep in as well.

Let’s see who climbs our personal PTB ladder on this occasion…

Ben Morse

5. ROB VAN DAM (2006)

Of the dozen guys who have won Money in the Bank, only two have ever “called their shot,” announcing in advance where and when they’d challenge for the title, giving the champion a chance to prepare. John Cena did it in 2012 and became the first guy to not cash in for a title; six years earlier, Rob Van Dam set his WWE title shot for ECW’s One Night Stand reunion show and got the win—over Cena.

Not only did RVD’s approach to Money in the Bank establish another way to use the briefcase—albeit one that’s rarely been used since—it also provided the momentum not only for him to break through to the main event for good, but also for ECW’s revival as a brand.

4. DANIEL BRYAN (2011)

When the 2011 Money in the Bank event came around, Daniel Bryan seemed more or less doomed to life in the mid-card. After being the talk of the business a year earlier, a lost U.S. title reign cooled him off and WWE then seemed to forget about him following a move to SmackDown.

Bryan’s surprising MitB win not only put him back on the map, it allowed for a variety of storyline options. First he had the plan to wait until WrestleMania so he could main event, which presented some intrigue, if not a lot of realism. When WWE course corrected—unless the WM deal had always been a bluff—and turned Bryan heel with a win over Big Show, they created a main eventer perhaps without even meaning to.

Given where he had been only a couple months earlier, it’s unlikely many expected Daniel Bryan to be any more than a placeholder for the World title in early 2012, but he took the ball and ran with it fiercely, showing off hidden depths of personality via his heel persona that WWE fans had never seen from him.

By the time he dropped the belt to Sheamus at WrestleMania, Daniel Bryan had already established himself a made man thanks to Money in the Bank.

3. CM PUNK (2008)

After CM Punk dropped the ECW title to Chavo Guerrero somewhat unceremoniously in early 2008 and then failed to regain it despite multiple shots, fans of the guy—like me—started to wonder if WWE had any planned direction for somebody who seemed like a surefire rising star. By WrestleMania XXIV, Punk seemed quite rudderless, and his victory in one of the more solid Money in the Bank matches seemed like a glimmer of hope.

When Punk won MitB, only Edge and Rob Van Dam— both far more established stars—had cashed in, placing the worry that this could be the exception that proved the rule. You had to figure at some point somebody would fail to capture the title, and this seemed primed to be that example.

That nagging doubt made the moment on June 30, 2008 when Punk pinned Edge to become World champion both surreal and so much sweeter. Edge had come out to interrupt Jim Ross’ farewell to Raw and taunt that the 2008 draft and failure of John Cena and Batista respectively to capture either of the major titles at the pay-per-view the night prior left the show without any championships. Batista interrupted and delivered a beat down, seemingly setting up the cash-in perfectly, but even after Punk’s theme hit, I kept waiting for the other shoe to drop; it didn’t and the Indy guy made good won the belt to a huge pop and for me one of the most shocking and feel good turns in recent WWE history.

2. CM PUNK (2009)

While CM Punk’s initial Money in the Bank win in 2008 led to one of my personal favorite moments, his follow-up victory the next year may represent one of his most crucial steps on the road to true superstardom.

Right off the bat, making Punk the first—and to date only—guy to claim the briefcase two years in a row upped his credibility as he beat out a field that included the likes of Kane, Christian, Mark Henry and others. However, far more importantly it allowed him to further develop a character that had started so hot a few year earlier, but stalled in the wake of abruptly halted pushes and being lost in the babyface shuffle.

Punk stands out as one of the first guys to really play up his ownership of the MitB contract, taunting opponents like Edge and John Cena as they went into grueling matches, reminding them he could screw them over. These subtle heel overtures exploded when he cashed in on the much beloved Jeff Hardy following a Ladder match and won his second World title.

Over the summer of 2009, many factors combined to make CM Punk red hot. He had the perfect opponent in Jeff Hardy, he cut amazing promos playing off the “straight edge makes me better than you” he perfected in ROH, and his matches were brilliant with a stacked roster of SmackDown talent to play off of. Yet without that Money in the Bank win, you wouldn’t have the awesome slow burn heel turn that really kicked it off. Going beyond that, without that heel turn, Punk would not have reached the level of credibility that allowed him to become entrenched in the main event and serve as one of WWE’s cornerstones of the last several years.

No one thing made CM Punk in WWE, but his second Money in the Bank win certainly served as a major turning point in his career.

1. EDGE (2005)

A tremendous amount of pressure sat on Edge’s shoulders as the very first “Mr. Money in the Bank.” If he couldn’t get the gimmick over, not only would it be a mark against him in his quest to break into the main event scene on a regular basis, it would also potentially shoot down the viability of using Money in the Bank beyond its initial foray.

Indeed for the bulk of the time Edge carried the briefcase, it served more a prop than anything else, with him rarely teasing the cash-in beyond a few times early on. Fortunately, the Rated R Superstar had other things on his plate for 2005, namely forming his classic pairing with Lita and entering into the feud with Matt Hardy that made him as a bonafide heel in a way that the 12 months prior had not. Going into 2006, nobody on the WWE roster had more heat and could draw heartier boos from crowds than Edge.

By the time Edge cashed in on John Cena at New Year’s Revolution in January 2006, many had forgotten he even had the ability to do so, which only heightened the excitement of the moment. Both Edge and Cena played their parts as opportunistic challenger and exhausted champion perfectly. Once the three count came down and we had a new WWE Champion, not only had a fresh main eventer been minted, Money in the Bank became instantly associated with unpredictability and excitement.

The reason Edge tops my list here has to do with the “what if” scenario had his run with Money in the Bank not been successful. If WWE had not exercised the patience to wait 10 months and if Edge didn’t possess the skills to get as over as he did with the briefcase as an enhancer but not a crutch throughout 2005, potentially we would not have gotten any other great MitB winners and moments. They had to wait that long for the cash-in to come out of nowhere; had they done it a night, week or month after as in later years that “anything can happen” feel would have been dead. However, that meant gambling Edge could sustain his top level heat for nearly a year, a roll of the dice which paid off but very easily could not have had he made any missteps along the way.

Edge lived up to the responsibility of being the inaugural Money in the Bank winner and then some; his first WWE title reign may have left something to be desired, but the gimmick made him and he made the gimmick.


 Callum Leslie

5. JOHN CENA (2012)

Okay, hear me out on this one. In assembling this list I’m not only looking at the effect on the individual of the MITB win, but also the effect on the company landscape at the time and going forward. This 2012 MITB match was all wrong; all former WWE champions, no up and coming guys who would get a leg up from winning the briefcase, and a crushing inevitability that John Cena was definitely winning. However, while there are still two MitB briefcases every year despite the lack of roster split, one of them will always have to be a throwaway—see Del Rio, and now Cena—done quickly and reasonably uneventfully. Cena winning the briefcase did a huge amount of good in just one aspect that is absolutely priceless to the company: he was the first to lose his cash-in. It had to happen eventually, and Cena was the only one who could do it and not be hurt by it.

4. THE MIZ (2010)

For me, this is the most surprising win of all, even more so than Daniel Bryan, with Miz winning the match ahead of Edge, Randy Orton, Chris Jericho and John Morrison. Miz was a long running U.S. Champion, and would hold the belt and briefcase simultaneously until September, eventually cashing in the briefcase in November against a prone Randy Orton. Miz would hold the belt for four months, including headlining WrestleMania with it. For somebody of his limited talent and obnoxious promos, that’s pretty good.

3. ROB VAN DAM (2006)

This goes down as one of the biggest wasted cash-ins in my mind, but the intention and execution were brilliant. Rob Van Dam was the first man to give his opponent notice, cashing in at the main event of One Night Stand 2006. Cena played his part brilliantly, working as a heel to the ECW crowd. This should have been the moment to properly kick off the new ECW brand, with RVD as its standard bearer, however a DUI bust would put an end to that.

2. EDGE (2005)

The original MitB winner who started it all. If it wasn’t for the way Edge cashed his briefcase in, I’m not convinced the match would have the status it does today. This cash-in established Edge as a top heel, and while he lost the title pretty quickly afterwards, he would go on to have many more reigns and be a top star for six years. He and Lita were the archetype heels; everything the crowd hated as well as what they wished they were. John Cena again played a big role here, helping to elevate Edge with a classic series of matches.

1. CM PUNK (2009)

CM Punk’s first cash in was something of a damp squib, and Punk ended up losing the title without being beaten. The second time around however, it was the catalyst for the development of one of the best heels of the last five years, and an outstanding rivalry with Jeff Hardy that was a highlight of 2009. His series of matches with the Undertaker also served to establish Punk as a top guy, a position he would stay in until the present day.


Michael Waldrop

In many ways, the Money in the Bank briefcase, throughout it’s almost decade long existence, has been more of a curse than a gift. The briefcase almost gives creative the right to book the wrestler holding it poorly in the build up, and the title reigns are often short and transitional. If you look at Dolph Ziggler, last year’s World Heavyweight title case winner, his time with the briefcase often saw him come out looking poorly, his cash in was great, and then an injury interrupted his reign before it could truly begin. Daniel Bryan’s 2011 win was someone I considered for my Top 5, but he was almost an afterthought in the WWE landscape, even with the title reign, until they paired him up with someone else with no long term plans, Kane, and the duo hit magic.

My criteria includes their cash-in moment as well as their overall title reign, and how it served them long-term with the company.

5. THE MIZ (2010)

The Miz has the longest title reign that’s come from a Money in the Bank cash-in, as he held the WWE Title for 160 days after cashing it in on Randy Orton. In fact, Miz is the only Money in the Bank cash-in to successfully retain his title at WrestleMania; that being said, this would be higher had the reign done more for Miz’s long-term WWE career or if it had been received better.

4. EDGE (2005)

Edge basically set the template for almost all future Money in the Bank cash-ins to follow when he hit the ring after the Elimination Chamber at New Year’s Revolution and defeated a weakened John Cena for the title. Edge’s reign seemed to be a trial run, and he quickly lost the title back to Cena, but it planted the seeds for what would be Edge’s best run in the company.

3. ROB VAN DAM (2006)

Van Dam had a great cash-in moment and a great wrestling moment in general, at ECW One Night Stand 2006. In fact, the entire ECW brand was rebooted with the idea of working it around him, and he was named ECW Champion while holding the WWE title. Had he not been arrested for marijuana possession he might have had a great run, if not with the WWE title then with the ECW strap at the very least. However, after the arrest, he lost both belts the same week, was suspended, and when he returned, never again put in a top position. He then left the company, had an unmemorable stint in TNA, and is just now returning to WWE on a part-time basis.

 2. EDGE (via MR. KENNEDY) (2007)

When Mr. Kennedy suffered an injury shortly after winning the Money in the Bank ladder match, the WWE made a choice that helped define SmackDown for four years. Edge won the briefcase from Kennedy on Raw, and then, the next night at the SmackDown taping, cashed in on the Undertaker to win the World Heavyweight title. The win was his first with the title. Before he retired in 2011, he would hold it another six times, making himself the record holder of the WWE version of that belt. There were skeptics about Kennedy winning the case and if he could have done business with a title, but the WWE pulled a great audible. If the 2005 run was planting the seeds, this move was letting them grow. And they grew into Edge’s “Ultimate Opportunist” character and a franchise player on Brand Blue.

 1. CM PUNK (2009)

Punk’s first run with the case and subsequent first World Heavyweight title reign, is indicative to many of the problems with the way Money in the Bank winners are treated. He had a brief, transitional reign that ended poorly when he forfeited the title. Honestly, the underdog babyface version of Punk was never going to be a major WWE star. One year later it was done right. Punk cashed in on Jeff Hardy, turning heel and launching the Punk character that has, with a tweak here or there, made him the number two face in the company. Punk and Edge were the only two who won the title and I genuinely feel helped their career take that next, necessary step to become true main event players. And for both, it was their second time holding the case.

Edge and MrKennedy WWE Raw 5 07 2007

 Steve Rogers

As someone who just went through the King of The Ring winners, I am interested in the “star making” aspect of the MiTB winners. Yes for every Daniel Bryan and Dolph Ziggler there is a John Cena and Kane where the storylines necessitated them to be the holders of the briefcase, but for the most part that is where I am going to go with this list. Well, maybe there is a deviation or two. However much like the King of The Ring, or the Royal Rumble and Wrestlemania title shot, there is something of a star making quality to the concept, and that is how this is going to go.

5. JOHN CENA (2012)

I know, I know, but it still was an interesting storyline device that they went with, and Cena is one of the few faces to capture the briefcase, and one of only two—the other ironically enough is Rob Van Dam AGAINST him in the second MiTB cash in—to announce exactly when and where he’d be cashing it in. The cash in was in vain for the first time, but still that part of Cena’s storyline for 2012 (boy, just like some golfers would love to have some of Tiger Woods’ down years, there are scores of under pushed wrestlers that would LOVE to have as bad of a year as Cena did in 2012) was a compelling one.

Could they have gone a different way? Probably. But, in some ways it also helped solidify CM Punk as a heel by getting cashed in on by the biggest face (despite how a very large segment of the fan base thinks of him) rival for his belt as opposed to another heel or elevating a face from the mid-card.

4. ROB VAN DAM (2006)

Again with a well established star I know, but like Cena’s it at least is built into a great storyline. The whole concept of his cashing it in got the ball rolling on the WWE’s revival of ECW. Granted it wasn’t as well received, and in execution seemed like, well, like the Las Vegas New York/New York Hotel and Casino. Yeah you have the broad strokes, but not the heart and originality…and to be honest, was ECW even that much better than a glorified indie that catered to the meta smark crowd?

But we are not here to debate the merits of WWE’s version of ECW and why they failed. We are here to talk Money in the Bank Winners, and Mr. Monday Night’s win and cash in being the catalyst of a “brand” that would last a few good years before being put back in mothballs in 2010.

3. CM PUNK (2009)

I am going with the heel turned Punk for his entry on the list. While his face run with the briefcase and title was fine, it is his “I’m better than you” heel personae, program with Jeff Hardy, and eventual messianic personae with both the SES and New Nexus that helped forge the angry and bitter character that gave that classic worked shoot on June 28th, 2011.

And it all can be traced back to Punk’s second MiTB win and cash in on Jeff Hardy. If you take out the fact that the WWE would probably never reference it, due mostly because Hardy is in TNA, it still was an important step in the evolution of The Best in the World!

2. EDGE (2005)

Along with CM Punk, the only other two time holder of a briefcase and the Ultimate Opportunist being the first MiTB winner got to show everyone how it is done. A long wait from winning the briefcase at WrestleMania to cashing it in at January’s New Year’s Revolution helped guarantee that the “this can happen at any time” nature of a cash in would be a well received one. Other years the wait, and teases would be more obvious with twists and turns that leave fans wondering if the briefcase holder would ever take the shot (see Ziggler, Dolph for example), but the template has to be started somewhere right?

Edge had been a well known and well decorated entity by this point with multiple tag titles, IC titles and the 2001 King of The Ring.  Yet now the Rated R Superstar was ready for his ascension to be a main event fixture for the rest of his career—and a perfect way to kick off the gimmick.

1.  DANIEL BRYAN (2011)

The road to glory for the bearded one began here with the SmackDown Money in the Bank briefcase. Already a rising star—and IWC favorite—Bryan seemed poised for greater things. He would cash it in, in an albeit sneaky heel fashion as is with most MiTB cash ins, and his legend would grow from there. First of course as the Honky Tonk Man version of the World’s Champion for 2011-2012, narrowly escaping in matches against Big Show and Mark Henry before losing in 18 seconds at WrestleMania to Sheamus.

This would ignite Bryan’s summer-long meltdown that made him quite an interesting character to follow as he admonished the fans for chanting his catchphrase, came very close to having his fiancé committed only to have her turn him down at the altar and him melting down and getting Rock Bottomed for his troubles, and finally went to anger management classes with Kane where the two forged an unlikely alliance as friends and tag team champions.

Could the former American Dragon win a second Money in the Bank match this month? We shall see, but his win in 2011 is a perfect example of how the gimmick can elevate the winner to great heights, and despite his self confidence issues of late, he is in no way a weak link in the WWE roster.


 Scott Criscuolo

5. CM PUNK (2009)

When Punk won MitB at WrestleMania 24 in Orlando, it was considered more of a “Well the fans really want him to win, even though we think he’s not ready” decision by WWE. Thus the reason when he cashed in the briefcase on a prone Edge on Raw the crowd went crazy but his reign was stunted by not getting the proper matches and feuds he needed and was more or less treated as a fluke. He was saved from being pinned by a Legacy attack before Unforgiven 2008 when Chris Jericho replaced him and won the Scramble to take his title. The following year he won in Houston at WrestleMania XXV but this time he took the initiative and took out a prone Jeff Hardy, also a fan favorite. That’s when the CM Punk everyone loved in Ring of Honor four years earlier took control. That’s when the CM Punk we now know was born. His feud with Hardy that year and subsequent creation of the Straight Edge Society was a stroke of genius. So even though he had won a briefcase already, this one was more important to his career.

4. THE MIZ (2010)

This was a booking roll of the dice for a guy no one wanted to take seriously when he became a full time competitor. For a while he was the Marty Jannetty to John Morrison’s Shawn Michaels. Finally, when they split he won the U.S. title and became a major mid-card player. But when he was inserted in the MitB match in July of 2010 many thought it was nothing more than a spot filler, and that either Edge, Orton or Jericho was the favorite. However he snatched the briefcase and, even better, he held it for a number of months. Kane cashed in his title shot that night on Rey Mysterio to become World champion so it was clear that Miz was not going to cash in on Sheamus at the end of the night after he beat Cena in a cage match. The crowd went nuts when he cashed in on Randy Orton that November, then to hold the title as long as he did AND retain the belt at WrestleMania was a testament to the growth of his character. He lost the belt to Cena the following month at Extreme Rules and then he was quickly shunted back to the mid-card. His babyface run is brutal, but we can remember that run from July 2010-April 2011 when he was on top of the world and the most entertaining heel on the roster.

3. EDGE (2005)

Edge was ready to burst as a main eventer when he turned heel in late-2004. We knew with roster shuffling and retirements that Edge would be given the spot he so coveted. So when he took the first MitB briefcase at WrestleMania XXI in Los Angeles, the only question that remained would be: when he would cash in? Of course John Cena had won his first WWE title that same night, so the clock would be ticking. Cena needed to be established before his growth could be stunted. Edge wouldn’t cash in on the other belt as Batista and Triple H were in their own stratosphere. So Edge was able to get into that hot summer feud with Matt Hardy to keep himself occupied while Cena battled studs like Jericho and Angle. The best part about this run was that everyone was involved in so much stuff that you almost forgot Edge had the briefcase. Sure he carried it around but because Cena was so engulfed with feuds involving Eric Bischoff and others that it never occurred to anyone that Edge would cash it in. It also helped that the concept was new so no one really knew how the whole process worked. When it finally happened in Albany at New Year’s Revolution after a bloodied Cena finished an Elimination Chamber war the place went crazy. Of course everyone snapped when Cena won it back two weeks later at the Royal Rumble. That was to set up Cena/Triple H at WrestleMania in Chicago. Many have gotten big cheers when they’ve cashed in, but the standard bearer for shocking cash-ins will always be the Rated-R Superstar that first year.

2. DANIEL BRYAN (2011)

This one was a big shock because that MitB match was the forgotten one at that PPV. The Raw MitB had more juice as well as the hyped Cena/Punk match since it was in Chicago. But the bookers realized that they had a jewel on their roster and it was time for him to show his stuff. That MitB ended up being the better of the two matches and it gave Bryan the much-needed credibility that would gain him even more fans than he had. This is the era of the Indy wrestler, and WWE fans (whether the brain trust wants to admit it or not) love Indy wrestlers and go to Indy shows. So Bryan winning his briefcase was a bigger deal in the long term, similar to Edge in 2005. He waited until the time was right, and even though he cashed in at TLC on a babyface Big Show, it was the right thing to do. Show is at the point of his career where his title reigns are transitional and trophy case creating, more than character-building. The fans wanted Bryan to cash in on somebody, it didn’t matter. As expected, his reign was solid but ended badly when Sheamus squashed him in 18 seconds at WrestleMania in Miami. But it still brought smiles to all the fans and Bryan has effectively shook it off due to his awesome matches with CM Punk later in 2012, his run with Kane in Team Hell No and his singles resurgence now in 2013. But it was this almost forgotten victory at MitB 2011 where Daniel Bryan began to put a foothold on his position in WWE as one of the top players.

1. ROB VAN DAM (2006)

For me, this was the perfect MitB storyline for many reasons. First off RVD was considered a main event underdog after his short-lived feud with Triple H and subsequent World title match loss at Unforgiven 2002. After that he never really sniffed another title shot and was relegated to being a top tag team guy and Intercontinental title regular. So when he won the MitB match at WrestleMania XXII in Chicago it was a big shock and a great moment for the fans. Second, instead of cashing in on anybody after a long match, he brought John Cena into the ring and effectively punked him out. He called his shot and asked for ECW One Night Stand at Hammerstein Ballroom. So not only did he do it the “good guy” way and planned the title shot out, he did it in his atmosphere at a time where the anti-Cena vitriol was really starting to bubble to the surface. The One Night Stand show from the year before was a huge success and many thought it was a one-time nostalgia thing. They decided to do it again since WWE was going to launch a separate ECW brand and it was going to spawn from this show. The title match that night was one of my favorite John Cena moments, as he actually worked as a heel and it was perfect. He walked down the aisle with the WWE title over his head, pretty much saying “You hate me but I have the gold so go fuck yourself.” The match was really good as Cena continued to work the heel route, but then the stunning Edge spear with the motorcycle helmet was the icing on the cake. I wasn’t a fan of Paul Heyman counting the pinfall but that’s minutiae. Rob Van Dam had realized the dream all his fans had been begging for since the late 1990s when he dominated ECW as the TV champion. He would hold the WWE title and the refreshed ECW World title simultaneously for a month. He’d lose both in separate instances and would eventually leave the company, but for those few months in 2006, RVD was “One of a Kind.”


And now, our overall Five Count…

5. THE MIZ (2010)

The cash-in got him over the hump to be a main eventer and he rode the momentum all the way to retaining the WWE title over John Cena at WrestleMania.

4. DANIEL BRYAN (2011)

Largely forgotten prior to his MitB win, the Indy darling broke through to play with the big boys and used that success to develop one of WWE’s most entertaining characters of the last several years.

3. ROB VAN DAM (2006)

Switched up the standard formula by “calling his shot,” utilized his cash-in for one of the hottest WWE title victories of all-time, and managed to resurrect the “dead” brand of ECW in a new environment along the way.

2. EDGE (2005)

The first man to ever cash in Money in the Bank created the template for all who came later and made himself a future Hall of Famer in the process. By keeping his heat for nearly a year without having to rely overly on the briefcase, Edge made the success of the gimmick possible.

1. CM PUNK (2009)

A close call for the number one spot—Edge and Punk received the same numerical totals but Punk got one more first place vote—however the proof can’t be denied. CM Punk transitioned his second MitB victory into a heel turn that allowed him to show off his full range of talent on the microphone and has become one of WWE’s main draws over the course of the past four years.


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