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Posted in: Requesting Flyby
REQUESTING FLYBY: Ranking The Money In The Bank Cash Ins (UPDATED THROUGH 2016)
By Maverick
Jun 18, 2017 - 10:26:50 AM

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Ranking The Money In The Bank Cash Ins

Greetings dear readers, and oh my gosh, didn’t Money In The Bank come around quickly this year? What started as a way to get upper tier midcarders with nothing better to do on the Wrestlemania billboard has turned into an institution that arguably rivals the Royal Rumble as a starmaking device and profoundly affects WWE booking through the twelve months after the match has taken place. While it certainly didn’t benefit from the inflation that inevitably took place when the pay-per-view started and two briefcases were fought over, the unification of the two world titles meant that the match (and pay-per-view) underwent a renaissance for a couple of years, most clearly visible from the way the event saw the first chapter in the Ambrose/Rollins saga in 2014, and the subsequent way The Architect cashed in at Wrestlemania XXXI, as well as kicking off the Wyatt vs Reigns feud in 2015. Now that the brand extension is back, Money In The Bank has become a single brand Smackdown event, with all the best performers on Smackdown lined up to put it all on the line to get the blue brand back some much needed momentum. With all that said, I thought it would be fun to revisit my ranking of the CASH INS from June 2015 with the two that have taken place since, as opposed to the ladder matches themselves. My main criteria are as follows:

The drama created by the moment of the cash in.
How the winner benefited after their cash in.
The quality of the actual cash in match.
Crowd response.
Historical perspective.

17) Jack Swagger won the World Heavyweight Championship after cashing in his Money In The Bank briefcase on Chris Jericho on Friday Night Smackdown, April 2 2010

After Edge and Jericho had gone back and forth at Wrestlemania XXVI, the Best In The World At What He Does found his smugness broken by yet another sneak attack spear from the vengeful Rated-R Superstar, which brought out the winner of the last Wrestlemania edition of the gimmick, Jack Swagger, who quickly used a gutwrench powerbomb to capture the title just four kayfabe days after he captured the briefcase. And that was essentially the problem. Swagger’s victory meant nothing because we had not got to see him get over properly, and although WWE deserve a small modicum of credit for trying something new, the All American American was not the performer to try it with. Following his win, Edge and Jericho continued their feud, meaning that Swags was denied the chance to get over by working with one of those workhorse vets. Instead, he took on Orton in a match that made no sense given that it was inter-brand, and then had to put up with a horribly out of shape babyface Big Show, followed by Rey Mysterio. Despite attempts to push him since, his toxic booking in mid 2010 is something he has never truly recovered from, hence why this places last on the list.

16) Alberto Del Rio won the WWE Championship after cashing in his Money In The Bank briefcase on CM Punk at Summerslam 2011

If ever there was a case of poor timing, this was it. I dare say that nobody would have had a problem with Del Rio holding that red case; it fit well with his “Destiny” gimmick and there were tonnes of good matches available to him once he became championship. The problem, of course, was that the moment WWE chose for him to cash in was CM Punk’s moment in the sun. Having defeated John Cena in the main event of both Money In The Bank and Summerslam, and having got over as an anti-establishment babyface, the very last thing Punk needed was the booking that followed the rematch with Cena. Even now, you have to wonder if WWE were consulting Vince Russo on the sly. A random Kevin Nash run in, Del Rio turning up with the briefcase (as he had in Chicago, only then it was just a tease to increase the drama), and a swift kick later, the Mexican Aristocrat was champion. More bizarrely still, the new champ went on to feud with Cena rather than Punk, while the Straight Edge Superstar ended up losing to Triple H and then tagging up with Hunter against The Awesome Truth. 2011, they did things differently then. Ironically, given such poor booking and writing, some good matches came out of both sides of the equation, but history does not look kindly on WWE’s decision making during this era.

15) Damien Sandow failed to win the World Heavyweight Championship after cashing in his Money In The Bank briefcase on John Cena on Monday Night Raw, October 28 2013

This is a funny one, because the match itself is absolutely fantastic. After Cena had come back from elbow surgery and beat Alberto Del Rio for the big gold belt at Hell In A Cell, the cerebral Sandow worked over the injured arm for some minutes before handing the briefcase over. In a highly competitive bout that foreshadowed the current U.S Championship Open that the Franchise Player is running, Sandow came up just short, but looked a million dollars. At the time, I and my co-hosts Mazza, Shinobi and ‘Plan said on LOP Radio’s The Right Side Of The Pond that it was all about the follow up for the Intellectual Saviour Of The Masses. His loss could’ve been the platform for him to go back into the midcard and show hunger and character development. Instead, he was bizarrely stripped of his gimmick, and then seemingly punished by having to do a humiliating series of impressions until his “stunt double” work for Miz got over with crowds for a time. What a tragic waste of a good performer. I only place this fifteenth because the Del Rio and Swagger cash ins are so widely acknowledged as disasters and because the match with Cena was so good.

14) CM Punk won the World Heavyweight Championship after cashing in his Money In The Bank briefcase on Edge on Monday Night Raw, June 30 2008

This is a case of the actual cash in working really well, but the follow up not quite being there due to the company not really knowing how to play to the strengths of a talented performer. After winning one of the better versions of the gimmick match at Wrestlemania XXIV, Punk was moved to Raw and found himself with the ideal opportunity to cash in when Batista decimated a smug Edge. People were hyped to see him turn up that night, and Edge sold the cash in beautifully, so that side of the equation worked fine. Sadly for Punk, the opponents he received thereafter were not exactly top drawer: a programme with an ageing JBL and a milquetoast babyface feud with Batista were followed by the booking of a Championship Scramble that Punk was written out of after he was punted by Randy Orton backstage, meaning that he did not even defend the title he lost that night. I actually enjoyed the babyface character Punk portrayed in 2008, but the way that his first championship reign was pushed into the midcard meant that he had to wait again for his chance to shine. Luckily for the Straight Edge Saviour, his second opportunity to cash in the briefcase would have a lot more heat attached to it.

13) The Miz won the WWE Championship after cashing in his Money In The Bank briefcase on Randy Orton on Monday Night Raw, November 22 2010

There’s no denying how over as a heel The Miz was through 2010, parlaying an excellent U.S Championship run into success at Money In The Bank, and using his role as Daniel Bryan’s “Pro” on NXT to garner serious heat with indy fanboys in a midcard feud that really stands the test of time. Therefore, when Orton was left vulnerable following a championship retention against Wade Barrett, “AWWWWWEEEESOME” coming over the PA got the crowd to pop big. After a brief struggle, the Tough Enough graduate planted The Viper with the Skull Crushing Finale to win the title. The cash in itself was, therefore, executed rather well. Trouble was, WWE booked The Miz very poorly following that win. The “lucky champion” gimmick is one that wrestling bookers need to be very careful with, since there’s a fine line between “lucky” and “weak”. In two rematches with Orton, Miz needed shenanigans to retain on both occasions, either side of a clean victory against Morrison on the New Year’s Day edition of Raw. Following the Rumble, Miz was booked in a title match against Jerry Lawler of all people, which gave him no momentum at all when placed up against Cena in the build to Wrestlemania XXVII, when he was overshadowed by the return of The Rock, whose every interaction with Cena hinted at a match between the two a year later. A magnificent hype package aside, Miz’s appearance in the main event of the Showcase of the Immortals was a dud, and he suffered the traditional depush that opponents of Cena tended to face back then in the aftermath of his retention that evening. I’ve always felt that Miz could have worked as a main eventer had the booking been better after his cash in.

12) Kane won the World Heavyweight Championship after cashing in his Money In The Bank briefcase on Rey Mysterio at Money In The Bank 2010

Unlike the situation with Jack Swagger earlier in 2010 where the briefcase holder was not established enough to make the cash in meaningful, Kane was a fifteen year veteran whose appearance with the case the same evening he won it was guaranteed to create some buzz. After only a single world title in his career to that point, the Devil’s Favourite Demon deserved his moment in the sun as a thank you for all of his hard work over the years and the heel turn that followed led to some of the best mic work of his career. I honestly feel that Kane’s work through 2010 has been chronically underrated over the years, because his title reign was a lot of fun, encompassing feuds with Mysterio, The Undertaker and Edge. The Big Red Monster was booked strongly for the most part and his twisted backstory was exploited to good effect throughout. The only black marks against this cash in was the the fact that the Smackdown brand was largely devalued by 2010, especially with the move to SyFy, and the fact that a thank you run doesn’t generally create a mass of heat for the cash in.

11) Sheamus won WWE World Heavyweight Championship after cashing in his Money In The Bank briefcase on Roman Reigns at Survivor Series 2015, November 22 2015

Sheamus was an underwhelming briefcase winner in 2015 to say the least, seemingly chosen at random after the booking decision was made to start the Reigns vs Wyatt feud with a run in where Roman had the victory cut out from under him by the Eater of Worlds. It wasn’t all that easy to see where a Sheamus push might go or when it might start, but Seth Rollins’ injury led to the tournament to crown a new champ at Survivor Series, which the Irishman crashed after Reigns had pinned his former Shield brother Ambrose in what basically amounted to a cynical re-run of the Randy Orton cash in on Daniel Bryan at Summerslam 2013 and an attempt to mine for the thousandth time the Vince McMahon heel boss character to get Reigns over as a face. The feud with Sheamus, Vince and the League of Nations was underwhelming, but I give the company credit for at least trying to create some drama at a big four event.

10) John Cena failed to win the WWE Championship after cashing in his Money In The Bank briefcase on CM Punk on Monday Night Raw, July 23 2012

I loved this angle at the time. Firstly, it made perfect sense for a stand up character like Cena to give his opponent a week to prepare; it would’ve been entirely ridiculous for Mr Hustle, Loyalty and Respect to cash in on a vulnerable opponent, and moreover, Cena’s history with CM Punk meant that there was obvious motivation for the briefcase holder to prove that he could beat his nemesis. It also meant that we got a marquee pay-per-view quality main event on an episode of Raw that was hyped in advance, something people usually cry out for. Raw 1000 was a fantastic show, and the main event was the feather in its cap. Punk and Cena showed their usual off the charts chemistry in their bout, which was interrupted by The Big Show, which also made sense as Cena had been feuding with the giant prior to winning the Money In The Bank ladder match, and the man with the ironclad contract would clearly want to screw the face of the company given their past interaction. The post-match beatdown of Cena by Show was interrupted by The Rock, which facilitated Punk’s planned heel turn when he clotheslined The Great One out of his boots. The aftermath of the match saw The Straight Edge Superstar grow more and more paranoid over his long championship reign ending, meaning that he joined up with Paul Heyman to form a heel dream team for the rest of that run. I honestly have no idea why anyone would dislike this failed cash in; it worked really well and it was great to see someone finally fail to win the title when handing over that case.

9) Dean Ambrose won the WWE World Heavyweight Championship after cashing in his Money In The Bank briefcase on Seth Rollins at Money In The Bank 2016, June 19 2016

The poetic justice of this one was just fantastic; after Ambrose had scratched and clawed his way to the briefcase, he watched his former Shield colleagues wrestle a classic in the main event and then picked his spot to deprive Seth Rollins of the title he had only just won back after a painful rehabilitation process. After all the times the heel Rollins character had screwed Ambrose, the Lunatic Fringe finally had his revenge, and his first world title, a fully deserved reward for a brilliant two years of work coming out of The Shield. The cash in led of course to the long awaited Shield triple threat and some stupendous TV singles matches between Dean and Seth, the standard bearers of their generation. Might there have been some mileage in having Ambrose taunt Rollins with the briefcase for a few months instead of cashing in right away? Absolutely, but with the brand draft fast approaching, WWE made the call to get the cash in out of the way first, and you know what? I loved it.

8) Dolph Ziggler won the World Heavyweight Championship after cashing in his Money In The Bank briefcase on Alberto Del Rio on Monday Night Raw, April 8 2013

The ultra hot crowd at the Izod Center the night after Wrestlemania XXIX reacted rapturously when Dolph Ziggler finally cashed in after 267 days holding the blue briefcase. The ascension of another internet favourite to championship gold was incredibly well received because not only had we waited for it for a long, long time, the actual match against a one legged Del Rio was incredibly dramatic, with a tease of The Show Off tapping out to the cross armbreaker before the injured leg became the Mexican Aristocrat’s downfall. Ziggler would run into concussion trouble following his victory, but this actually fed into an amazing reality era classic of a match between the two at Payback 2013 where the champion’s head was targeted by a ruthless challenger, and another excellent follow up at Money In The Bank 2013, where AJ Lee’s unhinged intervention cost Ziggler via disqualification. Unfortunately, the two were denied a big blow off match at Summerslam, and Dolph’s career would stall badly thereafter amidst rumours of backstage heat, but we’ll always have that Del Rio feud to remember his run as champ by, some of the best pay-per-view action of the decade.

7) Daniel Bryan won the World Heavyweight Championship after cashing in his Money In The Bank briefcase on The Big Show at TLC 2011

There are quite a few reasons why I look favourably on this cash in. First of all, the pop for an internet favourite like Bryan cashing in on a Big Show decimated by a vengeful Mark Henry just after Show had won the title from him was considerable (lots of rumours at the time had Bryan being the first man to lose a briefcase match) and it was a great moment to see a decade plus long career reach such a high point, especially given the scepticism some fans had about WWE’s attitude to D Bry. More importantly though, it was this match that started everything for Bryan in terms of his path to becoming the most over man in the business as he slowly and carefully turned heel over the next few weeks by beginning to arrogantly celebrate even the most insignificant victory in an obnoxiously over the top manner...and that was how the YES chant was born. If it hadn’t been for this cash in, the YES chant wouldn’t have existed, wouldn’t have got over, and Bryan’s heel antics wouldn’t have led to the huge backlash when he lost to Sheamus in 18 seconds at Wrestlemania XXVIII, which helped enhance his heel character even further. Therefore, if it wasn’t for this cash in, there wouldn’t have been anger management, or Team Hell No, or a growing desire among fans of all ages to see Bryan pushed to the main event. Historically, this is a very important cash in.

6) Edge won the World Heavyweight Championship after cashing in his Money In The Bank briefcase on The Undertaker on Friday Night Smackdown, May 11 2007

Edge became the first man to cash in the Money In The Bank briefcase twice after a legitimate injury to Mr Kennedy led to WWE calling an audible and having The Ultimate Opportunist win a “briefcase on the line” match. Just a day after (or three days in kayfabe), Edge cashed in on The Undertaker after a cage match Batista and an assault by Mark Henry had left The Deadman vulnerable. Edge was at his heel best, repeating the trick from two years before after the one year interlude where Rob Van Dam let Cena know in advance about the match at One Night Stand and living up to his character’s cunning nature by once again choosing the perfect time to strike. The cash in led to a year long feud with ‘Taker that didn’t finish definitively until a Hell In A Cell match at Summerslam 2008, meaning that this cash in led to a quality series of pay-per-view matches which will be long remembered. The only slight knock against the cash in is the fact that it had less impact due to the fact that we’d seen it once before. It was also a shame that Kennedy was stripped of the case given that his injury turned out to be not as serious as first thought; we’ll never know what the brash Wisconsin native might have become if he’d kept that contract opportunity.

5) Randy Orton won the WWE Championship after cashing in his Money In The Bank briefcase on Daniel Bryan at Summerslam 2013

Daniel Bryan’s stupendous clean win against John Cena in the main event of Summerslam 2013 was the beginning of a magnificent storyline cribbed from The Rock and Mankind in late ‘98/early ‘99 when the triumphant ticker tape celebration of the Yes Man was interrupted by a Pedigree from special referee Triple H, who promptly brought out the red briefcase holder at the time, Randy Orton, and crowned him the “Face of the WWE”. Heel turns for Orton and Triple H created The Authority stable which still dominates television almost two years on, sparking a chase narrative for Bryan where shenanigans- a fast count, Big Show causing a no finish, a crooked Shawn Michaels- constantly kept him away from the belt. All of this built into a frenzied Wrestlemania season where the bearded wonder would defeat Hunter and Randy on the very same evening to become the undisputed WWE World Heavyweight Champion in one of the greatest evenings of professional wrestling in history. Some went on record at the time and continue to go on record as saying that Bryan should have had a dominant face run with the belt after beating Cena; you won’t catch me saying that. I loved every moment of the Orton vs Bryan feud through mid to late 2013 and felt it was perfectly pitched and executed. The only slight problem I have with the scenario on the night of Summerslam was the gap between The Game’s Pedigree and The Viper’s cover, which was unreasonably long and made it a little hard to suspend disbelief in terms of Bryan staying down for the three; I might have preferred Orton picking up the fallen champ and hitting an RKO out of somewhere for good measure. But all in all, it was brilliantly judged cash in.

4) CM Punk won the World Heavyweight Championship after cashing in his Money In The Bank briefcase on Jeff Hardy at Extreme Rules 2009

CM Punk’s first experience with the Money In The Bank contract was not a happy one given that his babyface title reign suffered from dubious booking, but thankfully, Vince McMahon deciding to “see if [Punk] could run as a heel” led to a plan developing for the Straight Edge Saviour to win the ladder match at ‘Mania two years in a row and turn to the dark side via a cash in. An enthusiastic Phil Brooks, who had been desperate to be a villain ever since he signed with the company, had plenty of ideas about how to execute the turn. At Extreme Rules that year, Jeff Hardy and Edge’s decade long rivalry finally came to an end in a violent and exhausting ladder match, but the triumph of the Charismatic Enigma was short lived, as Punk’s music hit and he cashed in on the enduringly popular Hardy with a pair of Go To Sleeps. At first, Chicago Made retained his babyface persona, but ever so gradually, he moved into tweener territory by making his pronouncements about his straight edge lifestyle more holier than thou and also using these statements as pointed barbs against Jeff’s past indiscretions with illegal substances. As a slow burning heel turn, it was beautifully done, perhaps one of the best two or three examples of the trope I have seen. It led to an absolutely epic summer feud between the two men that culminated in a TLC match at Summerslam and a loser leaves town steel cage match on Smackdown not long after. Hardy put the up and comer over huge on pay-per-view and TV and it remains one of the best feuds of the last two decades, and one which all came about because of Punk’s second cash in.

3) Rob Van Dam won the WWE Championship after cashing in his Money In The Bank briefcase on John Cena at One Night Stand 2006

Rob Van Dam had been super over for years on end, and had already flirted with the main event during and just after the InVasion angle in 2001. Therefore, when ECW alumni were brought together for a nostalgic pay-per-view in 2006, it was the ideal opportunity to have Van Dam use his contract to set up a match with Cena at the event. In a Hammerstein Ballroom packed to the rafters with old school ECW fans, the “If Cena wins, we riot” meme was well and truly born in an electric atmosphere that probably, in hindsight, helped Cena come of age as a performer as he faced down incredible hostility despite nominally being the top face in the company. In a fantastic match filled with classic late 90s tropes like run ins and ref bumps, Van Dam had his three counted by Paul Heyman himself, bringing out the former ECW wrestlers to celebrate with their successful standard bearer. Sadly, RVD would undo his good work by being caught with marijuana not long after, but as a cash in match, this stands head and shoulders above the rest.

2) Seth Rollins won the WWE World Heavyweight Championship after cashing in his Money In The Bank briefcase on Brock Lesnar and Roman Reigns at Wrestlemania XXXI

Even though many of us had widely predicted that Rollins would cash in the briefcase that had become such an integral part of his character at Wrestlemania and save WWE from having to put the strap on a not-quite-ready-yet Roman Reigns, seeing it happen in the moment on the Network was one of the most fantastic mark out moments of my entire fandom. The fact that he picked his spot by making the match a triple threat rather than waiting for one of the two main event participants to win made it even better, as it was an original take on the cash in match, and the action that led to the one-two-three was breathless in its intensity and superbly choreographed. The moment where Rollins tried to Curb Stomp Lesnar and got lifted into the F5 position instead was heartstopping, and Reigns’ spear into the two of them perfectly timed. Rollins landing on his feet showcased the man’s unbelievable athletic ability and the Curb Stomp to Reigns that followed put over the improvisational skills of the character in grandstanding fashion. All of which begs the question, why is this not number one? Truthfully, it almost was, and it was a decision I agonised over, but Edge’s cash in of the first ever contract spawned a five year main event Hall of Fame career and an entire Ultimate Opportunist gimmick, and while I believe Seth Rollins will inevitably surpass Edge as a performer, if he has not done so already,, at the moment, he was standing on the shoulders of giants here, so the Wrestlemania heist sits at number two.

1) Edge won the WWE Championship after cashing in his Money In The Bank briefcase on John Cena at New Year’s Revolution 2006

Ultimately, there’s nothing like the first time, is there? Before Edge’s appearance at the conclusion of the New Year’s Revolution elimination chamber match, I had not fully considered the implications of the “at any time of the holder’s choosing” stipulation. I had always envisaged the RVD 2006 and John Cena 2012 model in my mind, but with the decision to have The Rated-R Superstar pick the bones of an exhausted champion, WWE changed the industry forever, to the point where the surprise cash in has, Rollins aside, become cliched in the extreme. None of that is Edge’s fault, however. It was an incredible moment at the time, and it remains so to this day. For whatever reason, The Ultimate Opportunist had been just outside that top bracket of main eventers before 2006, but this made him a member of the club for the rest of his career, and the work he did as a top heel over the next few years will always be remembered fondly as one of the few interesting things going on during a very bland time in professional wrestling history. Edge was always a wrestler who appreciated the business like no other, and his passion and innovation were both evident in his performance when he cashed in. I bet no pair of spears he ever hit felt quite so sweet as those on Cena that night in Albany. It felt pretty sweet for fans too, given how disgusted many adults were with the child friendly Franchise Player at that time. What a great memory to look back on.


Well folks, I’ve reached the end of the countdown, let me know what you thought about it in the comments section below, or tweet me here!

This is Maverick, requesting flyby!