WWE Money in the Bank Winners Ranked

This Sunday is the ninth WWE Money in the Bank PPV. It’ll give us the 23rd and 24th instances of the Money in the Bank ladder match, a part of WWE’s makeup that debuted at WrestleMania 21 back in 2005. Created by Chris Jericho (both in kayfabe and real life), the match has five-to-ten wrestlers battle it out to see who can climb up a ladder and retrieve the suspended briefcase first. By winning, the wrestler has the right to challenge the world champion whenever they want, up to a year.

The match is supposed to be what the Royal Rumble used to be: a high-profile multi-man match where the winner is propelled to stardom. As someone who has just rewatched every single one of these matches, it doesn’t work quite as well. Or at least, it doesn’t work as easily.

Unlike the Rumble, only the winner is the one who truly gets over. In the Rumble, you can lose but be known for lasting for a while, eliminating a bunch of guys, or even eliminating a huge name. The best you can do in Money in the Bank is pull off some cool spot and then immediately get knocked out of the ring before your momentum can really go anywhere.

Still, all the Money in the Bank matches are a fun time, even if a bit hollow. As we get ready for the next chapter, I’ve decided to rank all the winners. Kind of like what I did with all the Royal Rumble winners once upon a time.

I’m factoring four things into my rankings. First, their performance in the match itself. Did they really hold their own or did they just let everyone else do all the work and win anyway? Second, how their run as “Mr./Ms. Money in the Bank” paid off. Third, the actual cash-in where they try to win the title. Finally, there’s the aftermath, which speaks for itself.

Let’s start it off with the dirt worst and it shouldn’t be too big of a surprise.

22. DAMIEN SANDOW

Money in the Bank 2013

Opponents: Cesaro, Cody Rhodes, Dean Ambrose, Fandango, Jack Swagger, Wade Barrett

106 Days

Poor, poor Damien Sandow. A modern-day take on the Genius gimmick, the pompous know-it-all seemed like he was ready to ascend up the ladder in the metaphorical sense. The World Heavyweight Championship Money in the Bank match was held between seven heels and Sandow went into it acting like he was rooting for his Rhodes Scholars partner Cody Rhodes.

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As expected, Sandow turned on him to win and things took a nosedive for Sandow’s career.

Match Performance

At one point in his Money in the Bank match, Sandow was beaten mercilessly by Wade Barrett wielding a broken-off step of a ladder. That right there is the total of Sandow’s involvement in his match outside of double-crossing Cody at the very end. No Money in the Bank winner has done less in their match than this guy and it kind of sets the tone for his disastrous run as Mr. Money in the Bank.

Run with the Briefcase

Sandow feuded with Cody, who humiliated Sandow by stealing the briefcase and destroying it, causing Sandow to have it replaced with a more refined, classier case. Sandow handily lost their feud, which went well with the excessive amount of losses he endured throughout the months. I believe he had a single televised win during those 106 days.

The Cash-In

John Cena became World Heavyweight Champion despite having a hurt arm. Sandow figured the right thing to do was to mercilessly beat down on the arm with this briefcase, then cash in the contract. The two battled it out on Raw and had a really fantastic match. Buuuuut Cena won cleanly despite the odds against him, making Sandow the first man to ever cash in and outright lose.

The Aftermath

Sandow never really recovered from his loss to Cena. He was just a huge loser and proceeded to job continuously to the point that he became a joke character that dressed up as random guys like Bruce Springsteen and Magneto. This led to his run as Miz’s stunt double Mizdow, which was wildly popular for many months until WWE dropped the ball on the payoff and turned Sandow into a lousy Macho Man impersonator for a couple of weeks until simply forgetting about him.

21. CARMELLA (FIRST WIN)

Money in the Bank 2017

Opponents: Becky Lynch, Charlotte Flair, Natalya, Tamina

2 Days

The Princess of Staten Island had great charisma, very limited work rate, and a goofy sidekick in bottom-of-the-barrel jobber James Ellsworth. While seeing someone like Becky or Charlotte become the first Ms. Money in the Bank would come off as a top competitor earning her spot, Carmella was the picture girl for what the briefcase gimmick is meant to represent for heels: a conniving advantage acting as a crutch for someone who probably isn’t good enough to win championships on their own skill.

Carmella would go on to become a double winner over the course of a couple weeks. Unfortunately, there’s good reason for there being a do-over.

Match Performance

For a match with only five women in it, Carmella didn’t really do much at all. At one point she had a brawl with Charlotte on top of the ladder, only for Tamina to shove it over. That right there is the least interesting spot you can do in one of these matches. Towards the end, she took a nasty powerbomb off the ladder from Becky, which led to the infamous ending.

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Ellsworth got himself involved and took out Becky, meaning Carmella was the only one remotely stirring. Ellsworth tried to cheer her on, but since she was a bit out of it and couldn’t stand, he decided to simply climb up the ladder and get the briefcase for her. He removed the case, dropped it into her hands, and she won.

It’s an example of two great ideas that don’t work together, like brushing your teeth and drinking orange juice. Any other match, this would have been a prime ending, but this was the first women’s Money in the Bank match and they hyped the hell out of how important it was. During the entrances, they even took a break to show a video package of how special and momentous this whole thing was.

To do all that and go with “the weakest man on the roster wins the first ever all-women Money in the Bank match” was ill-chosen.

Run with the Briefcase

Carmella didn’t have any real run to speak about…

The Cash-In

Carmella didn’t even get a cash-in out of this. Due to the negative backlash of the Ellsworth stunt, SmackDown GM Daniel Bryan stripped Carmella of the briefcase and announced a second Money in the Bank match would happen. The redo would take place a week later.

The Aftermath

This is the one reason why Carmella at least out-ranks Damien Sandow. I’ll talk more about it later in the list, but the mulligan ladder match led to bigger and better things for her and she came out of this whole episode smelling like roses despite the very bumpy start.

20. MR. KENNEDY

WrestleMania 23 (2007)

Opponents: CM Punk, Edge, Finlay, Jeff Hardy, King Booker, Matt Hardy, Randy Orton

36 Days

Ken Kennedy seemed like a can’t-miss prospect. Even though his gimmick was essentially “says his name twice,” the guy had enough charisma to make people think that he was a definite future main-eventer. Money in the Bank was one of several instances where they were ready to pull the trigger on Kennedy, but outside forces got in the way.

Match Performance

Mr. Kennedy was in an eight-man match and did little to stick out in any way. For the most part, he existed to take rapid-fire finishers, like when Orton started handing out RKO’s to anyone nearby or when Edge speared everybody. Kennedy at least took a somewhat horrifying bump a few minutes in where he tried for a Kenton off the top rope onto Matt Hardy, missed, and nailed the back of his neck into a ladder. After that, he was gone for most of the match, only to return in the final two minutes, where he redeemed himself by hitting Hornswoggle with the Green Bay Plunge off the ladder, then having a rad final battle with CM Punk before claiming the briefcase.

Run with the Briefcase

During his time with the briefcase, Kennedy lost a bit more than he won, but it was nothing excessive. He just failed to come out of most situations looking strong. Though one thing that did seem interesting was his declaration that he was going to cash in his briefcase at WrestleMania XXIV.

If that was ever the plan, fate had other ideas.

The Cash-In

Kennedy is the glossed footnote of Money in the Bank history. For years, Michael Cole would have to claim that there was always a new champion crowned whenever somebody cashed in the briefcase. Not that every Money in the Bank winner would become champion.

It seemed that Kennedy had a major triceps tear and would need surgery, which would put him on the shelf for some time. Kennedy being gone for so long sent the powers that be into a panic and they did a segment on Raw where Edge brutalized Kennedy and goaded him into putting the briefcase on the line in an impromptu match. Kennedy gave in to the taunts and lost immediately.

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On the next SmackDown, due to World Heavyweight Champion the Undertaker also enduring an injury, Edge cashed in after a Mark Henry beatdown and pinned him easily.

Then it turned out that Kennedy’s injury wasn’t nearly as bad as it originally looked. Whoops!

The Aftermath

WWE kept trying to make Mr. Kennedy a thing, even with plans to reveal him as Vince McMahon’s long-lost son, but a combination of PED use, injuries, and complaints from high-ranking wrestlers sunk him again and again. The final straw was when he came back from an injury to take part in a ten-man tag match, where he proceeded to nearly break Randy Orton’s shoulder with a suplex. Orton and Cena complained to management and Kennedy was off to TNA.

19. JACK SWAGGER

WrestleMania XXVI (2010)

Opponents: Christian, Dolph Ziggler, Drew McIntyre, Evan Bourne, Kane, Kofi Kingston, Matt Hardy, MVP, Shelton Benjamin

2 Days (5 Days taped)

Jack Swagger looked to be one of the big success stories of WWE’s proto-NXT version of ECW. The amateur wrestling giant was like a cross between Biff from Back to the Future and Kurt Angle. Despite his lisp, he was filled with natural heel charisma as the kind of jock asshole you’d see in an ’80s high school movie. Although a big fish in ECW, he floundered just a bit when drafted to Raw. It didn’t ruin his potential, but he needed that extra bit of pep to get into the title picture.

Match Performance

Swagger’s lack of activity in this match wasn’t really his fault. It was a relatively short ten-man ladder match with very little emphasis on multiple-man spots. Granted, the brief moment he did get a spotlight was done for a seriously sweet and complex spot where Swagger was trapped inside a ladder by being poked/sandwiched between two other ladders. He just didn’t really do much other than be stuck. After that, he vanished from the match and trounced Christian in the end, rather abruptly.

Run with the Briefcase

While those before him waited weeks or months before attacking, Swagger intended to use his briefcase on WWE Champion John Cena almost immediately. Though Cena was weakened on the following Raw, he was still able to put up a fight and Swagger decided not to go through with the cash-in.

Luckily, his briefcase wasn’t dedicated to a specific world title belt.

The Cash-In

On SmackDown, World Heavyweight Champion Chris Jericho was coming off a successful WrestleMania title defense against Edge. Then again, after that match, Edge speared Jericho through a table. Ignoring the tape around his ribs, Jericho boasted about his win on SmackDown until Edge appeared and beat him up some more, dropping him with another spear.

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Jack Swagger ran out and KO’d Edge from behind with the briefcase. He entered the ring and frantically demanded his title match. One powerbomb later and Swagger was World Heavyweight Champion.

If anything, it was a really cool cash-in due to how unexpected it was for a heel to go after another heel.

The Aftermath

Swagger’s reaction upon getting the pin said it all. Instead of an enthusiastic jock narcissist, Swagger just remained still and calm. Because Chris Jericho’s slow-talking, suit-wearing heel persona was working so well, WWE tried forcing that style on others. This included Swagger, who lost all of his charm upon becoming champion.

Not only that, but he went down in WWE history as one of the all-time worst-booked champions. He lost an awful lot and rarely ever looked competent. His only saving grace was a clean win over Randy Orton that nobody really remembers. Otherwise, once he lost the title to Rey Mysterio, he fell out of the title picture for a long, long time.

18. BARON CORBIN

Money in the Bank 2017

Opponents: AJ styles, Dolph Ziggler, Kevin Owens, Sami Zayn, Shinsuke Nakamura

58 Days

Ever since the day when he beat up Apollo Crews on NXT and told him to, “Go back to Ring of Honor!” despite Crews never having competed in Ring of Honor, people could see a bright future for the lanky and gross-haired Baron Corbin. He started off as a Goldberg type who found his role as an insufferable biker bully once fans got tired of his shtick. He was a WWE creation through and through, making his eventual rise a done deal.

Once SmackDown’s quality died down, Corbin took a massive creative hit. He always seemed to be on the cusp of becoming big, but he was still stuck losing to the likes of Sami Zayn and Dolph Ziggler. It was time to step up…maybe.

Match Performance

Corbin was in the longest Money in the Bank match and didn’t take any impressive bumps or anything of note. The biggest thing he took was a Zigzag off the bottom of a ladder. If anything, Corbin looked absolutely rocking in the opening minutes. Not only did he jump Shinsuke Nakamura and put him on the shelf for most of the match, but with the opening chunk of the match being a whole lot of brawling, that was where Corbin was a Viking. He looked great overpowering nearly everyone in sight and only suffered a Ziggler superkick for his troubles.

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Unfortunately, he would be missing for so long at a time after taking very minimal damage. That’s par for the course in writing one of these matches, but the length of these segments made it seem like he was napping forever at times. He still got to show off some nice offense from time to time, like catching Ziggler with a Deep Six off the apron and chokeslamming AJ onto a ladder.

This all led to an ending where Corbin had things in hand, but Nakamura made his return and kicked his ass. Nakamura then focused on all the other opponents one at a time, escalating into an AJ Styles confrontation to hint at their eventual WrestleMania match. Corbin popped in at the end to throw them out of the ring and climb the ladder unopposed, which was a fantastic ending, but they really did spend too much time with AJ vs. Nakamura to the point that Corbin was in danger of being an afterthought.

Run with the Briefcase

All in all, Corbin did okay. He washed his hands of the Sami Zayn feud and moved on to feuding with Shinsuke Nakamura. Nakamura ended up winning that feud, which was understandable due to Nakamura moving into a title feud against Jinder Mahal. Corbin then got roped into a rivalry with John Cena in a time when Cena was known for putting over new talent. At first glance, things looked to be going great for the Big, Bad Wolf.

The Cash-In

John Cena had a match against Jinder Mahal one SmackDown and Corbin took that opportunity to run out and attack Cena. On the way out, he realized that he had a prime opportunity to cash in his briefcase and doubled back. He demanded a title match against the dazed Jinder, but once the bell run, Cena popped up on the apron. Corbin went after him, only to be rolled up by Jinder. Not only did Corbin lose his cash-in, but he lost in humiliating fashion.

The Aftermath

Things didn’t get much better for Corbin. Cena proceeded to clown him in their feud and ultimately won. Corbin never got to look all that good in his following storylines. Even when he became United States Champion, he lost it as part of a Dolph Ziggler storyline that ended up going nowhere. Corbin remained a force to be reckoned with at times (he did beat Miz in a US Champion vs. Intercontinental Champion match), but the company refused to get behind him in any meaningful way.

The company did finally start giving him a big push (too much one one, many would argue), but that was well after the fact.

17. ALBERTO DEL RIO

Money in the Bank 2011

Opponents: Alex Riley, Evan Bourne, Jack Swagger, Kofi Kingston, Miz, R-Truth, Rey Mysterio

28 Days

Alberto Del Rio was primed to rise to the top sooner than later, but WWE already screwed him up by having him win the 40-man Royal Rumble and then making him look like a total fool before, during, and after WrestleMania. There was still value in the Mexican Aristocrat and having him win the Money in the Bank match for the WWE Championship would be a good way to go about digging for that oil.

Match Performance

Del Rio was written out pretty quickly after being beaten by multiple ladders wielded by all of his opponents, sent to the outside, and then buried in some more ladders. A while later, he did recuperate, but failed to do anything meaningful outside of kayfabe injuring the Miz. Although he did take a sweet bump onto a ladder near the end, his tenure in this match wasn’t all that memorable outside of the brilliant plan to unmask Rey Mysterio in order to incapacitate him. Even then, Del Rio’s ladder fell over and he spent an extra moment or two setting it back up, which kind of killed the drama.

Run with the Briefcase

As WWE was in the middle of their red hot angle where CM Punk was threatening to win the WWE Championship and leave the company, McMahon tried to have Del Rio cash in to stop him. Del Rio immediately received a kick to the temple and got knocked out before the match could happen.

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After that, Del Rio spent the next month keeping a low profile as an eight-man tournament to crown a new champion took place. Del Rio lost a 5-minute opening round match to Kofi Kingston. Then at SummerSlam, Del Rio was on the losing team in a six-man tag match.

The Cash-In

SummerSlam 2011’s main event was WWE Champion CM Punk vs. WWE Champion John Cena with Triple H as the special guest referee. Punk ended up winning, though in a less-than-decisive way, and celebrated in the ring. Suddenly, Kevin Nash showed up out of nowhere and laid him out with a Jackknife Powerbomb. As almost an afterthought in this clusterfuck, Del Rio ran out and handed in his briefcase, allowing him to pin Punk and win the newly-unified championship.

This is the moment when their huge storyline went completely sour and it wasn’t a good look for Del Rio to be mixed up in there.

The Aftermath

Del Rio sidestepped the Punk/Nash/Triple H quagmire and went directly into a feud with John Cena. Del Rio didn’t come out of it looking all that good, not just thanks to Cena beating him for the title at the next PPV, but for Cena’s bizarre verbal burials where he not only pointed out that Del Rio’s tendency to drive fancy cars to the ring was just a fake wrestling gimmick, but also claimed that Del Rio was a coward who would fold the second he had to defend the title.

Note: Cena delivered that speech directly after Del Rio successfully retained against Rey Mysterio.

Del Rio eventually regained the title in a three-way Hell in a Cell against Cena and Punk and was able to retain against Cena in a Last Man Standing thanks to the assistance of Miz and R-Truth. Then he lost the belt shortly after to Punk, fell down the card, and spent the rest of his WWE career as an upper midcarder who would constantly lose to top faces.

16. JOHN CENA

Money in the Bank 2012

Opponents: Big Show, Chris Jericho, Kane, Miz

8 Days

John Cena had lost to the Rock at WrestleMania XXVIII and what followed was painted as the worst year in Cena’s professional career. Due to WWE’s fear of making Cena look too weak and affecting merch sales, saying Cena had a “bad year” is like whining because you won the lottery, but you only got $60 million after taxes. In a year that involved beating a returning Brock Lesnar, getting John Laurinaitis fired, winning a high-profile feud against Big Show, getting more main event spots than the actual WWE Champion, and winning the Royal Rumble, Cena also won a Money in the Bank ladder match.

Match Performance

You’d think that being in a five-man match that main-evented the show would mean we’d get a respectable amount of John Cena. Yet…not really. He started out strongly by sending Big Show through a table with an Attitude Adjustment, but then he somehow kind of got lost in a match of only a few competitors. He had a good enough showing, and the fact that being in a multi-man match allowed him to actually sell a sleeper hold without powering out was a truly welcome sight, but I figured we’d see more out of Big Match John.

Run with the Briefcase

Cena didn’t waste much time on his guaranteed title shot. On the next night on Raw, he didn’t have any matches, but he did show up during the main event of CM Punk vs. Big Show. Cena announced that on the following week, Raw’s thousandth episode, he would cash in against CM Punk.

The Cash-In

To add to the narrative that Cena was having a rough year, he failed to capture the title. Big Show ended up getting involved and attacked Cena, giving it a DQ finish and allowing Punk to remain champion. Despite technically winning, Cena became the first cash-in to fail.

The Aftermath

This one’s sort of hard to rate because on one hand, Cena went on to win the Royal Rumble and beat the Rock at WrestleMania for the WWE Championship. On the other hand, the Money in the Bank aspect was used in the story as this big moment of failure. It’s sort of the opposite of how the match is supposed to work. He remained super successful, but IN SPITE of being Mr. Money in the Bank.

15. SHEAMUS

Money in the Bank 2015

Opponents: Dolph Ziggler, Kane, Kofi Kingston, Neville, Randy Orton, Roman Reigns

161 Days

Sheamus had just returned from obscurity/injury to become a mohawked heel, terrorizing Daniel Bryan before Bryan was shelved for several years. He then got stuck in a stupid, stupid feud with Dolph Ziggler that he mostly dominated. They seemed to be serious about rebuilding his brand and bringing him back to the top.

Match Performance

Sheamus’ match performance was an interesting one because on one hand, he didn’t feel like the right choice and he was overshadowed by the storyline of, “Roman Reigns is supposed to win but, oops, sudden Bray Wyatt feud out of nowhere!” Even though Sheamus didn’t get involved in any interesting spots, he did get a lot of in-ring time, which did a really good job of selling him as deserving to win. In a match where nobody is able to stand tall forever until the final bell, Sheamus’ dominance tended to last long enough that he looked legitimately tough.

Run with the Briefcase

Sheamus got stuck in a boring feud with Randy Orton that never really went anywhere. Being 100% truthful and not joking, I can’t remember a single thing about any of it other than how they wrestled each other a bunch. Sheamus at least came out on top at the end. At least, that’s what I gather from checking Wikipedia to jog my memory. Otherwise, he just floated around the midcard, hung out with Bad News Barrett, and was treated as an afterthought.

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In fact, on the night of the cash-in, Sheamus was not only humiliated by enduring a massive ass-kicking in a Survivor Series tag match, but he preceded it by interrupting a New Day promo (his partners) and excitedly yelling, “We’re gonna get jiggy on these posers!” to the awkward sound of crickets.

That guy was going to be champion only a couple hours later. The “jiggy” guy.

The Cash-In

Survivor Series saw the end of a tournament to crown a new champion. The same tournament had Sheamus lose in the first round against Cesaro.

Roman Reigns won his first world title by pinning his bro Dean Ambrose. As an excessive amount of confetti dropped, Triple H offered his hand to him post-match. Reigns Speared Triple H instead, only to turn around into a Brogue Kick from Sheamus. Sheamus cashed in, hit another Brogue Kick, and left as the new corporate champion.

We all had a good laugh, though it was more at Reigns’ expense than caring about Sheamus being champ. Sheamus seemed secondary and therein lied the problem…

The Aftermath

Sheamus’ stock fell through the floor so hard that it’s totally hard to remember several months after the fact that he was once champion. His rivalry with Reigns made it apparent that he wasn’t in Reigns’ league and around that time, he started his unfortunate stable the League of Nations with Del Rio, Barrett, and Rusev.

Despite the talent involved, the League of Nations was a failure on every level and never made any impact. They lost to the New Day a bunch and although they were planned to feud with the Wyatt Family, Bray Wyatt got injured and they simply had the League implode.

Even though he got a big role in a popular summer movie, Sheamus’ TV role was roughly on the same level as Bo Dallas.

14. BRAUN STROWMAN

Money in the Bank 2018

Opponents: Bobby Roode, Finn Balor, Kevin Owens, Kofi Kingston, The Miz, Rusev, and Samoa Joe

70 Days

Braun is a lot like Sheamus in that his time as Mr. Money in the Bank is made up of extremes. In the months leading up to the show, Braun had been portrayed as powerful despite never getting any meaningful wins. He eliminated a bunch of guys in the Elimination Chamber without actually winning, he singlehandedly won the Raw tag titles alongside a child at WrestleMania, and he won the Greatest Royal Rumble.

With Roman Reigns continuing to lose to Brock Lesnar, it seemed like Braun was in line to be the new top guy.

Match Performance

Braun absolutely rocked this one. Most Money in the Bank matches are very blatantly every man or woman for themselves. Teamwork is short-term at best. In 2018, it was very much Braun vs. everyone. When Braun was active, it took the work of all of his opponents to keep him out of the picture, even for a few minutes.

read more: 100 Best Royal Rumble Moments

When Braun would recover, he’d rain Hell on everyone. This led to some amazing moments, like Braun emerging from underneath a pile of ladders to grab onto one that Finn Balor was trying to walk away with, throwing Kevin Owens off a massive ladder and through a table, and even running full-steam through a ladder being held by Finn and Roode.

This one made it look like unless all the other wrestlers agreed to take a dive and let someone else get the briefcase unopposed, they never had a chance. This was Braun’s playground.

Run with the Briefcase

Braun had an extremely one-sided feud with Kevin Owens. It was so one-sided that the only “win” Owens got out of it was winning a cage match via being thrown off the top of the cage and through a table. Braun put his briefcase on the line at SummerSlam and absolutely squashed Owens.

Then things got iffy. He appeared during the Brock vs. Roman main event as a threat to whoever won. Brock incapacitated Braun long enough that Roman could pin Brock and celebrate before Braun had a chance to do anything about it. The next night, Braun tried to jump Roman, only for the Shield to reunite and snuff out that idea.

The Cash-In

Braun cashed in ahead of time, allowing the company to promote a Hell in a Cell between Braun and Roman. It was a complete and utter disaster. The two knocked each other out for about ten minutes as their allies came out and did all the fancy stuntwork in their stead. Finally, Brock Lesnar appeared and F5’d each of them, meaning that a goddamn Hell in a Cell ended with a no contest.

THAT was Braun’s cash-in. Sheesh.

The Aftermath

Braun’s ill-advised heel turn was short-lived as Roman stepped down from the company for half a year due to illness. WWE kept building Braun up as a big deal, only in the sense that he could never get a major win. They built up a big, climactic match against Brock, only to chicken out because they didn’t want Braun to win and they didn’t want him to lose either.

He’s now more of a special attraction than a viable title contender.

13. CM PUNK (FIRST WIN)

WrestleMania XXIV (2008)

Opponents: Carlito, Chris Jericho, John Morrison, Mr. Kennedy, MVP, Shelton Benjamin

92 Days

CM Punk was getting a lot of love in WWE’s ECW and was slowly-but-surely rising up the ranks, but his Money in the Bank victory wasn’t the original plan. Jeff Hardy was gaining a lot of steam as a main event player and this was easily his ticket towards a title reign. Unfortunately, Jeff got busted with a wellness violation and was suspended, missing WrestleMania completely.

Time for plan B!

Match Performance

Punk did all right for himself in terms of his in-match performance. Truth be told, outside of hitting a Go to Sleep, he spent the entire match taking a lot of punishment and ladder shots. Then again, that might be on the head of Shelton Benjamin, who screwed up a spot and collapsed to the mat a moment before Punk was supposed to go in and stop him from winning. If Punk was going to do something cool right there, we never got to see it.

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Unlike the three winners who came before him, Punk actually spent a decent enough amount of time in the ring instead of sleeping on the outside and waiting for the ending. Despite eating ladder-laced finishers, Punk still came out on top, surviving a lengthy final clash with Chris Jericho.

Run with the Briefcase

Punk’s run was as middle-of-the-road as you can get. He won a bunch and he lost a bunch. He and ECW Champion Kane became uneasy allies against tag champs Miz and Morrison, eventually leading to Punk losing a regular title shot. Other than the hints that he might cash in against Kane (and possibly against Divas Champion Maryse), Punk merely used the briefcase as an accessory.

The Cash-In

Thanks to the WWE Draft, World Heavyweight Champion Edge was going to be traded to SmackDown. He cut a promo to taunt the crowd over how Raw would never have a world title defense again due to both top belts being on the other show. Batista, mad about Edge screwing him over in a previous title match, ran out and excessively destroyed him. He left Edge in a heap and walked away.

CM Punk took advantage, cashed in his briefcase, and easily pinned Edge with a Go to Sleep, poetically giving Edge a taste of his own medicine.

The Aftermath

Punk’s title reign lasted a respectable few months, but WWE never got behind him during this time and made it hard to take him seriously. He successfully feuded with JBL, but his title run felt almost sabotaged when he defended it against Batista, who was far more established and popular in comparison, meaning the crowd had little reason to cheer the champ. Punk still retained due to a DQ ending.

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The run came to an end when he was supposed to defend the World Heavyweight Championship in a Championship Scramble (man, remember those?). Backstage, he was attacked by Legacy and got punted in the skull by Orton, which made Punk forfeit the title. Punk never really got revenge on Orton or new champion Chris Jericho and instead just sunk back down into the midcard.

12. ALEXA BLISS

Money in the Bank 2018

Opponents: Becky Lynch, Charlotte Flair, Ember Moon, Lana, Naomi, and Sasha Banks

Less Than Three Hours

The powers that be couldn’t love Alexa enough. She went into WrestleMania as the top heel in the women’s division and only then finally dropped the Raw Women’s Championship to Nia Jax. Alexa lost the rematch and it appeared that she was going to be missing from the title picture for a little while.

Match Performance

Alexa was such a non-factor, especially for everything outside of the last several minutes. For the entire first two-thirds, all she did was spend her time resting on the floor and at one point dragged a ladder out of the ring, only to have Naomi splash onto her.

read more: 25 Weirdest Moments in Wrestling Games

She had more of a presence near the end and even pulled off a neat Yoshi Tonic, but it seemed pretty apparent that they were trying to protect her from having to take any physical risks.

Run with the Briefcase

There really wasn’t any to speak of…

The Cash-In

The Raw Women’s Championship was defended later that night in a match between Nia Jax and Ronda Rousey. Before Ronda could make Nia tap, Alexa ran in and attacked the two with her briefcase. She cashed it in, beat Nia handily, and became the champion again.

The Aftermath

Alexa first had to deal with Nia and ended their feud once and for all at Extreme Rules. Unfortunately for Alexa, the company decided it was time to pull the trigger on Ronda Rousey and had her challenge Alexa at SummerSlam. The match was a total squash and Alexa didn’t do so great in the rematch either.

Due to injuries, Alexa’s in-ring appearances in WWE have become more sporadic and she’s been gradually transitioning into a non-active role.

11. DOLPH ZIGGLER

Money in the Bank 2012

Opponents: Christian, Cody Rhodes, Damien Sandow, Santino Marella, Tensai, Tyson Kidd

267 Days

Ziggler always seemed to be on the cusp. Sure, he was World Heavyweight Champion once, but that was more of a technical thing and it barely even counted. He was a guy who got a bunch of title shots, but never got his chance to bask at the top of the food chain. It was time to finally pull the trigger on Mr. Ziggles.

Match Performance

Dolph Ziggler exists to take bumps and that’s just what he did right here. Outside of hitting a sweet Zigzag on Cody Rhodes, Ziggler spent the entire match getting thrown around. Tensai threw him like a ragdoll, he ended up getting faceplanted off a ladder, Tyson Kidd did some…twisting powerbomb thing, and Sin Cara completely botched a superplex (Sin Cara is to botches as Ziggler is to bumps). By the time Ziggler bypassed Christian and grabbed the briefcase, it felt like a bit of a letdown because he hadn’t done much else than get his ass thoroughly kicked for fifteen minutes.

Run with the Briefcase

Ziggler remained pretty high-profile and while he didn’t win all the time, he still seemed like he was a big deal. Sure, he lost a feud to Cena, but he recovered from it better than most. Ziggler attempted to cash in his briefcase multiple times, but whenever he did, someone he pissed off was always there to ruin his fun.

read more: A Look at the Undertaker’s First Year at the WWF

During this time, Ziggler started his own little faction with AJ Lee and Big E, which is really one of the highlights of Ziggler’s career. He also put his briefcase on the line against Chris Jericho’s career and won.

The Cash-In

At WrestleMania, Ziggler and Big E lost against Team Hell No in an attempt to win the tag titles. Regardless, the fans chanted hard for the heel to cash in against the World Heavyweight Champion Alberto Del Rio, who was exhausted after defeating challenger Jack Swagger.

The next night on Raw, Del Rio once again faced Swagger and once again won the battle, though at the cost of a heavily-damaged leg. Ziggler granted the post-Mania crowd their wish by setting up the impromptu title match. Del Rio fought hard and almost won, but Ziggler was able to exploit the bum leg and flattened him with the Zigzag, giving us one of the better post-Mania Raw moments.

The Aftermath

Things were looking good with Ziggler feuding with both Del Rio and Swagger at the same time. It looked like Ziggler had finally secured his spot as a top player.

Then Swagger accidentally gave Ziggler a major concussion. The decision was made to have Ziggler drop the title and they did it the best way possible. He faced Del Rio in a fantastic match that was able to pull off the rare double-turn. Del Rio viciously kept attacking Ziggler’s head to the point that the crowd turned on him. Ziggler lost and this newfound face turn should have helped his momentum.

Instead, Ziggler just fell away from the title picture. Since then, WWE never entertained the idea of making Ziggler important again. Even when he valiantly defeated Team Authority at Survivor Series by eliminating four of his opponents and being the sole survivor, his efforts were ignored so the narrative could give the credit to John Cena and Sting.

10. DANIEL BRYAN

Money in the Bank 2011

Opponents: Cody Rhodes, Heath Slater, Justin Gabriel, Kane, Sheamus, Sin Cara, Wade Barrett

154 Days

D-Bry always had a spot on Booker’s Fave Five list, but he was the constant target of Michael Cole, speaking on Vince McMahon’s behalf. Although he already had a US Championship reign under his belt, he didn’t seem to have much going on other than enduring midcard Hell. During a time when CM Punk was making waves, it made sense to give the briefcase to the vegan grappler.

Match Performance

For the first half of this rather lengthy Money in the Bank match, Bryan was barely there. He hit his trademark dropkick, hit his trademark dive, and that’s it. It wasn’t until the second half that he started to actually do stuff, usually in the form of fighting people by climbing the same side of their ladder. For a while, he came off as an annoyance who simply wouldn’t go down, but had nothing else to show for it. Durable and with heart, but nothing in his fists. It wasn’t until the final minutes when he started to come into his own, using his submission skills on Kane and Cody Rhodes, while outmaneuvering and outfighting Wade Barrett until he was the only one left standing.

Run with the Briefcase

Since Bryan was supposedly a champion in the making, wins were meaningless to him. At least, that’s what the humanoids in the writers’ room figured. Or just Vince. Bryan carried his briefcase to many matches and lost most of them. Wade Barrett and Cody Rhodes pinned him on a regular basis. Once Mark Henry – the dominant World Heavyweight Champion of the time – realized that Bryan was going to eventually target him, he spent weeks terrorizing him and handily beating him in matches.

read more: The 30 Best Wrestlers to Never Win the Royal Rumble

Bryan insisted that he’d cash in at WrestleMania, but his buddy Big Show kept pushing him to use it on Henry when the time was right. Bryan did give in and cashed in on Henry to pin him, but Teddy Long negated the decision because Henry wasn’t conscious at the time.

Michael Cole continued to rain on the insults. Bryan wasn’t looking so good, but at least he had that WrestleMania payoff sitting far in the distance.

The Cash-In

Mark Henry’s body couldn’t hold up too well and an injury meant they needed to get the belt off of him ASAP. At TLC, Henry and Big Show fought in a Chairs Match. Big Show won, only for Henry to lay him out afterwards. Bryan rushed to the ring and handed the briefcase to the ref, demanding the match. He pinned Big Show, who proved to be conscious as he lifted his shoulder up an instant too late.

Bryan celebrated his championship win as both Big Show and Michael Cole remained speechless.

Big Show dug his own grave. All this time he pushed Bryan not to wait for WrestleMania and Bryan listened.

The Aftermath

This altered storyline worked out great for Bryan’s career. He grew into a pompous ass, constantly high over his own success. He became a heel based on manipulating others, including his girlfriend AJ Lee, to help him remain champion. From this persona was born the “YES!” chant.

When WrestleMania time did come, he lost to Sheamus in eighteen seconds, but the fan backlash helped Bryan get over more than he ever been. It was that support that helped him become the star of WrestleMania XXX.

9. RANDY ORTON

Money in the Bank 2013

Opponents: Christian, CM Punk, Daniel Bryan, Rob Van Dam, Sheamus

35 Days

Randy Orton was always played as an important guy, but he was stuck with nothing to do. He briefly aligned himself with Daniel Bryan and Kane in order to combat the Shield and that trio became the first combination to actually stop the dominant squad. Orton had nobody to feud with after that, but at least he could earn himself an automatic title shot at the next PPV.

Match Performance

Orton did the least amount of work of all the guys in this match, though I’ll admit that for a guy ragged on for being boring on the reg, he did some beautiful mannerisms when he is in the ring. Even when it came time for him to grab the briefcase, he was the first winner to every take a second to scout around and make sure that everyone else was indeed out of the picture and that there would be no one to challenge his ascent.

read more: The Wrestlers Who Started the Royal Rumble Match

That said, this match was the first of a series of Money in the Bank matches that weren’t really about the winner winning, but about the would-be winners getting screwed over unfairly. In this case, it was Paul Heyman and Curtis Axel screwing over Daniel Bryan and then CM Punk. Orton’s win was almost a footnote.

In the end, this is one of the longest Money in the Bank matches ever and the winner doing a mere combination of dropkick, DDT, and RKO throughout that half hour is unacceptable.

Run with the Briefcase

Randy still didn’t have much to do, but he was Randy Orton as a face in WWE, so he just won. A lot. Despite not having any storylines to his name, Orton would just show up to work and have a match against whoever while always showing that he was good at winning fights and stuff.

The most he’d do with his Money in the Bank status was show up to warn John Cena and Daniel Bryan that he had absolutely nothing planned for SummerSlam and was more than capable of picking the bones of whoever won the big main event.

The Cash-In

At SummerSlam, Daniel Bryan took down John Cena cleanly with his big knee attack that commentary would just refer to as “The Knee that Beat John Cena.” As special referee Triple H made the count, Bryan beat the unbeatable opponent and stood tall as the brand new WWE Champion. It was a pretty big deal and everyone was pumped.

Randy Orton walked out, case in hand, and surveyed the scene. Yes, Bryan just had his match, but he still looked raring to go. Was cashing in a wise choice? Was Orton above this behavior as a face?

Triple H made the decision for him by turning on Bryan and planting him with a Pedigree. He invited the more marketable Orton to hand in the briefcase and Orton obliged, pinning Bryan with no trouble and ruining SummerSlam’s feel-good moment.

The Aftermath

This one’s something of a mixed bag. Although there were brief hiccups of losing to Bryan or having the championship vacated, Orton more or less remained champion for many months. The Authority made sure to keep Bryan from getting a true title reign and protected Orton as their top guy. Orton was able to beat Big Show at Survivor Series, get Cody Rhodes and Goldust fired via beating each of them, and even unified the WWE Championship with the World Heavyweight Championship by getting the best of John Cena.

Then again, he also lost cleanly to Kofi Kingston in a non-title match. This was pre-New Day Kofi who was a shell at this point and was on the same position of the totem pole as Zack Ryder.

Orton was WWE World Heavyweight Champion, but he didn’t seem like the most fearsome competitor. Regardless, the loss came at WrestleMania in a triple threat and he wasn’t even the one to take the fall. That’s not bad.

8. CARMELLA (SECOND WIN)

SmackDown Live 6/27/2017

Opponents: Becky Lynch, Charlotte Flair, Natalya, Tamina

287 Days

As we last left our heroine, Carmella won the first ever female Money in the Bank match…because her boyfriend won it for her. WWE decided, okay, fine, that was probably a bad look and decided to try again to give Carmella – and women in general – some actual dignity in her victory.

Match Performance

Carmella had more to do this time, but it wasn’t much to endear her despite being very entertaining. Like while the others brawled to open things up, Carmella grabbed a ladder and set it up to go for the quick win. This ended badly as all four opponents surrounded the ladder and knocked her off. She got thrown over a table by Tamina, Becksploder’d by Becky, and straight-up got beat up for most of her time in the bout. Outside of the ending, her one act of offense was jumping off the ladder and onto two of her opponents.

read more: Ranking Every Royal Rumble

All’s well that ends well as Carmella savagely showed up in the final moments to clobber Becky with a steel chair and climb the ladder herself.

Run with the Briefcase

Carmella went 287 days as Ms. Money in the Bank, which is the record for longest run with the briefcase. She never looked all that fantastic during that time, but that’s to be expected. The women’s division on SmackDown crumbled in terms of creative and nothing seemed to matter anymore for the female roster. Carmella was almost forgotten about, especially after James Ellsworth was fired. She was just kinda there.

She had a respectable showing at the Royal Rumble, but when they did the female battle royal at WrestleMania, Carmella was the first one eliminated.

The Cash-In

Even though WrestleMania was a bust for Carmella, SmackDown Women’s Champion Charlotte had a huge night as she not only successfully defended her title, but she became the first person to defeat Asuka. Two days later, Charlotte was attacked by main roster newbies the Iiconics and the two-on-one clash got the best of her. Carmella arrived, handed over her briefcase to a confused referee, and had an easy win.

The Aftermath

Her matches have been pretty bad and all, but she at least got to hold onto her title long enough to beat Asuka a few times. Carmella lost her championship without getting pinned in a triple threat at SummerSlam. Although she hasn’t been part of the title scene since, she’s still been doing all right for herself.

7. THE MIZ

Money in the Bank 2010

Opponents: Chris Jericho, Edge, Evan Bourne, John Morrison, Mark Henry, Randy Orton, Ted Dibiase

127 Days

In a time when Cena and Orton ran the show and nobody else could get over, Miz was really picking up steam by constantly upping his game. He had multiple tag title runs and had the United States Championship over his shoulder. At the time, he looked like he could be the breath of fresh air WWE needed. He simply had to be the next Mr. Money in the Bank.

Match Performance

Miz’s in-ring adventure was really what Edge’s should have been. His victory felt conniving, but at the same time, he did put enough of himself in there for it to feel right. About half of it was spent antagonizing John Morrison, which was on brand, but he also had a couple attempts at working alongside his fellow heels, which tended to blow up in his face…in the sense that he got a ladder smashed into his face. By the end of the match, everyone was broken and unconscious, meaning that Miz was able to act like a vulture and take the briefcase virtually unopposed.

Run with the Briefcase

Miz constantly scouted Sheamus, ready to strike and become champ, but repeated interruptions prevented the title matches from happening. Regardless, Miz did all right for himself by holding onto his United States Championship long enough. He was asked to join John Cena’s anti-Nexus team at SummerSlam and agreed to it last minute, only to discover that a returning Daniel Bryan took his place, meaning he had no reason to forego his opportunity to ambush Sheamus earlier that night.

read more: Everything You Need to Know About Money in the Bank 2019

He dropped the US title to Bryan afterwards, but didn’t break much stride. As he waited in the wings, Sheamus lost the WWE Championship to Randy Orton, who got busy with a feud against Nexus leader Wade Barrett.

The Cash-In

Barrett took on Orton for the title the Raw after Survivor Series. John Cena attacked Barrett and chased him off, which was the exact moment when the Nexus storyline truly died. Miz chose that opening to demand his title match against the fatigued Orton. Although Orton was still formidable, he went down to the Skull-Crushing Finale.

Even though the Money in the Bank gimmick had become old hat by this point, it was still a godly example of how great it could be. For one, it was immortalized by an audience reaction shot where a little girl looked like she was cursing demons onto Miz’s immortal soul via death glare.

Miz got pretty emotional over it, as did his apprentice Alex Riley, who excitedly yelled on live TV, “Your whole life, man! Your whole fucking life!”

The Aftermath

Miz was able to retain against Orton in their rematches thanks to a bit of cheating and help from Alex Riley and CM Punk. Then he had a couple matches with Jerry Lawler, which were very good, but didn’t help make Miz look world champion caliber. At least he also had a really good title defense against former partner John Morrison mixed in there.

He was doing fine, but then WrestleMania came and Cena was his opponent. Miz would brag for years that he won in the main event of WrestleMania, but it wasn’t in any way that made him look awesome. For one, he was the third wheel of what was essentially a John Cena vs. Rock feud and only won that match because of the Rock’s help.

In the follow-up matches with Cena, Miz lost the title and continued to look completely worthless in comparison, especially in an I Quit Match that was 99% Miz and Riley beating up Cena and 1% Cena doing the STF to win. Miz was able to recover and get some quality heat by teaming up with the psychotic R-Truth, but that was lead-up to a match against Cena and Rock.

Them losing wasn’t the problem. Miz and R-Truth getting beaten up by Cena singlehandedly a show or two beforehand the tag match was the problem. Miz plateaued and could never be a believable main eventer again.

6. ROB VAN DAM

WrestleMania 22 (2006)

Opponents: Bobby Lashley, Finlay, Matt Hardy, Ric Flair, and Shelton Benjamin

70 Days

RVD spent years as a popular WWE act after ECW folded, but he rarely got world title opportunities. As it turned out, Vince intended to bring back ECW as a third TV show/brand. It just needed a little extra promotion to get the ball rolling. Maybe a big title change that could get more eyes on the extended product…

Match Performance

In his Money in the Bank match, Rob Van Dam showed up every few minutes and then almost immediately disappeared. Outside of the final moments, he didn’t appear to be around for more than twenty seconds at a time. That said, he made those seconds count by putting his body on the line with some nasty bumps that believably kept him out of the match. By the time he took down Lashley at the end with a chair dropkick off the top rope, it wasn’t played up as just an opportune moment. RVD still had to fight off Shelton Benjamin and Matt Hardy before being considered the rightful winner.

Run with the Briefcase

Being an honorable face, RVD made no attempts to sneak attack anyone. Instead, he just carried it with him, coining the term “Mr. Money in the Bank.” He put the briefcase on the line against Shelton Benjamin’s Intercontinental Championship and came out on top. For his time as perpetual #1 contender, RVD cleaned up pretty well, winning nearly all of his matches and only losing a few due to overwhelming odds (ie. handicap match against the Spirit Squad).

The Cash-In

With the ECW One Night Stand PPV on the way, RVD announced ahead of time that he was going to face John Cena for the WWE Championship as the main event. Cena, the cheery poster boy of everything WWE, was forced into the lion’s den of ECW smarks who hated every fiber of his fictional being. The two had a hell of a battle, but Edge snuck in with a motorcycle helmet and Speared Cena to hedge the bets and make sure that RVD was the new champion.

It wasn’t the clean title change many hoped for, but it got the job done.

The Aftermath

Things were looking good from the get-go as RVD was not only WWE Champion, but also the new ECW Champion. Even if his WWE Championship reign was going to be a short one, at least he’d be able to carry ECW, right?

Not really.

RVD and Sabu got pulled over and were caught with drugs. This killed their prospects dead. Edge won the WWE Championship in a Triple Threat while Big Show dethroned RVD as ECW Champion and sent him off on a little vacation. RVD lost his status, which never again reached that height, and ECW lost its star.

But hey, at least they still had Kurt Angle! …Or, uh…at least they still had Chris Ben—okay, moving on.

5. CM PUNK (SECOND WIN)

WrestleMania XXV (2009)

Opponents: Christian, Finlay, Kane, Kofi Kingston, Mark Henry, MVP, Shelton Benjamin

63 Days

As I talked about earlier, WWE had Punk win the previous year out of necessity and made him World Heavyweight Champion, but didn’t really make him seem like a big deal. He was quietly taken out of the title picture and ended up back at square one. Luckily, second chances exist sometimes and Punk would go on to be the only male two-time Money in the Bank winner.

Match Performance

With the focus on Kane vs. Mark Henry early on, Punk immediately fell into the background and stayed there. The one good thing I can say here is that he appeared to be the first winner to have a fake-out bit where he was the only one in the ring, climbed the ladder, and almost got it before being interrupted. It’s just that it culminated in Christian hitting him with a Killswitch off the ladder and it looked really bad. Afterwards, Punk fought Christian once again in the end and was able to knock Kane off the ladder, allowing Punk to get his second consecutive win.

Run with the Briefcase

We already knew Punk’s intentions. He was the kind of face who would do the dishonorable thing and hit a champ when he was down. Since Edge soon after became World Heavyweight Champion, Punk was totally fine with déjà vu. The main reason he didn’t go all-in was that Umaga kept showing up to ruin his fun. Every time he’d go after the hurt champ, the Samoan Bulldozer would attack Punk.

This simply gave Punk something to do in the meantime and allowed him to wait it out for a bit while still looking good. He tangled with Umaga and laid their feud to rest at Extreme Rules in a Samoan Strap Match. He would no longer be blocked from championship gold.

The Cash-In

In the main event of that show, Jeff Hardy beat Edge for the World Heavyweight Championship. Punk then ran out and made the challenge. Hardy had very little left in the tank, but was able to surprise Punk a couple times in their very short title match by kicking out of the Go to Sleep and almost beating Punk with a roll-up pin.

Annoyed, Punk kicked him in the head and delivered a second Go to Sleep, double-hooking Hardy’s legs to make sure he had it. Punk became champion and the crowd wasn’t so happy.

As Punk pointed out, people loved the idea of him cashing in when it was Edge but Jeff Hardy was supposedly off-limits? That was against the rules?

The Aftermath

This was exactly what Punk needed to find himself. He remained something of a tweener for a month or so, but it soon became recovering drug addict Jeff Hardy vs. holier-than-thou straight edge champion CM Punk. Punk went full-on Evil Jesus with his savior gimmick and had one of the best ever WWE feuds against Hardy, made even better by the fact that Punk inadvertently won.

See, Punk beat Hardy in a Loser Leaves Match and sent him packing with the plan of Hardy taking a break from WWE and coming back later to exact revenge. Then he got caught with a ton of drugs a couple of days later, vindicating Punk’s on-air tirades and ruining the chance of extending the feud.

Punk moved on to a feud with Undertaker that was less than helpful, but even after dropping the title, he got a lot of mileage out of being the Straight Edge Savior.

Plus the time he came out dressed as Jeff Hardy and fooled the arena full of fans was outright godly.

4. EDGE

WrestleMania 21 (2005)

Opponents: Chris Benoit, Chris Jericho, Christian, Kane, Shelton Benjamin

280 Days

For a while it looked like WWE wanted to make Edge a believable title contender but weren’t sure how to make it work. They couldn’t just build up a match of Edge vs. whichever champ and have Edge cheat to win. They needed something special. Something unprecedented. Something that would make everyone identify him as a scheming, villainous mastermind.

As for why Edge isn’t on top of this list? Well…

Match Performance

The very first Money in the Bank is a great match. It’s also an extremely important Edge match. It’s just not a very good Edge match. Despite winning, Edge found himself being the most forgettable wrestler there. He started off doing the regular cannon fodder bumps (ie. catching a handful of dives alongside his opponents). Once that cleared up, he nailed a soft Spear to Kane and took a T-Bone Suplex from Shelton off the ladder. It was a nice bump, but it was overshadowed by everything else and Edge disappeared for the rest of the match.

Yes, it helped sell his Ultimate Opportunist persona, but it didn’t sell the basic concept of the match, which was, “Yes, you can have your automatic title shot, but you have to go through Hell to earn it.” Considering it was the first time they were doing that, it just rubbed me the wrong way.

Run with the Briefcase

Edge had a lot going on as the first Money in the Bank holder. For one, he held onto it for 280 days, a record that wouldn’t be exceeded for 13 years. For two, he took part in multiple feuds and constantly got to look victorious. He took down the likes of Chris Benoit, Kane, and a returning Matt Hardy, whose real-life drama with Edge and Lita brought the heels some very strong heel heat from those in the audience who were in the know.

Edge got injured and remained on the shelf, but made the best of it by starting his own Cutting Edge interview segment. He got to keep a strong TV presence while being immune to having to lose matches. Sweet gig.

He did start a feud with Ric Flair where Edge lost via roll-up at New Years Revolution, but the night wasn’t over just yet.

The Cash-In

John Cena defended his WWE Championship in an Elimination Chamber and barely came out of it the victor. Exhausted and covered in blood, he was taken aback when Vince McMahon arrived to announce an immediate title match between Cena and Edge. Through two Spears, Edge pinned Cena and excited those who were getting especially tired with Cena beating the odds every single time.

It was the original and in many minds it’s the best.

The Aftermath

This started out a little shaky but paid off in the end. Edge was the new champ and ratings kicked in because this was new and exciting. Unfortunately, they were really intent on doing Cena vs. Triple H for WrestleMania, so Edge lost the title within a couple weeks. D’oh.

Edge wouldn’t be deterred and solidified himself as one of the company’s top heels, spending years as a thorn in the side of Cena, Batista, Undertaker, and Triple H. Always thinking about the next step, Edge would constantly make up for his losses by scheming his way into yet another world title win.

3. SETH ROLLINS

Money in the Bank 2014

Opponents: Dean Ambrose, Dolph Ziggler, Jack Swagger, Kofi Kingston, Rob Van Dam

273 Days

Seth Rollins sold out his teammates in the Shield to become Triple H’s golden boy. As the saying goes, if you shoot at the king you best not miss, so if Rollins was going to betray and denounce one of the greatest stables in wrestling history (and I stand by that!), he needed to be damn sure it was worth it. Luckily, Money in the Bank was coming up and Rollins had the Authority watching his back.

Match Performance

No Money in the Bank winner put in a better performance than Seth Rollins. It’s not even close. The story of the match was essentially Dean Ambrose vs. Seth Rollins with a bunch of extra guys in there who didn’t have a chance. Rollins’ presence remained strong from beginning to end and he kept the fight going despite the fact that he ate shit repeatedly. For real, he took some nasty falls onto and/or off ladders and it’s a miracle he was able to climb the ladder at the end. Even though he won via Kane’s interference, his victory was still vindicated from the absolute amount of punishment he endured and fought through.

Run with the Briefcase

Becoming champion was still going to be tricky. It wasn’t just for the fact that Dean Ambrose was attacking him at every waking moment. The champions during this time were John Cena and later Brock Lesnar. Even in a weakened state, pinning either guy was not going to be easy.

Although Rollins was constantly being targeted by Ambrose, Rollins was still able to beat him at every turn, thanks mostly to Kane’s help. Rollins also jumped into the main event briefly to challenge Lesnar and Cena at the same time in a brilliant Triple Threat where even if he lost, he could still cash-in afterwards and try again. Rollins lost but still came out of it looking pretty damn good, seemingly like he could hold his own against the gods.

The Cash-In

At WrestleMania, Rollins lost a singles match to Randy Orton after taking the sweetest RKO. Also during that show, Dean Ambrose was hospitalized after taking some extensive damage in a Ladder Match. That meant nobody would be able to thwart Rollins if he decided to ask for his title shot.

The main event was Roman Reigns vs. Brock Lesnar for the WWE World Heavyweight Championship. It was telegraphed that Reigns was going to win and the crowd hated it. With both champion and challenger all-but spent and lying on the mat, Paul Heyman screamed at Lesnar to get up. His screams then became a look of horrified realization once Rollins’ music started playing.

Rollins bolted out and had it turned into a triple threat. Although overpowered by Reigns and Lesnar, Rollins was able to outsmart them and ended Reigns with the Curb Stomp. Rollins ended WrestleMania as the new champion, using the gimmick to the fullest.

The Aftermath

The good news was that Rollins remained champion for a very long time, getting past the likes of Ambrose, Orton, Reigns, Lesnar, Cena, Demon Kane, and even Sting. On paper, he was very successful.

In reality, he was the weeniest champion around. It wasn’t that he was willing to show ass as a heel. That kind of behavior is expected. It’s more that he was a champion who was horrified at the mere idea of ever having to wrestle. Like he forgot what his job was.

Triple H could tell him, “In six weeks, you’re going to defend your title against Xavier Woods,” and Rollins would stammer and go, “Whoa, whoa, whoa! What? Stephanie, can’t you talk some sense into him?!”

Then he’d usually win because of his subordinates or bizarre luck, like Undertaker’s teleporting dick kicks or Jon Stewart appearing with a chair and smark rage.

Still, a lengthy reign is a lengthy reign and Rollins only dropped the belt because he blew out his knee. Money in the Bank still made him a big deal.

2. KANE

Money in the Bank 2010

Opponents: Big Show, Christian, Cody Rhodes, Dolph Ziggler, Drew McIntyre, Kofi Kingston, Matt Hardy

Less Than an Hour

Kane was in the middle of a storyline where he was playing detective. The Undertaker was found beaten into a vegetative state and Kane declared that he would prosecute and persecute those responsible. Kane confronted all the top names on the SmackDown roster but found no answers. Anyone who knew hacky mystery reveals knew that Kane was secretly responsible, but his promos were still 100% badass.

Match Performance

Kane had two things going for him in this match. One, he was one of the two physical favorites alongside Big Show. Two, it was a very long match, clocking in at over 26 minutes. That meant that even though there was a big window of it that focused primarily on Big Show and his big-ass ultra ladder, there was so much time to kill that Kane got to actually do quite a bit. Whether he was enduring team-up beatings or going on rampages (near the end he just started kicking all the ass and it was great), Kane was the first Money in the Bank winner whose victory felt completely earned.

Run with the Briefcase

Kane got to hang out backstage for a spell. Maybe he got to chill and check out Alicia Fox vs. Eve Torres and the Hart Dynasty vs. the Usos on a nearby monitor. Whatever he did, he wasn’t losing matches or being made to look like a total doofus, so perfect score for the Big Red Machine.

The Cash-In

Jack Swagger’s attempt to regain the World Heavyweight Champion went up in smoke after Rey Mysterio pinned him. Swagger took out his frustrations by beating down the already weakened Mysterio, but Kane ran out to save the day. He attacked Swagger and chased him backstage while delivering blow after blow.

Mysterio took a second to enjoy his retained championship belt.

Then the pyro went off and Kane returned, briefcase in hand. He cashed in his title on the same show he won it against the same man he just rescued. Kane easily manhandled Mysterio and became the new World Heavyweight Champion.

As awesome as the ones for Edge and Rollins are, this one might just be my favorite cash-in moment. It’s so perfect.

The Aftermath

While his in-ring work was years past its prime, Kane was the final boss heel champion WWE had lacked for years. He beat Mysterio in their rematch and, as expected, it was revealed that Kane was the one behind the Undertaker’s epic beating. It didn’t matter because Kane spent several months defeating his brother again and again. This was sort of a big deal because it was the Undertaker’s final run as a regular part of the roster and he flat-out lost the feud at every turn.

Things weren’t perfect as Kane’s next challenger was Edge. Although a face, Edge’s superior mind games made him seem like an even bigger monster than Kane and Kane came out of the storyline looking like a dunce, peppered by losing his title.

Call it a gold watch title reign or bemoan the fact that a younger wrestler didn’t climb the ladder. In my opinion, Kane ruled more than anyone else when it came to Money in the Bank and deserved to be on top of this list.

That is, until…

1. DEAN AMBROSE

Money in the Bank 2016

Opponents: Alberto Del Rio, Cesaro, Chris Jericho, Kevin Owens, Sami Zayn

Less Than an Hour

Dean Ambrose hit a bit of a rut. In the lead-up to WrestleMania, he lost huge matches to Roman Reigns and Triple H. Then Brock Lesnar steamrolled him. He gradually started to get his mojo back by winning a feud with Chris Jericho, even if the payoff was a lame match. It meant little, though, as Roman Reigns was the reigning WWE World Heavyweight Champion and Seth Rollins returned to challenge for it. Ambrose was the odd man out.

Match Performance

Ambrose certainly put in his time and effort. Once the opening part with everyone doing their dives died down, Ambrose spent a LOT of the match just taking punishment. Very little offense but a lot of showing that he could endure a lot of pain and keep going. Considering the months he had going into this match, this was probably for the best way to tell the story. The way he took down Kevin Owens at the very end is one of the better final spots for one of these Money in the Banks.

Run with the Briefcase

Ambrose didn’t sit on his hands for very long. There was a very terrible Rusev vs. Titus O’Neil match afterwards, but after that was the main event of Roman Reigns vs. Seth Rollins. With briefcase in hand, Ambrose kept his eyes peeled.

The Cash-In

Seth Rollins cleanly defeated Roman Reigns as part one of Roman’s punishment for failing WWE’s wellness test. Ambrose’s music kicked in and as Rollins looked off to the entrance, Ambrose ambushed him with the briefcase and took him down. He cashed in the briefcase, hit Dirty Deeds, and won the title. While that’s heelish behavior, it worked as long game comeuppance for Rollins.

It also meant that in one night, all three members of the Shield were WWE World Heavyweight Champion.

The Aftermath

It was hard figuring out who had a better aftermath between Ambrose and Kane, but while Ambrose didn’t win a rivalry with the Undertaker, he also didn’t have to look like a total dunce in an Edge feud. The worst thing about Ambrose’s run as champion was that he took part in a ho-hum match with Dolph Ziggler at SummerSlam.

Otherwise, Ambrose did extremely well for himself. Not only did he get a couple clean wins over Rollins, but in the big Shield triple threat that people have been expecting for years, Ambrose pinned Roman himself. He went on to be champion in a vital time when Raw and SmackDown were being split up and got to spread his wings by being separated from his Shield brethren. He finally lost the title in a match against AJ Styles, which is not the worst thing in the world. Even then, before stepping down from the title picture, Ambrose got a clean win over John Cena.

Gavin Jasper writes for Den of Geek and still thinks it’s hilarious that Money in the Bank once took place at the TD Gardens. Read more of his articles here and follow him on Twitter @Gavin4L