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Ranking the Money in the Bank Winners

Alex loves writing about WWE and critiquing their major shows.

It’s that time of year again. It’s Money in the Bank time. Since 2005, the briefcase has been used to propel new stars to the next level. Unfortunately, it’s also been given to flashes-in-the-pan. Money in the Bank can be a fun a match, but since it’s become a staple of the company, it’s lead to WWE putting people in the main event even when they’re not ready.

But how have the Money in the Bank Winners ranked among each other? To figure that out, there are a lot of a different factors. It’s not just who deserved it, but what did they accomplish long term? How exciting was their cash-in? This ranking will go from worst to first.

Damien Sandow (2013)

Sandow was like the Elias of his day: He was an old-school obnoxious heel who was so hilarious in his smug trash-talking, fans loved hating him. (Come to think of it, the two even have similar faces.) When he won the briefcase, there was a lot of intrigue. After all, no one this low on the totem pole had ever won. Was this his next step into a larger world? Nope, he tried to cash-in on Cena and whiffed it. Not on a PPV, mind you but on Raw. (It was a cold comfort that - impromptu or not - it was a real match.) Did this change his character in any way? Was this part of a larger story? No, Sandow plummeted down the card so badly, being a mid-carder would’ve been a step-up. This was clearly just a sign that the World Heavyweight Title was circling the drain.

Baron Corbin (2017)

To Corbin’s credit, he’s more talented than some fans admit. The man has improved considerably since his debut. But he’s just not at a main event level. It’s never a good sign when Mr. Money in the Bank whiffing his cash-in is actually well-received. Having him lose the briefcase as part of a story felt like a smart move – in theory, that’s the kind of thing that can add gasoline to a raging fire of a feud. But Corbin’s feud with Cena was tepid. As was the blow-off match.

John Cena (2012)

Hey remember that tedious John Cena losing streak storyline? Cena won the briefcase in 2012 when he didn’t exactly need it. Little was accomplished other than a disqualification loss on Raw to CM Punk. Ironically, Cena’s star power not only makes this needless, it’s also what saves it from the bottom of the barrel. Unlike Sandow and Corbin, Teflon John wasn’t exactly hurt by it. Plus, it was at least part of a story—not a good story, but at least a story.

Jack Swagger (2010)

Even in 2010, this move felt baffling. This was the last Money in the Bank at Wrestlemania. Ever other person in the match felt like a more interesting choice—Christian, Ziggler, McIntyre. The company sent mixed messages with his push. Swagger scored a win against Orton—at the peak of his popularity—but wasn’t even allowed to pin The Big Show on PPV. The Big Show! After dropping the title to Mysterio, it was back to the mid-card for Swagger. While he had an inexplicable 2013 push out of nowhere, everything about the reign of Swagger indicated WWE didn’t have a lot of confidence in him. Might I add the World Heavyweight title started feeling like a B-championship around this time?

Mr. Kennedy (2007)

It… seemed like a good idea at the time. Only the third Money in the Bank winner was the first to flop at cashing in. To WWE’s credit, Mr. Kennedy was a good choice at the time. He was a solid worker and an even better talker with a great gimmick. Unfortunately, him losing the briefcase became a necessary evil when injury struck. He came back earlier than expected. Then it was discovered he lied about using steroids. It was all downhill from there. (Spoiler, this is not the last time you’ll hear this.) Kennedy was shown the door in 2009. He was at least a big deal in TNA when that kinda mattered, but his WWE career was a misfire.

Randy Orton (2013)

Randy Orton winning the briefcase was maligned at the time because he cut short Daniel Bryan’s first WWE Championship. On its own, that’s not a bad thing. Orton was a heel and raining on the fans’ parade is what heels do. However, the problems run deeper. The summer of 2013 felt like a changing of the guard and the beginning of some new blood. Daniel Bryan’s victory felt like the culmination of that. Orton’s win and the birth of the Authority felt like WWE rubbing it in fans’ faces that WWE would never change or give them their way. The next few months would see the title held “In Abeyance”, no winner in a vacant title match and Orton’s baffling feud with Big Show. It wasn’t until the fans spoke up that Daniel Bryan gave us the feel-good moment they wanted. Orton may be one of the best of our generation, but his win begot a lot of awfulness.

Sheamus (2015)

When Seth Rollins finally ascended to the world title, the company needed a few other top-level heels. Sheamus has been the victim of stop-start pushes. This felt like attempt number 2,600 to make Sheamus a main event guy. In theory, this was a good idea – something like Money in the Bank can give a person that jolt they need. Unfortunately, there was this distinct stench of “He has the briefcase, that’s all he needs, right?” Instead of carving a path of destruction, he had a directionless 50/50 feud with Orton. Let’s not forget the League of Nations – a stable of talented workers that made everyone actually look weaker. The need for a second heel became apparent when Rollins suffered injury. Sheamus cashed in on Reigns, which didn’t exactly set the world on fire. The Irishman didn’t get to hang around the main event after losing the title, creating the impression that he never belonged.

Alberto Del Rio (2011)

Not to sound like a broken record, but… It seemed like a good idea at the time. Hindsight is 20-20, but at the time, Del Rio seemed primed to be the next big thing. Even at the time there was an issue: The company didn’t count on CM Punk becoming the biggest thing in the company. Del Rio’s cash-in put the brakes on a storyline that managed to re-capture wrestling fans’ imaginations. But at the same time, Punk got there and Del Rio was a good heel for him. But after an injury, Del Rio was never the same. In the ring, he had a babyface push that killed all of his momentum. Outside the ring, Del Rio became one of the real life bad guys, who companies inexplicably keep hiring. Being a good idea at the time is still better than some winners.

Carmella (2017)

Such a rocky start for the first Ms. Money in the Bank. Carmella famously won the briefcase when her lackey James Ellsworth stole it for her. Heels using nefarious means to win is one of the foundations of wrestling. But the company shoved it down the viewers’ throats that this match was progress. If Carmella pulled this on maybe the second or third one, it would be fine. Not to mention Ellsworth was fired so his role was moot. (At least the re-do made it easier to scrub his role from history.) So why isn’t Carmella closer to the bottom? Well, being the first at least gives her SOME bragging rights. But more importantly, Carmella just owned being Ms. Money in the Bank.

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Kane (2010)

Remember how I said Money in the Bank could reinvigorate a stale character? This was an example of how. Kane had pretty much been relegated to jobber-of-the stars for a while. But in summer of 2010, he started cutting some insanely good promos. Remember when Kane started wearing his mask again? Remember how we thought it was the return of Kane’s viciousness? THIS was the Kane we all wanted. Plus, it was the first time someone cashed in the same night they won. (It was a clever spot too, with Kane pretending to be there to help Mysterio.) Kane even scored big wins over the Undertaker. But it wasn’t all sunshine and roses. His feud with Edge was absurd. And once Kane lost the gold – you guessed it – it was back down the card. Ever since Kane was essentially the go-to whenever the bookers didn’t have better ideas. But at least a talented veteran had his moment in the sun.

Dolph Ziggler (2012)

Ah, what could have been. When Ziggler finally won the briefcase in 2012, it felt like the man was finally earning his due. On his way to the cash-in, the man earned wins over Jericho and Cena. Dolph held the briefcase for a while until he cashed in on Del Rio after Wrestlemania. If you haven’t watched the clip, trust me: The crowd was behind Ziggler 110%. Finally, one of the most talented, charismatic workers was launched into the stratosphere. Not only that, but it added a little relevance to a title that was stagnating at the time. Then he suffered a concussion. Then Del Rio—who was ice cold at this point—won back the championship. By Summerslam, Dolph was a mid-carder again. Word is that despite supporters such as Pat Patterson, McMahon and Hunter don’t care for him because of his attitude. Despite glimmers of hope, it’s obvious Dolph is never going to be a top player.

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The Miz (2010)

If Kane was a return to glory, Miz was a full-fledged rise to stardom. Miz’s rise to the world title has a little rockiness (literally). As world champion, Miz always felt like second fiddle to someone—Nexus, Rock, Cena. But he did headline Mania. And he had victories over Cena and Orton. There was also an epic Raw match with John Morrison. And as weird as a match with Jerry Lawler sounds, Miz did carry the man to some good matches. While a lot of people fell down the card, Miz hung in there for most of 2011. Miz has rarely been a top guy or challenged for the world title after that. But after a 2016 reinvention, Miz has been a star in his own right. He’s even added some life to the once stagnant Intercontinental Title.

Dean Ambrose (2016)

Dean’s win and immediate cash-in was a layered story—a fan favorite getting his due, Dean getting revenge on Rollins, and all three Shield members being world champs within minutes. Plus, he won a big triple threat against Rollins and Reigns, where he received a hero’s welcome from the blue brand. Then… the Stone Cold interview happened. It may sound like a joke, but Dean’s stumbling, awkward interview hurt him a lot. He had an underwhelming feud with Ziggler. A lot of people saw their place on the card drop. Dean’s stock dropped in a different way: As he feuded with AJ Styles, the fans turned against him! The logic was that he was becoming lazy and that WWE vetoing his ideas put out his fire. But teaming with Rollins and the Shield reunion helped him find his mojo. Even with a recent injury, it is possible for him to rebound to that former glory.

CM Punk (2008)

The only two-time winner on this list, and the only person whose two wins tell different stories. CM Punk’s first win feels like a more optimistic version of Ziggler’s win. According to rumors, Jeff Hardy was supposed to win Money in the Bank at Wrestlemania XXIV. But his drug suspension put the kibosh on that. And that’s how Punk’s Money in the Bank win feels: Like they gave it to him before they really knew what to do with him. After he won the World Heavyweight Title, the company got cold feet about him pinning Batista. His only major win was against JBL was not exactly bragging rights. It doesn’t help that he was on Raw, which was stacked at the time with Cena, Batista, Orton and the epic Jericho/Michaels feud. He lost the title so unceremoniously people wondered if he implausibly violated the wellness policy. Still, his cash-in on Edge was an exciting moment and it was Punk’s first step into a larger world. While he spent sometime in mid-card limbo, Punk did rebound, but we’ll get there in time.

Rob Van Dam (2006)

The formula for Money in the Bank cash-ins has become a little obvious. Champion is vulnerable, suitcase holder runs out. The ECW original took things in a different direction. RVD informed Cena that they would face off at One Night Stand—not just a match, but a revival of ECW. Regardless of how the brand turned out, this show was one last hurrah for the original ECW. This was one of the rare instance where WWE actually created a brand vs. brand battle. In the Hammerstein Ballroom, Rob Van Dam was heralded as a hero. Cena faced a crowd so against him they literally threw his shirt back at him. It was obvious that even if he hadn’t been busted for weed, RVD was never going to stay in the WWE title scene. His only PPV title defense was fourth from the main event… over the Spirit Squad. Still a talented worker earned his moment in the sun. For being one of the most unique cash-ins, this earns points.

CM Punk (2009)

After his first Money in the Bank failed to live up to what fans hoped, this was the real deal. CM Punk turning heel and cashing in on Jeff Hardy may not have been as exciting as his first cash-in, but the aftermath more than made up for it. A lame DQ loss at The Bash that year made it seem like history would repeat itself. But when straight edge Punk feuded with Jeff Hardy, this was a chance for CM Punk to be the evil, sanctimonious cult leader heel we all knew he could be. While Raw was in the middle of its lame celebrity host phase, the Punk/Hardy feud made Smackdown feel like the real A-show. Edge suffered injury and Jericho’s character was neutered by the various guest hosts. So Punk and Orton felt like the true top heels in the company… until CM Punk backtalked the Undertaker and fell down the card. But two years later, he rebounded. But that's a whole 'nother Money in the Bank story.

Daniel Bryan (2011)

This was Daniel Bryan’s step to the main event. If there’s any criticism, it’s that the World Heavyweight Title had lost some stock by this point. On the flip side, Daniel Bryan’s stock skyrocketed. It wasn’t just a talented worker making it to the top, Daniel Bryan stepped up his character. Watch some interviews from around Money in the Bank—he stuttered through promos every now and then. But Bryan reinvented himself as a more entertaining character. The “Yes” movement, need I say more? Even when he was between world title pushes, he still proved his value with stuff like the anger management skits. At Summerslam 2013, he finally reclaimed the world title against Cena. Daniel Bryan was recently cleared to perform again, a definite gain for the company.

Edge (2005)

Do you know why Money in the Bank has been so successful? Because they got it right the first time. Being the first would give Edge a minimum of bragging rights. But it was also great storytelling. Edge held the briefcase for months. Cashing in on vulnerable champions has become the norm. But when Edge did it, it was such a new thing. Plus, he didn’t just do it after any match—he took advantage of Cena after a bloody Elimination Chamber match. Some people stumbled out of the gate. But Edge was a true star by this point. Even if he didn’t get the Wrestlemania main event, his brutal match against Mick Foley proved his worth. Edge wasn’t just some flash in the pan either: For the next five years, he had epic feuds and matches with Cena, Taker, Orton, Jericho. The R-rated superstar managed to reinvent himself as a face or heel. Sadly, neck injuries caused him to retire in 2011. But in a true sign of his star power, he retired as World Champion.

Seth Rollins (2014)

If Edge set the standard for slow burn, Rollins mastered the art. The signs were there that Rollins was meant for bigger things. Some people lose once they win the briefcase. WWE writers seem to figure “Eh, they’ll get the title anyway.” But Rollins scored big wins over guys like Dean Ambrose and even challenged for the WWE title in an epic battle at the 2015 Rumble. But what really puts Rollins over the top is HOW he cashed-in. Rollins crashed the main event between Reigns and Lesnar. Interrupting the match itself was a smart move because it added drama to the match and prevented the main event from being a micro-match. (I’m looking at you Wrestlemania 9.) Unfortunately, Rollins was a little hit and miss after his cash-in. As champion, he had big wins, held the title for a while and was even a dual-champion after beating Cena for the US title. But he lost all the time on TV before losing the title from injury. Sometimes Rollins has felt directionless since his 2016 face turn. But there have been highlights such as his feud with Triple H and the Shield reunion. As of this writing, Rollins is Intercontinental Champion and keeping that title prestigious.