5 Best (& 5 Worst) Money In The Bank Winners

WWE is very hit and miss with their gimmick concepts, but one idea has managed to stay exciting for over a decade — Money In The Bank. Debuting as a WrestleMania gimmick, the eight-man ladder bout for a WWE title match contract proved to be so popular it got its own pay-per-view. When it's done right, this match stipulation — and the resulting fallout — can be a star-maker, but not every winner is perfect. So, we’ve taken a look at every winner since the match’s debut in 2005 and we’ve determined the five best and the five worst.

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10 Best: Rob Van Dam

As a face, RVD couldn't copy what Edge did the year prior. So, instead of waiting to pick at the bones of a wounded champion, he made it clear that at ECW One Night Stand 2006, John Cena would defend his championship in front of a hostile crowd against the then-ECW champion.

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The match itself is a little frustrating to go back and watch. Cena got a majority of the offense in, but the crowd was so against Cena that it’s worth going back to experience it all over again. By the time the dust settled, RVD stood tall with both the ECW title and the WWE title — thanks to some help from Edge — and that moment of time made him one of the best to ever cash-in.

9 Worst: Damian Sandow

We hate that Damian Sandow is on this half of the list, but it’s hard to argue how much damage the Money In The Bank win did to his WWE career. To be fair, he was actually a good contract holder. He betrayed his tag-team partner Cody Rhodes, a hot feud fans were invested in coming out of the win, and had one of the nicest looking custom briefcases we’ve ever seen. But one terribly booked night made it all come crashing down.

The intellectual savior of the masses decided to cash in his contract after 106 days against John Cena, who hadn’t wrestled at all that night. Sure, Sandow gave him a good smacking with the actual briefcase, but it wasn’t enough to inflict critical damage on WWE’s Superman. That night, with one arm, John Cena defeated Sandow, crushing the hopes and dreams of internet fans across the globe, and the once-up-and-coming name saw his stock plummet.

8 Best: Dolph Ziggler

It may be hard to believe in 2019, but there was a point in time where Dolph Ziggler was so popular, he could have been the guy to carry the company into the future. While the stars didn’t align that way, his Money in the Bank win was something to remember.

Winning the contract in 2012, Ziggler held onto the briefcase for 267 days, leaving fans salivating to see how he’d do it. It wasn’t a quiet year either for him. In fact, he successfully defended the contract against Chris Jericho and John Cena — the former being a contract vs career match.

Finally, when he did cash in — on Alberto Del Rio no less — the crowd was all-in. His run was phenomenal, and it paid off in the best way possible. We don’t see this kind of commitment from WWE these days, but it’s a shame they were never able to follow up with this particular star after all that investment.

7 Worst: Jack Swagger

Jack Swagger had all the opportunity in the world to be a big deal, but it didn’t quite work out. Before all that, however, WWE gave him a chance to swim with the big fish by giving him the Money in the Bank briefcase, and it didn’t work. Not only that, but the particular match he won it in was filled with other stars fans preferred to see win. Veterans like Christian, Matt Hardy, and Shelton Benjamin faced off alongside younger stars like MVP and Dolph Ziggler gave this particular ladder match a feeling of unpredictability.

To WWE’s credit, they went with a wild card, and they at least tried to build up a name, but Swagger always lacked that “it” factor that would take him to the next level, and his run with the briefcase and the World Heavyweight Championship are largely forgotten.

6 Worst: John Cena

John Cena’s time with Money in the Bank came at a bad time. These days, WWE fans cheer on the rare occasion they see The Face That Ran The Place, but back in 2012, they were a little worn out. This didn’t help. Not only did John Cena not need to win the briefcase, but he also cashed in against internet favorite CM Punk. If that wasn’t bad enough, he technically won his title match but didn’t receive the title because it was by disqualification.

We get that sometimes, there isn’t a plan for who will win the contract, but this was a bad idea from the start and by the time it was done, the tires were still spinning in the mud.

5 Best: CM Punk

CM Punk is a two-time Money In The Bank winner, and he’s cashed in successfully both times. The second was against Jeff Hardy after a hard fought ladder match, but the first was against Edge — the man who put the briefcase on the map. 

Related: The 5 Best (&5 Worst) Money In The Bank Cash-Ins

Punk didn’t hold onto the contract for too long either. In fact, his first run lasted 63 days, while the second lasted 92. He’s also the first superstar to win the yearly ladder match on back-to-back occasions.

4 Worst: Baron Corbin

When Baron Corbin won his Money In The Bank briefcase, fans were surprised, to say the least. He was on the main roster for a short time before being put in this high profile match and beat out popular names like AJ Styles, Shinsuke Nakamura, Sami Zayn, and Kevin Owens. Jinder Mahal was there too.

While fans were sour at his win, he never really found his groove holding the contract and when it came time for him to actually cash-in, he did so at a really bad time by costing John Cena a match. So, in retaliation, he interfered in Corbin’s match causing him to lose. Not fully taking out his opponent, and the man he attacked from behind made him look like a fool, and losing the match all together made it impossible to take him seriously ever again. To his credit, however, he’s bounced back and is a pretty big piece of the main roster. In fact, he’s probably bounced back better than most on this part of the list.

3 Best: Seth Rollins

It was very clear after The Shield’s breakup that WWE had big plans for Seth Rollins, but nobody expected him to make history the way he did. After joining the Authority — which consisted of Triple H, Stephanie McMahon, Randy Orton, Kane, and later Joey Mercury and Jamie Noble — Rollins was the spoiled brat the evil WWE overlords were grooming while Randy Orton was the star of the present. His Money in The Bank win added just the right amount of tension between him and The Viper, and that’s without mentioning his issue with Dean Ambrose. His antics against his former Shield-brother made him absolutely hatable, and his cash-in at WrestleMania on his ex-tag team partner mid-match was nothing short of electrifying. In many ways, he was the last great winner, and WWE will have to do a lot to top this run.

2 Best: Edge

Edge is without a doubt the most successful winner — and not just because he did it twice. What makes him the perfect contract holder is his slimy “Ultimate Opportunist” persona. Believe it or not, there was once a time when a random title defense wasn’t lurking around every corner, but at New Year’s Revolution 2006, that all changed. Now, all of a sudden, we had a champion who metaphorically picked at the carcass of a dying animal in John Cena following an Elimination Chamber match to win the title. To make things even worse, he did it again to the Undertaker after he defeated Batista in a Cage Match on SmackDown Live.

There will never be a superstar more suited to carry that briefcase.

1 Worst: Mr. Kennedy

It’s hard to argue against Mr. Kennedy as the worst Money in The Bank winner, and it has nothing to do with his talent. In fact, when he won, most fans were pretty happy with the contract going to him. Yet, in a world as chaotic as professional wrestling, nothing is set in stone. In fact, due to an injury — at a really bad time too — Kennedy had to drop the briefcase to Edge, who went on to cash-in on a wounded Undertaker just one day later.

Next: 10 Best Money In The Bank Matches

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