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Ranking WWE's Money In The Bank Winners From Worst to Best

Unlike winning the Royal Rumble, winning the Money in the Bank allows a superstar to cash in when and where he pleases.

Winning the Royal Rumble gives a superstar the opportunity to vie for either the WWE World Championship or the WWE Universal Championship at WrestleMania. While this opportunity is one that any and every superstar would love to have, it isn't as surefire an opportunity at winning one of the aforementioned titles as winning the Money in the Bank briefcase is.

Unlike winning the Royal Rumble, winning the Money in the Bank allows a superstar to cash in when and where he pleases. This can be during a match; this can be at the conclusion of a match; this can be once the champion has been laid out; this can be during a promo; this can happen in a number of different scenarios. Throughout the years, a number of different superstars have won the illustrious Money in the Bank briefcase.

Here, we rank WWE's Money in the Bank winners from worst to best.

17 Mr. Kennedy

via FanSided.com

How do you assure that you're the worst Money in the Bank winner in the history of WWE? Simple, you pull a Mr. Kennedy and put your contract at stake and come out on the losing side of the matchup. Having won the prestigious Money in the Bank contract on April 1st, 2007 at WrestleMania 23, Mr. Kennedy paid homage to the date of April Fool's and made a massive fool of himself a little over a month later when he faced off against Edge for the contract. To make matters worse, Mr. Kennedy not only lost the contract that gives you the best opportunity to become WWE Champion, but his foe, Edge, cashed in the following day and became Smackdown's new World Heavyweight Champion.

16 Damien Sandow

via Damien-Sandow.com

In 2013, the "Intellectual Savior of the Masses", Damien Sandow, surprised the masses when he defeated the likes of Dean Ambrose, Wade Barrett, Cesaro, Fandango, Cody Rhodes and Jack Swagger to capture the contract that guaranteed him a shot at the World Heavyweight Championship. After holding the contract for 106 days, Sandow figured it was his time to capitalize against then World Heavyweight Champion, John Cena. Cena had been nursing an arm injury that Sandow felt was much worse then Cena had let on. Prior to cashing in, Sandow assaulted Cena's arm and once he felt he had neutralized the arm enough he cashed in. Unfortunately for Sandow, Cena still got the better of him and Sandow became the first, and still to this day only superstar to lose against his opponent in clean fashion upon cashing in his MITB briefcase.

15 John Cena

via AllwrestlingSuperstars.com

Instead of cashing in on a battered CM Punk, John Cena decided to do the noble thing (how noble of "Big Match John") and fight Punk the following week at the 1,000 episode of Monday Night Raw. The problem with not catching your opponent by surprise when you have the Money in the Bank contract is that you aren't truly taking advantage of cashing in whenever you like. Had Cena cashed in on the battered Punk the week prior, he likely would've hoisted another WWE Championship over his shoulders. Instead, he waited a week while Punk was at full strength (or at least in a much better position then the week prior). The Big Show decided to interfere and the match ended in a disqualification. As a result, Cena wasted a valuable opportunity. Not to worry, it's Cena he has gotten and will continue to get many opportunities at the company's highest prize until the day he calls it quits.

14 Sheamus

via Goliath.com

Coming out victorious at the 2015 Money in the Bank PPV against the likes of Kane, Kofi Kingston, Neville, Randy Orton, Roman Reigns and Dolph Ziggler, Beaker from the Muppets, I mean Sheamus, won his first ever Money in the Bank briefcase. Sheamus held onto the contract for just over four months at 161 days before he cashed in on Roman Reigns. With the League of Nations by his side, Sheamus defeated Reigns in five minutes and fifteen seconds. Not to forget, Sheamus and WWE made sure any and every one would know that he defeated Reigns in 5:15 as a "Sheamus 5:15" was available soon after the human jar of mayonnaise's victory. Unfortunately for Sheamus his reign was rather uneventful. He only held the belt for twenty-two days before Reigns reclaimed the belt.

13 Alberto Del Rio

via AllwrestlingSuperstars.com

Responsible for ending the "Summer of Punk" in 2011 with his cash in at WWE's self-proclaimed "Biggest Party of the Summer", the significant other of Paige, Alberto Del Rio, cashed in on CM Punk after Kevin Nash delivered a power bomb to the "Straight Edged Superstar". Less than a month earlier, Punk had captivated both casual and diehard fans by baiting them into thinking he was quitting the company and leaving with the WWE Championship as well. Punk became champion and wrestling had one of its hottest angles to date. Yet, inexplicably, the WWE had Del Rio cash in on Punk less than a month earlier to end the "Summer of Punk" before it had barely gotten started. To make matters worse, this reign only lasted thirty-five days for Del Rio.

12 Kane

via WWE.com

In 2010, the first ever Money in the Bank PPV took place, with the Money in the Bank matchup having taken place at WrestleMania prior. The winner of the briefcase for Smackdown's World Heavyweight Championship was Kane as he beat out the likes of the Big Show, Christian, Matt Hardy, Kofi Kingston, Drew McIntyre, Cody Rhodes and Dolph Ziggler. Kane wasted no time as he cashed in his MITB briefcase that very same night. Kane became the third champion of the night as Jack Swagger was the champion going into the PPV, only to defeated by Rey Mysterio, who was defeated by Kane. Kane ended up holding the "big gold belt" for a respectable 154 days in his first, and to date only run with the championship.

11 Jack Swagger

via Goliath.com

Facing off against a record nine competitors, Jack Swagger came out victorious in the final WrestleMania Money in the Bank match on March 28th, 2010 in Glendale, Arizona. The Perry, Oklahoma born Swagger cashed in his briefcase in a mere two days as he capitalized on a beaten down Chris Jericho who had just been speared by the "Rated R Superstar", Edge. While Swagger can forever lay acclaim to being the last person to win the MITB briefcase at WrestleMania and defeating nine adversaries in the match, he can't lay acclaim to having a memorable title reign. Swagger held the World Heavyweight Championship for less than three months as he came out on the losing side in a Fatal 4-Way match at the PPV with the same name. Seven years later and Swagger has still never regained the championship.

10 Dolph Ziggler

via wwe.com

The night after WrestleMania has become the Raw of Raws in recent years and this was no different in 2013 when Dolph Ziggler cashed in his Money in the Bank briefcase against Alberto Del Rio. Ziggler easily received the biggest reaction for a cash in, as the East Rutherford, New Jersey crowd simply erupted when he handed over his briefcase to the referee. While the cash in will forever be remembered as a thunderous one, the same cannot be said of Ziggler's reign. The majority of this stemmed from the fact that Ziggler ended up sustaining a legitimate concussion at the hands of Jack Swagger. This caused Ziggler to miss a month of television time. The reign only lasted sixty-nine days and when combining that with the time Ziggler missed it isn't hard to see why this reign didn't materialized into much for the beach blonde haired Ziggler.

9 Rob Van Dam

via wwe.com

Claiming victory against Shelton Benjamin, Finlay, Ric Flair, Matt Hardy and Bobby Lashley at WrestleMania 22, Rob Van Dam ended up winning the WWE Championship in one of the most raucous wrestling environments ever. In front of 2,460 diehard and rabid ECW fans in New York City's Hammerstein Ballroom, RVD defeated "Mister Hustle, Loyalty and Respect" to become WWE Champion. Soon after, RVD would add the newly reinstated ECW World Heavyweight Championship to his collection which made him the first person to ever hold both belts at the same time. But, RVD screwed himself over in epic fashion. Busted for having eighteen grams of weed and five Vicodin pills, RVD lost both belts in early July as the drug bust was grounds for him receiving a thirty day suspension. You truly are "one of a kind" RVD, you truly are.

8 CM Punk (2008)

via ballsandbrawls.com

Since its inception in 2005, CM Punk is not only the lone wrestler to repeat as the year's Money in the Bank winner, but he is the lone wrestler to win the prestigious contract on two occasions. In 2008, the Chicago native came out on the winning end against Shelton Benjamin, Carlito, Chris Jericho, Mr. Kennedy, John Morrison and MVP. Less than three months later, Punk was drafted to Raw and he made a name for himself on his first night. Capitalizing on Batista's attack on then World Heavyweight Champion, Edge, Punk cashed in and claimed his first World Heavyweight Championship. Less than three months later, Punk was forced to relinquish the title as he was unable to defend it in a match against Batista, JBL, Kane and Rey Mysterio. Punk didn't forfeit the belt as a result of a legitimate injury; he forfeited the belt as a result of a kayfabe injury meaning the E had little to no faith in the tatted superstar. This proved to be a lackluster reign at its finest.

7 Randy Orton

via Pinterest.com

Likely "hearing voices in his head", Randy Orton made his way to the ring at the 2013 SummerSlam PPV and cashed in his MITB contract immediately after Triple H delivered a pedigree to newly crowned WWE Champion, Daniel Bryan. While Orton put a halt to the "Yes Movement", he didn't fully put an end to it. Orton lost the championship back to Bryan at the following paper, but Bryan wasn't exactly champion. To add on, Bryan won the belt as a result of a fast count. The championship remained vacant from September 15th to October 27th, when Orton finally got the better of Bryan. Orton also became the first every WWE World Heavyweight Champion during this reign as he defeated John Cena in a match that had both Orton's WWE Championship and Cena's World Heavyweight Championship up for grabs.

6 Dean Ambrose

via dailyddt.com

On June 19th, 2016, Seth Rollins had completed his mission of "redesigning, rebuilding and reclaiming" as he defeated Roman Reigns to become the new WWE World Heavyweight Champion. Unfortunately for Rollins, his other former Shield brethren, Dean Ambrose, had just won the Money in the Bank briefcase earlier in the evening and he had no intentions of holding his briefcase for long. Ambrose ended up cashing in immediately after Rollins defeated Reigns and via hitting his Dirty Deeds finisher became WWE World Heavyweight Champion for the first time in his career. Ambrose came out on top against the likes of Rollins (in a rematch) and Dolph Ziggler before he lost his title to AJ Styles at Backlash. Ambrose held the belt for eighty-four days and had one of the more memorable cash ins since the briefcase had been introduced.

5 Edge

via Dailymotion.com

The winner of the first ever Money in the Bank at WrestleMania 21 in 2005, Edge still holds the record for holding the briefcase longer than any other wrestler at 280 days. Despite holding the briefcase for close to 300 days, it was well worth it for the "Ultimate Opportunist" as he cashed in the following calendar year in January and got the one, two, three over John Cena to claim his first ever World Heavyweight Championship. Edge followed his victory up with a "live sex celebration" the following night on Raw which was an unprecedented thing to do in the 2006 landscape of WWE. Nonetheless, Edge's segment garnered Raw a 5.2 viewership rating which was its highest mark in over a year, so credit to Edge (and Lita)! However, regrettably, Edge's reign only lasted a minuscule three weeks.

4 CM Punk (2009)

via cbslocal.com

A tad over a year after he had won his first Money in the Bank briefcase, CM Punk repeated with a back-to-back victory in 2009. Unlike his first run with the briefcase, his second run with the briefcase was much more eventful. Having been a fan favorite at the time of his win of the briefcase, fans were torn when Punk cashed in and claimed the World Heavyweight Championship over fan favorite Jeff Hardy. This led for an immensely intriguing feud throughout the months as Punk would turn full out heel and reference his Straight Edge lifestyle as to why he was superior to Hardy. To further help Punk's cause, and to further hurt Hardy's cause was the fact that Hardy had real life drug abuse problems. Punk's reign lasted just forty-nine days, but his feud with Hardy was extremely compelling and arguably the best feud of 2009.

3 The Miz

via AllwrestlingSuperstars.com

In 2010, Miz somewhat shockingly surprised everyone when he hoisted the Money in the Bank briefcase from atop the ladder against the likes of Evan Bourne, Ted DiBiase, Edge, Mark Henry, Chris Jericho, John Morrison and Randy Orton. Cleveland, Ohio's Miz held the briefcase for just over four months at 127 days when he decided to finally turn the briefcase in to the referee. Orton, who had just fought Wade Barrett was winded, and Miz capitalized to become WWE Champion for the first time in his career. Miz ended up holding the belt for over five months and as a result of his cash in was able to main event WrestleMania XXVII. Not only did Miz main event 'Mania, but he came out victorious against John Cena with the tile at stake (with a tad bit of help from the "Great One"). Miz's cash in and reign is to this day one of the most successful of all-time.

2 Daniel Bryan

via WWE.com

Before Sami Zayn was dubbed the "Underdog from the Underground", Daniel Bryan filled that role, without being given the actual nickname. In 2011, Bryan shocked the world when he came out victorious against the likes of Wade Barrett, Justin Gabriel, Kane, Cody Rhodes, Sin Cara, Sheamus and Heath Slater. Granted, Bryan's victory wasn't as shocking as a victory by Slater would've been, but it was a welcomed surprise nonetheless. Bryan was adamant that he would hold his briefcase until WrestleMania and would then cash in at the "Grandest Stage of them All". Bryan caught everyone by surprise when he cashed in on newly crowned champion the Big Show on December 18th, 2011 after Show had just defeated Mark Henry for the belt. The reign lasted over three months when Bryan was defeated in eighteen seconds by Sheamus at WrestleMania. At the time, it looked like a decision that would bury Bryan for years to come; in reality, it was the best thing that could've happened to Bryan as his character benefitted from it immensely.

1 Seth Rollins

via ophephotography.blogspot.com

Daniel Bryan had aspirations to hold his Money in the Bank briefcase until WrestleMania and cash in then; Seth Rollins actually did so. Cashing in during the Brock Lesnar and Roman Reigns main event, Rollins delivered his now banned curb stomp finisher to Reigns (who had just speared Lesnar out of the ring) to claim his first ever WWE World Heavyweight Championship. Rollins reign was a lengthy one as it concluded at 220 days. As if that wasn't good enough, Rollins also didn't actually ever lose his belt. Rather more, Rollins had to vacate his belt as he suffered a torn ACL, MCL and damaged meniscus at a live event against Kane. However long Rollins reign was supposed to go is anyone's guess, but Rollins easily has the most memorable cash in and one of, if not the most successful reigns of a Money in the Bank winner.

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Ranking WWE's Money In The Bank Winners From Worst to Best