Examining Superstars Who Failed to Capitalize on Money in the Bank Win

Ryan Dilbert@@ryandilbertWWE Lead WriterJune 23, 2014

Winning the Money in the Bank briefcase is supposed to be a set of wings designed to carry a WWE Superstar to a higher tier, but for some, the wings' wax melted quickly and soaring turned to plunging.

Dolph Ziggler, Damien Sandow, Jack Swagger and Mr. Kennedy didn't reap the benefits that their fellow Money in the Bank winners did. Valleys followed that peak for those four men, the midcard and below awaiting them.

Money in the Bank is a clever concept, although someone in Sandow's position may fail to see the truth in that statement right now.

Wrestlers on the verge of being ready to headline are offered an opportunity to force their way into championship status. It's a way to ease a star into a marquee role as WWE did with CM Punk and Daniel Bryan.

Those two stars both first won the World Heavyweight Championship via Money in the Bank before becoming WWE champ, before reaching their career peaks. Punk held the WWE Championship for 434 days. Bryan became the company's hottest star and ended WrestleMania 30 as the victor in the night's most prominent match.

Money in the Bank came before those achievements. The briefcase catapulted rising stars toward the clouds.

Last year, Randy Orton, an established vet in need of momentum, won the briefcase and soon found himself in main events once again, including at WrestleMania against Bryan and Batista.

For the following men, success was far more fleeting. Injury, lack of opportunity or floundering under the spotlight kept them from leaving the ground for long.


Mr. Kennedy

Rather then become the third man to turn a contract in a briefcase into a world championship, Mr. Kennedy became the answer to a trivia question: Who is the only Superstar to win Money in the Bank only to watch someone else cash in?

He outlasted his foes in the Money in the Bank Ladder match at WrestleMania 23. The rising star and charismatic villain never got a chance to see the fruits of that win, though.

Many saw a future main eventer in him, but bad luck and injury kept tripping him up.

A torn triceps had officials and Mr. Kennedy thinking he was going to be out for a long stretch. WWE decided to take the briefcase away from him, having Edge beat him for it on May 7, 2007.

The injury wasn't as bad as previously thought. As Mr. Kennedy told Mike Mooneyham of The Post and Courier, "They told me I was going to be out for seven months, but it turned out to be only a slight tear, and I was only out for a few months."

He returned to the ring, but not for long. As of Greg Oliver of Slam! Sports writes, Mr. Kennedy "was one of the wrestlers named on the Orlando-based Signature Pharmacy list" for receiving banned substances, which led to him serving a 30-day suspension.

Top stars have been both injured and suspended before, but a large percentage of Mr. Kennedy's time was spent on the operating table and out of the ring.

That stigma stuck to him when he returned. He feuded with Shawn Michaels and William Regal, but momentum was never his again. Long after Mr. Kennedy left for TNA, Ziggler would reportedly be labeled "snakebit" and "injury prone," per PWInsider Elite (via Wrestling Inc).

Unfairly or not, that's likely how officials viewed Mr. Kennedy as well.

Just two years after raising the Money in the Bank case in the air at WrestleMania, Mr. Kennedy was gone from the company. WWE released him on May 29, 2009.


Jack Swagger

The last Money in the Bank Ladder match at WrestleMania crowned Swagger as victor. WWE chose him out of a crowded field of competitors to chase the world title.

Swagger earned early comparisons to Kurt Angle thanks to a strong amateur wrestling background and his use of Angle's Ankle Lock. The powerhouse, though, lacked the presence that made Angle a star, as WWE would eventually find out.

On March 30, 2010, Swagger cashed in on Chris Jericho, winning the World Heavyweight Championship.

The spotlight then zeroed in on Swagger, but he couldn't hold up under its heat. His promos lacked spark. His magnetism was spotty.

WWE took the title off him after just two months. He would never hold it again.

Months later, WWE tried to tweak Swagger's gimmick by having an eagle mascot join him. Edge confronted both eagle and former Mr. Money in the Bank and called the whole setup "stupid." The more popular star speared the mascot after Swagger had scurried away.

This was not where Money in the Bank was supposed to take him.

WWE's confidence in him seemed to dissipate in the years to follow. When WrestleMania arrived, Swagger wasn't competing. Instead, he served as Michael Cole's trainer. 

He hung around, battling Evan Bourne, teaming with Ziggler and later holding the United States Championship for less than two full months. Before trying to resurrect him with his current anti-immigrant gimmick with Zeb Colter, Swagger went on a losing streak that saw him fall to men like Brodus Clay with little resistance.

Just when he seemed to have his mojo flowing once again and was being pushed by WWE toward world title contention, Swagger was arrested, according to TMZ.com, for driving under the influence and marijuana possession. 

WWE never suspended Swagger and didn't pull him out of his world title match with Alberto Del Rio at WrestleMania 29. He surely hurt his chances of ever taking that title home again, though.

He has since watched Cesaro join and then leave his side and now finds himself sinking down the card. Swagger recently lost to Adam Rose, WWE using the Oklahoma native as fodder for a goofy newcomer.

That's surely not what he and the company envisioned for him back in 2010.

For so many stars, their popularity ballooned after winning Money in the Bank. They found ways to milk more of their potential. Swagger never did.

His ceiling wasn't as high as WWE imagined. He's a powerful, talented mat worker who's best suited for battles on the midcard. No briefcase could change that.


Dolph Ziggler

After winning his Ladder match at Money in the Bank 2012, The Show-Off took nearly a year to successfully cash it in. When he finally stomped on Del Rio's injured ankles and snatched the world title from him, the fans in attendance howled in excitement. 

The celebration didn't last.

In a brawl with Swagger in May of 2013, Ziggler took a kick to the head that left him with a nasty concussion. Of the injury, he told WWE.com, "I didn't know what day it was; I didn't know what month it was. I've had a couple of concussions before and just had a headache. I've never not remembered entire days, like someone in a movie."

WWE was patient with him, keeping the championship on him while he recovered. He didn't compete again until June 16 at Payback where Del Rio dethroned him.

That was it for Ziggler as world champ. 

The company instead placed him in contention for the U.S. title and Intercontinental Championship. He lost out to men like Curtis Axel, Big E and Dean Ambrose.

It didn't matter how spectacular these matches were or how impressive he was in them. He seemed to be sent out to boost other guys, not elevate himself. He must hear the referee counting to three in his dreams now.

A concussion in early 2014 scared officials from putting him in a prominent spot. According to PWInsider, via Marc Middleton of Wrestling Inc, folks backstage believe that Ziggler can't be trusted to be a top guy "because he's injury prone and has a history of taking time off."

Once someone slaps a label like that on you, it's hard to peel off. Ask Mr. Kennedy.

Money in the Bank brought Ziggler his career peak but few moments to celebrate ever since.

He hasn't held a championship of any level since losing to Del Rio a year ago. An unfair perception that he's an injury waiting to happen has instead made him the go-to guy for aiding other stars.


Damien Sandow

Sandow's viciousness in the ring and his top-tier mic skills seemed to have him poised for a climb up WWE's ladder. He won the Money in the Bank briefcase on July 14, 2013, and it soon become the center of his feud with Cody Rhodes.

He waited three months to cash it in, using the briefcase to assault an already injured John Cena. Sandow battered the champion, hurling him into the ring steps and stomping on his surgically repaired arm.

Even that wasn't enough to keep Cena down.

Sandow joined what is now a two-man list of Superstars who have failed to take home the title after cashing in. The result gave Cena-bashers new ammunition and frustrated many fans pulling for Sandow. Mick Foley tried to spin things in a positive way, though.

Foley couldn't have known what awaited Sandow.

That loss didn't propel him; it fitted him with concrete shoes. Sandow found himself losing often and in quick fashion. For some losses, Sandow must have wished that they would come quickly.

Ziggler stuffed him inside a drum in one match, and Mark Henry used cupcakes and a Christmas tree as weapons in another, one where Sandow was dressed as Santa Claus.

Sin Cara joined forces with Scooby-Doo on March 24, knocking off the former Mr. Money in the Bank with ease. WWE refused to use Sandow as anything other than a pushover. He seemed to be being punished for some backstage infraction.

The company turned him into a weekly punchline.

He began to dress in ridiculous costumes, adding sight gags to his defeats. As D-Sizzle, Magneto and a ribbon dancer, Sandow made the announcers chuckle and made the memory of his Money in the Bank win feel like a daydream that fans all had together.

WWE got gun-shy with Kennedy and Ziggler because of their injury history. With Swagger, the company pulled him off center stage after a brief run as one of the lead performers. Sandow never got the chance—and no torn muscle or head injury got in his way.

A lack of faith from company officials brought him failure after Money in the Bank instead, stuffing him into a hole he will struggle to ever climb out of.

WWE has to avoid repeating this mistake. Rather than build a new star, it worked to ruin a promising wrestler in Sandow post-Money in the Bank. That's waste of that oft-effective tool.

The Money in the Bank concept is designed to uplift, but only if there isn't someone holding down the winner's wings.


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