Since 2005, Money in the Bank match has essentially acted as a launchpad to catapult WWE Superstars from the mid-card to Championship glory, or at the very least the illusion of being a main event level player, even if they aren’t quite there yet.

For some performers that have been an unqualified success, with the likes of Edge, CM Punk, Seth Rollins, Rob Van Dam and Dean Ambrose using it to ascend to the next level. There have been those who have had mixed fortunes like Dolph Ziggler, Alexa Bliss, Kane and Sheamus who had forgettable experiences with the briefcase. Then there are those whose run with the briefcase was a disaster, and while this is far from an exhaustive list, let’s take a look at the five worst Money in the Bank Ladder match winners, in no particular order.

Jack Swagger

When I think of Money in the Bank winners who were neither deserving of the accolade, nor particularly successful as champion after cashing in their contract, Jack Swagger immediately comes to mind. The “All American American” had been kicking around the mid-card for a couple of years by the time he reached up and struggled for what felt like an eternity to bring down the prize, and while he had impressed on his initial run in ECW he never seemed to really develop any further. So it was quite the shock when he was selected in 2010. Swagger’s cash-in on Chris Jericho was sudden, only two days later on SmackDown Live, but it was unspectacular, hurried and lacked impact. His reign as World Heavyweight Champion was mediocre with unconvincing victories over Randy Orton and Big Show, and a laughable angle with Bunkhouse Buck playing his father before he dropped the belt to Rey Mysterio.


Some would argue that Carmella was the logical choice to win the first women’s Money in the Bank ladder match. With Becky Lynch (long before she became The Man), Charlotte Flair, Tamina and Natalya all in the match, Carmella would seem to be the person who would benefit most from being elevated by winning the contract. Although she was not always the standout talent in-ring compared to her peers, she had a strong look and a well-defined character. However, the manner in which she won the briefcase with James Ellsworth getting involved, and then subsequently being stripped of the contract only to win it again in screwy circumstances devalued the win hugely. I know she’s a heel, but needing the help of Ellsworth made Carmella feel like far less of a threat to the division, and I’m not sure it elevated her. This feeling was compounded when she actually cashed in, with a title reign that was treated like a joke and one that left her back in the middle of the card. With the exception of a catchphrase, Carmella gained very little from the Money in the Bank win and arguably advanced her carer more by winning the Mixed Match Challenge.

Damien Sandow

Looking back, it feels almost bizarre that the man dubbed the “intellectual saviour of the WWE” won the right to a guaranteed title shot. Although John Cena may have been the first man to actually fail to successfully cash in his contract, Damien Sandow was the first who seemed like he was set up to fail. Sandow had been a midcarder for some time after a lengthy stint in developmental, with a gimmick that was one dimensional and a limited shelf life. In many ways, his win was to set up a feud and facilitate a babyface turn for Cody Rhodes. The programme between the two with Rhodes throwing the briefcase in a river, and Sandow bringing out a lather case was enjoyable, but it was not the kind of booking that was destined to properly either man to the top, making Sandow’s failure all the more telegraphed. That said, there is an argument to be made that this started Rhodes on a road (pun intended) that would lead him feuding with The Authority, the Stardust character, his eventual frustration with the company and his release which has allowed him to blossom outside the confines of the WWE machine. It’s a stretch, granted, but there has to be something positive to take from what was otherwise a huge waste of a Money in the Bank win.

Baron Corbin

Probably the most high profile, well publicised “winner” on this list is Baron Corbin. After a so-so run in NXT, he was called up to the main roster with a bang, winning the André the Giant Memorial Battle Royal at WrestleMania 32. Again, after that, he had a middling run on the main roster before winning the briefcase in 2017. Corbin has all the tools, size, speed, agility, charisma of a sort (when given the opportunity), athleticism and he can talk. However, he has never quite been able to put all those things together. But in 2017, before his run as “constable” of RAW, he was poised to go all the way. Then, out of nowhere, he failed in his cash in attempt against Jinder Mahal on an episode of SmackDown Live. Rushed and abrupt are perhaps the best words to describe the situation. Seemingly Cobin’s big chance had been squandered to further a feud with John Cena, which he would eventually lose. Perhaps the office got cold feet on him, or maybe he was in the dog house but this was a major waste, and I’m not sure Corbin has recovered as yet.

Mr Kennedy

Finally, we come to one of the more interesting anomalies in the history of Money in the Bank. Mr Kennedy…Kennedy. From his first match on SmackDown Live in 2005 it was clear that Mr Kennedy was a can’t miss star in the making. He was excellent on the microphone, he oozed charisma, his ring work was of a very good standard, he had a superstar look and he had “it”. Major feuds and title matches with the likes of Batista, The Undertaker and DX would come and go, and while he wasn’t quite at the highest echelon, he seemed destined to get there. However, Kennedy might be one of the unluckiest performers in WWE history. Every time he seemed poised to get a big break, he got injured or suspended, His Money in the Bank briefcase was no exception. Kennedy would reach up and grab the briefcase at WrestleMania 23, and the next night he proclaimed he would cash it in at WrestleMania 24. However, Kennedy would lose the briefcase to Edge in a short match only a week later after suffering what was thought to be a serious tricep tear that would keep him out for months. It turned out not to be serious and he was back only a few weeks later, by which time Edge had already cashed in. In truth, Kennedy was his own worst enemy and that is what cut his WWE career short, but he will go down in history as the only person (so far at least) to win the Money in the Bank briefcase, but never get a chance to cash it in.

With the 2019 edition of Money in the Bank quickly approaching, it remains to be seen who will take home the briefcase this year, and where it will take them over the next twelve months. However, one thing is for sure, they would do well to avoid the paths laid out by the five previous winners listed above if they want to reach new heights as Mr or Ms Money in the Bank.


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