At the upcoming Money in the Bank event, six of the most popular stars in the WWE today will compete in the 17th Money in the Bank ladder match. A staple of the company since 2005, the Money in the Bank briefcase grants the holder a World Title shot whenever they choose for up to one year. Since its inception, fifty different men have competed for the briefcase, while only sixteen have gone on to win the match. Out of those sixteen men, thirteen of them managed to successfully cash in the briefcase, two failed to do so (John Cena and Damien Sandow), and one never even got the opportunity to cash in (Mr. Kennedy would lose his briefcase to Edge). Speaking of Edge, he and CM Punk are the only superstars to have cashed in the briefcase on two separate occasions. CM Punk also holds the record for the most Money in the Bank ladder match victories with two, one at WrestleMania XXIV and one at WrestleMania XXV. This also makes Punk the only man to have won the briefcase two years in a row, a feat which will not be repeated for quite some time. With so many different superstars being involved in these matches over the years, it’s a given that some men may have been more deserving of the win than others. In fact, when one looks back at the history of the match itself, some of the greatest superstars of this generation have failed to attain the briefcase. Here are the top fifteen superstars that have shockingly never won a MITB ladder match.
15 Ric Flair (MITB Record: 0-1)
By the time that Ric Flair had participated in his first (and only) Money in the Bank ladder match, his legendary career was already starting to wind down. Despite also competing in his first tables, ladders, and chairs match earlier that year (2006), no one truly believed that Flair stood at chance at winning the briefcase. Still, Flair managed to put on an admirable effort during the match, especially when you consider that he was fifty-seven years old at the time. After taking a superplex off the top of a ladder, Flair would clutch his knee and was helped backstage, with fans assuming they had seen the last of Flair on that night. However, Flair still had some gas left in the tank and, later on in the match, he limped back down to the ring. Dismantling the competition with a flurry of chops and punches, Flair made his way back up the ladder and was inches away from grabbing the briefcase….until Finlay and his Shillelagh knocked Flair off the ladder. Even though Flair lost the match, the effort that he put into making his performance memorable made sure that the loss didn’t hurt him in the slightest.
14 Booker T (MITB Record: 0-1)
After winning both the King of the Ring and the World Heavyweight Championship in 2006, Booker T looked to continue his new-found success by winning the Money in the Bank briefcase at WrestleMania 23 in 2007. In one of the most star-studded Money in the Bank ladder matches ever, Booker T managed to hold his own and put on an entertaining performance. At one point in the match, Booker T looked like he had the match won, as he was just seconds away from unhooking the briefcase. Unfortunately Matt Hardy, another participant in the match, proceeded to grab Booker T’s wife Sharmell and threatened to hurt her unless Booker T made his way back down. Although the briefcase was within his grasp, Booker T decided that love was more important than glory, so he hopped down the ladder and went after Hardy. Sadly this would be the last we would see of Booker T in the match because moments later, Hardy would hit the Twist of Fate on Booker T, effectively ending his involvement in the match.
13 Big Show (MITB Record: 0-2)
Despite the fact that Big Show can boast that he is the largest athlete to ever compete in a Money in the Bank ladder match, he unfortunately has never won one. His first attempt at the briefcase occurred at the first ever MITB pay-per-view back in 2010 and it seemed hard to believe that anyone could stop him from winning the match. The only concern fans had during the contest was what ladder would possibly be able to support the weight of Big Show. This issue was solved during the match when Show unveiled his own monstrosity of a ladder, which seemed capable of holding the combined weight of all the superstars in the match. Even with this personalized weapon at his disposal, Show was unable to attain the briefcase. Fast forward two years and once again Show was competing in a MITB ladder match. Just like before Show would lose, but on this occasion, it at least came down to him and everyone’s favorite superhero John Cena.
12 Ted DiBiase Jr. (MITB Record: 0-1)
When Ted DiBiase Jr. first arrived on the scene back in 2008, he seemed destined for success in WWE. Being paired with Cody Rhodes and Randy Orton only added to that belief, with the three men dominating the RAW scene during their time together as Legacy. Following their split in 2010, DiBiase managed to gain the lovely Maryse as both his onscreen girlfriend and valet. Combined with his athletic prowess, it seemed like it was only a matter of time before DiBiase’s singles career really took off. Heading into the first ever Money in the Bank event in 2010, he looked to become the first superstar to ever win the RAW brand’s briefcase. During the match, DiBiase would have a strong showing, but unfortunately for him he was unable to win, losing to The Miz. In a desperate attempt to not lose the momentum he had gained up until that point, DiBiase brought back his father’s famous Million Dollar Championship belt and claimed it as his own. He would transition into a feud with Goldust over the belt and this would be end up being the closest DiBiase came to tasting singles success in the company.
11 Roman Reigns (MITB Record: 0-1)
For the past two years, it seems as though Roman Reigns is able to plow through any challenge that stands before him. Whether it be AJ Styles, Daniel Bryan, or even Triple H, Reigns has made a career out of always coming out on top. Although this has earned him the ire of fans, the fact of the matter is he has improved his craft considerably since his arrival back in 2012. To date, Reigns has only competed in one MITB ladder match and that was actually the most recent one which occurred at last year’s event. Near the tail-end of the match it seemed as though Reigns was poised to grab the briefcase, but interference from Bray Wyatt made sure that this result wasn’t to be. Now although it was smart to not to go with the predictable Reigns win in this case, the fact that it came at a cost to Bray Wyatt’s career was a sad sight to see. Reigns would go on to exact his revenge on Wyatt, defeating at both the 2015 editions of SummerSlam and Hell in a Cell.
10 Matt Hardy (MITB Record: 0-4)
Throughout the years, both Matt Hardy and his brother Jeff have made themselves famous by performing death defying stunts. While many consider Jeff to be the more popular and charismatic brother, it can be argued that Matt is the better in-ring performer of the two. Because of this (and strong fan support), Matt has found opportunity at his doorstep time and time again. In many instances, he has used these opportunities to his advantage and has found success, but this isn’t the case when it comes to MITB. From 2006 to 2010, Matt competed in four MITB ladder matches, coming up short in every time. It can be argued that Matt never had a legitimate chance of winning these matches, as he was likely put into them given the history he’s had with ladder matches. Whatever the reason, with Matt currently wrestling for TNA, the door may be forever closed when it comes to him fighting for the briefcase.
9 Dean Ambrose (MITB Record: 0-2)
One of the most popular superstars in WWE today, Dean Ambrose hopes that the third time will be a charm when it comes to him and MITB matches. Arriving on the main roster scene in 2012 with his Shield brethren Roman Reigns and Seth Rollins, Ambrose immediately seemed as though he was the standout member of the group. He was the first to win a singles championship out of the three (the United States Title) and was even given the honor of wrestling The Undertaker in what was probably his final SmackDown match. Ambrose was likely the fan favorite to win SmackDown’s MITB contract back in 2013, although like the others on this list he suffered a crushing defeat. As time progressed, his former teammates Rollins and Reigns found themselves on the receiving end of more and more success, while Ambrose has had difficulty reaching the heights that they have reached. With the Money in the Bank event being just a few weeks away, there’s a chance that Ambrose could finally break through the glass ceiling and once again be treated as an equal to Rollins and Reigns.
8 Drew McIntyre (MITB Record: 0-2)
At one point in time, it seemed as though the powers that be had high hopes for Drew McIntyre. Personally endorsed by Vince McMahon when he first made his way to SmackDown back in 2009, McIntyre wasted no time and quickly won the Intercontinental Championship from John Morrison. He would go on to be a heavy fixture on SmackDown for the first half of 2010, but all of that would change following back to back MITB losses. Derailed by the sudden loss of momentum, McIntyre would attempt to regain some credibility by winning the WWE Tag Team Championship alongside Cody Rhodes. The two would quickly lose the titles to the unlikely team of John Cena and David Otunga, and that would be all she wrote for McIntyre. Ignoring a mildly entertaining run with Jinder Mahal and Heath Slater as 3MB, McIntyre would never come close to the level he was in 2010, going down in history as one of WWE’s most disappointing stories of “what could’ve been.”
7 Wade Barrett (MITB Record: 0-2)
When Wade Barrett first debuted back in 2010, he didn’t seem as though he was someone that was going to attain the success that he did. Appearing alongside his “coach” Chris Jericho during the first season of NXT, Barrett seemed like a big man who wouldn’t last very long in the company. Almost instantaneously that opinion was changed by many when Barrett returned as the leader of The Nexus and for several months he dominated the main event scene. Despite failing to win the WWE Championship, the future seemed very bright for the young superstar. Barrett would go on to compete in two MITB ladder matches during his career and rather surprisingly came up short in both. If rumors are to be believed, Barrett was at one point considered to win the briefcase at WrestleMania XXVIII, but an injury caused those plans to be scrapped. Although Barrett wouldn’t attain the briefcase during his tenure in WWE, he did manage to become a five time Intercontinental Champion and the 2015 King of the Ring. After recently parting ways with the company, it’ll be interesting to see where Barrett goes from here.
6 Kofi Kingston (MITB Record: 0-6)
Long before he was one-third of the insanely popular New Day, Kofi Kingston enjoyed moderate success as a singles star. In fact, he was already a former Intercontinental and World Tag Team Champion by the time he participated in his first MITB ladder match at WrestleMania XXV. Despite coming out on the losing end of the match, 2009 would still end up being a great year for Kingston (he even admitted so on RAW recently). Since his first appearance in the match over seven years ago, Kingston has gone on to compete in five more MITB matches, each time failing just as he did before. Although Kingston is still an active member of the WWE roster (and likely will be for some time), it’s unlikely that he’ll ever possess the briefcase. With that being said, he still does have a very lucrative and successful road ahead of him with New Day.
5 Shelton Benjamin (MITB Record: 0-5)
During the first couple of years that the MITB ladder matches were around, part of what made them amazing revolved around what could Shelton Benjamin possibly do to top himself year after year. Similar to how Kofi Kingston has amazed us with his Royal Rumble acrobatics, Benjamin always found a way to showcase his athletic ability. You could make an entire list based solely off of what the man has done in MITB matches. However, despite all of the risks that he took during his attempts to win the briefcase, he was unable to attain it. As the years progressed, Benjamin was hardly ever considered a favorite to win, as he was only there to add athleticism and death defying leaps to the match. The one good thing that came from this though was that fans around the globe came to have a strong respect for the man and he build a strong following of fans because of it. He would go on to have moderate success as a singles star throughout his career, but one has to wonder how Benjamin’s career would’ve panned out had he won the briefcase at some point.
4 John Morrison (MITB Record: 0-2)
Looking back, it’s hard to believe that John Morrison was unable to win the MITB briefcase during the latter portion of his WWE career. When he first arrived on the scene, Morrison (originally Johnny Nitro) managed to draw interest as a tag team competitor, but as a singles competitor he struggled to find his stride for some time. Thankfully after several years of putting on good matches and finding a persona that fit him, Morrison would start to find true success in the company. He would go on to win the Intercontinental and Tag Team Championships multiple times throughout his career, and starting in 2008 he first started to go after the MITB briefcase. After failing to win it at WrestleMania XXIV, Morrison would try once again during the 2010 edition of Money in the Bank. Just like before, Morrison was unsuccessful in his attempt to win, only this time he wouldn’t have another opportunity down the road. In 2011, he left WWE and now he’s competing for the popular wrestling program Lucha Underground.
3 Cody Rhodes (MITB Record: 0-4)
First arriving in WWE alongside his father Dusty Rhodes back in 2007, Cody Rhodes managed to grow leaps and bounds as a performer during his nine year stint on the main roster. Going from the overshadowed member of Legacy to one of the longest reigning Intercontinental Champions of the last decade wasn’t an easy journey for Cody, but his dedication and athletic prowess ensured that he got there. Now Cody had a number of great moments during his time in WWE, but one moment that never occurred (but should’ve) was him winning the coveted MITB contract. This was never more apparent than at the 2013 instalment of the Money in the Bank event, where Cody absolutely cleaned house during SmackDown’s ladder match. The live Philadelphia crowd was firmly behind the young competitor and it seemed for just a moment that Cody was about to get one step closer to becoming a World Champion. In the end Cody lost the match when his tag team partner at the time, Damien Sandow, pushed Cody off the ladder and claimed the briefcase for himself. Sadly, this turned out to be the closest Cody ever got to the main event scene. With his time in WWE firmly behind him, it’s the hope of this writer that Cody Rhodes has success come his way in the near future.
2 Christian (MITB Record: 0-6)
A former two time World Heavyweight Champion in WWE, Christian never got to win the briefcase. Even though he did compete in several Money in the Bank ladder matches throughout his career, Christian was never truly considered to be an odds on favorite to win. The only time where he really had a chance of winning was all the way back at WrestleMania XXVI. Surviving until he and Jack Swagger were the only two men left standing in the match, Christian would disappointingly lose to the younger and inexperienced superstar. Two years later he would go on to compete in the final RAW Money in the Bank ladder match, but yet again failed to attain the briefcase. It was at this point that his career would slowly start to die down. By 2014, the veteran had ceased competing inside a WWE ring, mostly due to concussions he had sustained throughout his storied career.
1 Chris Jericho (MITB Record: 0-4)
Topping off the list is the innovator of the Money in the Bank ladder match himself, Chris Jericho. Participating in four MITB matches thus far (soon to be five), Jericho can be considered to be one of the most experienced competitors of all time. With the sheer amount of times he’s participated in these matches, it’s hard to believe he hasn’t one at least one. He’s even had the briefcase cashed in on him before (courtesy of Jack Swagger), but unfortunately the briefcase may be one of the few things Jericho will be unable to obtain in his storied career. The closest Jericho ever came to winning the briefcase was at WrestleMania XXIV, where after a two year absence he looked to get back in the World Title scene. While Jericho didn’t win the briefcase on that night, he did manage to go on and dominate RAW throughout the rest of 2008. This is just one of many examples that shows that even without ever winning the briefcase, Jericho can at least say that he’s had (and will continue to have) an incredible career.