The “Money in the Bank” concept has been a very successful one for WWE since its creation in 2005. It has spawned a ton of new stars and turned very deserving wrestlers into world champions when they wouldn’t necessarily get a shot otherwise.
On the other hand, ideas that have been around as long as MITB tend to burn out, especially with split brands and the need for multiple ways to book the briefcase and try to keep the concept fresh. Sometimes it works, like making Kane the first person to win and cash in on the same night. Other times, not so much.
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Here are the six most egregious examples of when winning the briefcase wasn't “money in the bank” for the winner.
1. Damien Sandow (2013)
Much like his WWE career, Sandow is jerking the curtain in this list as well. In 2013 he was part of a midcard tag team with Cody Rhodes called Team Rhodes Scholars. This was during the period when every tag team had to have “Team” in their name for some reason. They did a breakup story line that was pretty well received. Cody seemed destined to become the team's star and win the briefcase for Smackdown. Instead, Sandow won the match and the briefcase in a baffling decision that still doesn't make sense.
After that win, he lost match after match on TV, although the feeling from fans was that guys get beaten a lot when they have the briefcase because you want the eventual cash-in to be a big shock. Sandow lost pretty much every match for three months and then waited for world heavyweight champion John Cena to be worn down by a match on “Raw” in the fall, at which point he went out and cashed in his title shot.
And then he lost cleanly in what was a complete squash by the champion. This was the first, and to date only, time a briefcase holder challenged for the title and lost. WWE made no effort to rehabilitate Sandow afterward, and he basically became a jobber.
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The decision to go this route remains a real head-scratcher. The prevailing theory is that WWE wanted to try some clever story where Cody Rhodes challenged Sandow for the case at SummerSlam and ended up winning it from him, which would put the story line back in the direction everyone assumed it was going. Instead, Sandow got his one win on PPV and then went hurtling back down to the undercard. This was the very definition of a wasted briefcase win.
2. John Cena (2012)
Although Sandow was the first person to cash in and lose, he wasn’t the first person to cash in and not win.
Cena won the briefcase in 2012 in the midst of the “John Cena has the worst year of his life” story line, where he still won titles and made millions of dollars and did all the other things that 99 percent of the population wishes it could do. This one was at least an understandable experiment on WWE’s part, because having a bunch of midcarders in the main event wasn’t a great way to boost PPV numbers. Instead, it had an “All-Star” Money in the Bank match for “Raw” that year, with only Cena, Big Show, Chris Jericho, the Miz and Kane involved. The idea was that CM Punk was WWE champion and was going to hold it for another eight months, so WWE needed to have someone fail the cash-in without hurting the challenger. And since Cena is bulletproof, he was the guy to do it.
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Shortly after winning the briefcase, Cena challenged Punk for the main event of “Raw” on whatever anniversary they were celebrating that year, and cashed in the briefcase in advance to hopefully draw a big rating for the show. Cena was only the second person to give advance notice of his cash-in, after Rob Van Dam did the same thing to Cena in 2006. Cena, of course, had the match and the title won against Punk, but Punk ended up getting himself disqualified to save the title, thus turning heel and continuing the miserable existence that was John Cena’s year in 2012.
You’ll note, of course, that Cena didn’t actually lose the match but rather just failed to win the title. He might have been having the worst year of his life, but there was no need to be crazy about it.
3. Sheamus (2015)
This was another baffling decision, and one that didn’t help anyone. Basically everyone assumed Roman Reigns was walking out with the briefcase because he was the guy who was supposed to be the big star of the future; instead, we got “swerved” and Sheamus ended up winning. Then he got sucked into the incredibly lame “League of Nations” faction and mostly did nothing with the case because the WWE world champion was Authority-endorsed Seth Rollins and there really wasn’t a story line there.
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In fact, there wasn’t a logical place to slot Sheamus into the main event scene until Rollins suffered a fluke injury in the fall and was forced to vacate the belt. A tournament was held at Survivor Series 2015 to crown a new champion, and Reigns beat bestie Dean Ambrose in a disappointing finale. This was finally the time for Sheamus to cash in. He won the title with the Brogue Kick, giving the world the meme of Roman sobbing on the mat afterward. The company almost immediately changed its mind and Reigns won the title back on “Raw” a month later, thus rendering the entire exercise pointless.
Sheamus wasn’t elevated by it at all. He was left looking like the fluke transitional champion that he was, and Reigns was no more over for beating him. In retrospect, WWE should have just given it to Reigns and been done with it.
4. Mr. Kennedy (2007)
Kennedy was supposed to have an epic 2007. He was selected to be the guy to carry the briefcase, and he was going to be revealed as Vince McMahon’s illegitimate son before winning the world title and taking over the company. The first step came at WrestleMania 23, when he won the third Money in the Bank briefcase and held it for a little over a month. He had previously announced that he would wait until WrestleMania 24 and cash it in against one of the champions at that point, which was a bold move if nothing else.
Unfortunately for him, he suffered a severe arm injury, which was thought to keep him out of the ring for up to seven months. The solution was to have Edge win the briefcase instead on an episode of “Raw." This is the only time someone has won a briefcase in a match other than the MITB ladder match itself. Edge cashed in the next day and became world champion while Kennedy sat on the sidelines. Kennedy then suffered the double-whammy of being nailed in the Signature Pharmacy scandal.
In hindsight, it’s kind of a good thing Ken didn’t get busted and suspended while world champion, but he still ranks of one of the lamest choices for briefcase winner, a flash in the pan who would be gone from the company a year later.
5. CM Punk (2008)
Put down the pitchforks; I’m talking about his first one.
Punk won the briefcase at WrestleMania 24 in what was his breakthrough moment. He went from loser brand ECW to the main roster and in the process became a big star.
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His cash-in against Edge was a great moment, with Batista getting revenge on Edge by softening him up for Punk to beat, but his title reign was forgettable, at best. His main opponent was washed-up JBL, in a feud where Layfield mostly made him look like a job guy who was lucky to be in there with him. Further, Punk was not treated as any kind of legit world champion or main eventer; he was frequently shunted to the middle of the show while bigger stars like John Cena or Randy Orton wrestled in the main event. In fact, Punk was way down the card at SummerSlam 2008 when he faced JBL in a title match that was barely treated like a title match while Batista and Cena were in the main event.
Punk held the title for a few months before he was stripped of the belt in September 2008 after getting attacked by Orton and being unable to defend it at the Unforgiven PPV, and that was that.
Yes, Punk’s second briefcase win in 2009 was much better (and ironically the result of a drug suspension to rumored winner Jeff Hardy), but his first one might as well not have happened at all.
6. Jack Swagger (2010)
Finally, our poster boy for lame briefcase holders. Swagger won an overstuffed MITB ladder match at WrestleMania 26, and the result made no sense. Swagger showed star power as ECW champion the year before and looked like someone who should be a star, but he was never able to put the pieces together in the ring.
There were mitigating circumstances around this bout, though. This was the last year to feature the briefcase being contested at WrestleMania instead of the standalone Money in the Bank PPV, and WWE had already announced the debut of that standalone show for later in the year, so clearly it had to get rid of the briefcase early so there wouldn’t be multiple ones around to confuse the issue.
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Unfortunately for Swagger, he has a lisp, which means Vince McMahon was unlikely to fully get behind him as a top guy. That was never more apparent than his rushed cash-in. He beat Chris Jericho for the world heavyweight title after holding the briefcase for only a couple of weeks, and then, much like CM Punk, immediately plummeted back down to the midcard. Although he retained the title against Randy Orton a month after winning it, he quickly dropped it to Rey Mysterio in a four-way match and then moved on to hanging out with Chavo Guerrero in an eagle costume.
He got more shots at being elevated here and there, but he never again got close to the world title level. He has become mostly a footnote in the history of the "Money in the Bank" briefcase. Given this list of also-rans, that’s saying something.
