With Money in the Bank 3 weeks away, I’ve been pondering on some of my favorite cash-ins. When a superstar runs down that aisle with briefcase in hand, it presents one of the most exciting moments in WWE. The spontaneity, the suddenness of the moment, and the near guarantee of a new champion. There are so many factors that make a Money in the Bank cash-in exciting, and I believe these 10 have stood out from the rest. They’ve certainly been my favorites. With that said, here are my 10 favorite Money in the Bank cash-ins in the history of WWE.
10. Rob Van Dam cashes in on John Cena at One Night Stand (2006)
Rob Van Dam was the 2nd Money in the Bank winner, but he instantly tried to stand out from those who would come after him, because he actually told John Cena well in advance when he was going to cash in his Money in the Bank contract, taking away the advantage of being able to score a victory over a disadvantaged John Cena. Ironically, he cashed it in on the only other superstar in WWE history to tell his opponent when he was going to cash in the contract, as John Cena told CM Punk he was going to cash in his contract for the WWE Title at Raw 1000. The actual match wasn’t really anything special, and it is more known for the chaotic environment that both men wrestled in if anything. However, the atmosphere was absolutely electric, and when Paul Heyman came running down to make the winning pinfall, Rob Van Dam, a fan favorite in his prime won the WWE Championship for the first time in his career. Unfortunately, the biggest push of his career would be short-lived, due to being busted for doing weed and drugs with Sabu. It especially sucks because Rob Van Dam was the only superstar in WWE history to hold the WWE and ECW World Titles simultaneously, and he would drop both world titles to Edge and The Big Show the following two days.
9. Kane cashes in on Rey Mysterio at Money in the Bank (2010)
Money in the Bank was made into its own exclusive PPV in 2010, and while there wasn’t anything particularly unique about this PPV, it did have one special moment. Kane outlasted a litany of superstars to win the Money in the Bank contract to earn a shot at the World Heavyweight Championship. However, Kane would set a different standard for Money in the Bank cash-ins, because he would be the first superstar to cash in the contract the night he won it. And it was an ingenious move because no one saw it coming. Of course, Kane benefited from the fact that he was the first person to do it, thereby adding more shock to the moment.
Rey Mysterio successfully defended the World Heavyweight Championship against Jack Swagger, but he didn’t leave the match unscathed, as Jack Swagger attacked Rey Mysterio after the match. Kane came out and it was initially thought he may be coming to Rey Mysterio’s aid. But once his pyro hit, it was clear what his intentions are. Kane made short work of Rey Mysterio and won the World Heavyweight Championship. Kane’s world title reign would be uneventful, however, as he would go through a horrible feud with The Undertaker in the fall of that year and eventually lost it to Edge at TLC.
8. Edge cashes in on The Undertaker (2007)
Edge was known as the Ultimate Opportunist in his storied WWE career, and he only perpetuated that moniker on one SmackDown night in 2007. Edge was involved in the Money in the Bank ladder match at WrestleMania 23, but he would, unfortunately, come up short. Then, Edge taunted and goaded the winner of the match, Mr. Kennedy, to the point where Mr. Kennedy accepted a challenge from Edge where his briefcase was up for grabs. Edge, ever the opportunist, attacked Mr. Kennedy before the match even began, and all it took was one spear when the match became official, and Edge was once again Mr. Money in the Bank.
The eventful week for Edge wouldn’t end there, because while he was a Raw superstar at the time, the briefcase was brand-neutral before 2010, meaning you can crossover and cash in on any world champion of the winner’s choosing. Since Edge already cashed in on the WWE Champion at the time, John Cena, he chose for a bigger fish in the sea, The Undertaker. After a grueling steel cage match against Batista, and a post-match attack from Mark Henry, The Undertaker was left battered and bloodied, but still, World Champion, until Edge came in. It wasn’t easy and took more than just one pin to finish him, but with one spear, Edge became World Champion.
Funny thing is Edge was fortunate here because this was supposed to be Mr. Kennedy’s moment. However, injuries plagued Mr. Kennedy for his WWE career, but this time, WWE misdiagnosed his injury and gave the briefcase to Edge. He was originally reported to have torn his right triceps completely to the bone and be out for 5-7 months, but he actually only had a massive hematoma and would have recovered with normal rehab. A big what-if in WWE history. Ironically, Edge himself would have to relinquish the World Title himself not long after his victory due to a right pectoral muscle tear.
7. Daniel Bryan cashes in on The Big Show at TLC (2011)
The sheer dynamics of this cash-in is what makes this moment particularly special. Probably the smallest guy on the roster in terms of weight, Daniel Bryan, cashing it in on someone over twice his height and size. The Big Show had finally captured the World Heavyweight Championship from Mark Henry, but he, like many others on this list, suffered the trope of the post-match attack leading to the cash-in. Daniel Bryan’s music hit and everyone knew what was happening. The only thing that was questioned was whether or not Daniel Bryan would be able to pull it off, because in a straight-up match, even if he’s hurt, Daniel being able to get a huge behemoth for a pinfall or submission victory would be difficult. Fortunately, Mark Henry softened him up to the point where only one pinfall attempt was enough for Daniel Bryan to capture the World Heavyweight Championship for the first time in his career.
Daniel would go on to be the face of SmackDown from late 2011 to early 2012 until his reign ended in 8 seconds at WrestleMania 28 at the hands of Sheamus.
6. Randy Orton cashes in on Daniel Bryan at SummerSlam (2013)
Randy Orton is one of my favorite superstars in WWE history, so this being on the list was a given. However, this cash-in set the stage for a much bigger purpose down the line. Anyway, Daniel Bryan and John Cena finished one hell of a match that saw Daniel Bryan won the WWE Championship clean. It was a great moment and the entire Staples Center was hot on fire that Daniel Bryan finally held WWE’s top title. However, the celebration was short-lived as we were interrupted by Randy Orton’s music. He ran out with the briefcase but started to give it second thoughts. He raised the contract high above his head as a reminder of what’s in store for him in the future……or immediate future. He retreated, but not before looking back one last time. Then, the special guest referee for the WWE Championship match, Triple H, shockingly pedigreed Daniel Bryan from behind. Randy Orton, like a snake, slithered to the ring, one pinfall, and just like that, Randy Orton was once again WWE Champion.
While the return of Evolution that people predicted wouldn’t happen after WrestleMania, the bigger purpose behind all of this was the stage set for Daniel Bryan’s long journey to reclaiming what he never fairly lost. He did win the title back around 4 weeks later at Night of Champions, but it was stripped away from him due to a fast count from the referee. Randy Orton remained WWE Champion for most of the time period after Daniel Bryan lost it until he won it back from Randy Orton at WrestleMania 30 in a triple threat match involving the two of them and the winner of the Royal Rumble, Batista. This was the start of a journey that had a satisfying payoff.
5. The Miz cashes in on Randy Orton (2010)
The Miz began his WWE career as a Diva talent search host and exiled from the locker room over spilled fried chicken. However, you can’t help but feel that he’s laughing at everyone as he is a grand slam champion and one of the most all-around successful personalities in WWE history. The Miz’s meteoric rise came in 2010 when he won the Raw Money in the Bank ladder match. The Miz waited for the right moment, and one came when an injured Randy Orton just finished a WWE Title defense against Wade Barrett. Randy Orton was vulnerable with an injured leg, and this was the perfect opportunity for The Miz to cash in, and he did just that. Randy Orton actually fared well to begin and it looked like he may actually survive it. However, his bad leg wouldn’t allow him to get enough elevation on an RKO, and one Skull Crushing Finale later won The Miz his first WWE Championship in what must have been an emotional moment for him.
Many people deemed The Miz’s main event title run as a failure and one of the worst main events in WrestleMania history with John Cena resulted in WrestleMania 27. He was basically the third string in a match that was used to build towards a much bigger WrestleMania main event one year later, in John Cena vs. The Rock. However, I guarantee that if The Miz was world champion now, and with everything he’s developed and learned since then, it’d truly be……awesome.
4. Dean Ambrose cashes in on Seth Rollins at Money In The Bank (2016)
Dean Ambrose was sort of going through the motions in 2016. He had a disappointing match with Brock Lesnar at WrestleMania and was in passable, but unmemorable feuds with Triple H and Chris Jericho. However, his fortune would come at Money in the Bank in 2016. He won the contract, and while he did tease that he could potentially cash in his contract on the winner of the Seth Rollins vs. Roman Reigns main event the week prior, we didn’t think it would actually happen because you don’t normally reveal your plans in advance. However, Dean Ambrose stuck to his guns and came out, and blindsided Seth Rollins from behind and won the WWE Championship for the first time in his career, becoming the final member of The Shield to hold the title.
There’s a couple of reasons why this moment was special. Firstly, all 3 members of The Shield held the WWE Title on the same night. But more importantly, it was a culmination of a trio of moments between Dean Ambrose and Seth Rollins which little realized. At Money in the Bank 2014, Seth Rollins won the Money in the Bank contract after Dean Ambrose was screwed over by Kane. At Money in the Bank 2015, Seth Rollins defeated Dean Ambrose for the WWE Title in a ladder match in which the title literally slipped from Dean Ambrose’s fingertips. But the third time would prove to be the charm, as Dean Ambrose would make sure he didn’t leave Las Vegas without the WWE Championship.
3. Dolph Ziggler cashes in on Alberto Del Rio (2013)
The night after WrestleMania 29 was one of the most special nights in RAW history because you had an electric East Rutherford, New Jersey crowd putting themselves over and having one hell of a blast. However, the night was remembered for Dolph Ziggler finally cashing in and winning the World Heavyweight Championship from Alberto Del Rio. Dolph Ziggler had the 4th longest cumulative time holding the briefcase at 267 days, which was 2nd longest to Edge at the time he cashed it in. It got to a point where people thought he would never cash it in or not cash it in successfully. People were actually anticipating Dolph Ziggler to cash it in the night before at WrestleMania 29 after the snoozefest of Alberto Del Rio/Jack Swagger. As a matter of fact, the anticipation of a cash-in was the only thing keeping the crowd awake during the match. When it became apparent that a cash-in wasn’t happening, people started to give up hope, but lo and behold, a swerve. Dolph Ziggler cashed in the Money in the Bank contract and Dolph Ziggler received one of the biggest pops in WWE history when he won.
Dolph Ziggler finally reached the brass ring, but he would seemingly lose it just as much as fast as he won it. Shortly after winning it, he suffered a real concussion from Jack Swagger and subsequently lost the World Title back to the man he won it from at his first title defense at Backlash. This would be his last World Title reign, and we are starting to wonder if he will ever reach it again.
2. Edge cashes in on John Cena at New Year’s Revolution (2006)
While there’s one more entry on this list, rarely anything beats the original. Edge held the Money in the Bank contract tightly for 280 days. Holding it for that long built up anticipation every time he came out, and every time a world champion was involved in a match because he could show up at any time. However, Edge set the standard for a Money in the Bank cash-in. You can cash in the contract at any time, and the wisest thing is to do it when a superstar least expects it or when they are heavily fatigued. Edge had lost the opportunity to become Intercontinental Champion against Ric Flair earlier in the evening and it appeared his night was over. However, John Cena just went through a grueling Elimination Chamber match and came out bloodied, but on top with the title.
However, Vince McMahon came out to everyone’s surprise because we didn’t know what was going on. He came out to announce that we would have a championship match, courtesy of Edge wisely choosing to cash in. While Edge needed not one, but two spears to finish the job, Edge finally reached the brass ring after 8 years in the industry and became WWE Champion in one of the best moments in WWE history. Unfortunately for Edge, this was merely a transitional run for him, because he only held the title for 3 weeks and lost it back to John Cena pretty handily at the Royal Rumble.
1. Seth Rollins cashes in on Brock Lesnar at WrestleMania 31 (2015)
The main event of WrestleMania 31 had many people guessing. Would Brock Lesnar resign with WWE? Would WWE pull the trigger on Roman Reigns and have him win the title? Or will the night end with Seth Rollins cashing in the briefcase? We didn’t know what was going to happen, but when the main event of Brock Lesnar and Roman Reigns began, we didn’t care because we were all so immersed at the moment. Brock Lesnar and Roman Reigns had an incredible physical war before WWE started to saturate these two with the same spots and the same moves at this match. However, this match at WrestleMania 31 was deserving of the main event slot. It was brutal, it felt like a real fight, and Suplex City was on the rage. Brock Lesnar had Roman Reigns up for a F-5 and connected but couldn’t finish the job. Then, Seth Rollins’ music hit and he ran down the WrestleMania aisle.
Normally, someone will cash in Money in the Bank when a match is finished. However, Seth Rollins cashed it in mid-match, thereby making it a triple threat match. Meaning he didn’t have to be involved in the decision to foil his briefcase. However, with some fortunate timing, Seth managed to escape disappointment, curb stomped everyone in sight and left with the WWE Title to complete one of the more improbable endings in WrestleMania main event history. Edge’s victory had more historical significance, but if you want the most memorable cash-in, look no further than The Kingslayer.