Best MITB Cash-Ins In WWE History

The Money in the Bank match has become massive for the WWE. It has been a core part of WWE history for just under 20 years now, if you can believe it. This is incredible to think about, considering most of us probably remember the first one. Since the first cash-in, fans have been invested in the briefcase winner(s) and how they might cash in. The best MITB cash-ins usually have something special about them. It might revolve around a hot star at the time or someone people really liked. It also might just happen in a cool way. Regardless, these cash-ins are memorable and important to WWE fans.

The Money in the Bank ladder match began at WrestleMania 21 and would remain a staple match for five years. By 2010, WWE had the idea to give the Money in the Bank concept its own PPV on the calendar annually. This was a time in the company when former WWE Owner Vince McMahon was trying to garner interest in the PPVs. The company had not been getting proper PPV buys for a while. People were not buying nearly as much as they used to. He figured it was because of old PPVs and ignored the fact that his creative problems were a core issue.

Therefore, gimmick PPVs were attempted massively. The Money in the Bank PPV (now PLE) has been one of the few gimmick PPVs that have survived since then. Having one of the best MITB cash-ins can really help a wrestler. That is a proven fact that some of the people listed below can relate to. That said, let’s get started on our list of the best MITB cash-ins in WWE history!

EDGE

• Cash-In: New Year’s Revolution – 2005

Edge won the first Money in the Bank match at WrestleMania 21. At the time, Chris Jericho just came up with the idea. Vince loved the concept, but no one really knew what to do with it. The winner of the case has a guaranteed title match, sure. However, should this give them the right to face a champion at a specific PPV? Technically, the Royal Rumble match already did this. It would be weird to have two things that did the same thing. Would it allow the person to pick a match date with a champion, in any match they wanted? This had promise…but it still didn’t fit.

That was when Edge and Vince started talking, where Edge came up with the concept that the person should be able to cash in whenever. As long as a referee was around, they had the right to cash in the case on the champion of their choosing any time, any place. Edge was being called “The Ultimate Opportunist” at the time, so what better rule could there be for a guy like that? He would wait until the WWE Champion, John Cena, went through a grueling Elimination Chamber match.

He’d win the match, but Vince McMahon came out to announce that Edge will now cash in the MITB briefcase. With Cena barely surviving the chamber while Edge was fresh as a daisy, he stood no chance. Edge did not have to do much before he hit a spear and pinned Cena, securing the first World Championship of his career. This still stands out as one of the best MITV cash-ins ever.

THE MIZ

• Cash-In: WWE Monday Night RAW – November 22, 2010 

In 2009 & 2010, WWE had been making The Miz into something pretty special. He ditched his shorts and tank top for normal trunks and wrestling attire, changing his look. WWE slowly began to give him bigger and bigger opportunities, leading to an Undisputed Tag Team Championship run and even a long run with the WWE United States Championship. He won the RAW Money in the Bank match at the 2010 Money in the Bank PPV, which was big. He held the case and the U.S. Title together for a bit, but fans knew something might be changing soon after.

A few months later, he lost the U.S. Title to Daniel Bryan. Most felt this was a sign that WWE was now planning to have Miz cash in the briefcase, and we were right. On November 22, 2010, in an episode of WWE Monday Night RAW, the WWE Champion, Randy Orton, was beaten down by Nexus and their leader, Wade Barrett. Of course, Barrett injured Orton’s leg, but the champion won his match with Wade. This was the perfect time to take advantage of the fallen champion, though.

Now hurt, Orton was a perfect victim for The Miz, who would come out to cash in his briefcase. Orton put up a fight, but it was not for very long. Miz hit his Skull Crushing Finale finisher, pinning and beating Orton for his first World Title reign. It was a big moment for Miz, but fans loved it too. We all felt Miz had earned this over the last several years, so it was a nice moment. Miz took that momentum to the main event of WrestleMania 27, too!

CM PUNK

• Cash-In: Extreme Rules – 2009

CM Punk is the only person to have won two Money in the Bank matches. While Edge & Miz both cashed in twice, they won their second briefcase off of the winner of that year’s MITB match. Edge took it off Mr. Kennedy, while Miz took it off Otis. That said, Punk won both the 2008 & 2009 Money in the Bank ladder matches at WrestleMania. This makes him the only man to cash in a briefcase twice in consecutive years. His first cash-in was cool as he took the World Heavyweight Championship off of Edge, who was headed to SmackDown from RAW due to the WWE Draft.

That cash-in was cool, but it did not really help Punk. Not only did he have his title taken away from him in a match he was not involved in, but fans started to turn on him slowly. WWE decided to turn Punk into a heel by 2009 fully. Jeff Hardy, who was always a risk as a World Champion, had won the World Heavyweight Championship from Edge. Hardy was beaten badly in the match but won the title despite the pain he put himself through. Punk knew this was the perfect time to strike.

Hardy lost the title to Punk, who was booed by the fans for taking the title away from the fan favorite. This led to Punk’s first heel run, where he became the “Straight Edge Savior.” Due to Hardy’s history of abusing drugs and alcohol, it was the perfect gimmick for Punk to switch to and came at a perfect time. It all started with the big win over Hardy, which is why it was one of the best MITB cash-ins of all time.

BAYLEY

• Cash-In: Money in the Bank – 2019

Fans loved Bayley during her run on the NXT brand. She was the NXT Women’s Champion there and could do no wrong. Most felt she could be the female John Cena when she ended up on the main roster. However, when she arrived, she went from being booked by Triple H to being booked by Vince McMahon. This changed her entire dynamic, leading fans to experience a totally different Bayley from what they knew. It hurt her, the character, and much more. WWE tried to utilize her at the top as much as possible, even giving her a run with the WWE Raw Women’s Championship.

However, things did not seem to work. This is why 2019 was such a big year for Bayley, as she needed to make a change. That all started by winning another World Championship. She’d win the 2019 Women’s Money in the Bank match but did not like the idea of waiting. After Becky Lynch lost her match with Charlotte Flair later that night, Flair showed signs of weakness. To be fair, Flair had already been overused at the top, and fans were tired of seeing it. Beating Lynch just added fuel to that.

Bayley came out and successfully cashed in her briefcase on Flair to become the SmackDown Women’s Champion. Not too long after, Bayley realized she needed to make a big change. She’d turn heel for the first time, killed the Bayley Buddies (wacky inflatable arm-flailing tube men), and even cut her hair. It led to one of the best versions of Bayley there has ever been. From how and who she cashed in on to the character change, this was one of the best MITB cash-ins of all time.

DANIEL BRYAN

• Cash-In: November 25, 2011 episode of SmackDown & WWE TLC – 2011

This entry is controversial, but Daniel Bryan won the SmackDown Money in the Bank briefcase at the 2011 Money in the Bank PPV. However, an issue came up when he tried to cash in his MITB case. Big Show & Mark Henry were involved in a rivalry together where the two big men would put on some great matches. One of those even involved breaking the ring, too. That said, they were battling over Henry’s World Heavyweight Championship.

On November 25, 2011, Big Show & Mark Henry were in the ring doing a segment on SmackDown where Big Show punched Henry. Due to Show’s punch being called the WMD, one punch could knock a person out. That said, the champion was out, so Daniel Bryan rushed down to the ring, where he successfully pinned Henry. However, this is where the controversy came up. SmackDown General Manager Teddy Long claimed Henry was “not medically cleared to compete” when Bryan cashed in.

This is complete crap and does not matter, but WWE’s story-telling was nonsense during this time. That said, Henry remained champion…until the WWE: Tables, Ladder, & Chairs PPV a month later. Big Show actually won the match, defeating Henry. Mark was upset and attacked Big Show, beating him down badly. Bryan then rushed down to the ring to cash in yet again, this time winning the title.

We feel this is one of the best MITB cash-ins of all time because Bryan had to cash the case in twice, both times winning over much larger men.

DEAN AMBROSE

• Cash-In: Money in the Bank – 2016

Dean Ambrose has one of the shortest runs with the Money in the Bank briefcase there has ever been. At the 2016 Money in the Bank PLE, Ambrose won the Money in the Bank match. It was a big moment for the Lunatic Fringe, as he was the only Shield member to have never won a World Championship in WWE up to that point. When he won the case, everyone was pretty happy to see it. The best part was that he now could cash the case in at any time, which made some of us come up with all of these crazy things Ambrose might do.

However, the Lunatic Fringe has never been able to stop himself from taking a risk when the reward could be huge. That said, just over an hour later, he decided to make his move.

Seth Rollins returned to WWE after missing several months of action due to a severe knee injury. He attacked WWE World Champion Roman Reigns at the previous PLE, leading to the two facing off at the Money in the Bank PLE. Rollins defeated Reigns, but just as he would start to celebrate, Ambrose came out of nowhere. He hit Rollins from behind with the case and then cashed it in. He’d beat Seth, which offered such sweet revenge for Dean.

Most people love this cash-in moment, as do we. This is why we feel it is one of the best MITB cash-ins ever.

DAMIAN PRIEST

• Cash-In: WrestleMania 40

Damian Priest cashed in his MITB briefcase just recently at WrestleMania 40. Going into the WrestleMania 40 WWE World Heavyweight Championship match between Seth Rollins and Drew McIntyre was simple. Rollins, who was returning from a legitimate knee injury, wrestled on Night #1 of WrestleMania on the night before. Drew was fresh, avoiding any action before Night #2. The two even opened the show for Night #2. Drew was in a storyline rivalry with CM Punk at this time, too.

He invited Punk to sit at the announce table to see him beat Rollins. Punk did just that as Drew beat the relatively injured Rollins. However, he celebrated a lot and got into Punk’s face. This led to an altercation, resulting in Drew being thrown for a loop. Priest took this opportunity to come out and attack McIntyre. Drew’s hubris was his downfall, as Priest beat him for the title.

We rank it among the best MITB cash-ins because it just made sense. Plus, it was the absolute perfect time to do it, too. Priest might have lost the WWE Undisputed Tag Team Titles the night before for Judgment Day. However, he left WrestleMania as the WWE World Heavyweight Champion. One could not ask for more from the guy.

LIV MORGAN

• Cash-In: Money in the Bank – 2022

Liv Morgan has one of the best MITB cash-ins of all time, likely due to how unexpected it was. It also helped that she would cash the briefcase in on one of the most feared women in WWE, Ronda Rousey. It is worth noting that Morgan has one of the shortest runs with the briefcase. She did not want to wait for months, prowling around to different brands and merely attempting to make at least two “think” she might cash in the case. She was not interested in all of that.

Rather, Morgan realized that no one would think she’d cash in the night of the Money in the Bank event. Moreover, she’d never cash in on Rousey. Yet just as Rousey beats Natalya to retain her championship, the slightly wounded champion would see Liv come for her. It was not as if Morgan was fresh, as she had a ladder match earlier in the night. Morgan attacked Rousey, only to be put into an anklelock by the champion.

However, Morgan managed to get out and would roll her up to get the shock win. While Morgan’s reign with the WWE SmackDown Women’s Championship was not incredible, she’d somehow manage to beat Rousey in a rematch. This made her the only woman in history to beat Rousey twice in consecutive matches. That said, her shocking cash-in is still one of the best ever.

DOLPH ZIGGLER

• Cash-In: RAW after WrestleMania 29 – 2012

Dolph Ziggler was a veteran in WWE who had all the tools to be a World Champion. He held the WWE Intercontinental & United States Championships and even held the WWE Tag Team Titles. The man had charisma and was one of WWE’s best “sellers.” He deserved to hold a World Championship in WWE, and by this point in his career, he’s in his prime. Ziggler also could not have been more “over” with fans, even as a heel.

WWE recognized this, allowing him to win the Money in the Bank briefcase. While he did tease some cash-in attempts, the big one came on the night after WrestleMania 29. It could not have been a more perfect time to do it. Ziggler had the longest run with the case, and some assumed he might cash it in at WrestleMania. The RAW after WrestleMania is always a hot show, and people from all over the world are in attendance.

These people loved Ziggler. When the World Heavyweight Champion, Alberto Del Rio, beat Jack Swagger in a match…he was glad it was over. During the match, he injured his ankle and was not in a good place physically. Ziggler was like a shark that smelled blood and came out to cash in. Del Rio tried to fight Dolph off and did well initially before Ziggler went for his ankle and hit his finisher.

The pop that Ziggler got when he won is still one of the best and biggest we’ve ever heard. This makes us feel it is one of the best MITB cash-ins in history.

SETH ROLLINS

• Cash-In: WrestleMania 31

Is there a better cash-in than this? Honestly, we’re not sure there ever will be. The small backstory is that Seth Rollins had gone heel the year before this, as he turned on Dean Ambrose (Jon Moxley) & Roman Reigns. That effectively ended the Shield faction, as Rollins joined The Authority. Money in the Bank came up shortly after, where Rollins won the briefcase. He teased a cash-in often but never pulled the trigger. The WWE was heavily behind Roman Reigns then, but fans weren’t digging him.

Still, Reigns won the Royal Rumble, which earned him the right to headline WrestleMania 31 with Brock Lesnar for the WWE Championship. Seth, meanwhile, wrestled Randy Orton on the card. He took one of the best RKOs in WWE history to end that match. We thought Rollins’ night was over after that, but he had more in store for us.

People were not looking forward to Reigns/Lesnar, but in all fairness to both men, they put together an incredibly physical match. Yet fans were still not sold on Reigns, so Vince McMahon pulled the trigger to have Seth cash in. WWE wanted to end this event with a new era and a young star on top of the company, but it would not be Reigns leading that. Seth cashed in and won the title in dramatic fashion.

It was shocking, and everyone loved it. If you ask any wrestling fan their favorite cash-in, this will likely be one of the first they mention. That makes it worthy of being considered one of the best MITB cash-ins ever.