At time of writing, the 2020 Money in the Bank (MITB) pay-per-view (PPV) is set for Sunday, May 10th. With all that is going on with the world right now, it's hard to say if the WWE will go through with the event; however, if WrestleMania 36 rolled on, there's a very good chance MITB will, too.
With the event mere weeks away, it's only natural to be reflective about who's won in the past and the incredible briefcase cash-ins the WWE Universe has seen along the way.
10 Bayley - 2019
A babyface Bayley would make history in 2019 as the third female superstar to be crowned Miss MITB during last year's PPV. While many within the WWE Universe were rooting her on, she would turn around and shock the live crowd and audience at home when she cashed in her briefcase on the same night she won it.
Charlotte Flair was able to pull out a win on Becky Lynch that night, turning the champ into just the RAW Women's Champion, but before Flair could truly celebrate, Bayley ran down from the ramp and pulled a fast one on The Queen by cashing in her contract and beating Charlotte to become the new SmackDown Women's Champion.
9 Randy Orton - 2013
Daniel Bryan had hit some huge momentum in 2013 with his "YES!" movement and was slated for a major match come SummerSlam that year against John Cena for the WWE Championship. Bryan would pull off an incredible victory, but, before he had a chance to truly get those YES! chants going, along came Randy Orton poised to cash-in his MITB briefcase.
Thanks to a little interference from guest referee Triple H, Daniel's championship dreams were shattered, and the corrupt era of The Authority was born, where the faction dominated Monday Night RAW for months.
8 The Miz - 2010
As memorable as The Miz's Raw 2010 MITB cash-in was, what was even more memorable was the live audiences' reaction, moreover that angry little girl who was clearly not pleased with the Miz's championship win, an image that continues to live on in memes everywhere! Whatever happened to her? Regardless, the Miz would not only move on to become the WWE Champion but would also defend the title in the main event at WrestleMania 27 the following year against John Cena.
7 CM Punk - 2008
CM Punk has some major bragging right around MITB, winning two consecutive ladder matches to attain briefcases in both 2008 and 2009. His 2008 cash-in hits this list, thanks to a couple of things.
First off, he was drafted in June of that year to RAW, and, during his first official night the week after his draft, he'd successfully cash-in on the then-champ, Edge. This would be the first of three incredible WWE World Championship reigns for Punk, helping to carve a solid yet sometimes controversial legacy for the superstar.
6 Carmella - 2017
Carmella hit a lot of milestones when she scored the Miss MITB title. Not only was she the first woman to win the ladder match, but she also became the first female superstar to successfully cash-in her briefcase the following year, as well as being the longest MITB winner to hold onto their contract before cashing it in at 287 days.
While she had teased a cash-in plenty of times while she held the MITB briefcase, two days after WM 34, she defeated Charlotte Flair to snag the SmackDown Women's title after the Queen was attacked by the IIconics.
5 RVD - 2006
As memorable as "angry little girl" was during The Miz's 2010 MITB cash-in, so was the infamous "If Cena Wins We Riot" sign from Rob Van Dam's win in 2006.
Picture it: ECW's One Night Stand PPV, where the impossible finally became possible, when anti-establishment hero (a.ka. RVD) took on the company face that ran the place back then (a.k.a. John Cena) when he cashed in his MITB briefcase and defeated the Cenation leader to become the new WWE Champion. It happened, and it was wonderful, right down to Paul Heyman hitting the three-count for RVD's win.
4 Edge - 2006
Speaking of 2006, the OG MITB winner Edge was the very first superstar in history to win the coveted briefcase, during the first MITB ladder match that took place during WM 21, back in 2005. The Rated-R Superstar would move on to cash-in his contract against John Cena in 2006 during the New Year's Revolution PPV, taking advantage of the fact that the champ had just finished a grueling Elimination Chamber match. Edge would score the win to become champion, setting a trend of sorts for MITB winners—especially heels—to wait patiently for the opportunity to cash-in on a "vulnerable" opponent.
3 Dolph Ziggler - 2013
With A.J. Lee and Big E. by his side, Dolph Ziggler successfully cashed-in his MITB contract during the April 8th edition of RAW that year against Alberto Del Rio. He caught Del Rio off guard after just finishing up a win over Jack Swagger and his manager Zeb Colter in a handicap match. Ziggler would hold that briefcase for nine months that year, and his win over Del Rio that night signified his second reign as WWE World Champion.
2 Dean Ambrose - 2016
Dean Ambrose made history in 2016 when he become the MITB winner that year, cashing the contract in on the very same night. He also didn't cash-in on any old match, he barged into the main event for the PPV that saw Seth Rollins go toe-to-toe against Roman Reigns, his old faction brothers.
The Hounds of Justice experienced an unofficial reunion when Roman Reigns started out as the WWE Champion early on in the night, only to lose the title to Seth Rollins during the match and then have Dean Ambrose cash-in and walk out as the one with the gold. In one night—one single match—the WWE Universe bore witness to all three members of the Shield as champion at one point or another.
1 Seth Rollins - 2015
Speaking of history being made, when Seth Rollins arrived on-ramp during the WrestleMania 31 main event against Brock Lesnar and Roman Reigns, he blew the MITB and WM history books right out of the water. He became the first superstar to cash in during a WM, first superstar to cash-in during a single main event WM match —thus, turning the bout into a triple threat match—first MITB contract cash-in in the middle of any match, for that matter. He walked out of WM 31 as WWE Champion and changed the MITB game forever.