WrestleMania 21 hosted the very first Money in the Bank ladder match in 2005. The Money in the Bank ladder match has become so popular, that five years later it became its very own pay-per-view. Winning the Money in the Bank ladder match generally guarantees a World Championship reign. Nine out of the first 10 different Money in the Bank ladder match winners went on to win to clinch a World Championship by successfully cashing in their Money in the Bank contract.
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Unfortunately, some Money in the Bank winners who won the WWE or World Heavyweight Championship had a dreadful World Title reign. However, some benefited from winning the Money in the Bank briefcase as they went on to secure their first World Championship, and they took the ball and ran with it by having a successful World Title reign.
10 Randy Orton
Randy Orton winning the Money in the Bank ladder match in 2013 was a bit of a surprise. However, the Viper's face run had run its course and for the first time in three years, Orton turned heel at SummerSlam alongside his former Evolution mentor Triple H. Orton successfully cashed in his Money in the Bank briefcase with Triple H planting Daniel Bryan with a Pedigree, and Orton captured his 10th World Championship.
Fans were displeased as Bryan was the hottest commodity in WWE in 2013. However, Orton's latest World Title tilt wasn't long for this world. He held the WWE Championship for just one month as Bryan regained the title at Night of Champions.
9 Dolph Ziggler
Dolph Ziggler has been on the cusp of greatness throughout his WWE career, but he has never had a meaningful run with the World Title. Ziggler bided his time and he held the Money in the Bank briefcase for 267 days. On the Raw after WrestleMania 29, the Showoff dethroned Alberto Del Rio for his second World Heavyweight Championship reign.
This was the perfect time for Ziggler to go on and prove himself as a worthy World Champion. Unfortunately, he sustained an untimely concussion. The Showoff was champion for 70 days, and he only defended the title once, which was dropping the title back to Del Rio at Payback 2013.
8 Alberto Del Rio
Alberto Del Rio made history in 2011 as he became the first man to win the Royal Rumble match and the Money in the Bank ladder match in the same calendar year. He almost cashed in the contract at the Money in the Bank event, the same night that he won the briefcase.
CM Punk had beaten John Cena to become the Undisputed WWE Champion at SummerSlam 2011. However, Kevin Nash attacked the Straight Edge Savior. Punk had little resistance, and Del Rio was crowned as the new WWE Champion. Del Rio successfully retained the title once against Rey Mysterio the night after on Raw, but John Cena beat him for the gold at Night of Champions, just five weeks later in a lackluster title reign.
7 Jack Swagger
The final Money in the Bank ladder match to take place at WrestleMania was at WrestleMania 26. Jack Swagger emerged victorious in a jam-packed field. On the following episode of SmackDown, the All-American, American defeated a less than 100% Chris Jericho to win the World Heavyweight Championship for the first time.
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Swagger's World Heavyweight Title run was dismal and he didn't look like a top star throughout his championship run. He managed to score a handy win over Randy Orton at Extreme Rules 2010. His feud with Big Show did him no favors, and Rey Mysterio ended his 82-day World Heavyweight Championship run in a fatal-4-way match.
6 Rob Van Dam
Rob Van Dam had to wait a long time to get his hands on a World Championship. RVD won the Money in the Bank ladder match at WrestleMania 22, and admirably, he announced that he would cash in his briefcase at ECW One Night Stand 2006. John Cena was the reigning WWE Champion, and he received a hostile reception in the Hammerstein Ballroom.
RVD and Cena hit a home run in an excellent WWE Championship match. Moreover, with a helping hand from Edge, RVD secured the WWE Championship. Before RVD's title reign could gain any traction, he got caught by police as he had marijuana. RVD was the reigning WWE Champion and ECW Champion but he dropped both titles to Edge and Big Show respectively, three weeks after winning the WWE Championship.
5 Edge
Arguably, Edge's Money in the Bank cash-in is still the greatest cash-in, in WWE history. The Rated-R Superstar won the inaugural Money in the Bank ladder match at WrestleMania 21. He waited nine months before he cashed it in on a wounded John Cena at New Year's Revolution 2006 to become WWE Champion for the first time.
The Rated-R Superstar was understandably emotional as he achieved his goal of winning the WWE Championship. Although Edge's cash-in was great, his WWE Championship reign wasn't. He beat Ric Flair in a TLC match, but he dropped the title three weeks later back to Cena at the Royal Rumble. Unquestionably, Edge's WWE Championship reign should have lasted longer than it did.
4 Kane
Surprisingly, Kane won the Money in the Bank ladder match at the inaugural Money in the Bank event in 2010. The Big Red Machine had been a prolific performer in Money in the Bank ladder matches. Nevertheless, Kane wasted no time as he made history as the first man to cash in the Money in the Bank briefcase on the same night.
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Kane dethroned Rey Mysterio for the World Heavyweight Championship, and it was his first World Title reign in 12 years. The Devil's Favorite Demon's World Title run was decent, and he beat The Undertaker in three straight World Title matches to retain his title. His 154-day run as champion was ended by Edge in a fatal-4-way TLC match at TLC 2010.
3 CM Punk
CM Punk made history as the first back-to-back winner of the Money in the Bank ladder match at WrestleMania 24 and 25. The Second City Saint's maiden World Heavyweight Championship came at the expense of Edge in June 2008.
Punk feuded with the likes of Batista and JBL during his first World Title run. He wasn't beaten when his first World Title reign was ended at Unforgiven 2008. However, the second time around, Punk turned heel after he cashed in his briefcase on Jeff Hardy at Extreme Rules 2009. Punk feuded with Hardy, and his title reign only lasted a month with Hardy reclaiming the gold at Night of Champions.
2 Daniel Bryan
Fans were pleased when Daniel Bryan won the Money in the Bank ladder match in 2011 for a future World Heavyweight Championship opportunity. Moreover, Bryan took advantage of Big Show, who had just beaten Mark Henry for the World Heavyweight Title in a chairs match.
At TLC, Bryan cashed in his Money in the Bank contract and he captured the World Heavyweight Championship. Bryan turned heel during his title reign, and he did a good job with the Big Gold Belt. He overcame Show and Henry in a triple threat steel cage match at the 2012 Royal Rumble, and he retained the title in an Elimination Chamber match. Infamously, his 105-day championship run was ended by Sheamus at WrestleMania 28 in the curtain-raiser in just 18 seconds.
1 The Miz
The Miz doesn't get the credit he deserves at times, but he finally proved naysayers wrong when he cashed in his Money in the Bank contract on Randy Orton on an episode of Raw in November 2010 to clinch the WWE Championship.
Miz beat Orton in back-to-back bouts at TLC 2010 and the 2011 Royal Rumble to remain as WWE Champion. However, the highlight of his 160-day WWE Championship reign was defeating John Cena in the main event of WrestleMania 27. That was a shocker, but Cena brought the curtain down on Miz's title run at Extreme Rules in a triple threat steel cage match that involved John Morrison.
