The majority of Money in the Bank ladder match winners went on to become certified main eventers during their WWE careers. However, some of the first 10 to win it was amongst the very best, and others were questionable.
Gimmick matches come and go but WWE has nailed it to perfection with the Money in the Bank ladder match. The first six MITB ladder matches were featured exclusively at WrestleMania, but the event was so successful that it attained its own pay-per-view in 2010.
Winning a Money in the Bank ladder match definitely suits a heel more than a babyface as a heel will attack a champion when they are vulnerable. Some of the very best to hold the MITB briefcase have gone on to become a World Champion and ensured that their cash-ins were memorable.
10 Mr. Kennedy
When Mr. Kennedy won the Money in the Bank briefcase at WrestleMania 23, it was well deserved and Kennedy was destined for greatness. Unfortunately, the issue with Kennedy was that he always ended up getting injured at the wrong time.
WWE panicked and thought that Kennedy's right tricep injury was worse than it actually was. Therefore, he dropped the Money in the Bank contract to Edge on the May 7, 2007, edition of Raw which would have been a bittersweet moment for Kennedy.
9 Jack Swagger
The Money in the Bank ladder match at WrestleMania XXVI was one of the worst iterations of the match. Jack Swagger emerged as a surprise winner, and he had trouble unhooking the briefcase which has been edited out on the WWE Network.
Swagger was far from a popular choice to win it as veterans Matt Hardy or Christian were favored amongst the fans to get their moment as a World Championship contender. The All-American American wasted no time in cashing in his contract on Chris Jericho just days later for his maiden World Heavyweight Championship reign. Swagger's World Title reign was forgettable, and he was barely featured in the World Title picture after he dropped the strap.
8 Alberto Del Rio
Alberto Del Rio won the 40-man Royal Rumble match at the 2011 Royal Rumble but failed to convert his Rumble victory into the World Heavyweight Championship at WrestleMania XXVII. Nevertheless, The Mexican Aristocrat was knocking on the door of greatness and he prevailed in a dreadful MITB ladder match at Money in the Bank 2011.
Mr. McMahon forced Del Rio to cash in his contract to stop CM Punk "leaving" WWE with the WWE Championship. Ultimately, his cash in was voided as Punk attacked him. Finally, Del Rio became a World Champion in WWE when he dethroned Punk at SummerSlam by cashing in his contract with a little help from Kevin Nash. Del Rio's time as Mr. Money in the Bank wasn't great and fans hated the fact that he ended Punk's reign early.
7 Kane
The inaugural Money in the Bank pay-per-view extravaganza occurred in 2010 and it kicked off with SmackDown's MITB ladder match. Kane had been a mainstay in WWE for over a decade and he triumphed over the likes of Big Show, Cody Rhodes, Kofi Kingston, Christian, Matt Hardy, Dolph Ziggler, and Drew McIntyre.
SmackDown's Money in the Bank ladder match was one of the longest MITB ladder matches in history. Whilst the match was not great, Kane made up for it as he cashed in the Money in the Bank briefcase, ending Rey Mysterio's World Heavyweight Championship reign emphatically.
6 Rob Van Dam
At WrestleMania 22, Rob Van Dam was on the cusp of becoming a future World Champion. Fans rejoiced when RVD outlasted Shelton Benjamin, Ric Flair, Finlay, Bobby Lashley, and Matt Hardy to become the second holder of the Money in the Bank briefcase.
Van Dam also made history as the first man to hold a title when he owned the MITB briefcase. He captured the Intercontinental Championship from Shelton Benjamin at Backlash 2006. However, RVD was admirable when he announced that he was going to cash in his Money in the Bank contract against John Cena at ECW One Night Stand. RVD dethroned Cena for the WWE Championship with a little help from Edge but to do it at the Hammerstein Ballroom was a hallmark moment for Van Dam.
5 Daniel Bryan
Daniel Bryan was the perennial favorite to win SmackDown's MITB ladder match at Money in the Bank 2011. Bryan certainly deserved to win the match, and Bryan did a decent job as Mr. Money in the Bank.
At TLC 2011, Big Show had just defeated Mark Henry for the World Heavyweight Championship but Henry was angry and viciously assaulted Big Show with a steel chair. Bryan picked up the scraps and became the World Heavyweight Champion by pinning Show. Bryan turned heel during this time frame, and his maiden World Title run in WWE is memorable for losing the title to Sheamus in just 18 seconds at WrestleMania XXVIII.
4 The Miz
Whilst The Miz's WWE Championship reign may have not been the best, his time as Mr. Money in the Bank was certainly awesome. The Miz outlasted a strong field that featured Edge, Randy Orton, Mark Henry, Chris Jericho, Evan Bourne, John Morrison, and Ted DiBiase.
Miz was the reigning United States Champion and he was an obnoxious heel when he held the contract. Finally, on the Raw after Survivor Series 2010, Miz took advantage of a weakened Randy Orton to become the new WWE Champion.
3 Dolph Ziggler
Dolph Ziggler's time as Mr. Money in the Bank was one wild rollercoaster. Ziggler held the briefcase for 267 days, but it did not come easy. The Showoff actually defended the briefcase twice, when he defeated Chris Jericho in August 2012, and overcame John Cena in a ladder match at TLC 2012.
Despite being a heel and having Vickie Guerrero in his corner, Ziggler was one of the most popular Superstars on the roster. On the Raw after WrestleMania 29, Ziggler cashed in his Money in the Bank contract on Alberto Del Rio, and he captured his second World Heavyweight Championship. The raucous ovation he received was spine-tingling and one of the best moments on Raw.
2 CM Punk
When you think about Money in the Bank winners, CM Punk often comes to mind. The Second City Saint made history as the first back-to-back Money in the Bank ladder match winner at WrestleMania XXIV and the 25th Anniversary of WrestleMania.
Punk successfully cashed in his contract on both occasions. He defeated Edge on an episode of Raw in June 2008 after Batista laid The Rated-R Superstar out. Punk's maiden World Heavyweight Championship run wasn't great but a year later he had his redemption. More polished as a top Superstar, Punk cashed in on a wounded Jeff Hardy for his second World Heavyweight Title run and he turned heel during his reign.
1 Edge
Edge had been knocking on the door as a World Championship contender for many months but needed a push to get over the line. That came at WrestleMania 21 when Edge defeated Christian, Chris Jericho, Kane, Shelton Benjamin, and Chris Benoit to become the inaugural Mr. Money in the Bank.
The Ultimate Opportunist lived up to his moniker in arguably the greatest cash-in in WWE history. Edge picked his opportune moment to end John Cena's 280-day reign as WWE Champion at New Year's Revolution 2006. The tears flowed, and whilst Edge's reign only lasted a meek three weeks, he certainly arrived as a permanent fixture in the main event scene.