Six WWE superstars with the highest number of Money in the Bank ladder match appearances

Money in the Bank has been here for almost fifteen years, and it still produces a world of fun in each instalment. This is one of the few gimmick matches which is pretty much always entertaining and high in quality. A bunch of WWE superstars have made their name for themselves in the Money in the Bank ladder match, before ascending to the main event.

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The likes of Edge, CM Punk and Seth Rollins come to mind while talking about the bonafide stars created by this match. However, these three have had a total of eight ladder matches between them. That is just one more than the person who has competed in the most Money in the Bank ladder matches to date.

Out of the six most frequent competitors in this match, only two of them have won the briefcase. They have provided us with countless memorable ladder and briefcase moments throughout the year. Out of the eighteen men's Money in the Bank matches, sixteen of them have featured at least one of these superstars. Let's see who has had the most Money in the Bank experience as of writing.

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#5 (tie) - Chris Jericho (5)

Chris Jericho won the MITB match in Appleton.

Chris Jericho came up with the idea of the Money in the Bank ladder match when WWE didn't have any plans for him and a bunch of upper mid-carders on Raw for WrestleMania. That makes it surprising that he hasn't won one yet. Or did he win, as he claimed to have done so in Appleton?

Jericho took part in the first match, before going on a two-year-long hiatus. He made his WrestleMania return in the 2008 version of the risk-filled match. Further appearances in the 2010 and 2012 matches for the Raw briefcase added to his collection of MITB matches.

However, his most entertaining involvement in anything MITB related was during the build towards the 2016 ladder match. His epic comedic timing and instant chemistry with Kevin Owens shone through. It laid the groundwork for the highly entertaining best friends angle between the two in the latter part of the year.

#5 (tie) - Shelton Benjamin (5)

Shelton Benjamin was the MITB MVP in its early days.

Shelton Benjamin was the highlight of the first portion of Money in the Bank matches when they were held at WrestleMania. In fact, he was part of five out of the first six matches of this kind. Pretty much every year, Benjamin would come up with more and more dangerous spots.

He never failed to deliver in a Money in the Bank ladder match, shocking the WWE universe with his bruising leaps and bumps. His quick sprint up a leaning ladder was the biggest spot of the first ever MITB ladder match at WrestleMania 21. Since then, he has been trying to better himself every time.

At WrestleMania 24, Shelton took a terrifying fall through a horizontal ladder. The ladder he was on got tipped over and he took a front flip before crashing through the ladder. It remains one of the biggest crashes in the history of this match. It's a shame that WWE failed to utilize his massive potential and push him above the mid-card. He deserved to win the briefcase at least once in his career.

#2 (tie) - Christian (6)

Christian would have been one of the more interesting MITB winners in history.

Christian is one of the most criminally under-appreciated wrestlers in WWE history. His tag team work with Edge was stellar, before playing a dastardly heel. He was part of the WrestleMania 21 ladder match as well, before leaving WWE for a few years. Upon returning in 2009, he played the valiant babyface on the revived ECW brand.

He also competed in the last two Money in the Bank ladder matches at WrestleMania, before wrestling his second MITB match in the same year when he took part in the Smackdown briefcase match at the first ever pay-per-view named after the match. He would also play a part in two other ladder matches, in 2012 and 2013.

The MITB briefcase would have been perfect for somebody like Christian, who needed that extra something to win their first world title. He could have been turned into a main event player through Money in the Bank, like his best friend Edge. Fortunately though, he did win the World Heavyweight Championship twice in his career.

#2 (tie) - Kofi Kingston (6)

Kofi Kingston is a genius in gimmick matches.

At six Money in the Bank ladder matches, Kofi Kingston is tied with Christian. But he has had more memorable moments in this match than Captain Charisma. Kingston took over Shelton Benjamin as the Money in the Bank MVP. His genius has formed some of the most innovative spots in MITB history.

As the ladder was being set up, Kingston tried to run up the ladder and grab the briefcase at WrestleMania 25. He almost won the match at WrestleMania 26 using a ladder broken in two halves as a pair of stilts. His risk-taking ability is incredible as well; his Boom Drop onto Drew McIntyre through the announce table at Money in the Bank 2010 is a classic WWE moment.

He appeared in the 2011, 2014 and 2015 ladder matches as well. As a member of The New Day, Kingston could possibly enter his seventh Money in the Bank ladder match this year. He is a natural in this setting and is likely the best fit for the match from all three members. Hopefully, Kingston will win the briefcase at some point or he will likely go down as the greatest MITB competitor never to win it.

#2 (tie) - Dolph Ziggler (6)

Dolph Ziggler went on a stellar run as Mr. MITB.

After cashing in his briefcase on Alberto Del Rio on the Raw after WrestleMania 29, Dolph Ziggler would have been regarded in the same vein as guys like Edge and CM Punk - main event superstars made by Money in the Bank. Unfortunately, concussion issues forced him down the card in no time at all. However, Ziggler has still stolen the show in multiple MITB matches over the years.

WrestleMania 26 and Money in the Bank 2010 were his first two ladder matches, before picking up singles gold for the first time. In 2012, Ziggler won the briefcase and went on an incredible run as Mr Money in the Bank. He ousted Chris Jericho from the company, captained his Survivor Series team to victory as the sole survivor, retained his briefcase in a ladder match with John Cena, and was the iron man in the 2013 Royal Rumble match.

After winning and losing the World Heavyweight Championship, the Showoff took part in the 2014, 2015 and 2017 versions of the stunt-filled car crash. He never threatened to win it again but is a solid addition to any ladder match. His selling can make many superstars look good in environments like these.

#1 - Kane (7)

Kane was the first man to cash in his MITB contract on the same night he won it.

The surprising leader on this list is none other than the Big Red Machine, Kane. When you think about Money in the Bank ladder match veterans, you would think of the previous names like Jericho, Kofi and Ziggler. You wouldn't think of Kane. However, Kane has taken part in seven MITB ladder matches in the past.

He did not have many impressive individual spots but was always an intimidating figure in his matches. He was part of the first one at WrestleMania 21 when all the ladders caught fire during his entrance in a spectacular scene. Since then, he's competed at the last two Money in the Bank ladder matches at WrestleMania, the Smackdown briefcase match in 2010 and 2011, and the Raw briefcase match in 2012.

His last Money in the Bank appearance was in 2015 as Corporate Kane, but he had parts to play in other years as well. He was scheduled to be part of the Raw briefcase match in 2013 before he was removed, following an attack from a debuting Wyatt Family. Kane also appeared in the 2014 ladder match to help Seth Rollins win the briefcase.

Kane was the first person to win the briefcase and cash it in on the same night. This happened at the first ever Money in the Bank pay-per-view in 2010. He does have a pretty prominent legacy in Money in the Bank history, more than we thought.