The Money in the Bank ladder match is one of the biggest WWE creative successes of the 21st century.

In what was supposed to be a one-off at Wrestlemania 21, the ladder match transformed into a yearly event and then a stand-alone show that could be argued as a new entry into WWE’s “big four” premium live events. It is a built-in event that allows the company to tab one superstar on its male and female rosters for future success.

The fact that this title is handed out on an annual bases means there have been some truly awful decisions made on WWE’s part as they booked themselves into a corner, but that isn’t very surprising now is it? In the end, this match type is one that has benefitted WWE greatly in its pursuit to create moments and stars.

Here are the very best superstars to have taken claim to the title of Mr. or Mrs. Money in the Bank.

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7. Big E (2021)
This may be an underrated addition, but it is one that cannot go unmentioned.

The Money in the Bank briefcase is often reserved for younger talents or as a way to just improve the list of accolades on an established main event veteran. Big E’s win in 2021 was a mix of both. The New Day star was already well on his way to the hall of fame by Summer 2021, but had yet to have any true singles success. In one night, WWE changed all of that by giving him the briefcase which allowed him to truly break through two months later when he defeated Bobby Lashley for the WWE Championship. Though the less said about his reign is for the better, Big E finally got his big moment due to this win.

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6. Daniel Bryan (2011)
Daniel Bryan’s path to Wrestlemania 30’s main event started two years earlier when he lost the World Heavyweight Championship to Sheamus in an 18-second match at Wrestlemania 28.

He doesn’t have that loss, or all of the fan support that came with it, if it weren’t for his Money in the Bank win in 2011. Bryan was also able to parlay the briefcase and subsequent title win into his first great run, becoming an annoying heel who didn’t realize that he needed to cheat to win all of his matches. It was the start of something truly special for one of the greatest ever.

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5. CM Punk (2008 and 2009)
We’re lumping these two wins together because, well, one was very good and one was very bad.

Luckily for WWE, they were able to make up for the bad win with the good one. In 2008, CM Punk won the Money in the Bank at Wrestlemania 24, cashed in on Edge to a huge babyface pop and would lose the title in a backstage segment. That’s bad. In 2009, he won the briefcase at Wrestlemania 25 (not the 25th anniversary like WWE wants you to believe) and cashed it in on Jeff Hardy. The difference? Punk was booed by the fans for stealing the title off Hardy though he didn’t do anything different from his cash in the year prior. That influenced a heel turn and a solid run with the title that helped the Straight Edge Savior find his footing.

4. Dolph Ziggler (2012)
This one boils down to the cash in.

Dolph Ziggler has never been able to find his footing in the main event, but his best moment in that spot came on the night after Wrestlemania 29 when he cashed in on Alberto Del Rio. The end of his 267-day reign with the briefcase produced one of the loudest pops of the decade and a tremendous moment for fans of the underdog.

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3. Bayley (2019)
WWE has this weird obsession with only allowing the women on their roster to hold the briefcase for one day, with five of the first six winners cashing in within 24 hours.

This is the best of the bunch.

Bayley was treading water as a boring babyface when she won the briefcase in 2019. That night she would go on to make a save while Charlotte and Lacey Evans were putting the boots to Becky Lynch, before cashing in on Charlotte to win the title. During that reign, she turned heel and sparked a career resurgence that made her one of the most popular stars on the roster.

It only takes a day.

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2. Seth Rollins (2014)
It took 10 years for WWE to finally allow a Money in the Bank winner to cash in at Wrestlemania.

The wait was worth it.

Seth Rollins won the briefcase in June 2014. In that time, he became the face of the biggest heel stable in the business and workshopped a snotty heel gimmick that had people clamoring for him to get what was coming to him. Instead, they got the coolest Money in the Bank cash in of all time and a tremendous reign that only came to an end due to injury. There wasn’t a single thing wrong with Rollins’ win and subsequent reign, it just isn’t No. 1.

1. Edge (2005)
It’s rare for WWE to knock something out of the park on their very first try, (There’s a reason why we haven’t seen many “cry baby” matches.) but they couldn’t have nailed this one more if they tried.

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The creative powers at WWE finally decided to give Edge the main-event push that had eluded him for nearly six years when deciding to make him the first Mr. Money in the Bank in 2005. In playing a sniveling and conniving heel, Edge was the perfect first winner as his character would love to take advantage of the opportunity that the briefcase gave him. The future Hall of Famer carried the case around for 280 days before cashing in on a bloodied and battered John Cena to secure his first world title. His reign kickstarted the stipulation we all know and love.

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