The Money in the Bank allows WWE Superstars to cash-in their briefcase for a title match against any world champion, and every Superstar hopes to hold the briefcase one day.

There have been no less than 25 Money in the Bank briefcase winners thus far (21 men and 4 women). The men have had eight out of ten successful cash-ins for the WWE Championship and seven out of eight successful cash-ins for the WWE World Heavyweight Championship.

Over the years, a few of the Money in the Bank briefcase winners have shared interesting stories regarding their cash-in attempts, allowing fans an insight on what goes on behind the scenes to make the magic happen.

In this article, we will look at five WWE Superstars who’ve shared interesting details regarding their Money in the Bank cash-ins.

#5 Baron Corbin (WWE Money in the Bank 2017 winner)

While Baron Corbin has only won a single title in his WWE career, he has won the Andre the Giant Memorial Battle Royal, Money in the Bank briefcase, and the King of the Ring Tournament.

Along with that, Corbin has also been trusted with some major matches and rivalries on WWE RAW and SmackDown which shows that the company has faith in him.

In 2017, Corbin became Mr. Money in the Bank and had the chance to win his first world title in the company. On an episode of WWE SmackDown, Corbin unsuccessfully cashed in his briefcase against Jinder Mahal.

Corbin was recently interviewed by All Things Wrestling Radio and he spoke about when he found out about the fact that he had to cash in his briefcase:

Unlike a few other entries on the list, Corbin had very little time to prepare for his Money in the Bank cash-in. He was unfortunate in not being able to cash-in the briefcase successfully.

#4 Damien Sandow (WWE Money in the Bank 2013 winner)

A lot of people believe that Damien Sandow could have made it huge in WWE had he been booked properly. With his in-ring talent and mic work, few can doubt the fact that he had the potential to make it big.

In 2013, it seemed like Sandow was ready to get a massive push as he won the Money in the Bank briefcase. He cashed it in over 100 days later against John Cena, but fell prey to the Attitude Adjustment after a really good match that ended in an unsuccessful cash-in.

Sandow opened up about his Money on the Bank cash-in during the Why It Ended with Robbie E podcast.

Sandow was not happy with his cash-in as he believed WWE could have done so much more with him and the opportunity at hand.

Kevin Eck, a former WWE writer, took to SportingNews.com to talk about what went wrong during Sandows’ rise and fall when he held the Money in the Bank briefcase.

Looks like WWE had the right intentions for Sandow early on, but their bookings made them lose faith in an extremely talented Superstar who was released from the company in May 2016.

#3 Dean Ambrose (WWE Money in the Bank 2016 winner)

While Seth Rollins and Roman Reigns were steam-rolling their way to the top of WWE, their Shield brother Dean Ambrose was trying to find his way to the top too.

In 2016, Ambrose won the Money in the Bank contract and held it for just 57 minutes before deciding to cash it in on Rollins later in the night. Rollins was fresh off a 26-minute contest against The Big Bog where he managed to retain his WWE World Heavyweight Championship.

Ambrose arrived right after Rollins’ victory, attacked him from behind with the briefcase, and hit him with the Dirty Deeds to win the match and the title in just nine seconds.

Talking to 98.5 The Sports Hub after the event, The Lunatic Fringe told the bizarre story of why he did not even wait an hour before cashing in:

Ambrose now performs for All Elite Wrestling (AEW) as Jon Moxley, and his MITB and WWE World Heavyweight Championship victory on the same night in 2016 was one of the high points of his career.

#2 Edge (WWE Money in the Bank 2005 winner)

Edge won the Money in the Bank briefcase in 2005 at WrestleMania 21 and held the briefcase close to his heart.

At New Year’s Revolution 2006, John Cena successfully defended his WWE Championship against Carlito, Chris Masters, Shawn Michaels, Kane, and Kurt Angle in an Elimination Chamber match.

Cena was visibly tired after the near 30-minute match, and that’s when The Rated-R Superstar struck and cashed in his briefcase, delivering two Spears to Cena to become the WWE Champion.

The Rated-R Superstar later revealed that he had told Vince McMahon that he wanted to cash in his briefcase at a time when the Champion was at his worst so that he could draw more heat towards himself as a heel.

Edge revealed the following during a talk on his own podcast:

This was the first-ever Money in the Bank cash-in, and Edge picked the perfect time to cash-in his contract.

#1 Seth Rollins (WWE Money in the Bank 2014 winner)

Seth Rollins pulled off the “Heist of the Century” when he became the first man to cash-in the WWE Money in the Bank contract during the main event of WrestleMania 31.

As Brock Lesnar and Roman Reigns competed for the WWE Championship during the main event, no one was ready for Mr. Money in the Bank, Seth Rollins, to run out to the middle and cash-in his briefcase mid-match to become the new WWE Champion.

Rollins recently opened up about the heist he pulled off at WrestleMania 31 during a conversation with WWE India.

Rollins and the WWE creative team put a lot of thought into this cash-in, and they managed to pull it off perfectly, giving the WWE Universe a moment to remember.

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