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WWE Money in the Bank Winners Relive Their Best Moments, Reunite With Briefcases

There's nothing like seeing an old friend again! For these WWE Superstars, that old friend is the coveted Money in the Bank briefcase. 

By Chris Phelan
Four wrestlers climb ladders to get to the Money In The Bank briefcase

With Money in the Bank 2023 less than a week away, it's more than timely to look back at forgotten moments in the history of WWE's upcoming premium live event. From ladder match wins to historic contract cash-ins, this trip down memory lane has plenty of room!

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Of course, it helps when WWE Superstars reminisce about Money in the Bank personally. Recently, WWE cameras caught up to a handful of previous men's and women's winners and presented them with their old briefcases! For many Superstars, it would be the first time they had seen their briefcases in years.

It's clear that these ladder match victories hold a special place in these athletes' hearts – you can tell by their smiles. With that being said, let's look at some forgotten Money in the Bank moments that the WWE Universe will be well-served to freshen up on!

Sheamus' Upset Victory (2015)

While Money in the Bank is usually a stepping stone for up-and-coming future champions to prove their worth to the WWE Universe, sometimes it's the perfect platform for an established Superstar to remind the world that they still have what it takes! The Celtic Warrior accomplished exactly that in 2015 when he defeated an impressive field of ladder match participants en route to capturing his second all-time briefcase win.

RELATED: The Humble Beginnings of WWE's Money in the Bank Event

The 2015 match is notable because Roman Reigns was the odds-on favorite to secure the briefcase. Against those odds, Sheamus made it a point to overcome the champ and four other Superstars to cement his place in history. To make matters worse for future Tribal Chief, Sheamus added insult to injury months later when he cashed in his Money in the Bank contract on Roman Reigns and defeated him to capture the World Heavyweight Championship. Overall, 2015 was not a bad year for the Celtic Warrior! 

It sounds like Sheamus has Roman Reigns' number. We'd love to see him step up in 2023 and challenge The Tribal Chief for the Undisputed WWE Universal Championship!

The Miz's Historic Cash-In – 2010

Historic cash-ins begin and end with Miz's unforgettable moment on RAW in 2010 against Randy Orton. What's even more interesting is how Miz used the Money in the Bank briefcase in real life before he cashed it in! 

"I never utilized it for anything," Miz confessed to WWE cameras. "It was just a contract within it, and I just walked around with it. If you're in an airport, you have to explain a million times what the Money in the Bank contract is, which I didn't mind because it's truly an honor to hold this briefcase and this contract. This changed my life and changed my career. I don't know if I didn't win this contract, if I would have become the Superstar that I am today."

The Miz isn't wrong. He set the high watermark for dramatic cash-ins. His shocking pinfall win over Orton let his fellow WWE Superstars know that the best strategy for using your Money in the Bank contract is to utilize the element of surprise. 

Bayley Cashes In On the Queen – 2019

There has yet to be a Superstar with a career trajectory like Bayley's. Her evolution is impressive, from her humble beginnings as a WWE superfan-turned-wrestler in NXT to the condescending villain she is portraying on Monday Night RAW. As we all know, the key to WWE longevity is constantly reinventing yourself, something that even the reigning World Heavyweight Champion knows!

Bayley's memorable 2019 cash-in on Charlotte Flair served as a catalyst for the conniving woman she is in present-day WWE. Until that fateful night, Bayley was content to let moments, wins, and championships come to her, constantly biding her time, waiting for the perfect moment. The WWE Universe could see it in her eyes on that night in 2019 – she knew the Bayley of old wouldn't cash in on Charlotte when the champion was in such rough shape. 

But, as we all know, Bayley embraced the moment she found herself in and pulled the trigger, putting the women's locker room on notice as someone who conquered the Queen herself. 

Asuka's Balcony Dive – 2020

With the pandemic raging worldwide, the Money in the Bank ladder matches of 2020 took place inside a never-before-used building: WWE headquarters in Stamford, Connecticut. Both male and female competitors started on the ground floor of the building, fighting their way up the dozens of floors until they reached the roof, where a proper WWE ring was set up with briefcases hanging high above the Stamford sky. 

It was one of the most unforgettable Money in the Bank matches ever. Still, Asuka stole the show en route to winning the women's Money in the Bank briefcase – courtesy of a thrilling high-dive off an interior balcony onto her fellow competitors! While Asuka is currently enjoying a dominant WWE Women's title reign, as the video above shows, she's always been at the top of the mountain in the women's division. 

Austin Theory's Brock Lesnar Dents – 2022

Being the Money in the Bank winner isn't all glitz and glamor – especially when you draw the constant ire of Brock Lesnar! WWE cameras caught up with Austin Theory, and he admitted being the briefcase holder in 2022 did have one severe drawback.

"The thing that sucks is I carried around a briefcase that was so dented up," Theory said. "And the sad part was a lot of those dents were Brock Lesnar beating the crap out of me with it."

We feel your pain, Theory, and appreciate your honesty. Let's hope Lesnar doesn't get his hands on your United States Championship.

Here's to hoping the 2023 winners of the Money in the Bank ladder matches have long, healthy runs with the briefcases as they wait for the picture-perfect moment to cash in – and we'll cross our fingers that they stay out of Brock Lesnar's sight.

You can tune in to Peacock to watch WWE's Money in the Bank on July 1. In the meantime, catch up on all things WWE Universe on Peacock as well.

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