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#4 Damien Sandow- 2013 Money in the Bank winner
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At Money in the Bank 2013, Damien Sandow shocked the WWE Universe when he won a shot at the World Heavyweight Championship. He managed to defeat Cesaro, Dean Ambrose, Fandango, Wade Barrett, Jack Swagger, and Cody Rhodes.
Rhodes was pegged by many fans as the next Mr. Money in the Bank, and it seemed like he was destined to fulfill those hopes at the event. Unfortunately, he was betrayed by his Rhodes Scholars partner, Damien Sandow.
The Intellectual Savior of the Unwashed Masses would eventually model the briefcase to better suit his character. A fancier leather case definitely fits the bill. Eventually, he'd cash in on John Cena and lose following a pretty great match between the two.
Following that, he became Damien Mizdow before ultimately leaving the company in 2016. He's now working with NWA as one-half of the tag champions alongside JR Kratos as Aron Stevens.
#3 Brock Lesnar- 2019 Money in the Bank winner
Remember when Brock Lesnar won a match that he wasn't even involved in and aggravated the entire WWE Universe?
Now, remember when he turned the Money in the Bank briefcase into a boombox and repeatedly danced to the ring? With the bad comes the good, and Boombox Brock is definitely good.
At Money in the Bank 2019, Ricochet, Finn Balor, Andrade, Mustafa Ali, Randy Orton, Drew McIntyre, and Randy Orton all battled for a chance at the briefcase. Unfortunately for all of them, they forgot the fine print of every match in the company. Brock Lesnar does what he wants!
With almost everyone down around the ring, Mustafa Ali had his hands on the briefcase when Lesnar's music hit. Instead of finishing the match and pulling the prize down, Ali stared in stunned silence. Lesnar would climb up the ladder to claim the briefcase.
Lesnar would cash in on Seth Rollins at Extreme Rules in 2019 before losing the Universal Title back to The Messiah at SummerSlam. Currently, Lesnar is no longer under a WWE contract. However, he's expected to join back up as soon as the company begins touring again.
