#2 Jon Moxley fka Dean Ambrose - 2016 Money in the Bank Winner
Money in the Bank 2016 will go down as one of the greatest in the events' history because of one simple, yet wildly impressive stat. In one night, all three former members of The Shield held the WWE Championship.
Heading into the pay-per-view, Dean Ambrose (now Jon Moxley) was added to the Money in the Bank ladder match. Roman Reigns would defend the WWE Title against Seth Rollins in the main event. Ambrose bested Alberto Del Rio, Cesaro, Chris Jericho, Kevin Owens, and Sami Zayn to win a shot at that same belt.
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Seth Rollins defeated Roman Reigns in a fantastic main event match-up, leading to the crowd erupting for the Architect. However, they only grew louder once we saw Ambrose was cashing in on him. The Lunatic Fringe dropped Rollins with Dirty Deeds, capturing his first and only WWE Championship during his run with the company.
He'd leave WWE in 2019 and would quickly join AEW, where he'd become the second-ever World Champion of Tony Khan's promotion.
#1 Braun Strowman- 2018 Money in the Bank winner
Man, nobody expected Braun Strowman to be let go by WWE this year. The Monster Among Men was a major attraction for the company for years and was a part of some incredible storylines with Roman Reigns, Brock Lesnar, and more.
In 2018, after his fantastic feud with Reigns, Strowman captured the Money in the Bank contract. Strowman plowed through the competition which included Bobby Roode, Finn Balor, Kevin Owens, Kofi Kingston, Rusev, The Miz, and Samoa Joe. Strowman's target? His number one rival, Roman Reigns. On August 27th, he made it clear he'd challenge The Big Dog for the Universal Title at Hell in a Cell.
That would wind up being one of the worst Money in the Bank cash-ins of all time. Not because of Strowman or Reigns, of course. Their chemistry was always fantastic. But their Hell in a Cell match ended in a no-contest when Brock Lesnar broke the cage door and laid everyone out.
That would leave Strowman as the only Money in the Bank winner whose cash-in ended in a no contest. It was also the second Hell in a Cell match to end without a definite result. Strowman would go onto win the Universal Championship at WrestleMania 36 by beating Goldberg.
Strowman was one of many WWE releases in the past few months, and the biggest name to be included.