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#2 Otis (Money In The Bank 2020)
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Money In The Bank 2020 presented WWE with a unique opportunity. With this being the first pay-per-view since WrestleMania 36 during the pandemic, the company wanted to try something new. The titular ladder match would be a cinematic match with both men and women competing at the same time in a race up to the top of WWE Headquarters.
This was a wild, ridiculous contest that saw a Brother Love and Paul Heyman cameo, a random clown, a food fight and superstars being thrown off the roof. Otis was the man to retrieve the briefcase following AJ Styles having it slip out of his hands. This was a surprise winner for many.
Otis had momentum after his entertaining feud with Dolph Ziggler that saw him defeat his rival and kiss his crush, Mandy Rose at WrestleMania 36. However, his victory at Money In The Bank 2020 felt like a huge jump up the card. He was featured throughout his reign with the briefcase, but it never felt like he was on the cusp of becoming a world champion.
He was mostly featured in tag team matches with his Heavy Machinery tag team partner, Tucker, or side character in the rivalry between Mandy Rose and Sonya Deville. Otis eventually found himself against The Miz, who felt like he was not deserving of the Money In The Bank contract.
The feud with The Miz felt very low-brow and beneath what they were fighting over with the Money In The Bank briefcase made into a lunch box by Otis and a goofy court case that set up a match at Hell In A Cell 2020 with the contract on the line. This is where Tucker turned on Otis and cost him the contract.
This killed any elevation that Otis got during his time with the briefcase and broke up a successful tag team in Heavy Machinery. WWE simultaneously split the babyface tag team, devalued the Money In The Bank contract and killed an organically over-babyface with one reign with the briefcase.
