By the end of 2019, Otis entered into a romantic storyline with Mandy Rose. On the February 14, 2020 episode of "SmackDown", Otis had a date with Rose, but Dolph Ziggler appeared in Otis's place during the date, the storyline then evolved into a love triangle involving a feud between Otis and Ziggler over Rose. On the April 3 episode of "SmackDown", it was revealed that Sonya Deville was working with Ziggler to keep Otis from Rose. At WrestleMania 36, Otis defeated Ziggler with the help of Rose, who kissed him after the match. On the May 1 episode of "SmackDown", Otis defeated Ziggler to qualify for the Money in the Bank ladder match. At the Money in the Bank pay-per-view, Otis won the Money in the Bank ladder match, earning him a world title match at the time of his choosing. On the September 11 episode of Smackdown, Otis and Tucker began a feud with The Miz and John Morrison after they stole the Money in the Bank briefcase from Otis. However, the briefcase did not contain the Money in the Bank contract as the contract was inside Otis' lunchbox. On the September 18 episode of SmackDown, Otis was sued by Miz and Morrison and was told to relinquish the contract but Otis refused and opted to go to court instead.