As part of the 2019 Draft in October, Black was drafted to the Raw brand. Over the following weeks, Black would develop a winning streak, squashing his opponents. On 18 November episode of "Raw", Buddy Murphy went to Black's locker room to challenge him, but Black was absent and Murphy claimed that Black was all talk and no fight. The following week, Black appeared and attacked Murphy after his match. A match between Black and Murphy was scheduled for , which Black won. At the Royal Rumble pay-per-view on 26 January 2020, Black entered the Royal Rumble match at number 28, but was eliminated by Seth Rollins. On 24 February episode of "Raw", Black was attacked by The O.C. (AJ Styles, Luke Gallows, and Karl Anderson) backstage. The next week on "Raw", Black faced The O.C. members in separate matches, and suffered his first pinfall loss on the main roster, to AJ Styles. At Elimination Chamber on 8 March, Black defeated Styles in a no disqualification match, with interference from The Undertaker. At WrestleMania 36 on night two of the event, Black defeated Bobby Lashley, by accidental distraction from Lashley’s kayfabe wife, Lana (wrestler). On 20 April episode of "Raw", Black defeated Austin Theory to qualify for the Money in the Bank ladder match at Money in the Bank. At the event, Black failed to win the match, being the 2 people, along with Rey Mysterio to be thrown off the roof of the building.