It was announced on May 20, 2021, that YouTuber-turned-professional boxer Jake Paul had signed a promotional deal with American television network Showtime, an agreement that would see his next bout aired on the network.
His fight against former UFC Welterweight Champion Tyron Woodley was announced on July 12, 2021, with the venue and date set to be in Paul's hometown of Cleveland on August 29, 2021.