Pleasants (6-7, 330) originally entered the NFL after signing with the Jacksonville Jaguars as an undrafted free agent on April 27, 2020. Throughout his five-year NFL career, he has spent time on the practice squads with the Jaguars (2020), Carolina Panthers (2021-22), Los Angeles Chargers (2022-24), Chicago Bears (2023-24) and Arizona Cardinals (2023-24) and has appeared in two games with the Panthers and Chargers. In 2024, Pleasants spent time on the Chargers, Cardinals and Bears practice squads prior to being released from Chicago's practice squad on December 3.