Cleveland attended Bethel High School in Spanaway, Washington.

[1] He committed to Boise State University to play college football.

[4][5] After his junior season in 2019, Cleveland entered the 2020 NFL draft.

On October 31, 2023, Cleveland was traded to the Jacksonville Jaguars in exchange for a sixth-round pick of the 2024 NFL draft.

[11][12][13] On March 8, 2024, Cleveland signed a three-year contract extension with the Jaguars.