Leatherwood enrolled at Alabama a semester early and played in seven games as a true freshman. He saw significant playing time in the 2018 CFP National Championship Game, entering the game at left tackle after starter Jonah Williams was injured in the third quarter.[5] He was moved to right tackle during spring practice and moved again to right guard during fall training camp, winning the starting job going into his sophomore season.[6] He started all 15 of the Crimson Tide's games, giving up 21 pressures, and was named second-team All-Southeastern Conference (SEC) by the league's coaches.[7][8]
Leatherwood was moved back to the left tackle position following the season.[9] He was named first-team preseason All-SEC and a second-team preseason All-American by Sporting News entering his junior season.[10] He was placed on the Outland Trophy watchlist midway through the season.[11] Leatherwood started every game for Alabama and was named first-team All-SEC by the league's coaches and second-team by the media and was named first-team All-America by the American Football Coaches Association.[12] After considering entering the 2020 NFL Draft, Leatherwood announced that he would return to Alabama for his senior season.[13]
Leatherwood was selected by the Las Vegas Raiders with the 17th overall pick in the 2021 NFL draft.[18] On May 24, 2021, Leatherwood signed his four-year rookie contract with Las Vegas,[19] a four-year, fully guaranteed deal worth $14.39 million.[20] He moved to offensive guard due to struggles at tackle as a rookie and was waived on August 30, 2022.[21]
Chicago Bears
On August 31, 2022, Leatherwood was claimed off waivers by the Chicago Bears.[22] He was placed on the reserve/non-football illness list on September 14, 2022.[23] He was activated on October 28.
On August 27, 2023, Leatherwood was released by the Bears.[24]
Cleveland Browns
On August 30, 2023, Leatherwood was signed to the practice squad of the Cleveland Browns.[25] His contract expired when the team's season ended January 13, 2024.
Los Angeles Chargers
On May 29, 2024, Leatherwood signed with the Los Angeles Chargers.[26] He was released on August 27, and re-signed to the practice squad.[27][28] Leatherwood was released by the Chargers on December 10.[29]
Personal life
In June 2020, Leatherwood wrote a screenplay for a video in support of the Black Lives Matter movement. He appeared in the video along with other Alabama players and their head coach, Nick Saban.[30]