Bailey signed with the Denver Broncos as an undrafted free agent following the 2019 NFL draft on April 30, 2019.[2] He was waived during final roster cuts on August 31, 2019,[3] and signed to the team's practice squad the next day.[4] He was promoted to the active roster on December 24, 2019.[5]
The next season, Bailey was again waived during final roster cuts on September 5, 2020,[6] and re-signed to the practice squad the next day.[7] He was elevated to the active roster on November 14 for the team's week 10 game against the Las Vegas Raiders, and reverted to the practice squad after the game.[8] He signed a reserve/future contract on January 4, 2021.[9]
On August 31, 2021, Bailey was waived by the Broncos and re-signed to the practice squad the next day.[10][11] He was promoted to the active roster on January 7, 2022.[12]
On August 30, 2022, Bailey was waived by the Broncos and signed to the practice squad the next day.[13][14] He was promoted to the active roster on November 19.[15]
On August 1, 2024, Bailey was placed on injured reserve with an ankle injury, missing the entire 2024 season.[16] After the end of the season, he became a free agent.
