Montgomery began his collegiate career at Holmes Community College. As a sophomore, he caught 36 passes for 991 yards and ten touchdowns and was named first-team All-State.[1] He was rated a three-star prospect and committed to transfer to Austin Peay for his remaining eligibility.[2]
Montgomery became a starter in his first season with the Governors and finished second with 19 receptions and 228 receiving yards with three touchdowns.[3] As a senior, he caught 42 passes for 797 yards and ten touchdowns[4]
Montgomery signed with the Cleveland Browns as an undrafted free agent on May 3, 2019.[6] He suffered a hamstring injury during training camp and was placed on season-ending injured reserve on August 21, 2019.[7] The Browns waived Montgomery on August 19, 2020.[8]
New York Jets
Montgomery was claimed off waivers by the New York Jets on August 30, 2020.[9] He was released before the start of the regular season and re-signed to the Jets practice squad.[10] Montgomery remained on the Jets' practice squad for the entirety of the 2020 season and signed a reserve/futures contract with the team on January 4, 2021.[11] He was waived at the end of training camp on August 31, 2021, and was re-signed to the practice squad the next day.[12] Montgomery was elevated to the active roster on December 12, 2021, for the team's Week 14 game against the New Orleans Saints.[13] He signed a reserve/future contract with the Jets on January 10, 2022.[14] He was waived on May 10, 2022, then re-signed on May 24, 2022. He was waived on July 26.[15]
On August 18, 2023, Montgomery signed with the Colts.[21] He was waived on August 29, 2023 and re-signed to the practice squad.[22][23] He was signed to the active roster on December 14.[24]
Montgomery was released by the Colts on August 27, 2024, and re-signed to the practice squad.[25][26]