Callaway played at the University of Tennessee from 2016 to 2019 under head coaches Butch Jones and Jeremy Pruitt.[4][5] Callaway had 92 receptions for 1,646 yards and 13 receiving touchdowns in his four seasons at Tennessee.[6][7]
On April 27, 2020, Callaway signed with the New Orleans Saints as an undrafted free agent after the 2020 NFL draft.[10] He made his NFL debut in Week 2 against the Las Vegas Raiders playing on offense and special teams.[11] In Week 4 against the Detroit Lions, he had his first professional reception on a 16-yard catch in the 35–29 victory.[12] In a Week 5 matchup against the Los Angeles Chargers, Callaway was targeted six times and made four receptions for 34 yards.[13]
On October 25, 2020, in a game against the Carolina Panthers, Callaway caught Drew Brees’ 7,000th completion.[14] He finished the game with eight receptions for 75 yards, both team highs.[15] He was placed on injured reserve on December 5, 2020.[16] He was activated on December 24.[17] As a rookie, he appeared in 11 games, of which he started three. He finished his rookie season with 21 receptions for 213 receiving yards.[18]
Callaway's role expanded in the 2021 season. He scored his first professional receiving touchdown on a seven-yard reception from Jameis Winston in the 28–13 victory over the New England Patriots in Week 3.[19] In Week 5, against the Washington Football Team, he had his first multi-touchdown game in the 33–22 victory.[20] In Week 15, against the Tampa Bay Buccaneers, he had six receptions for 112 receiving yards in the 9–0 victory.[21] On the 2021 season, Callaway appeared in all 17 games. He finished with 46 receptions for 698 receiving yards and six receiving touchdowns.[22]
In the 2022 season, Callaway appeared in 14 games. He finished with 16 receptions for 158 receiving yards and one receiving touchdown.[23] Callaway did not receive a qualifying offer following the 2022 season and became a free agent on March 15, 2023.[24]
Denver Broncos
On March 24, 2023, Callaway signed with the Denver Broncos.[25] He was waived on August 29, 2023.[26]
On November 21, 2023, Callaway was signed to the Saints' practice squad.[29] He appeared in three games for the Saints in the 2023 season.[30] He was not signed to a reserve/future contract and thus became a free agent at the end of the season.[31]
Pittsburgh Steelers
On January 17, 2024, Callaway signed a reserve/futures contract with the Pittsburgh Steelers.[32] On July 30, Callaway was released by the Steelers.[33]
New Orleans Saints (third stint)
On August 1, 2024, Callaway signed with the New Orleans Saints.[34] On August 11, Callaway was released by the Saints.[35]
Tampa Bay Buccaneers
On October 16, 2024, Callaway was signed to the Tampa Bay Buccaneers' practice squad.[36] He signed a reserve/future contract on January 14, 2025.[37]
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