Before WKU: Montgomery arrived at WKU after starting his college career as an offensive lineman at Alabama. In his first season with the program in 2023, he appeared in two games before redshirting. He played in 12 games on special teams while also rotating along the offensive front in 2024, and he did not see any game action during the 2025 season.
HS/Misc.: Montgomery prepped at Anniston High School in Alabama, where he was rated a four-star prospect by Rivals and On3. He was considered the No. 11 offensive guard and the No. 21 overall player in the state of Alabama, according to Rivals, and he was considered by On3 to be the No. 26 player at his position in the country and No. 20 in the state. He was rated a three-star prospect on the 247Composite rankings, checking in as the No. 26 interior offensive lineman and the No. 22 player from Alabama. He was No. 31 offensive lineman and No. 21 in the state on the On3 Consensus. He was ESPN’s No. 206 player in the Southeast Region, No. 21 offensive guard and No. 23 player from the state.
