Montgomery was selected in the 39th round of the 2018 Major League Baseball draft by the Chicago White Sox, but opted not to sign with the team.
[1] Montgomery played college baseball for the Texas Tech Red Raiders for three seasons.
[3] After signing with the team he was assigned to the Rookie-level Florida Complex League Rays, where he allowed one earned run and struck out 20 batters in 10+2⁄3 innings pitched.
[5] In 27 starts split between Bowling Green and the Double–A Montgomery Biscuits, he accumulated a 6–3 record and 2.10 ERA with 171 strikeouts across 124 innings.
[7] Montgomery began the 2024 campaign with Triple–A Durham, compiling a 1–7 record and 6.26 ERA with 105 strikeouts over 31 games (14 starts).