Selected by the Chicago White Sox in the 1st round (No. 22 overall) of the 2021 MLB Draft out of Southridge High School in Huntingburg, Indiana... signed with the White Sox on July 20, 2021... made his pro debut on Aug. 6, 2021 with the Arizona Complex League White Sox... hit .287 with seven RBIs and 16 runs in 94 at-bats over 26 games in his first season in the Minors... made his full-season debut with Kannapolis on April 8, 2022.
Played basketball at Southridge High, where he averaged 24 points and eight rebounds in his senior year... he finished his high school basketball career as the school's all-time leading scorer in a career that included a school boys basketball record 41-point game as a junior; his younger sister, Myah, set the Southridge record with 42 points and committed to Kentucky Wesleyan College for basketball in 2021... Montgomery committed to play baseball at Indiana during his junior year of high school and had planned to be a walk-on for the Hoosiers' men's basketball team... as a senior, he hit .333 with seven homers, 23 RBIs and 24 stolen bases, leading the Southridge Raiders to their first-ever IHSAA state championship... trained in the off-season with fellow White Sox first-round pick Jake Burger.