[10] In 2021, his senior baseball season, he batted .333 with seven home runs, 23 RBIs, and 24 stolen bases, and led Southridge to their first ever IHSAA state championship.
[11][12] Following the end of the season, he traveled to Cary, North Carolina, where he participated in MLB's first ever Draft Combine.
[16] He made his professional debut with the Rookie-level Arizona Complex League White Sox.
[18] Montgomery was assigned to the Kannapolis Cannon Ballers of the Single-A Carolina League to begin the 2022 season.
[27] Montgomery was assigned to the Charlotte Knights of the Triple-A International League to open the 2024 season.