Montgomery grew up in Bloomsburg, Pennsylvania until moving to Lewisberry, Pennsylvania when he was in middle school.[1] He attended Red Land High School. As a sophomore, he batted .359 with 23 RBIs as the Patriots won the AAAAA State Championship.[2] Montgomery committed to play college baseball at the University of Virginia over offers from Stanford University, Duke University and the University of North Carolina earlier in his sophomore year.[3] His junior season in 2020 was canceled due to the COVID-19 pandemic and he played in the Perfect Game All-America game that summer, where he won the event's home run derby.[4][5] Montgomery also played in the East Coast Professional Showcase, the Area Code Games, and the Baseball Factory All-Star Classic.[6][7][8] Montgomery entered senior season as the top collegiate outfield prospect and as a top prospect for the upcoming Major League Baseball draft.[9][10][11] In 2021, as a senior, he led Red Land to the AAAAA State Championship game again and was named the Pennsylvania Gatorade Player of the Year.[12][13] He ended his senior year batting .420 with seven home runs, 22 RBIs, and 19 stolen bases.[14]
Montgomery spent the 2023 season with the High–A Spokane Indians, playing in 109 games and batting .251/.336/.370 with 10 home runs, 51 RBI, and 18 stolen bases.[19]
Montgomery was assigned to the Double–A Hartford Yard Goats to begin the 2024 season. In 11 appearances, he hit .283/.313/.500 with two home runs, 10 RBI, and three stolen bases. On May 12, 2024, Montgomery underwent surgery to repair a left shoulder injury.[20]