Montgomery split the 2023 campaign between Double–A Montgomery and the Triple–A Durham Bulls. In 29 starts split between the two affiliates, he compiled a 7–4 record and 3.98 ERA with 144 strikeouts over 124+1⁄3 innings pitched.[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). On September 5, 2024, Montgomery was selected to the 40-man roster and promoted to the major leagues for the first time.[8] He made nine appearances for Tampa Bay during his rookie campaign, compiling a 1.86 ERA with 17 strikeouts across 9+2⁄3 innings pitched.[9]
On June 18, 2025, Montgomery recorded his first career win, tossing a scoreless inning against the Baltimore Orioles.[10] He made 57 appearances for the Rays on the year, posting a 1–3 record and 5.67 ERA with 63 strikeouts and one save over 46 innings of work.[11]
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