[1] The New York Yankees selected Cowles in the 10th round of the 2021 MLB draft.
[2] He began the 2022 season with the Tampa Tarpons and received a midseason promotion to the Hudson Valley Renegades.
[3] Returning to Hudson Valley in 2023, Cowles set a franchise record for consecutive games reaching base safely.
[5][6] On July 30, 2024, the Yankees traded Cowles and Jack Neely to the Chicago Cubs in exchange for Mark Leiter Jr.[7] In 4 games for the Double–A Tennessee Smokies, he went 1–for–13 (.077) with 2 walks.
Following the season, the Cubs added Cowles to their 40-man roster to protect him from the Rule 5 draft.