In 2015, Baldwin split the season between the rookie-level GCL Red Sox and the Low-A Lowell Spinners, slashing .288/.359/.399 in 50 games between the two teams.

The following season, Baldwin split the year between the Single-A Greenville Drive and Lowell, accumulating a .266/.305/.372 batting line with 4 home runs and 37 RBI.

For the 2018 season, Baldwin played for the High-A Salem Red Sox, slashing .233/.282/.371 with 7 home runs and 27 RBI.

[2] Baldwin only appeared in eight games between Lowell and the GCL Red Sox in 2019, missing much of the year with a broken ankle.

[3] The Red Sox invited Baldwin to spring training in 2020,[4] but he did not play in a game in 2020 due to the cancellation of the minor league season because of the COVID-19 pandemic.

Baldwin elected free agency following the season, but later re-signed with the Red Sox on a minor league deal on February 1, 2022.