Freeman opened the 2022 season back with Birmingham, but missed nearly three months due to injury.[9] Over 14+1⁄3 innings pitched with Birmingham, he posted an 8.79 ERA with 14 walks and 15 strikeouts.[10] He returned to Birmingham to open the 2023 season and also spent time with the Charlotte Knights, posting a 3.71 ERA and 38 strikeouts over 34 innings for the season.[11] Freeman returned to Birmingham for the entirety of the 2024 season, going 2-5 with a 3.92 ERA and 56 strikeouts over 43+2⁄3 innings.
Freeman was assigned to Birmingham to open the 2025 season, and was promoted to Charlotte in April.[12] On May 4, 2025, the White Sox purchased Freeman's contract and added him to their active roster.[13][14] He made his MLB debut the next day versus the Kansas City Royals. Freeman pitched one inning in relief in which he gave up one earned run and collected his first major league strikeout against Salvador Pérez.[15] In five appearances for Chicago, he recorded a 5.40 ERA with three strikeouts across 3+1⁄3 innings pitched. Freeman was designated for assignment following the promotion of Jake Palisch on June 20.[16] He cleared waivers and was sent outright to Triple-A Charlotte on June 23.[17] Freeman elected free agency following the season on November 6.[18]
