The Chicago White Sox selected Fry in the third round,with the 77th overall selection,of the 2014 MLB draft.[8] He signed with the White Sox,receiving a $760,000 signing bonus,and assigned him to make his professional debut with the Great Falls Voyagers of the Rookie-levelPioneer League and spent the whole season there,posting a 1–0 record and 2.79 ERA in 9+2⁄3 innings.[6] Fry began the 2015 season with the Winston-Salem Dash of the High-ACarolina League. In June 2015, he underwent his second Tommy John surgery.[9] Prior to his surgery, he was 1–8 with a 3.63 ERA in ten starts. He missed the 2016 season while rehabilitating from the surgery. The White Sox invited Fry to spring training in 2017.[10] In 2017, he pitched for the Birmingham Barons of the Double-ASouthern League where he went 2–1 with a 2.78 ERA with 52 strikeouts in 45+1⁄3 relief innings pitched.[11]
On September 5, 2017, Fry was selected to the 40-man roster and promoted to the major leagues for the first time.[12] He made 11 appearances for Chicago during his rookie campaign, struggling to a 10.80 ERA with three strikeouts across 6+2⁄3 innings pitched.[13] In 2018, his first full season with the team, Fry recorded a 4.38 ERA with 70 strikeouts and 20 walks in 51+1⁄3 innings.[14] The following season, Fry's ERA regressed to 4.75 as he walked 43 batters in 55 innings; he also logged a 3-4 record and 68 strikeouts.[15]
With the 2020 Chicago White Sox, Fry appeared in 18 games, compiling a 0–1 record with 3.66 ERA and 24 strikeouts in 19+2⁄3 innings pitched.[16]
In January 2021, Fry underwent a microdiscectomy, making him likely to miss the first month of the season.[17] On April 8, Fry was placed on the 60-day injured list.[18] He was activated on June 26, and optioned to the Triple-A Charlotte Knights.[19] Fry posted a 10.80 ERA in 6 appearances with Chicago in 2021. On November 5, Fry was outrighted off of the 40-man roster and elected free agency.[20]
Washington Nationals
On March 19, 2022, Fry signed a minor league contract with the Washington Nationals.[21] Fry made 15 appearances for the Triple-A Rochester Red Wings, working to a 3–0 record and 3.77 ERA with 20 strikeouts in 14+1⁄3 innings pitched. He was released by the Nationals organization on June 22.[citation needed]
Philadelphia Phillies
On June 29, 2022, Fry signed a minor league contract with the Philadelphia Phillies organization. Fry pitched in 18 games for the Triple-A Lehigh Valley IronPigs, but struggled to a 1–2 record and 6.75 ERA with 20 strikeouts in 16 innings of work. He elected free agency following the season on November 10.[22]
Detroit Tigers
On February 15, 2023, Fry signed a minor league contract with the Detroit Tigers organization.[23] Fry made 7 appearances for the Triple–A Toledo Mud Hens before he was placed on the injured list with left elbow inflammation on April 27.[24] On June 8, Fry was released by the Tigers organization.[25]
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