Josh Winckowski

Winckowski is from Toledo, Ohio. He attended Toledo Mud Hens games at Fifth Third Field as a child, but moved to Florida for high school.^[1] Winckowski attended Estero High School in Estero, Florida.^[2] The Toronto Blue Jays selected him in the 15th round of the 2016 MLB draft.^[2][3] Winckowski played in the Blue Jays' farm system from 2016 through 2019, reaching the High-A level with the Dunedin Blue Jays.^[4] In four seasons with the Toronto organization, Winckowski made 54 appearances (50 starts), compiling an 18–17 win–loss record with a 3.35 earned run average (ERA).^[4]

On January 27, 2021, Winckowski was traded to the New York Mets alongside Yennsy Díaz and Sean Reid-Foley in exchange for Steven Matz.^[5] On February 10, Winckowski was traded to the Boston Red Sox with Franchy Cordero and three players to be named later in a three-team trade, where the Kansas City Royals acquired Andrew Benintendi and the Mets received Khalil Lee.^[6] Winckowski began the year in Double-A with the Portland Sea Dogs and was promoted late in the season to the Triple-A Worcester Red Sox.^[4] Overall with both teams, he appeared in 23 games (22 starts), compiling a 3.94 ERA and 9–4 record while striking out 101 batters in 112 innings.^[4] After the regular season, Winckowski was selected to play for the Scottsdale Scorpions of the Arizona Fall League.^[7] On November 19, in advance of the Rule 5 draft, the Red Sox added Winckowski to their 40-man roster.^[8][9]

Winckowski began the 2022 season with Worcester.^[10] The Red Sox activated him on May 28 to start the second game of a doubleheader against the Baltimore Orioles at Fenway Park.^[11] Winckowski allowed four runs on six hits in three innings, taking the loss.^[12] He was returned to Worcester the following day.^[13] Winckowski was next recalled for a start on June 15,^[14] and registered his first MLB win after pitching five scoreless innings in a 10–1 victory over the Oakland Athletics at Fenway.^[15] Winckowski remained in the starting rotation until being placed on the COVID-related list on July 14;^[16] he rejoined the team on July 26.^[17] Through the remainder of the season, he split time between Worcester and Boston.^[18][19][20] In 15 games (14 starts) with Boston, Winckowski posted a 5–7 record with 5.89 ERA while striking out 44 batters in 70+1⁄3 innings.^[21]

For the 2023 season, Winckowski appeared in 60 Red Sox games (one start) and posted a 4–4 record with three saves and a 2.88 ERA while striking out 82 batters in 84+1⁄3 innings.^[21] Winckowski opened the 2024 season as a member of Boston's bullpen, until being optioned to Worcester on May 12; at the time, he had a 3.33 ERA in 24+1⁄3 innings.^[22]

Winckowski was optioned to Triple-A Worcester to begin the 2025 season.^[23] He was with Boston for nine days during April.^[24] On June 7, 2025, he was placed on the 60-day injured list with an elbow issue.^[25] Winckowski was designated for assignment by the Red Sox on November 18.^[26] On November 21, he was non-tendered by Boston and became a free agent.^[27]

On December 31, 2025, Winckowski signed a two-year minor league contract with the Toronto Blue Jays; it was also revealed that he had recently undergone internal brace surgery and would miss the majority of the 2026 season.^[28]

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