Toronto Blue Jays 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. Winckowski attended
Estero High School in
Estero, Florida. Winckowski played in the Blue Jays'
farm system from 2016 through 2019, reaching the
High-A level with the
Dunedin Blue Jays. 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. 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. After the regular season, Winckowski was selected to play for the
Scottsdale Scorpions of the
Arizona Fall League. On November 19, in advance of the
Rule 5 draft, the Red Sox added Winckowski to their 40-man roster. Winckowski began the 2022 season with Worcester. The Red Sox activated him on May 28 to start the second game of a
doubleheader against the
Baltimore Orioles at
Fenway Park. Winckowski allowed four runs on six hits in three innings, taking the loss. He was returned to Worcester the following day. Winckowski was next recalled for a start on June 15, and registered his first MLB win after pitching five scoreless innings in a 10–1 victory over the
Oakland Athletics at Fenway. Winckowski remained in the starting rotation until being placed on the COVID-related list on July 14; he rejoined the team on July 26. Through the remainder of the season, he split time between Worcester and Boston. In 15 games (14 starts) with Boston, Winckowski posted a 5–7 record with 5.89 ERA while striking out 44 batters in innings. 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 innings. Winckowski was optioned to Triple-A Worcester to begin the 2025 season. He was with Boston for nine days during April. On June 7, 2025, he was placed on the 60-day injured list with an elbow issue. Winckowski was
designated for assignment by the Red Sox on November 18. On November 21, he was non-tendered by Boston and became a free agent.
Toronto Blue Jays (second stint) 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. ==References==