Josh Winckowski Bio
Joshua Winckowski, born June 28, 1998, is an American professional baseball pitcher who is currently a free agent. He has previously played in Major League Baseball (MLB) for the Boston Red Sox, where he worked as both a starter and a reliever. Listed at 6 feet 4 inches (1.93 m) and 202 pounds (92 kg), he throws and bats right-handed.
A graduate of the Toronto Blue Jays’ farm system, Winckowski has been active in professional baseball since 2016. He became a free agent in November 2025 after spending the bulk of his major league career with the Red Sox organization.
Early Life and Background
Joshua Winckowski was born on June 28, 1998, in Toledo, Ohio. Growing up in Toledo, he frequently attended Toledo Mud Hens games at Fifth Third Field, where his early interest in baseball took root. The familiar surroundings of minor league baseball gave him regular exposure to the sport during his childhood.
Winckowski later moved to Florida for high school, where he attended Estero High School in Estero. The change in climate and competition helped shape his development as a pitcher and prepared him for a professional career. His combination of size and right-handed delivery made him an appealing prospect among amateur evaluators.
Path to Professional Baseball
Winckowski’s path to professional baseball began in the 2016 MLB draft, when the Toronto Blue Jays selected him in the 15th round. That selection launched his career in the Toronto farm system, where he worked his way up through the lower levels of the organization.
From 2016 through 2019, Winckowski pitched in the Blue Jays’ minor league system, reaching the High-A level with the Dunedin Blue Jays. Across four seasons with the Toronto organization, he made 54 appearances, including 50 starts, and posted an 18-17 win-loss record with a 3.35 earned run average (ERA). That track record helped establish him as a legitimate starting pitching prospect entering the next phase of his career.
Josh Winckowski Career
Toronto Blue Jays Farm System (2016-2019)
Winckowski spent his first four professional seasons within the Toronto Blue Jays organization after being drafted in 2016. He progressed steadily through the lower levels, ultimately reaching High-A with the Dunedin Blue Jays. His time in the Blue Jays’ system gave him the foundation he needed to develop into a starting pitcher capable of handling advanced competition.
Following the 2019 season, the Blue Jays traded Winckowski. On January 27, 2021, he was sent to the New York Mets alongside Yennsy Díaz and Sean Reid-Foley in exchange for Steven Matz. Just two weeks later, on February 10, he was traded again, this time to the Boston Red Sox as part of a three-team deal that also sent Franchy Cordero and three players to be named later to Boston.
Boston Red Sox (2021-Present)
After joining the Red Sox organization, Winckowski began 2021 in Double-A with the Portland Sea Dogs. He was later promoted to the Triple-A Worcester Red Sox late in the season. Across both affiliates, he appeared in 23 games, making 22 starts, and compiled a 3.94 ERA with a 9-4 record while striking out 101 batters in 112 innings. After the regular season, he was selected to play for the Scottsdale Scorpions of the Arizona Fall League, and on November 19, 2021, the Red Sox added him to their 40-man roster ahead of the Rule 5 draft.
Winckowski made his MLB debut in 2022 after being activated on May 28 to start the second game of a doubleheader against the Baltimore Orioles at Fenway Park. He took the loss in that outing, allowing four runs on six hits in three innings, and was returned to Worcester the following day. He was recalled again on June 15 and earned his first MLB win after pitching five scoreless innings in a 10-1 victory over the Oakland Athletics at Fenway. He remained in the starting rotation until a July 14 placement on the COVID-related list, then rejoined the team on July 26. Across 15 games and 14 starts with Boston in 2022, he posted a 5-7 record with a 5.89 ERA and 44 strikeouts in 70+1⁄3 innings.
In 2023, Winckowski transitioned into a relief role. He appeared in 60 Red Sox games with just one start, posting a 4-4 record with three saves and a 2.88 ERA while striking out 82 batters in 84+1⁄3 innings. The strong bounce-back season established him as a reliable bullpen option for Boston. He opened the 2024 season in the Red Sox bullpen before being optioned to Worcester on May 12, at which point he had a 3.33 ERA across 24+1⁄3 innings.
Free Agency (2025)
Winckowski was optioned to Triple-A Worcester to begin the 2025 season. He spent nine days with Boston in April before a longer absence. On June 7, 2025, he was placed on the 60-day injured list with an elbow issue, ending his major league action for the year. On November 18, the Red Sox designated him for assignment, and on November 21, Boston non-tendered him, making him a free agent.
Driving Style and Strengths
Winckowski’s imposing 6-foot-4 frame and right-handed delivery give him a power pitcher’s profile. He has demonstrated he can handle the responsibilities of both a starting pitcher and a late-inning reliever, a flexibility that has helped him remain valuable at the major league level. His 2.88 ERA across 60 appearances in 2023 showed he can thrive in high-leverage relief situations.
Notable Events and Milestones
One of the defining moments of Winckowski’s career came on June 15, 2022, when he earned his first MLB win with five scoreless innings against the Oakland Athletics at Fenway Park. His 2023 season, which featured a 2.88 ERA and three saves in 60 appearances, marked his most productive major league campaign to date.
Josh Winckowski Career Highlights
Joshua Winckowski has compiled a varied major league resume across starts and relief appearances. He has been part of postseason-caliber rosters in Boston and has contributed both as a starter and as a bullpen arm during his time with the Red Sox.
Boston Red Sox Highlights
Winckowski’s most prolific major league season came in 2023, when he appeared in 60 Red Sox games and posted a 4-4 record with three saves and a 2.88 ERA while striking out 82 batters in 84+1⁄3 innings. In 2022, he made 15 appearances, including 14 starts, finishing 5-7 with a 5.89 ERA. His first MLB win came on June 15, 2022, against the Oakland Athletics, when he tossed five scoreless innings in a 10-1 victory at Fenway Park.
Other Performances
In 2021, after joining the Red Sox organization, Winckowski posted a 3.94 ERA with a 9-4 record across 23 minor league games, splitting time between Double-A Portland and Triple-A Worcester. He was also selected to the Arizona Fall League that offseason.
Josh Winckowski Family
Family Background and Personal Life
Joshua Winckowski is originally from Toledo, Ohio, where he grew up attending Toledo Mud Hens games at Fifth Third Field. He later moved to Florida, where he completed his high school education at Estero High School. Public details about his immediate family remain limited.
Personal Life
Winckowski resides in the United States and has built his professional life around baseball since being drafted in 2016. He has not publicly shared extensive personal-life information, and verified details about a spouse or children are not available.
2025 Season Performance
Joshua Winckowski began the 2025 season with Triple-A Worcester after being optioned by the Red Sox. He spent nine days with the major league club in April before a longer absence. His most significant stretch of the year came when he was placed on the 60-day injured list on June 7, 2025, due to an elbow issue that kept him out of major league action for the remainder of the season.
Following the season, the Red Sox designated Winckowski for assignment on November 18, 2025, and non-tendered him on November 21, making him a free agent. He ended his time in the Boston organization with a varied resume that included both starting and relief work.
As a free agent, Winckowski enters the next chapter of his career with experience as both a starter and a reliever. His 2023 bullpen success suggests he could be a useful addition for clubs looking to add right-handed depth, and his recovery from the 2025 elbow issue will be a key storyline heading into 2026.