Josh Winckowski Bio
Joshua Winckowski, born on June 28, 1998, in Toledo, Ohio, is an American professional baseball pitcher. He is listed at 6 feet 4 inches and 202 pounds, throws right-handed, and bats right-handed. Winckowski has played in Major League Baseball (MLB) for the Boston Red Sox and is currently a free agent.
Originally drafted by the Toronto Blue Jays, Winckowski spent several years developing in the minor leagues before reaching the majors with Boston. He has worked as both a starter and a reliever throughout his professional career.
Early Life and Background
Joshua Winckowski was born and raised in Toledo, Ohio, where he developed an early love for the game of baseball. As a child, he attended Toledo Mud Hens games at Fifth Third Field, an experience that helped spark his interest in pitching. His exposure to professional baseball in his hometown laid the foundation for his future career on the mound.
During his high school years, Winckowski relocated to Florida to continue his baseball development. He attended Estero High School in Estero, Florida, where he refined his skills as a pitcher. The move south allowed him to play year-round in a warmer climate and against stronger competition, helping him grow as a prospect.
Path to Baseball
Winckowski’s path to professional baseball officially began when the Toronto Blue Jays selected him in the 15th round of the 2016 MLB draft. Coming out of Estero High School, he joined Toronto’s farm system as a young pitching prospect with a strong frame and a heavy right-handed delivery. The Blue Jays saw potential in his arm and gave him the opportunity to develop at the minor league level.
From 2016 through 2019, Winckowski worked his way through Toronto’s minor league system, steadily climbing the ranks. He reached as high as the High-A level with the Dunedin Blue Jays, where he gained valuable experience against advanced hitters. Over 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), establishing himself as a reliable starting pitcher in the making.
Josh Winckowski Career
Early Career (2016–2019)
Winckowski’s early professional career was spent entirely within the Toronto Blue Jays organization after being drafted in 2016. He developed as a starting pitcher across several minor league affiliates, working on his command and pitch arsenal. His time in the lower levels helped him adjust to the rigors of professional baseball.
By the time he reached High-A Dunedin, Winckowski had become a dependable starter in Toronto’s system. His 3.35 ERA across 54 appearances showed consistency, even as he continued to refine his game. The Blue Jays eventually moved him at the major league level, opening the door for a new chapter in his career.
Boston Red Sox Era (2022–2025)
Winckowski’s journey to Boston began with a pair of trades in early 2021. On January 27, 2021, he was traded to the New York Mets alongside Yennsy Díaz and Sean Reid-Foley in exchange for Steven Matz. Shortly after, on February 10, he was part of a three-team trade that sent him to the Boston Red Sox, with Franchy Cordero and three players to be named later going to Boston as well, while Andrew Benintendi was dealt to Kansas City.
He spent most of 2021 in the minor leagues, splitting time between Double-A Portland and Triple-A Worcester. In 23 games with 22 starts, he posted a 9–4 record with a 3.94 ERA and 101 strikeouts over 112 innings. After the season, he played for the Scottsdale Scorpions of the Arizona Fall League. On November 19, ahead of the Rule 5 draft, the Red Sox added Winckowski to their 40-man roster.
Winckowski made his MLB debut with Boston on May 28, 2022, starting the second game of a doubleheader against the Baltimore Orioles at Fenway Park. Although he took the loss in that debut, he earned his first MLB win on June 15 against the Oakland Athletics, pitching five scoreless innings in a 10–1 victory. He split time between Worcester and Boston for the rest of the year, finishing his rookie season with a 5–7 record and a 5.89 ERA in 15 games.
In 2023, Winckowski transitioned to a relief role, appearing in 60 games with one start. He posted a 4–4 record with three saves, a 2.88 ERA, and 82 strikeouts in 84⅓ innings, becoming a dependable arm out of the Red Sox bullpen. He opened the 2024 season in the bullpen before being optioned to Worcester in May. In 2025, he began the year in Triple-A, spent nine days with Boston in April, and was placed on the 60-day injured list on June 7 due to an elbow issue.
Toronto Blue Jays Return (2025–Present)
On November 18, 2025, Winckowski was designated for assignment by the Red Sox, and on November 21, he was non-tendered, making him a free agent. Shortly after, on December 31, 2025, he signed a two-year minor league contract with the Toronto Blue Jays, the organization that originally drafted him. The signing was accompanied by news that he had recently undergone internal brace surgery and was expected to miss the majority of the 2026 season.
Driving Style and Strengths
Winckowski’s 6-foot-4 frame and 202-pound build give him a strong presence on the mound, allowing him to generate good angle and downhill plane on his pitches. He has demonstrated the ability to work both as a starter and a reliever, showing durability and consistency. His right-handed delivery and growing pitch mix have helped him succeed in a variety of roles.
Notable Events and Milestones
One of the most memorable 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, in which he appeared in 60 games with a 2.88 ERA and three saves, marked his emergence as a reliable bullpen arm for the Red Sox.
Josh Winckowski Career Wins
Joshua Winckowski has accumulated victories at both the minor league and major league levels throughout his professional career. In the minor leagues with Toronto’s system, he posted an 18–17 record across 54 appearances, and in 2021 with Boston’s affiliates, he went 9–4. In the majors, he has recorded wins with the Boston Red Sox, including his first career MLB victory in June 2022 against Oakland.
MLB Highlights
Through the 2025 season, Winckowski’s major league statistics include a 13–14 win-loss record, a 4.20 ERA, and 195 strikeouts. His 2023 campaign stands out as his strongest, with a 2.88 ERA and three saves across 60 appearances out of the Red Sox bullpen.
Other Wins & Performances
In addition to his major league work, Winckowski has logged strong performances in the minor leagues, including his 9–4 record with Portland and Worcester in 2021. His selection to the Arizona Fall League that same year also highlighted his standing as a notable prospect within the Red Sox organization.
Josh Winckowski Family
Family Background and Racing Lineage
Joshua Winckowski was born in Toledo, Ohio, but public details about his parents and family background are limited. His upbringing in Toledo and early attendance at Toledo Mud Hens games played an important role in shaping his love for the game.
Personal Life
Limited public information is available regarding Winckowski’s personal life, including marital status or children. He continues to focus on his professional baseball career and his recovery from elbow surgery.
2025 Season Performance
Winckowski began the 2025 season with Triple-A Worcester after being optioned by the Red Sox. He joined Boston briefly in April for nine days before returning to the minors. On June 7, 2025, he was placed on the 60-day injured list due to an elbow issue, cutting his major league season short.
His 2025 campaign was overshadowed by injury, as the elbow problem limited his availability and ultimately led to his designation for assignment by Boston in November. Following his non-tender, he signed a minor league deal with Toronto, though he is expected to miss most of 2026 while recovering from internal brace surgery.
Looking ahead, Winckowski’s outlook centers on rehabilitation and a return to the mound with the Blue Jays organization. His two-year minor league contract provides a pathway back to the majors once he has fully recovered from surgery.