Joshua Winckowski Bio
Joshua Winckowski is an American professional baseball pitcher who most recently played in Major League Baseball (MLB) for the Boston Red Sox organization. Born on June 28, 1998, in Toledo, Ohio, Winckowski has built a professional career spanning multiple organizations and levels of competitive baseball. Listed at 6 feet 4 inches (1.93 meters) and 202 pounds (92 kilograms), he throws and bats right-handed. Winckowski began his professional journey after being selected in the 15th round of the 2016 MLB Draft by the Toronto Blue Jays and eventually worked his way up to the major leagues, making his MLB debut with Boston in 2022. He has accumulated a career MLB record of 13 wins and 14 losses with a 4.20 earned run average and 195 strikeouts across his time with the Red Sox.
Early Life and Background
Joshua Winckowski grew up in Toledo, Ohio, where he developed an early passion for baseball by attending Toledo Mud Hens games at Fifth Third Field as a child. His connection to the local minor league team helped shape his understanding and love for the sport during his formative years. However, his family relocated to Florida during his high school years, setting the stage for his eventual path into professional baseball through the American baseball system rather than remaining in his Midwestern roots.
Winckowski attended Estero High School in Estero, Florida, where he refined his skills as a pitcher and caught the attention of MLB scouts. His performance in high school baseball demonstrated the talent and potential that would eventually lead to his selection in the 2016 MLB Draft. The combination of his Ohio baseball upbringing and Florida high school development provided him with a diverse foundation for his professional career.
Path to Professional Baseball
Winckowski’s journey to professional baseball began when the Toronto Blue Jays selected him in the 15th round of the 2016 MLB Draft. The selection marked the start of his professional career within the Blue Jays organization. He immediately began his minor league development, steadily progressing through the developmental ranks while honing his pitching craft and building the foundation for his future major league aspirations.
From 2016 through 2019, Winckowski played exclusively within the Toronto Blue Jays farm system, climbing from lower levels to eventually reach High-A baseball with the Dunedin Blue Jays. In his four seasons with the Toronto organization, he made 54 appearances with 50 starts, compiling an 18 win and 17 loss record with a 3.35 earned run average. These numbers demonstrated his ability to compete at the minor league level and positioned him for eventual major league consideration.
Joshua Winckowski Career
Toronto Blue Jays to Boston Red Sox (2021)
Winckowski’s career trajectory changed significantly in January 2021 when the Toronto Blue Jays traded him to the New York Mets alongside Yennsy Diaz and Sean Reid-Foley in exchange for Steven Matz. The trade represented a notable transaction involving a player who had spent his entire professional career with one organization. However, Winckowski did not remain with the Mets for long before his path would lead him to Boston.
Less than two weeks later, on February 10, 2021, Winckowski was traded again as part of a three-team deal involving the New York Mets and Kansas City Royals. The Boston Red Sox acquired Winckowski along with Franchy Cordero and three players to be named later, while the Royals obtained Andrew Benintendi and the Mets received Khalil Lee. Winckowski began the 2021 season in Double-A with the Portland Sea Dogs before receiving a late-season promotion to Triple-A with the Worcester Red Sox.
Combined between both minor league levels that season, Winckowski appeared in 23 games with 22 starts, compiling a 3.94 earned run average and a 9 win and 4 loss record while striking out 101 batters in 112 innings pitched. His strong performance earned him recognition, leading to his selection to play for the Scottsdale Scorpions in the Arizona Fall League following the regular season. In November 2021, the Red Sox added Winckowski to their 40-man roster ahead of the Rule 5 draft, officially protecting his professional rights.
MLB Debut and Early Boston Career (2022)
Winckowski began the 2022 season with the Triple-A Worcester Red Sox, continuing his development in the minor leagues. He received his first major league promotion on May 28, 2022, when the Red Sox activated him to start the second game of a doubleheader against the Baltimore Orioles at Fenway Park. In that debut appearance, Winckowski allowed 4 runs on 6 hits over 3 innings of work and took the loss in the contest. The Red Sox returned him to Worcester the following day to continue his development.
Winckowski was recalled again for a start on June 15, 2022, and achieved a significant milestone by registering his first MLB victory. He pitched 5 scoreless innings in a 10-1 victory over the Oakland Athletics at Fenway Park, marking a turning point in his major league career. He remained in the starting rotation through mid-July before being placed on the COVID-related list on July 14. He rejoined the team on July 26 and continued contributing to the rotation for the remainder of the season.
Throughout the 2022 season, Winckowski split time between Worcester and Boston, appearing in 15 games with 14 starts for the Red Sox. He posted a 5 win and 7 loss record with a 5.89 earned run average while striking out 44 batters in 70 and one-third innings pitched. The rookie season provided valuable experience at the highest level of professional baseball.
Breakthrough Season (2023)
The 2023 season marked a significant breakthrough for Winckowski as he established himself as a valuable member of the Boston Red Sox pitching staff. He appeared in 60 games with only one start, demonstrating his versatility in transitioning to a bullpen role. Winckowski posted a 4 win and 4 loss record with 3 saves and a stellar 2.88 earned run average while striking out 82 batters in 84 and one-third innings. His performance represented a dramatic improvement from his rookie campaign and showcased his ability to succeed as a reliever at the major league level.
2024 and 2025 Seasons
Winckowski opened the 2024 season as a member of the Boston Red Sox bullpen. His performance remained solid through early May, as he carried a 3.33 earned run average into mid-May before being optioned to Worcester on May 12. The assignment represented a continued pattern of movement between the major league club and Triple-A affiliate that characterized much of his Red Sox tenure.
To begin the 2025 season, Winckowski was optioned to Triple-A Worcester, where he began the year developing his craft at the highest minor league level. He was called up to Boston for a brief stint lasting nine days during April, providing bullpen depth when needed. However, his season encountered a significant setback when he was placed on the 60-day injured list on June 7 due to an elbow issue that required medical attention. The injury interrupted what had been a challenging season at the Triple-A level.
Driving Style and Strengths
Winckowski has demonstrated versatility throughout his professional career, successfully transitioning between starting and relieving roles. His ability to work as both a starter and reliever has provided the Red Sox with valuable roster flexibility. His 6-foot-4 frame generates good pitch plane angle, and he has shown the ability to work through opposing lineups multiple times when functioning as a starter while also possessing the stuff to provide effective innings out of the bullpen.
Notable Events and Milestones
Winckowski achieved his first MLB win on June 15, 2022, against the Oakland Athletics at Fenway Park, pitching 5 scoreless innings in his second major league appearance. The milestone represented a career highlight and validated his progression from the minor leagues to MLB. His 2023 season with Boston, where he posted a 2.88 ERA across 60 appearances, stands as his most accomplished major league campaign to date.
Joshua Winckowski Career Statistics
Winckowski has accumulated a career MLB record of 13 wins and 14 losses with a 4.20 earned run average and 195 strikeouts across his seasons with the Boston Red Sox. His career spans portions of five professional seasons since being drafted in 2016, with development work across multiple minor league levels and organizations. His minor league career includes a combined 18 win and 17 loss record with a 3.35 earned run average in 54 appearances with Toronto from 2016 to 2019.
Boston Red Sox Highlights
Winckowski’s most productive MLB season came in 2023 when he appeared in 60 games and posted a 2.88 earned run average with 4 wins, 4 losses, and 3 saves. His 2022 rookie campaign provided the foundation for his success, as he earned his first career victory and gained invaluable experience facing major league hitters. The combination of his 2022 and 2023 seasons established him as a capable major league pitcher capable of contributing in various roles.
Minor League Career
Winckowski’s minor league career includes four seasons with the Toronto Blue Jays organization from 2016 to 2019, where he compiled an 18 win and 17 loss record with a 3.35 earned run average in 54 appearances. He reached the High-A level with Dunedin and continued his development through 2021 with Portland and Worcester in the Red Sox system, where he posted a 9 win and 4 loss record with a 3.94 earned run average in 23 appearances. His Arizona Fall League participation with the Scottsdale Scorpions further enhanced his professional profile.
Joshua Winckowski Family
Personal Life
Winckowski grew up in Toledo, Ohio, where his childhood experiences watching Toledo Mud Hens games at Fifth Third Field helped spark his interest in professional baseball. His family later relocated to Estero, Florida, where he completed his high school education at Estero High School before embarking on his professional baseball career. Information regarding his current family situation remains private and has not been publicly disclosed through verified sources.
2025 Season Performance and Future Outlook
The 2025 season presented significant challenges for Winckowski as he struggled with an elbow injury that ultimately required placement on the 60-day injured list in June. Prior to the injury, he had been working primarily at the Triple-A level with Worcester after beginning the season in the minor leagues. His brief call-up to Boston during April provided limited opportunities to contribute at the major league level before the injury halted his progress.
The elbow issue that landed Winckowski on the injured list represented a serious setback in his career trajectory. After the season concluded, the Boston Red Sox designated him for assignment on November 18, 2025, and ultimately non-tendered him on November 21, making him a free agent. The decision marked the end of his tenure with the Red Sox organization, which had begun in February 2021 when they acquired him in a three-team trade.
Following his departure from Boston, Winckowski signed a two-year minor league contract with the Toronto Blue Jays on December 31, 2025, returning to the organization that originally drafted him in 2016. However, it was revealed that he had recently undergone internal brace surgery, a procedure that would require an extended recovery timeline. As a result of the surgery, Winckowski is expected to miss the majority of the 2026 season while rehabilitating from the procedure. The signing represents a homecoming of sorts for the Ohio native, who will look to recover from injury and potentially contribute to the Blue Jays organization in the future once he has fully healed.