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Josh Winckowski

Joshua Michael Winckowski (born June 28, 1998, in ) is an American professional baseball pitcher for the Boston Red Sox of (MLB). Standing at 6 feet 4 inches (1.93 m) and weighing 215 pounds (98 kg), he bats and throws right-handed. Winckowski grew up in Fort Myers, Florida, where he attended Estero High School. Winckowski was selected by the Toronto Blue Jays in the 15th round (462nd overall) of the 2016 MLB Draft, signing for a $125,000 bonus after forgoing a commitment to . He began his professional career in the Gulf Coast League that July, progressing through Toronto's system to reach Double-A by 2020. In January 2021, the Blue Jays traded him to the as part of a deal for pitcher ; less than a month later, on , the Mets sent him to the Red Sox in a three-team trade that brought outfielder to New York from . Winckowski made his MLB debut with the Red Sox on May 28, 2022, and has since appeared in 121 games through the 2025 season, primarily as a reliever with occasional starts. Over his career, he holds a 13–14 record with a 4.20 (), 195 strikeouts in 242.1 , five saves, and 23 holds, including a career-high 19 holds in 2023. His pitching arsenal features a reaching 94–96 mph, an 83–87 mph , and an 89–91 mph , positioning him as a potential multi-inning reliever or back-end starter, though command and secondary pitch consistency remain areas for improvement. In 2025, Winckowski's season was limited by right elbow inflammation, which placed him on the in ; he made six MLB appearances with a 3.86 over 11.2 before further setbacks, including a flexor strain in May that sidelined him for much of the year. He also pitched effectively in Triple-A with the , posting a 2.21 in 20.1 . Earlier in his , he missed time in 2019 due to a finger injury. As of November 2025, Winckowski remains with the Red Sox organization, having completed his fourth season with three years of service time.

Early life and amateur career

Early life

Joshua Winckowski was born on June 28, 1998, in Toledo, Ohio. He spent the early years of his childhood in Toledo, where he developed an initial passion for baseball through attendance at local minor league games with his father and grandfather, including school field trips to watch the Toledo Mud Hens. He also played travel baseball with the Ohio Diamond Hawks, where he first realized his talent in the sport. His family provided strong support for his athletic pursuits during this period, fostering his early interest in the sport without further public details on siblings or heritage. Shortly before high school, Winckowski and his family relocated to the Fort Myers, Florida area. There, as a teenager, he immersed himself in the local culture by frequently attending games of the Boston Red Sox and , which helped nurture his ambitions in the sport.

High school career

Winckowski began his high school career at Cypress Lake High School in Fort Myers, Florida, before transferring to Estero High School as a . At Estero, Winckowski quickly gained attention for his strong arm and potential as a right-handed , which scouts noted as one of the hardest-throwing in the area with good velocity and command. His grew during his year, where he was seen as a projectable talent despite needing refinement in control. In a standout performance as a senior on March 8, 2016, he pitched six innings against High School, allowing just two hits and striking out nine batters to secure a 4-3 victory, helping Estero maintain a first-place tie in Class 7A-District 12. During his senior season at Estero, Winckowski posted impressive statistics, including a 5-5 record, a 1.41 over 54.2 , and 85 strikeouts. These performances elevated his profile among scouts, leading to his selection by the Blue Jays in the 15th round (462nd overall) of the out of Estero High School.

Professional career

Toronto Blue Jays

Winckowski was selected by the Blue Jays in the 15th round, 462nd overall, of the 2016 MLB Draft out of Estero High School in , and he signed with the organization on July 11 for a $125,000 . He began his professional career that summer in rookie ball with the Gulf Coast League Blue Jays, where he made five appearances (one start), posting a 2-2 record with a 4.61 over 13.2 innings and 13 strikeouts. In 2017, Winckowski returned to rookie-level ball with the of the , appearing in 12 games (11 starts) and recording a 2-2 with a 5.33 in 54 innings while striking out 45 batters. His performance improved significantly in 2018 at short-season in the , where he went 4-5 with a 2.78 in 13 starts, logging 68 innings and 71 strikeouts, helping to establish him as a promising starter in the system. Winckowski advanced to full-season affiliates in 2019, beginning the year with low of the , where he excelled with a 6-3 , 2.32 , 73.2 innings, and 71 strikeouts in 13 starts; he was promoted midseason to high of the , finishing 4-5 with a 3.19 in 11 starts over 53.2 innings and 37 strikeouts, for a combined 10-8 and 2.69 across 24 starts and 127.1 innings that year. However, his 2019 season was interrupted by a stint on the 7-day retroactive to April 29 while with Lansing due to a finger injury. The 2020 minor league season was cancelled due to the , preventing Winckowski from building on his momentum. On January 27, 2021, the Blue Jays traded Winckowski, along with pitchers Sean Reid-Foley and Yennsy Díaz, to the in exchange for left-handed starter . Shortly thereafter, on February 10, 2021, Winckowski was included in a three-team trade that sent him from the Mets to the Boston Red Sox, with the Red Sox sending outfielder and cash to the , the Royals sending outfielder to the Red Sox, and the Royals sending a to the Mets.

Boston Red Sox

Winckowski was acquired by the in a three-team trade on February 10, 2021, that also brought outfielder from the to . Winckowski made his MLB debut on May 28, 2022, starting the second game of a doubleheader against the at , where he pitched 3.0 innings, allowing 4 earned runs on 6 hits and 3 walks while striking out 4 batters in a 4-2 loss. In 2022, Winckowski primarily served as a for the Red Sox, making 14 starts across 15 appearances and posting a 5-7 record with a 5.89 over 70.1 , including 44 strikeouts. He earned his first career win on June 15, 2022, against the , delivering 5 scoreless with 3 strikeouts in a 10-1 victory. By 2023, the Red Sox transitioned him to a role, where he appeared in 60 games with just 1 start, recording a 4-4 mark, 2.88 , and 3 saves over 84.1 while fanning 82 batters. In 2024, Winckowski took on mixed duties, blending relief outings with spot starts in 6 games, finishing 4-2 with a 4.14 and 2 saves across 76.0 and 60 strikeouts in 40 appearances. In 2025, Winckowski's season was limited by injuries, beginning with right inflammation that placed him on the in April; he made six relief appearances with a 3.86 over 11.2 and 9 strikeouts before a flexor strain in mid-May at Triple-A , leading to his placement on the 60-day on June 7. He pitched effectively with the , posting a 2.21 in 20.1 . The Red Sox activated him from the on November 6, 2025, only to designate him for assignment that same day amid roster adjustments. Through four MLB seasons with , primarily as a reliever by 2025, Winckowski compiled a 13–14 record, 4.20 , and 195 strikeouts in 242.1 across 21 starts and 121 appearances.

Pitching style

Pitch repertoire

Josh Winckowski's pitch repertoire features five offerings: a , sinker, , , and , with no in regular use. His averages 94.7 mph in the 2025 season, an increase from 92-93 mph prior to 2023 following offseason velocity training. The sinker, clocked at a similar 94.7 mph, emphasizes arm-side run and downward movement to induce groundballs. The , introduced at the end of 2021 and incorporated into his rotation by 2022, averages 89.6 mph and provides a harder breaking option with minimal horizontal and vertical break to jam hitters. Winckowski's primary breaking pitch is , thrown at 86.2 , which he refined post-2022 with a new grip for sharper movement and added velocity, enhancing its swing-and-miss capabilities. , used occasionally, averages 91.8 with significant arm-side fade, serving as a complementary against opposite-handed batters. In 2025, Winckowski leans on his fastball-sinker- combination for about 71% of his pitches (29% four-seamer, 19% sinker, 23% ), while deploying at 13%—often higher in roles for —and at 16%. These adjustments, including the sharper , have boosted his rates to around 9 K/9 in seasons like 2023.

Mechanics and development

Winckowski employs a high three-quarters arm slot in his right-handed , allowing for consistent release points while varying his position slightly to exploit advantages against left- and right-handed hitters. His motion features a repeatable with a short, somewhat stiff arm action that includes a subtle stab in the back, contributing to solid extension off the averaging approximately 6.5 feet across his pitch arsenal. This extension helps maximize perceived by reducing the batters have to react, though Winckowski has emphasized maintaining arm slot consistency to avoid inconsistencies that could diminish his fastball's effectiveness. A key development milestone came between the 2022 and 2023 seasons, when Winckowski increased velocity by about 1.5 mph on his fastball, sinker, and slider through a combination of mechanical adjustments in the Red Sox organization, including a revamped windup and grip modifications on select pitches. These changes, part of an aggressive offseason overhaul, were supported by the team's strength and conditioning program, which focused on building lower-body power and core stability to sustain higher arm speeds without compromising control. Post-2022, his command improved notably, with a walk rate stabilizing around 3.5 BB/9 in subsequent seasons, reflecting better overall delivery repeatability. Winckowski's transition from starting to roles, particularly intensified in 2023 and 2024, contributed to a right flexor strain sustained in mid-May 2025 while pitching at Triple-A , highlighting the physical toll of adapting to shorter, higher-intensity outings after extended starter workloads. , which sidelined him for the remainder of the season after placement on the 60-day in June, prompted a protocol centered on gradual arm conditioning, including structured throwing progressions to rebuild forearm strength and prevent recurrence. Scouting evaluations note that while his primary pitches have gained reliability, ongoing refinement of secondary offering consistency remains a focus in his development, with the Red Sox pitching staff emphasizing tweaks to enhance shape and location variability.

References

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