Why Josh Winckowski could be an impact pitcher for Blue Jays next season

As the Toronto Blue Jays turn the page and look forward to the 2027 season, having enough arms that can be trusted will be among the team's priorities. One such pitcher in the organization may be a dark horse candidate to provide that kind of impact.

Josh Winckowski, 28, is a middle reliever and swingman with four seasons and 242.1 innings of major-league experience. He hurt his elbow in 2025, then signed a two-year minor-league deal with Toronto in December. Unfortunately, Winckowski spent most of 2026 recovering from an internal brace surgery for that elbow, which is similar to Tommy John, except the recovery period is shorter than the typical 18 months for TJ surgery.

The right-hander made six appearances with Single-A Dunedin and Triple-A Buffalo this season. Combined, Winckowski posed a 0.66 ERA and 0.95 WHIP over 13.2 innings, while striking out 17 with five walks. His fastball touched 94 mph and averaged around 92 mph during the rehab outings.

Josh Winckowski on track to returning to the big leagues with Toronto in 2027

This is Winckowski's second stint with the Toronto organization. He was drafted out of high school by the Blue Jays in 2016, then traded in 2021 to the New York Mets in the Steven Matz deal, then shipped to the Boston Red Sox in a three-team deal a few weeks later. He made the majors with Boston in 2022, but struggled and moved to the bullpen in 2023. Winckowski excelled in his new role, posting a 2.88 ERA in 60 games.

Winckowski was in Boston's bullpen again in 2024, pitching to a 4.14 ERA in 40 games, while spending some time down in Triple-A. He started 2025 in the minors, but made it back to Boston for just 11.2 innings before his elbow injury landed him on the Injured List in June. After the season ended, the Red Sox designated Winckowski for assignment, then non-tendered him, making him a free agent in November.

The strikeout totals are key to Winckowski's effectiveness. In 2022 and 2024, he posted underwhelming strikeout numbers (44 strikeouts in 70.1 innings and 60 in 76 innings respectively), likely due to a drop in velocity. In 2023, Winckowski struck out 82 in 84 innings.

Winckowski told Rogers Sportsnet's Blake Murphy what encouraged him to sign with Toronto was the team's philosophy and direction. He caught a glimpse of those ideals when he was with the organization in 2020 and 2021, before he was traded. Toronto's player development complex, which opened in 2021, was also a major benefit that appealed to Winckowski.

Aside from encouraging him to be the best version of himself, Winckowski told Sportsnet the plan is for the Blue Jays to make him a starter in 2027. Given Toronto's starting rotation was more of rotating door this season, the plan makes sense. Winckowski throws five pitches; fastball, slider, changeup, sinker and a cutter, which is the kind of repertoire a starting pitcher would have.

Winckowski has a variety of pitches and above average control, which makes him an ideal candidate to be a starter, or at least a reliable arm in the bullpen. This could be one less arm the Blue Jays will have to find for 2027.

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