Josh Winckowski Signs Minor League Deal with Blue Jays During Elbow Rehab.

The Toronto Blue Jays added pitching depth this offseason by signing right-hander Josh Winckowski, though the move is focused more on the future than immediate impact. Winckowski is recovering from elbow surgery and is not expected to pitch during the 2026 season. Winckowski, who has spent his entire Major League career with the Boston Red Sox, underwent internal brace surgery earlier this month after dealing with an elbow strain that sidelined him during the 2025 season. Because of the lengthy recovery timeline associated with the procedure, Toronto signed him to a two-year minor league contract, allowing him to rehabilitate without pressure to return quickly. The agreement was first reported by Steve Adams of MLB Trade Rumors, though the Blue Jays have yet to make an official announcement. According to Adams, the organization hopes Winckowski can return late in 2026, with a plan to gradually build him back up as a starter once he is healthy. The signing also represents a reunion of sorts. Although Winckowski debuted in the majors with Boston in 2022, he was originally drafted by the Blue Jays in 2016 out of high school. After moving through several trades, he eventually reached the big leagues with the Red Sox.

Winckowski’s early Major League experience came as a starter, posting a 5–7 record and a 5.89 ERA during his rookie season. He found greater success after transitioning to the bullpen in 2023, when he emerged as one of Boston’s most reliable relievers. That season, he appeared in 60 games and recorded a 2.88 ERA with 82 strikeouts over 88 innings.

Before his injury in 2025, the 27-year-old showed promise once again, pitching in six games and finishing with a 3.86 ERA and nine strikeouts in 11 innings. While his long-term role—starter or reliever—remains uncertain, the Blue Jays are offering him the opportunity to fully recover and redefine his career path within a competitive organization.