Josh Winckowski Joins Blue Jays Organization While Rehabbing Elbow Surgery
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The Toronto Blue Jays' most recent addition to their pitching staff is in a different scenario than their other acquisitions this offseason. He is highly unlikely to see the field in 2026 for the organization as it is probable he will miss the year as he only underwent surgery on his arm this month.
Josh Winckowski has spent the bulk of his professional career with the Boston Red Sox, including 2025, but he didn't play much. Back in May he suffered an elbow strain that would eventually lead to an internal elbow brace being put into his arm this month.
His agreement with the Blue Jays was reported by Steve Adams of MLB Trade Rumors. The Blue Jays have not formally announced the deal.
Unfortunately this procedure means that there is no expectation for him to pitch this coming season which is why the Jays and him agreed to a two-year minor league deal even though he has been pitching in the Majors since his debut in 2022.
A two-year contract gives Winckowski the chance to rehab this injury properly without any added pressure that he will lose his spot with the ballclub if he doesn't throw a pitch in the next year.
Quick Look at Winckowski's Career Thus Far
This will actually be somewhat of a reunion for both Winckowski and the Blue Jays. Even though he has only pitched for the Red Sox it was actually Toronto that kick started his career as they were the team to draft him back in 2016 fresh out of high school.
A series of trades eventually landed him in Boston which is where he made his debut back in in 2022 as a starter. In his debut year he went 5-7 with a 5.89 ERA and only 44 strikeouts in over 70 innings. It was the following year that he found his place in their bullpen.
Source: Right-hander Josh Winckowski is signing a two-year minor league deal with the #BlueJays. Had internal brace surgery earlier this month. Hoping to pitch late in 2026. Plan right now is to build him back up as a starter when he’s healthy.
— Steve Adams (@Adams_Steve) December 31, 2025
In 2023 Winckowski was one of the Red Sox best relievers which is why he was utilized in 60 games where he posted a 2.88 ERA to complement 82 strikeouts in 88 innings worth of work.
The 27-year-old had started 2025 off strong as a reliever. The Red Sox had used him in six games and his quick season ended with a 3.86 ERA and nine strikeouts in 11 innings.
There isn't necessarily a clear path as to whether or not he will step back into the majors in a starter or reliever's role, but he has to be glad that he has a chance to figure it out with a team as good as the Blue Jays.
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Maddy Dickens resides in Loveland, Colorado. She grew up with two older brothers, where their lives revolved around sports. She earned a master's degree in business management from Tarleton State University while simultaneously playing basketball and competing in rodeo at the collegiate level. She successfully parlayed a reserve national championship into a professional rodeo career and now stays involved in upper-level athletics by writing for On SI on several different MLB teams' pages, along with some NCAA sites.