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Red Sox free agent pitcher signs with AL East rival that once traded him
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- Red Sox free agent pitcher signs with AL East rival that once traded him
The Red Sox ended Josh Winckowski’s tenure with the organization in November. designating him for assignment amid a roster crunch. Now, he’s headed to an American League East rival — and a club that’s very familiar to him.
Winckowski has signed a two-year minor league contract with the Blue Jays , according to MLBTradeRumors’ Steve Adams . For the 27-year-old, it’s a return to the organization that drafted him (in 2016), then traded him five years later before he was flipped to Boston in another trade.
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According to Adams, Winckowski — who didn’t pitch after May 11 at any level due to a nebulous elbow injury — recently underwent an internal brace (Tommy John alternative) surgery on his throwing arm and is likely out for most of the 2026 season. Thus, the Jays will oversee his rehab process in hopes he can contribute in 2027.
Winckowski moves on following a four-year stint with the Red Sox in which he made 121 appearances (21 starts) and logged a 4.20 ERA. Winckowski had a breakout season as a reliever in 2023, logging a 2.88 ERA in 60 appearances (84 ⅓ innings). He wasn’t a perfect match for new pitching coach Andrew Bailey when he took over in 2024 and posted an uneven season (4.14 ERA, 4.48 FIP in 76 innings). In 2025, Winckowski didn’t make the Opening Day roster and totaled just 11 ⅔ innings over six April games before being sent down to Triple-A Worcester. He was designated and subsequently non-tendered in November.
In his first stint with the Jays, Winckowski only reached High-A (in 2019) before COVID wiped out the 2020 minor league season. Toronto traded him to the Mets for Steven Matz in January 2021, then flipped him to Boston in the three-team deal that sent Andrew Benintendi to Kansas City just two weeks later.
In 2023, Winckowski acknowledged a “grudge” against Toronto for trading him.
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“I’ve always been a big chip-on-my-shoulder guy and sometimes I do the ‘fake fire’ stuff, so I still hold a grudge against them, to this day, even though it’s probably not warranted,” Winckowski said. “I just fake it. Anytime I play them, I just want to do extremely well. Even just giving up a hit to them drives me crazy.
“I think the Blue Jays thought I was a good pitcher but as any team does, they had their guys that they had an explicit trust and belief in,” Winckowski added. “At the end of the day, there was a price for me. It’s a business and I get it. They saw one year of Steven Matz worth losing me for.”
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