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Toronto Blue Jays Sign Former Boston Red Sox Pitcher After World Series Run
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- Toronto Blue Jays Sign Former Boston Red Sox Pitcher After World Series Run
The Toronto Blue Jays are reportedly signing former Boston Red Sox pitcher Josh Winckowski to a two-year contract.
Boston designated the 27-year-old Winckowski for assignment earlier this winter, and he later opted for free agency. According to MLB Trade Rumors' Steve Adams, Winckowski hopes to pitch late in the 2026 season after undergoing internal brace surgery.
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Winckowski recorded a 3.86 ERA with a 9-5 strikeout-to-walk ratio in 11⅔ innings for the Red Sox last season. However, he went on the injured list in May with a flexor strain and did not return.
Adams shared that the Blue Jays intend to use Winckowski as a starter once he is healthy.
What to Know About Josh Winckowski and the Toronto Blue Jays
Boston Red Sox relief pitcher Josh WinckowskiEric Canha-Imagn Images
Toronto and Winckowski are familiar with one another. The Blue Jays selected Winckowski in the 16th round of the 2016 MLB Draft, but they traded him — along with pitchers Yennsy Díaz and Sean Reid-Foley — to the New York Mets for starting pitcher Steven Matz in January 2021.
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The Mets then dealt Winckowski to the Red Sox in a three-team trade with the Kansas City Royals less than a month later. He made his MLB debut in May 2021 and posted a 5.89 ERA and minus-0.4 bWAR in 15 appearances, including 14 starts.
Winckowski transitioned to a full-time relief role in 2023, recording a 2.88 ERA, an 82-31 strikeout-to-walk ratio, three saves, and 1.9 bWAR across 60 appearances. His ERA climbed to 4.14 over 76 innings the following season.
Winckowski now rejoins a Blue Jays team fresh off winning the American League and reaching the World Series for the first time since 1993. Toronto and the Los Angeles Dodgers met in a tightly contested Fall Classic, though the Dodgers prevailed in seven games.
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The Blue Jays already made a splash this offseason, signing San Diego Padres pitcher Dylan Cease to a seven-year, $210 million contract in December. Toronto has also been linked to Chicago Cubs All-Star outfielder Kyle Tucker , while veteran second baseman Bo Bichette remains a free agent. Bichette, who has been with the Blue Jays organization since 2016, has repeatedly said he wants to return to Toronto if given the opportunity.
FanDuel Sportsbook lists the Blue Jays at +1700 odds (bet $100 to win $1,800) to win the World Series as of Jan. 1. That ranks fifth in the American League behind the New York Yankees (+800), Seattle Mariners (+1300), Red Sox (+1400), and the Houston Astros (+1600).
Toronto opens the 2026 season against the Athletics on Thursday, March 26.
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Related: MLB Insider Shares Update on Kyle Tucker-Blue Jays Free Agency Rumors
Related: Alex Rodriguez's Hall of Fame Progress Is Quickly Accelerating Ahead of 2026 Election
This story was originally published by Athlon Sports on Jan 1, 2026, where it first appeared in the MLB section. Add Athlon Sports as a Preferred Source by clicking here.
