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Boston Red Sox designate former Toronto Blue Jays pitcher for assignment ahead of Rule 5 deadline


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Roger Macpherson
November 18, 2025  (8:02 PM)
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Josh Winckowski is 1-0 with a 1.02 ERA and 16 strikeouts over 17 2/3 innings in his last three starts. (Cliff Welch/MiLB.com)
Photo credit: Cliff Welch-MiLB.com

With the Rule 5 deadline approaching, many teams are forced to make difficult decisions.

The Boston Red Sox are no different.
On Tuesday, hours before the Rule 5 deadline, Boston designated infielder Nathaniel Lowe and pitcher Josh Winckowski for assignment, removing both from the 40 man roster, and clearing the way for other players to be protected in advance of the Rule 5 draft.
Lowe is a former Gold Glove and Silver Slugger winner who was signed by the Red Sox after his release from the Washington Nationals in August.
Winckowski has been with the BoSox since 2021.
The #RedSox are Designating RHP Josh Winckowski for assignment, a league source tells @7News

Winckowski had a 4.20 ERA with the Red Sox in 121 appearances and 242.1 IP between 2022-25.
A 15th round pick of the Toronto Blue Jays in 2016, Winckowski laboured in the Jays farm system for four years, only ever reaching Single-A with the Dunedin Blue Jays.
In four seasons with the Toronto organization, Winckowski made 54 appearances (50 starts), compiling an 18-17 win-loss record with a 3.35 ERA.
He got traded twice within the span of a month in 2021. In January, he was shipped to the New York Mets along with Yennsy Diaz and Sean Reid-Foley in exchange for starting pitcher Steven Matz.
Two weeks later, the Mets flipped him to the Red Sox for Franchy Cordero and three players to be named later, in a deal that also involved the Kansas City Royals.

Made his major league debut in 2022.

After one season in Boston's minor league system, Winckowski finally made his major league debut, getting the call at the end of May.
While he had some success, he never stuck around for a full season, bouncing back-and-forth between Boston and Triple-A Worcester.
For his career, Winckowski is 13-14 with a 4.20 ERA.
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Boston Red Sox designate former Toronto Blue Jays pitcher for assignment ahead of Rule 5 deadline

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