Boston Red Sox Option Former Trade Acquisition, Big Bullpen Piece to Triple-A

Josh Winckowski, who was acquired in the trade of Andrew Benintendi, is headed to Triple-A Worcester despite an accomplished track record.

Josh Winckowski, a pitcher for the Boston Red Sox pitches in relief during a Spring Training game against the Baltimore Orioles at JetBlue Park in Fort Myers on Monday, March 17, 2025. | andrew west / USA TODAY NETWORK via Imagn Images

The Boston Red Sox are on the verge of optioning reliever Josh Winckowski to Triple-A Worcester, according to Chris Cotillo of MassLive.

It appears Josh Winckowski is another reliever being optioned, though no confirmation from the team yet. https://t.co/zcmwPVu23D

— Chris Cotillo (@ChrisCotillo) March 19, 2025

This seems like a bit of a surprising decision for the Sox, considering Winckowski has spent the last two seasons featuring prominently on the roster. The 26-year-old was acquired in 2021 in the trade that sent Andrew Benintendi to the Kansas City Royals

He's made 115 appearances in the last three years, including 100 in the last two years combined. He was dynamite as a reliever in 2023, going 4-4 with a 2.88 ERA. While he regressed in 2024, he still was 4-2 with a 4.14 in 40 appearances. He did made seven appearances at Triple-A last season as well.

The fact that he's being sent down seemingly shows the improvements that the Red Sox made to their bullpen this offseason. They added veteran Aroldis Chapman, as well as Justin Wilson. They also will get a full year of Liam Hendriks, whom they signed before the 2024 season.

Boston is coming off a season in which it was 81-81 and missed the playoffs by finishing third in the American League East. However, with an improved bullpen and additions of Garrett Crochet, Alex Bregman and Walker Buehler, the expectations are certainly higher this year.

The Red Sox will open the regular season on March 27 at the Texas Rangers, while the "WooSox" will open their season a day later.

It's unclear if Winckowski will function as a starter or a reliever in Triple-A. He does have 21 major league starts.

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