Red Sox May Cut Ties With 27-Year-Old Pitcher Shortly After World Series

Has this righty reached the end of the road in Boston?

May 27, 2025; Milwaukee, Wisconsin, USA; A Boston Red Sox hat and glove sit in the dug out before a game against the Milwaukee Brewers at American Family Field. Mandatory Credit: Michael McLoone-Imagn Images | Michael McLoone-Imagn Images

Managing the 40-man roster during the Major League Baseball season often means teams have to rid themselves of talent.

The Boston Red Sox are going to be in a tough situation once the official league year ends after the World Series. Because they had so many injuries this season, their 40-man roster didn't include a large handful of players who went on the 60-day injured list. As those players return to the picture, some people will necessarily be squeezed out.

In fact, before the Red Sox make a single trade or free-agent signing, they'll likely have to cut ties with at least one player. Insider Chris Cotillo provided an intriguing option as to who that player could be.

Will Red Sox designate Josh Winckowski for assignment?

Apr 14, 2025; Tampa, Florida, USA; Boston Red Sox pitcher Josh Winckowski (25) throws a pitch against the Tampa Bay Rays in the seventh inning at George M. Steinbrenner Field. Mandatory Credit: Nathan Ray Seebeck-Imagn Images | Nathan Ray Seebeck-Imagn Images

On Tuesday, Cotillo suggested that right-handed pitcher Josh Winckowski had made himself expendable over the last couple of seasons and might be designated for assignment when the roster crunch arrives.

"The free agent departures puts the Red Sox at 32 on the 40-man roster," Cotillo wrote. "The club then needs to reinstate nine players ... from the 60-day IL, which doesn’t exist in the offseason. That means there will likely be 41 players for 40 spots. The Red Sox will then need to make a cut to fit everyone on.

"There are some depth options on the roster who are candidates to be designated for assignment like lefty Jovani Morán and righty Josh Winckowski."

Winckowski, 27, was an important bullpen piece for the Red Sox in 2023, making 60 appearances to the tune of a 2.88 ERA over 84 1/3 innings. But Boston burned his last two minor-league options over the following seasons, as he put up a 4.11 ERA in 46 major league outings since the start of 2024.

The right-hander also finished the season as one of those players on the 60-day IL, having sustained a flexor strain to his throwing elbow.

While Winckowski has certainly flashed the talent to be a staple of a major league bullpen, it wouldn't be shocking at this point to see the Red Sox let him try to find success elsewhere.

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