Red Sox DFA 27-Year-Old Pitcher After Four Seasons In Boston

The Boston Red Sox have just a few days to make decisions for the big deadline around Major League Baseball.

Tuesday is the deadline for players who have been tendered the qualifying offers to decide whether to accept the offer or not. Boston doesn't have to worry about that deadline. Lucas Giolito was the lone guy who seemingly had a shot at the qualifying offer, but the Red Sox didn't make the offer.

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The next deadline for the Red Sox to be on the lookout for is Nov. 21st. That is the deadline for teams around the league to tender contracts to arbitration-eligible guys with the organization. This also means that it is the deadline for teams to non-tender eligible players on the roster. This essentially means that the Red Sox have just a few days to decide which arbitration-eligible players the club wants to keep, and which ones the team wants to let walk to free agency. Rumors have been flowing for days about who the Red Sox could cut ties with. On Tuesday, Boston got out ahead and one move it made was reportedly designating 27-year-old hurler Josh Winckowski for assignment, per 7News Boston WHDH's Ari Alexander.

The Red Sox are moving on

Apr 8, 2025; Boston, Massachusetts, USA; Boston Red Sox relief pitcher Josh Winckowski (25) pitches against the Toronto Blue Jays during the eighth inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

"The Red Sox are Designating RHP Josh Winckowski for assignment, a league source tells 7News," Alexander reported. "Winckowski had a 4.20 ERA with the Red Sox in 121 appearances and 242.1 IP between 2022-25."

MassLive.com's Chris Cotillo also reported the news, while sharing that he will be non-tendered on Friday.

"Josh Winckowski designated for assignment by Red Sox, source says," Cotillo wrote. "Red Sox have to add players to 40-man today so need to clear spots. Ari Alexander on it. Winckowski will be non-tendered (effectively released) Friday, just like Nathaniel Lowe."

This wasn't the only move of the day either. Boston also traded Luis Guerrero to the Tampa Bay Rays for Tristan Gray and designated Nathaniel Lowe for assignment.

Winckowski has pitched in 121 big league games over the last four seasons and has a 4.20 ERA to show for it in 242 1/3 innings pitched. In 2025, the Red Sox used him in just six games in the big leagues, which is why the move makes sense here. The Red Sox built one of baseball's best bullpens. They finished the regular season with the second-best bullpen ERA at 3.41, despite the fact that Winckowski didn't get many opportunities.

Boston's bullpen is in a good place headlined by Aroldis Chapman, Garrett Whitlock, Greg Weissert, and Justin Slaten. Jordan Hicks is an expensive option for the team with upside, despite a bad 2025 season. Brennan Bernardino is another guy who should be a shoe-in for a consistent role. Plus, there have been reports out there that the Red Sox could look to bring in a bullpen arm, like Devin Williams.

Winckowski wasn't a shoe-in for a consistent role, so it makes sense to move on and save a bit of cash in the process.

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