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Red Sox pull off late trade to get roster back to 40

Boston made a small deal late on the final day of the Winter Meetings, adding a minor-league reliever to fill a roster spot.

A view of the Red Sox logo outside of Fenway Park. (Maddie Meyer/Getty Images)
Maddie Meyer/Getty Images

The Boston Red Sox had an opening to fill on their 40-man roster after trading Vaughn Grissom for a lower-level minor leaguer. They decided to fill it with a reliever acquired in a trade late on the final day of the Winter Meetings.

As announced by the team Wednesday night, the Red Sox traded for right-handed pitcher Ryan Watson from the Athletics, in exchange for minor league utility player Justin Riemer and cash considerations. The move puts the Red Sox' 40-man roster back at the maximum, as they head into the post-Winter Meetings phase of the offseason.

Watson, 28, was originally a 39th-round pick of the Los Angeles Dodgers in 2016. He played four years of college ball at Auburn, where he made the 2020 honor roll in Supply Chain Management and graduated that same year. Watson first joined the pros with the Baltimore Orioles, where he spent seven seasons working his way up to Triple-A. The Orioles traded him to the Giants for cash in 2024, then he stayed in the San Fran organization until he was left unprotected in Wednesday's Rule 5 draft. The A's then selected him, and later traded him to Boston. He has yet to pitch in a major league game.

A 6-foot-5 reliever, Watson has made 157 career minor-league appearances with 34 starts. He throws a fastball, slider, and cutter, with his heater clocked at an average of 94.4 mph in 2025 (via Fangraphs). It's certainly not unprecedented for a veteran minor-leaguer to finally crack the majors, and even make an impact, in his late-20s. But at this stage, Watson should be considered a long shot to be a difference-maker for the 2026 Boston Red Sox.

In the wake of the Winter Meetings, as of Thursday morning, the Red Sox have had a disappointing week. Despite being linked to several big-name infielders and Craig Breslow publicly addressing the team's need for a middle-of-the-order bat, Boston has yet to make a significant addition. They struck out on free agents Pete Alonso and Kyle Schwarber, and Alex Bregman remains on the open market.

Matt, a North Andover, Massachusetts native, has been with The Sports Hub since 2010. Growing up the son of Boston University All-American and Melrose High School hall-of-fame hockey player Steve Dolloff, sports was always a part of his life. After attending Northeastern University, Matt focused his love of sports on writing, extensively writing about all four major Boston teams. He also is a co-host of the Sports Hub Underground podcast and is a regular on-air contributor on the Sports Hub. Matt writes about all New England sports from Patriots football to Boston Celtics and Boston Bruins.