As the 2026 season inches closer, let’s take a look at the Boston Red Sox notable moves this offseason and give some grades. This will also cover one notable departure.
Three Major League Arms Traded
The Red Sox started by trading three separate pitchers who had major league experience. LHP Brennan Bernardino, LHP Chris Murphy and RHP Luis Guerrero were all shipped out to separate teams. In exchange, the Red Sox got back some minor league depth prospects.
Overall, none of the prospects the Red Sox received project as anything more than borderline major league talent, if that. However, the Red Sox simply made these moves to clear up space on their 40-man roster.
Grade: C
Trading for Sonny Gray
The first notable acquisition for Boston came courtesy of their former general manager Chaim Bloom. Bloom, now at the helm of the St. Louis Cardinals, had some pieces to trade off for future pieces. He did just that, trading starting pitcher Sonny Gray to the Red Sox for LHP Brandon Clarke and RHP Richard Fitts.
Gray, a 13-year veteran, pitched to a 101 ERA+ in his past two seasons as a member of the Cardinals. However, he was an innings eater, finishing in the top 20 in the majors with 180 2/3 innings pitched last season. Gray projects as a steady middle-rotation guy who can take some stress off the bullpen when Garrett Crochet isn’t pitching.
Overall, this trade works out great for the Red Sox. They received a stern presence in the middle of the rotation so that guys like Payton Tolle and Connelly Early don’t have to shoulder as much of the load. This is a very valuable piece in exchange for a long-term project and an injury-prone major leaguer.
Grade B+
Password Is Gone
The Red Sox, with an outfield logjam, were predicted to be trading one of their major league outfielders this offseason. Although not too many people predicted this one. Jhostynxon Garcia and RHP Jesus Travieso were dealt to the Pittsburgh Pirates. In exchange, the Red Sox received RHP Johan Oviedo, LHP Tyler Samaniego and C Adonys Guzman.
Oviedo, recovering from Tommy John surgery, made nine starts in the 2025 season. He would record career-best numbers in WHIP, hits per nine, and strikeouts per nine. He has some upside value, as his fastball, curveball, and slider were plus pitches in 2025.
Garcia, currently ranked the 85th best prospect in the minor leagues, was known for raking in the minors like leaves in the fall. His home run power is legit, while still maintaining most of his athleticism despite added muscle mass.
Overall, Oviedo is a bit of a project, but he can become a solid hand for the rotation if things go right. Garcia projects as a possible starter come opening day for the Pirates. Both guys were logjammed by superior talent at their positions, so it made sense for both sides.
Grade: C+
Willson Contreras Trade
The Red Sox were in desperate need of power, and three days before Christmas, they finally got some. In exchange for RHPs Hunter Dobbins, Yhoiker Fajardo and Blake Aita, the Red Sox got first baseman Willson Contreras.
Contreras, during his time as a Cardinal, notched a 127 OPS+ while hitting 55 home runs in three seasons, even after converting from catcher to a full-time first baseman in the 2025 season. Even in an abbreviated 2024 season, he clobbered 15 home runs in 84 games.
Overall, Contreras stands out as the clear starting first baseman in 2026 for the Red Sox. Trading him for a couple of prospects and a pitcher that became obsolete due to previous trades was a great deal for Boston.
Grade: B+
Losing Out on Bregman
After signing him to a three-year deal last offseason, Alex Bregman opted out to test free agency once again. After a reported five-year, $165 million offer was given to Bregman by Red Sox Chief Baseball Officer Craig Breslow, it seemed Bregman might return. Alas not, as the Chicago Cubs outbid them, dealing a five-year, $175 million deal to steal him away from the Red Sox.
This is also considering the fact that Bregman allegedly told the Red Sox that he had a better offer elsewhere. Reportedly, according to A.J. Pierzynski, the Red Sox scoffed at the idea of Bregman having a better offer on the table.
If all of this is true, Breslow should be ashamed of letting Bregman go. Someone who was highly praised for being a clubhouse leader, and a much-needed help in the offensive core.
Grade: F-
Closing Out the 2025 Boston Red Sox Offseason
Although the offseason technically isn’t over yet, the Red Sox most likely won’t go after any more notable free agents, although they are “interested” in Bo Bichette. Considering the expectations the Red Sox came in with, the 2025 offseason was a severe disappointment.
Overall Offseason Grade: D+
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