The Boston Red Sox’s season ended Oct. 2. As of writing this, it has been 102 days since the Red Sox have played any sort of baseball. That was also enough time for my river of tears to evaporate and for my broken television to be fixed.
Now that the MLB season has ended, the sport has entered one of its most highly anticipated periods: offseason free agency. A period where ball clubs make moves and chief baseball officer Craig Breslow hibernates. The time frame started poorly for the Red Sox, as third baseman Alex Bregman elected to pursue free agency instead of re-signing, as did a large part of the pitching staff, including starting pitcher Lucas Giolito.
This may not have been a huge loss, as the free agent class this year was strong, headlined by National League home run leader Kyle Schwarber, first baseman Pete Alonso and starting pitcher Dylan Cease.
The Red Sox were in the market for all three of these players. Did they get a single one of them? No. They did not. The club did, however, acquire 36-year old pitcher Sonny Gray from the St. Louis Cardinals for a modest return. Gray appears to share a burning hatred for the New York Yankees, securing my nomination and wholehearted support for the American League Cy Young Award in 2026.
The Red Sox were relatively quiet for the rest of the month, improving their pitching staff by acquiring right-handed pitcher Johan Oviedo from the Pittsburgh Pirates and left-handed pitcher Jake Bennett from the Washington Nationals.
That was until Breslow decided to wake up and provide Red Sox fans with an early Christmas present, trading for 2016 World Series champion and first baseman/catcher Willson Contreras. It was a strong move for the Red Sox, which are in a position of need, especially as previous first baseman Nathaniel Lowe opted for free agency and the future of first baseman Triston Casas is uncertain. Things weren’t all sweet, however, as the signing of Contreras may have spelled the end of the rope for Casas, who now appears to be limited to a backup role in the foreseeable future.
It wouldn’t be silly season without numerous trade rumors. A primary trade candidate appeared in outfielder Jarren Duran. The American League leader in triples and Boston fan favorite appears to be on the wrong end of an outfield logjam as his compatriots, right fielder Wilyer Abreu and center fielder Ceddane Rafaela, were Gold Glove winners in 2025. (Rafaela should have won the Platinum Glove, but that is a conversation for another time.) Duran still has trade value, with the Kansas City Royals being a prominent suitor for the one-time all-star. However, negotiations have stalled between the two teams, as Boston’s asking price is steep.
There is still a lot of time left in the free agency period and the offseason. The Red Sox still need to strengthen their pitching staff and attempt to lock down Bregman. Hopefully, Breslow and the Red Sox front office are able to make a few more moves and elevate this team to the contender it deserves to be.
