Following a highly anticipated 2025 Winter Meetings, the Boston Red Sox left Orlando without a single major league signing or trade. Chief Baseball Officer Craig Breslow stressed the importance of being “aggressive and decisive” following the acquisition of Sonny Gray from the St. Louis Cardinals, leaving many fans and analysts expecting fireworks over the Winter Meetings. Instead, Kyle Schwarber resigned with the Philadelphia Phillies, and Pete Alonso signed with the Red Sox’ division rival, the Baltimore Orioles. While the offseason is certainly not a failure yet, Boston’s options are thinning, and they must make a move soon.
Diamandbacks Receive: Hunter Dobbins, Payton Tolle (Red Sox #1), Franklin Arias (Red Sox #2), Luis Perales (Red Sox #4)
Red Sox Receive: Ketel Marte
It’s no secret that the Red Sox are still searching for a middle-of-the-order bat to remedy the hole Rafael Devers left in their lineup, but multiple factors have stood in the way of that possibility. Breslow’s model is against the idea of long-term contracts for aging players, poor defenders, and designated hitters. Positional and lineup versatility has been a point of emphasis in his tenure, and that will continue to be the case, limiting their interest in free agents such as Schwarber and Alonso. Marte, on the other hand, has been a plus defender at second base his entire career, a position of need for Boston. Posting the sixth-highest OPS in baseball over the last two years, he would provide a level of production in the lineup that the Red Sox haven’t seen in the 2020’s. While the price would certainly be steep, it’s one that they can meet with their surplus of MLB-ready pitching depth. Marte would immediately slot in as Boston’s best hitter on a talented roster.
Brewers Receive: Noah Cameron, Blake Mitchell (Royals #2), Mikey Romero (Red Sox #6), Drew Beam (Royals #10)
Royals Receive: Jarren Duran
Red Sox Receive: Freddy Peralta
With the Kansas City Royals’ surplus of starting pitching and desperate need for outfield production, there’s been plenty of trade speculation involving the Red Sox in 2025. In this trade, the Royals help Boston facilitate a deal for the Brewers’ ace. With Milwaukee working under a budget, they’ve shown interest in moving on from Peralta in the final year of his contract. This trade allows them to replace him with a young, controllable lefty in Cameron, as well as to receive an assortment of prospects from Boston and Kansas City. The Royals fill one of their outfield spots with Duran, and the Red Sox add a surefire #2 starter to their rotation.
Red Sox Sign Kazuma Okamoto: 5 years – $90 MM
In signing Okamoto, the Red Sox would make the final addition to their lineup. The Japanese corner infielder would provide a better fit for Breslows’ model than Alonso or Schwarber. Okamoto projects as an average defensive third baseman and a great defensive first baseman. He provides 20+ homerun potential while limiting strikeouts, a point of emphasis for Boston in 2026. Despite already being 29, Okamoto would only be signing a 4-5 year contract, limiting the potential for the deal to go underwater for an extended period of time. While he’d likely play both positions, Okamoto could move to first and allow Marcello Mayer to handle the opening day third base role.
While they’d still have to make a few moves around the edges, this offseason plan would provide a feasible route for the Red Sox to take in order to greatly improve their roster. Whether fans like it or not, Boston will likely try to stay under the first CBT threshold surcharge at $264 MM, and this plan would give them a realistic chance to do so. While letting Alex Bregman walk in free agency would hurt, Boston would still feel much better about their linuep than they did at the end of 2025. This new-look Red Sox team would provide better defensive potential and a significantly stronger rotation behind Garrett Crochet.
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