The Boston Red Sox have been one of the more active teams this offseason, reshaping their roster with a clear eye on both immediate improvement and long-term flexibility. After losing Alex Bregman to the Cubs in free agency, the front office responded by bolstering the pitching staff-most notably with the addition of Ranger Suárez-giving them a 10-deep rotation mix that should keep them competitive over the grind of a 162-game season.
But while the rotation looks deeper than it has in years, the infield remains a work in progress. And with that in mind, Boston is reportedly open to dealing from its surplus-particularly in the outfield and designated hitter spots-to address that need.
At the center of those trade discussions is Masataka Yoshida, the 32-year-old designated hitter who’s in the middle of a five-year, $90 million deal. According to reports, the Red Sox would “love” to move on from Yoshida and his contract this winter. That’s not exactly a surprise.
Yoshida’s 2025 season was a tough one. In just 55 games, he slashed .266 with a .696 OPS-the lowest mark of his Major League career. And while his numbers in the two seasons prior (.765 and .783 OPS) weren’t disastrous, they also didn’t come close to justifying the hefty investment Boston made when they brought him over from Japan.
The challenge now? Finding a trade partner willing to take on the final two years of that deal, which runs through 2027. With Yoshida’s production dipping and his defensive limitations keeping him locked into a DH role, the market for him is understandably limited.
That’s where names like Jarren Duran, Wilyer Abreu, and Ceddanne Rafaela come into play. All three offer more upside, positional flexibility, and-most importantly-cost control. If the Red Sox want to land an impact infielder, packaging one of those outfielders with a prospect like Yoeilin Cespedes, Wikelman Gonzalez, or another young arm might be the more realistic path.
Still, it’s clear that Boston’s front office, led by chief baseball officer Craig Breslow, would prefer to move Yoshida if they can. The current roster construction has created a bit of a logjam between the outfield and DH spots, and something has to give. Trading Yoshida would not only clear that space, but also free up payroll for potential in-season moves or future flexibility.
Whether or not a deal materializes remains to be seen. But one thing is clear: Boston is looking to evolve. And moving on from Yoshida-if they can find a taker-would be a step toward building a more balanced, dynamic roster heading into 2026.