3 Upgrades Red Sox Could Pursue to Fix Season-Defining Roster Issues

Ultimately, all these areas need to improve

Sep 24, 2026; Chicago, Illinois, USA; Chicago Cubs right fielder Seiya Suzuki (27) hits a home run during the fifth inning against the Miami Marlins at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images | IMAGN IMAGES via Reuters Connect

The offseason is going to be extra painful for the Boston Red Sox this year, both because of what came before it and what's coming soon.

After being swept out of the playoffs in just two games by the arch-rival New York Yankees, the Red Sox could have a long time to sit with their failure. An impending Major League Baseball work stoppage threatens to cancel games during the 2027 regular season.

For now, we'll act like free agency and trades this winter will still matter, even if they have fewer games to play next year than usual. And if that's the case, the Red Sox can't afford to sit on their hands, so we found them some potential upgrades.

Seiya Suzuki - RF/DH, Chicago Cubs

The Red Sox's clearest flaw was their lack of thump, but there are very, very few impact power bats available this winter. Suzuki, who enters his age-32 season next year, has a 128 career OPS+ in five years with the Cubs, and this past season was his best showing yet.

Though he's not a lock for 30 home runs (only did it last season out of his five years in Chicago), Suzuki topped five bWAR for the first time this year and could take a leap in the power category at Fenway Park, similarly to Willson Contreras this past season.

Yandy Díaz - 1B/DH, Tampa Bay Rays

Sep 4, 2026; Arlington, Texas, USA; Tampa Bay Rays designated hitter Yandy Diaz (2) follows through for a double against the Texas Rangers during the fifth inning at Globe Life Field. Mandatory Credit: Jim Cowsert-Imagn Images | IMAGN IMAGES via Reuters Connect

Similarly to Suzuki, Díaz profiles more as a really good hitter than one with game-changing power. But it's also easy to picture the career .293 hitter raising his power ceiling at Fenway Park. He's never hit 30-plus home runs in the big leagues, but has 22 or more in three of the last four years.

In Boston, Díaz would likely fill the designated hitter slot on four days out of five, which means they'd be creating problems elsewhere on the roster to resolve one of the big issues. Far from a perfect fix, but it's not like the Red Sox can take Junior Caminero away from the Rays instead.

Re-sign Sonny Gray OR bring in Michael King

Sep 30, 2026; Bronx, New York, USA; Boston Red Sox pitcher Sonny Gray (54) delivers a pitch in the first inning against the New York Yankees during game two of the Wildcard round for the 2026 MLB Playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | IMAGN IMAGES via Reuters Connect

It's pretty clear that the Red Sox needed a commanding veteran presence in the rotation this season, which Gray provided. The rotation outside of Gray was also dominated by lefties, making his righty presence all the more valuable.

Gray has hinted at retirement, but even if he comes back, there's a possibility that the Red Sox are moved instead to pursue King, who is coming off a career-high 185 innings in the regular season and is five years younger. Either way, they need that extra top-of-the-rotation arm.