The Boston Red Sox's rotation projects to be their biggest strength yet again next year, especially if Garrett Crochet is back to full health. But Sonny Gray seems like a goner, and it'll be important to replace his presence on the roster, even if there's no replacing his production.
According to Sean McAdam of MassLive on the latest episode of "The Fenway Rundown" podcast, the organization plans to reserve most of their resources to address this offense, leaving the lower tiers of the free-agent pitching market available to the front office. He did suggest that this will likely take the form of some "back-end guys," but being fiscally responsible doesn't mean the Red Sox have to punt on upside completely.
They might just have to take on a little more risk than usual to get some in the building.
3 high-upside pitchers Red Sox should seek out to fill rotation needs at a meager cost
Clay Holmes
Holmes is listed here first because he might be a little pricier than the range of free agents McAdam is referencing, but he's the ideal target for the Red Sox in this tier of pitcher.
The right-hander made a wildly successful transition from the bullpen to the rotation after switching New York teams a few years ago, and he looked like a surefire All-Star this year before a comebacker fractured his right leg in May. He wound up sitting out until getting moved to the Cubs at the trade deadline, with whom he proved to be healthy and effective (4.09 FIP) following that freak injury.
Thanks to a still-dominant sinker, Holmes is elite at keeping the ball on the ground and off the barrels of opposing hitters. That should make him a perfect fit for Fenway Park (he has a career 3.48 in 20⅔ innings there) and as close to a one-to-one replacement for Sonny Gray as the Red Sox will find this offseason.
If his injury-plagued season forces him to settle for a prove-it contract, Craig Breslow has to be all over Holmes' market.
Brandon Woodruff
Woodruff will be the ultimate blind dart throw this winter, a former ace who hasn't been able to stay on the field in recent years due to various injuries (most of which have been located in his throwing shoulder).
Of course, we know Breslow and the Sox aren't scared by pitchers with lengthy injury histories; they've signed guys like Patrick Sandoval, Michael Fulmer, Lucas Giolito, and Liam Hendriks while knowing they were going to miss excessive time with their respective rehab processes. Woodruff, who was added to the Brewers' World Series roster at the last minute, should be healthier right now than any of those prior examples.
Even though he hasn't tossed more than 67 innings in a campaign since 2023, the right-hander remains electric when he is able to get on the mound. His 3.11 ERA over the past two seasons would look fantastic in the Red Sox's rotation, even if he can only give Chad Tracy 10-15 starts total.
After earning more than $22 million this year on the qualifying offer, expect Woodruff to settle for a more affordable deal this winter after another mostly lost season.
Zac Gallen
The temptation to predict an unlikely reunion with someone like Giolito or Walker Buehler was strong here, but ultimately, I remain committed to the pursuit of upside at the expense of certainty.
Gallen was a top-five Cy Young finisher as recently as 2023, a feat he also achieved the year before that. He was one of the best starters in the game for a handful of years, even leading the Diamondbacks to the World Series as their Game 1 starter that postseason.
Unfortunately, the regression monster has claimed him and hung on tight in recent years, with an ugly 5.27 ERA to his hame since the start of the 2025 season. He was really bad this year before elbow inflammation knocked him out in July, but he made an encouraging return in September before the D-backs bowed out of the playoff race.
He'll have to accept a meager contract after falling so far from such great heights, but he's a 31-year-old just a few years removed from an elite peak. The Red Sox could strike an absolute bargain here.
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