The Red Sox may be ready to spend their bigger money elsewhere, but that doesn’t mean the rotation market is off limits. With Garrett Crochet’s health looming as a major factor and Sonny Gray looking like a loss, Boston still has a real need to patch the back end of the staff.
On the latest episode of “The Fenway Rundown” podcast, Sean McAdam of MassLive said the club appears prepared to steer most of its resources toward offense, which would leave the lower end of the free-agent pitching pool for the front office to work with. McAdam framed that group as likely consisting of some “back-end guys,” but there’s still room for the Red Sox to chase upside if they’re willing to accept a bit more risk than usual.
That’s where names like Clay Holmes, Brandon Woodruff and Zac Gallen come into play.
Holmes is the most natural fit of the three, even if he might come in a little above the price range McAdam was talking about. The right-hander has already shown he can make the leap from reliever to starter, and after a move to New York a few years ago, he looked every bit like an All-Star this season before a comebacker fractured his right leg in May. He didn’t return until after a trade deadline deal to the Cubs, and once he got there, he still looked healthy and effective, posting a 4.09 FIP.
The appeal is obvious. Holmes’ sinker is still a weapon, and it does exactly what the Red Sox would want in a pitcher: it keeps the ball on the ground and keeps hitters from squaring it up.
Fenway Park hasn’t been a problem for him, either, with a career 3.48 in 20⅔ innings there. If Boston is looking for the closest thing to a Sonny Gray replacement on the market, Holmes makes a lot of sense.
If his injury-hit year pushes him into prove-it territory, Craig Breslow should be in on him.
Woodruff would be the swing-for-the-fences option. He’s the kind of former ace who turns into a fascinating winter gamble because of the injuries that have piled up, most of them tied to his throwing shoulder.
But the Red Sox have not shied away from that type of profile before. They’ve already taken shots on pitchers such as Patrick Sandoval, Michael Fulmer, Lucas Giolito and Liam Hendriks, all while knowing rehab time would be part of the equation.
Woodruff’s situation is different in one key way: he was added to the Brewers’ World Series roster at the last minute, which suggests he should be healthier now than some of those previous bets. He hasn’t thrown more than 67 innings in a season since 2023, but when he’s on the mound, he still brings impact stuff.
His 3.11 ERA over the past two seasons would be a strong addition to Boston’s rotation, even if the Red Sox only get 10-15 starts out of him. And after making more than $22 million this year on the qualifying offer, he’s expected to be cheaper this winter after another season cut short by injury.
Then there’s Gallen, the upside play that comes with the loudest reminder of how quickly things can turn. The temptation to circle a reunion with someone like Giolito or Walker Buehler was there, but the case here is simple: upside matters more than certainty.
Gallen was a top-five Cy Young finisher in 2022 and again in 2023, and during that stretch he was one of the best starters in baseball. He also helped lead the Diamondbacks to the World Series as their Game 1 starter.
The last couple of seasons, though, have been rough. Since the start of the 2025 season, he’s carried a 5.27 ERA, and this year got away from him before elbow inflammation sidelined him in July.
He did show something encouraging when he returned in September, even if Arizona’s playoff run was already slipping away by then. For a Red Sox team trying to balance cost and ceiling, that makes Gallen a tough but intriguing name to monitor.
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