This story was excerpted from Ian Browne’s Red Sox Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.
BOSTON -- For the 2026 Red Sox, offseason evaluations will be challenging for chief baseball officer Craig Breslow’s staff, given the erratic nature of the team’s season.
From Opening Day until June 24, the Sox were 32-46 and looked like they may be sellers at the Aug. 3 Trade Deadline. Then came Boston’s summer surge that defied anyone’s imagination. The club went 32-5 in 37 games from June 25 to Aug. 7, and a franchise-best 27-3 in 30 games from July 1 to Aug. 7.
And then there was the final stretch after the surge, in which the club went 21-24 and were swept by the Yankees in two games in the American League Wild Card Series.
“This season in particular was incredibly unique, but we didn't capitalize on our summer success,” said Breslow. “I think that’s the feeling that's echoing in my head. I think this was more than just a run. I think it showed some true underlying talent. But we obviously have a lot of work to do to get where we want to go heading into 2027.”
Given that, what are the biggest questions facing the Sox entering the offseason?
1. Will Roman Anthony be healthy in ‘27?
Touted as MLB Pipeline’s No. 1 prospect in 2025, Anthony more than lived up to the hype after being called up in June last season, producing 3.3 bWAR and an .859 OPS in 303 plate appearances. But on his last at-bat of the ‘25 campaign, Anthony suffered a left oblique strain on a check swing that ended his season on Sept. 2, knocking him out of the postseason.
There was no reason to think that Anthony's injury would linger into 2026, and it didn’t. Anthony came out firing for Team USA in the World Baseball Classic, being named an outfielder on the All-Tournament team. But after a slow start to the regular season, Anthony endured another injury on a swing on May 4 -- this one a partially torn carpometacarpal/CMC ligament, which is located at the base of his right ring finger.
It seemed Anthony was on the road to recovery when he returned to action on Aug. 30. However, he lost his momentum when he reinjured his hand in Game 1 of the AL Wild Card Series and had to be taken off the roster. New imaging showed a reinjury of the joint that included additional strains.
Breslow said the 22-year-old outfielder won’t need surgery. However, it’s hard for the Red Sox to know just what they can expect going forward from Anthony, who is considered a franchise cornerstone.
2. Can Garrett Crochet return to form?
Crochet was one of the best pitchers in baseball when the 2025 season ended, finishing second to Tarik Skubal in the AL Cy Young Award race. But in '26, things were never right for Crochet, even in Spring Training, when he fought with his mechanics and velocity. Crochet’s final start of the season was on April 25, and it was his best, when he pitched six scoreless innings in Baltimore to lower his ERA to 6.30. Unsurprisingly, an injury developed and he was placed on the injured list with left shoulder inflammation. Crochet was eventually reinstated on Sept. 29, in time to make a relief appearance in Game 2 of the AL Wild Card Series on Sept. 30. The good news is that, unlike Anthony, Crochet’s offseason is expected to be normal and not filled with rest and rehab.
“He obviously pitched [in the playoffs], and the velo and the stuff looked pretty good. Kind of vintage Garrett Crochet,” said Breslow. “He came out of it the next day feeling good. So he'll go into the offseason fully healthy.”
3. Can Breslow find the power?
Last offseason, Breslow said one of his key goals was to find a big bat to put in the middle of the order. Though Willson Contreras, who hit a career-high 27 homers this season, was added to the mix, it was a net-neutral gain after Alex Bregman departed in free agency to the Cubs.
While the Red Sox had one of the best pitching staffs this season, the offense lagged behind, with the exception of that sizzling summer stretch. The Sox hit 163 homers, which ranked 26th in the Majors. In ‘25, they belted 186 homers, which ranked 15th in the league. Breslow needs to find a way to make his lineup more formidable so the elite pitching desn’t go to waste.
4. What happens with Jarren Duran?
An All-Star for the 2024 Red Sox, Duran’s bWAR was 9.0 in that special season before dipping to a respectable 4.9 in ‘25. However, Duran’s bWAR took a precipitous dip to 0.4 in ‘26, mainly due to his mighty struggles on offense, posting a .207/.266/.361 batting line in 151 games. Duran is arbitration-eligible and will likely jump up to an eight-figure salary through that process. That is, unless the Red Sox decide to non-tender him. Logic stands that Boston will explore trading Duran before the Nov. 20 non-tender deadline. Replacing Duran’s lefty bat with a righty slugger makes a lot of sense for a club that is trying to find a better fit for its home ballpark.
5. What can Curtis Mead bring to the offense?
On July 25, Mead, in the midst of the best hitting stretch of his career, was acquired by the Red Sox for starting pitcher Connelly Early. Two days later, on July 27, in Mead's second at-bat with the Red Sox, he suffered a fractured left wrist that kept him out for the rest of the season.
While building the club’s offense for 2027, it will be interesting to see how much the Sox expect from Mead, who is supposed to become the team’s starting second baseman. While with the Rays and White Sox before landing with the Nationals, Mead had trouble producing enough to earn playing time. Can he carry his Washington momentum to Boston? If so, that could be a big lift in the Red Sox’s quest to score more runs.