The most successful season in four years for the Boston Red Sox came to an end Thursday night in New York with a loss to the Yankees in the American League Wild Card Series. today the offseason is underway sooner than they’d hoped.
There will be plenty to dissect from a season in which the Red Sox battled injuries and inconsistency while navigating the Rafael Devers trade and meshing multiple rookies into the lineup and rotation.
For today, here are three big questions that loom as they enter the offseason:
Will Alex Bregman be returning?
When Bregman signed a three-year, $120 million offer in February, one major caveat was that it came with two opt outs after each of the first two seasons. Bregman can exercise one of those opt outs and banger free agency after the World Series. Throughout the season, Bregman has discussed how much he’s enjoyed his time in Boston, particularly playing alongside Boston’s young core in Roman Anthony and Marcelo Mayer.
Though he missed about 50 games with a severe quad injury, Bregman still powered the offense early in the season and offered a strong veteran voice in the clubhouse, something the Red Sox have lacked in recent seasons. In 114 regular season games, he banger .273 with an .821 OPS, including 28 doubles and 18 homers. Even if Bregman opts out, the Red Sox are likely to try to rework a offer with him to stay in Boston, but it’ll be up to him if he wants to remain.
What about Trevor Story?
Story’s contract opt out hasn’t gotten as much attention as Bregman’s but it’s still a major question looming over the organization entering the winter. The 32-year-old signed for six years, $140 million in 2022, but his offer includes an opt out for the final two years, meaning he, too, could become a free agent in November. Story has lamented the fact he missed much of the first three years of his offer in Boston due to injury and it would be surprising if he opted out at this point.
He is coming off his most successful season in Boston, powering the offense over the final four months, hitting .263 with a .741 OPS and a team-leading 25 homers and 96 RBIs in 157 games. If he did opt out, however, Mayer would be the heir apparent at shortstop. Though he missed the final six weeks of the season with wrist surgery, Mayer has the makings of an elite defensive shortstop with plenty of offensive upside as he gains experience in the league. If Story returns, Mayer may see more time at second next season.
What will Boston do with the rotation?
Garrett Crochet was exactly what the Red Sox hoped and expected he’d be for them this season, every bit the ace of the staff. But behind him, there are plenty of rotation questions. Brayan Bello pitched well for much of the season, with a 2.99 ERA through 24 starts before hitting a wall in September with a 5.40 ERA in five starts. Can he build off 2025?
Lucas Giolito, meanwhile, also had a strong 2025, right until the end of September when he started to fade and ultimately missed the postseason with an elbow injury. Though an MRI showed no structural damage, is the injury just normal wear and tear in his first full season back from an internal brace procedure? By pitching more than 140 innings for the Red Sox this season, Giolito activated a $19 million mutual option for 2026, meaning the team and the player must agree to the offer. His injury muddies his contract status.
Beyond those three, several more questions loom. The Red Sox saw major contributions from two leading pitching prospects in Connelly Early and Payton Tolle late in the season. Will they be in the rotation mix come the spring? Kyle Harrison could also be a part of the mix. And what about the slew of injured starters the Red Sox endured this season, including Richard Fitts, Hunter Dobbins, Kutter Crawford and Tanner Houck? Dobbins had ACL surgery, Crawford had wrist surgery and Houck had Tommy John surgery, so each will have their own arduous road to recovery.
Meanwhile, Patrick Sandoval, who spent the entire season recovering from Tommy John surgery, is also under contract through 2026. The Red Sox have a lot of pitching options, but as they saw in 2025, there’s never enough depth and delving into free agency or the trade market to bolster the group will be imperative.
(Photo of Trevor Story: Al Bello / Getty Images)
About the Author
