As the free agency clock officially begins Thursday at 5 p.m. ET, the Boston Red Sox — along with 29 other teams — can start rebuilding their roster for the upcoming season.
Several key decisions have already been made ahead of the deadline, including Alex Bregman and Lucas Giolito opting out of their deals with the Red Sox and Trevor Story opting to remain with the club. Meanwhile, the team reworked Jarren Duran’s 2026 contract rather than pick up his option.
Rob Refsnyder, Justin Wilson, Steven Matz and Dustin May are the other players from the 2025 roster who’ve entered free agency.
The last decision for Boston due by 5 p.m. is whether to extend a one-year, $22.05 million qualifying offer to Giolito.
So what does all this mean for the Red Sox as they enter the offseason with the General Managers Meetings next week in Las Vegas?
Here’s a look at where things stand:
Will Red Sox extend a qualifying offer to Lucas Giolito?
It seems likely the Red Sox will extend the qualifying offer to Giolito. If he accepts, they have a solid starter for the rotation at an affordable rate of $22.05 million for one year. If he declines and signs elsewhere, Boston will pick up an extra draft pick in 2026.
Giolito initially signed a two-year, $38.5 million deal in 2024 before missing the entire first season with an internal brace procedure. This season, he made a triumphant return with a 3.41 ERA over 26 starts as a key piece of the rotation. His deal included an option for 2026 that would vest to $19 million if he hit 140 innings, which he did. So a $22.05 million salary would be a modest increase. But given the season he had and the overall dearth of starting pitchers in free agency, Giolito declined his Red Sox option in search of a longer deal, likely with the potential of a 2027 MLB lockout in mind.
If the Red Sox don’t extend a qualifying offer to Giolito, it could mean they feel he has not bounced back from elbow soreness that forced him to miss the postseason. The right-hander visited the doctor who performed his internal brace procedure in September and was told that there was irritation in his forearm, but nothing structurally wrong. Giolito has since resumed throwing.
If he receives the offer, Giolito has until Nov. 18 to decide whether to accept. Since he’s likely pursuing a longer deal for more security, the expectation is that he would decline. If he does so, the Red Sox would get an extra draft pick after the fourth round next season. If the club had not exceeded the $241 million luxury tax threshold, it would have been after the second round.
As the Red Sox seek to bolster their rotation, keeping Giolito, 31, in the mix would help. The club could choose to re-sign him on a longer deal if they believe he’s healthy, and The Athletic’s Tim Britton projects Giolito to sign a three-year, $57 million deal. But the Red Sox may opt to use that money to sign a bona fide No. 2 starter like Dylan Cease, Framber Valdez, Ranger Suárez or Michael King.
As it stands now, the Red Sox rotation for 2026 has just two spots locked up in Garrett Crochet and Brayan Bello. Rookies Connelly Early and Payton Tolle will be in the mix come spring training, as will young lefty Kyle Harrison, acquired in the Rafael Devers deal. Several pitchers coming off injured seasons like Patrick Sandoval, Kutter Crawford, Hunter Dobbins and Richard Fitts will compete for spots as well, but none are guaranteed a spot as of now.
Tanner Houck is expected to miss all of 2026 recovering from Tommy John surgery.
Will Alex Bregman re-sign with the Red Sox? If not, what are their options?
Last offseason, Bregman’s market was dampened a bit by having a qualifying offer attached, meaning clubs signing him would lose a draft pick, something the Red Sox deemed necessary and palatable given they’d gained a draft pick when Nick Pivetta declined his offer earlier in the offseason.
This time around, Bregman does not have the offer attached and is hoping for greater control of his market. He opted out of the final two years and $80 million remaining on his contract with the Red Sox, but that doesn’t mean he won’t re-sign with the club on a longer deal.
Bregman, 31, played an integral role on the club last season not only as a mentor for a young team, but in offering advice to veteran hitters and scouting reports to his pitchers on how to attack opponents. His bold, outspoken voice in the clubhouse was something the team had not had in recent years.
The Red Sox valued that.
“I will not miss an opportunity to talk about his contributions on the field, in the clubhouse, to the coaching staff, to the front office,” chief baseball officer Craig Breslow said at the end of the season in discussing Bregman’s future. “Every conversation we’ve had, I learned something. I think that impact and influence has rubbed off on his teammates, and by all accounts, he’s loved his time in Boston as well.”
Alex Bregman (left) played an integral role last season as a mentor to a young team, offering advice to veteran hitters and providing scouting reports to pitchers. (James A. Pittman / Imagn Images)
Britton projects Bregman to sign a six-year, $171 million deal. Though his production at the plate was impacted by missing 41 games with a quad strain, he still hit .273 with an .821 OPS in 114 games while offering right-handed balance to the lineup and strong defense at third base.
The Red Sox have given every indication they’ll remain engaged with Bregman this offseason. Whether they meet his asking price and how his time in Boston affects his desire to return are the main questions.
Even if the Red Sox re-sign Bregman, they still likely will want to add another power bat with Pete Alonso and Kyle Schwarber as two leading candidates. Japanese power hitters Kazuma Okamoto and Munetaka Murakami, projected as first basemen, are other options the Red Sox are likely to explore as power bats.
The other issue, if Bregman does not re-sign, is what to do about third base. Marcelo Mayer played well at third when Bregman went on the injured list this summer, posting 2 Outs Above Average in 39 games at the spot this season. Though he is an option to take over at third come next season, some with the team feel Mayer could use more time in Worcester. In 44 games, he hit .228 with a .674 OPS, but racked up strikeouts with a 30 percent strikeout rate. Still, if the Red Sox cannot find a third baseman in place of Bregman, Mayer is the clear frontrunner to fill the role.
What does Trevor Story’s return mean?
When Story signed his six-year, $140 million deal in 2022, there was an opt-out after the 2025 season, meaning if he took the opt-out, he’d become a free agent and attempt to sign a larger deal than the two years, $55 million remaining on his current one.
Instead, Story chose to stay with the Red Sox. Throughout the season, Story said he felt he owed the club for having missed so much time due to injury over the first three years of the deal. This season, he showed what he’s capable of when healthy by hitting .263 with a .741 OPS in 157 games.
Story stabilized Boston’s defense for much of the season, though he did have a rash of throwing errors at the end of the year, likely due to fatigue after playing his first full season since 2021. He finished the year averaging 82.3 mph on his throws, the hardest he’s thrown since 2020. The Red Sox may consider moving Story to second base, where he played to accommodate Xander Bogaerts in 2022, but it seems likely he’ll stick at shortstop. Mayer, again, is an option at second.
The Red Sox could explore the trade market for a second baseman or consider signing Bo Bichette, a natural shortstop, and one who may be willing to move spots. But Bichette is expected to sign a deal north of $200 million, and the Red Sox may want to pour their money into a bigger power bat or No. 2 starter.
Where do things stand with Jarren Duran?
The Red Sox needed to resolve a contract decision on an $8 million option for Jarren Duran by Thursday. On Tuesday, the team declined the option but signed Duran to a $7.7 million deal for 2026. The contract indicated that Duran and his agent felt he would not receive the $8 million if Duran and the Red Sox went to an arbitration hearing.
Even with the new deal, Duran still may be traded this winter. At 29 and with three years of control left, Duran is the most obvious candidate to trade in Boston’s crowded outfield.