Trevor Story’s place in Boston is suddenly one of the biggest open questions of the Red Sox winter.
The two-time All-Star could still be the club’s shortstop when 2027 arrives, but that is far from the only possibility. Boston could slide him to another spot on the field, maybe second base or even designated hitter.
There’s also a real path where he’s no longer in the organization at all. For now, the Red Sox are staring at a winter with multiple ways this could go.
MassLive.com’s Chris Cotillo said Boston “go big for a long-term star shortstop” this offseason, then Story’s outlook in the organization would be “squarely in doubt.”
“A massive shakeup could occur if the Red Sox decide to go big for a long-term star shortstop, should one become available,” Cotillo wrote. “That puts Story’s future in the organization squarely in doubt, especially considering his contract status and the fact he was unable to build off a strong 2025 and instead went backwards (especially on the health front) in 2026.”
Boston already explored that kind of move before the 2026 trade deadline, with Zach Neto of the Los Angeles Angels, CJ Abrams of the Washington Nationals and Elly De La Cruz of the Cincinnati Reds all linked to the club at different points.
The contract situation adds another layer. Story has one season left on his deal for the 2027 campaign at $25 million, followed by a $25 million club option for 2028.
Cotillo pointed to the middle infield as the most complicated part of the roster, and it’s not hard to see why. At the moment, Story and Curtis Mead would appear to be the leading options at second base and shortstop.
But Franklin Arias is part of the equation too, as are outside additions and depth pieces such as Nick Sogard. Boston has a stack of choices to sort through this winter.
Cotillo went a step further in his prediction, saying Story’s time in Boston will end this winter. That does not lock anything in, but it comes from one of the most connected Red Sox voices around.
The talent has never been the issue. When Story is healthy, he can swing games with his bat and legs. He showed that in 2025, when he hit 25 home runs, drove in 96 runs, stole 31 bases and batted .263 in 157 games, worth 4.1 WAR.
But that season also stands out for another reason: it was the only year in his five-year stretch in which he played more than 94 games. His 2026 season started with him clearly not at full strength, then he had sports hernia surgery and finished strong, but still appeared in only 64 games.
If Boston does decide to move on, it would create room for Arias at shortstop or for another external addition. It would also make the designated hitter spot easier to use for another bat.
The challenge is obvious. It’s hard to see another team taking on the money still left on Story’s deal.
So for now, the Red Sox have options, and plenty of uncertainty. Once the World Series ends, clubs across the league will begin making more concrete decisions, and Boston’s Story situation should start to come into focus.
In Other News...
Willson Contreras Just Addressed A Growing Red Sox Concern
After a wild-card exit that left Boston with only two runs across two games against the Yankees, the conversation around the Red Sox quickly shifted from the ending to what comes next. Willson Contreras did not hide his frustration with the teams approach, but he also said he met with club officials and came away with a clearer sense that both sides are on the same page as the organization heads into the winter.
For a Red Sox club trying to sort through an ugly finish, that matters. Contreras also said he is feeling better physically after dealing with injuries, and with his contract running through 2027 plus a club option for 2028, he remains part of the longer-term picture as Boston looks for answers beyond one disappointing postseason. [Read more 🡒]
Red Sox Just Sent An Early Offseason Roster Message
The first little roster move of the offseason has already given a glimpse of how Boston plans to manage the back end of its roster. The Red Sox re-signed minor league reliever Angel Bastardo and made room by moving Nate Eaton to Oakland, a transaction that also brought in a young arm in 18-year-old pitching prospect Jareth Rayo.
It is the kind of housekeeping that often says as much about the months ahead as it does about the player involved. Boston was looking to open a 40-man spot as the offseason gets underway, and with more reinforcements expected to come off the injured list, the Red Sox are already starting to shape the roster for what comes next. [Read more 🡒]
Red Sox Keep Intriguing 24-Year-Old Arm In The Mix After World Series
Boston is keeping Angel Bastardo in the fold for another look, signing the right-handed pitcher to a minor league contract for 2027 with an invitation to Major League Spring Training. The 24-year-old spent the 2026 season at Triple-A Worcester, where the organization continued to treat him as one of its more intriguing bullpen depth options and someone who is close enough to the majors to remain on the radar.
Bastardos path back to this point has already been a little unusual. Toronto picked him in the 2024 Rule 5 Draft before returning him to Boston, and since then the Red Sox have kept him nearby as a developmental arm with some upside. The spring invite gives him another chance to show he can stay in the mix when the club starts sorting out its pitching options again. [Read more 🡒]