Red Sox 2025 Free Agents, Trade Targets, Offseason Guide After Wild Card Loss
The Boston Red Sox's season is over, as their playoff fate was sealed with a wild card series loss to the New York Yankees.
Even if they didn't get back to the World Series for the first time since 2018, the Red Sox can still look back on their 2025 campaign as a success. They snapped a three-year playoff drought, and they're heading toward 2026 with room to improve on their 89-73 record.
For the long haul, they know they have a generational ace in Garrett Crochet, a strong offensive core centered on breakout rookie Roman Anthony and do-it-all outfielder Jarren Duran, plus a manager in Alex Cora who ranks among the best string-pullers in the game.
What the Red Sox lacked in 2025—particularly toward the end of the year—was depth on both sides of the ball. They especially need to address an offense that was short on firepower and a pitching staff that needed more talent in between Crochet and resurgent closer Aroldis Chapman, who's already back in for 2026.
To this end, how the Red Sox conduct their offseason will be crucial. They have major contract decisions looming, and their fanbase is sure to have high demands for spending now that Rafael Devers' contract is off the books.
Ahead, we'll break down which players stand to become free agents and throw out targets for them to pursue on the free-agent and trade markets.
Traditional Free Agents
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OF Rob Refsnyder
As a tormenter of left-handed pitching (.959 OPS in 2025) who can handle himself in both corner outfield spots, Refsnyder has made his value clear as a platoon option in his four seasons with the Red Sox. He also loves it in Boston, so it wouldn't be surprising if the team found a way to bring him back for his age-35 season next year.
LHP Justin Wilson
Wilson had a solid year overall, posting a 3.35 ERA in 61 appearances out of the bullpen. He also fulfilled his primary function as a silencer of left-handed bats, with lefty hitters finishing with only a .574 OPS against him. Even if he's more of a nice-to-have than a must-have in the bullpen, he's a candidate to come back if his market value doesn't go well beyond the $2.25 million he made this year.
RHP Dustin May
May was one of the shockingly few additions for the Red Sox at the trade deadline, and his tenure in Boston is one that won't be remembered fondly. He posted a 5.40 ERA in only six appearances before elbow neuritis ended his season in early September. He'll be a worthwhile target as a reclamation project for someone in free agency, but he probably won't be a priority for Craig Breslow this winter.
LHP Steven Matz
Matz was the other notable addition for Boston at the deadline, and he fared better than May in pitching to a 2.08 ERA in 21 appearances out of the bullpen. That was with only 12 strikeouts in 21.2 innings, however, so the general profile remains that of a mop-up man and lefty specialist. As with May, he's unlikely to be a priority for Boston this winter.
Contract Option Decisions
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3B Alex Bregman: 2-year, $80 million player option
As reported by ESPN's Jeff Passan in September, Bregman is expected to opt out of his deal this winter. Despite a quad injury that sidelined him for a big chunk of the summer, the veteran earned his keep with a 128 OPS+ and 3.5 rWAR on the field and with his leadership in the clubhouse.
The Red Sox should probably be prepared to spend upwards of $150 million to keep him around. That is territory they have tried to avoid in free agency in the last decade or so. But since they're no longer paying Rafael Devers and generally good on the revenue front, there should be no doubt that the Red Sox can afford Bregman if they want him.
SS Trevor Story: 2-year, $55 million player option
Story also has the opportunity to opt out, though Mark Feinsand of MLB.com wrote in August that it "would be shocking" if he took it.
He had his best year yet as a member of the Red Sox, tallying 25 homers, 31 stolen bases and 3.8 rWAR. But he's also a 32-year-old with a recent history of injuries and basically league-average hitting, so whether there's more than $55 million out there for him is a genuinely good question.
RHP Lucas Giolito: $19 million mutual option
This was a $14 million club option, but Giolito turned it into a mutual option when he crossed the 140-inning plateau in September. At that point, opting into free agency seemed all but certain.
The situation is now less certain after an elbow injury sidelined the 31-year-old righty for the playoffs, but he at least avoided what would have been his third major elbow surgery. Testing the market remains a solid bet, even if his next contract is likely to be heavily laden with incentives.
RHP Liam Hendriks: $12 million mutual option
After missing all of 2024 and posting a 6.59 ERA in only 14 appearances this season, Hendriks has felt like a likely goner from Boston for a while now. Now his exit seems all but certain after he had ulnar nerve transposition surgery in September.
Hendriks was once one of the top relievers in the game, but various health scares (including non-Hodgkin lymphoma) have limited him to 19 appearances in the last three seasons. The 36-year-old wants to keep pitching, but interest in him may be limited to minor league offers.
OF Jarren Duran: $8 million club option
Duran's option is a mere formality, as he is arbitration-eligible through 2028 no matter what. The Red Sox will presumably pick up his option, though what will really be intriguing is if they choose to shop him on the trade market this winter. They have a surplus of outfielders, and interest in him has been strong in the past.
Biggest Needs
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Third Baseman
The assumption here is that Bregman will indeed opt out, which would open up a sizable hole at the hot corner in Boston.
One option would be to anoint Marcelo Mayer as Bregman's heir at third base, but that avenue is dripping with risk. Mayer's injury history is just too scary, and it would come with the downstream risk of giving Kristian Campbell another shot at second base. Both players should have to earn jobs next spring.
For the Red Sox, there's a straightforward solution here: If Bregman opts out, move quickly to re-sign him.
First Baseman
Casas wasn't hitting well before he got hurt, and the Red Sox never really figured first base out after he was lost for the season. Ultimately, the position yielded a .691 OPS and 0.3 rWAR.
As Chris Cotillo of MassLive wrote in July, the Red Sox understand that Casas' "return to being a lineup force isn't a sure thing considering the severity of his knee injury." If so, they'll need to have a Plan B at first base this winter.
Designated Hitter
The Red Sox were set at designated hitter when Rafael Devers was around, but not so much after he left. Masataka Yoshida got the bulk of the action there down the stretch, and he didn't do much designated hitting. He finished with a .696 OPS.
Yoshida has become an unwelcome reminder of the Chaim Bloom years. Even if it means eating the $37.2 million they still owe him, the Red Sox would do well to move on from him.
Relief Pitching
Despite Aroldis Chapman's brilliant work throughout 2025, the Red Sox still managed to rank among MLB's leaders with 27 blown saves.
This speaks to how shaky the bridge to Chapman was at times, particularly when Greg Weissert was on the mound. Don't let his 2.82 ERA fool you, as he didn't miss many bats and was responsible for nine of those blown saves.
The Red Sox did extend Chapman through 2026 in September, but it would be a mistake to assume he can be as effective at 38 as he was at 37. They'll need an insurance policy who could otherwise be an effective setup man for him.
Free-Agent Targets
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Third Base: Alex Bregman
This doesn't need to be complicated. Bregman and the Red Sox were a perfect match on paper when they joined forces, and that is still the case now.
Bregman can and should do better than his current deal on the open market, with Matt Chapman's six-year, $151 million contract representing a relevant price point. The 31-year-old is worth such a deal just in terms of what he can do between the lines, and his clubhouse presence only further escalates his value.
First Base: Pete Alonso
The Red Sox were never really big players in Alonso's free agency last winter, but they've already been floated by Jon Heyman of the New York Post as a fit for him this offseason.
Alonso isn't going to come cheap in terms of average annual value, but the 30-year-old should only be looking at a new short-term deal upon declining his player option for 2026 with the New York Mets. His right-handed power would help the Red Sox, even if it meant living with his poor defense at the cold corner.
Designated Hitter: Eugenio Suárez
This one is a bit of a wild card, as Suárez has only started 30 games at DH in his 12 years as a major leaguer.
Yet, at 34, he is getting a little old to play third base every day. And if the Red Sox are going to sell him on a shift to DH duty with only occasional action at third base and first base, the best way to do it would be by hyping how well his right-handed pull power would fit at Fenway Park.
Relief Pitcher: Ryan Helsley
Helsley tanked his value after the trade deadline, with his 22 appearances for the Mets yielding a 7.20 ERA. He may be a candidate for a one-year pillow contract in free agency as a result.
As Helsley is a guy with triple-digit heat and questionable control, the Red Sox could do for him what they've done for Aroldis Chapman. Maybe it wouldn't be as basic as simply telling Helsley how and where to throw the ball, but there must be some kind of fix that would get this two-time All-Star back on track.
Trade Targets
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3B José Ramírez, Cleveland Guardians
Hey, there's nothing wrong with aiming big. And if the Red Sox can't retain Bregman this offseason, there would be no downside to reaching out to the Guardians to gauge their interest in trading Ramírez.
That interest should be nonexistent, but you just never know with the Guardians. They're always playing Jenga with their roster and payroll. And given that he's 33 and owed $69 million through 2028, they may not have many more golden opportunities to get anything for Ramírez.
His credentials as a star are basically unblemished. He's been an All-Star seven times and has averaged a 30-30 season with 6.3 rWAR since 2017.
1B/DH Yandy Díaz, Tampa Bay Rays
This assumes the Rays exercise the $12 million option they hold on Díaz for next season, which seems like an easy call. For the last four seasons, he's been a .301 hitter who has twice topped 20 home runs.
The Red Sox were reportedly coveting the 34-year-old veteran ahead of the trade deadline. Were they to do so again, they would stand to gain a high-reliability hitter who could work as their everyday DH and platoon with Triston Casas at first base.
LHP Reid Detmers, Los Angeles Angels
Talented relief pitchers are a dime a dozen these days, but not all of them are former first-round picks with no-hitters under their belts.
Detmers is, and his move to the pen has helped stabilize a career that had been going awry. Even if his 3.96 ERA doesn't jump off the page, his chase, whiff and strikeout rates all rank in the top 10 percent among all pitchers.
The 26-year-old is controlled through 2028, so convincing the Angels to part with him may not be easy. But then again, you have to figure they'll come to their senses and starting planning for the future eventually.
Projected 2026 Opening Day Roster
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Starting Lineup
LF Roman Anthony
3B Alex Bregman
CF Jarren Duran
SS Trevor Story
RF Wilyer Abreu
DH Yandy Díaz
1B Triston Casas
2B Marcelo Mayer
C Carlos Narváez
The Red Sox re-signing Bregman should be one of the bigger slam dunks of the winter, and they could conceivably leave their lineup alone otherwise. Instead, we have them trading for Díaz and salary-dumping Yoshida on someone else.
Bench
C Connor Wong
OF/INF Ceddanne Rafaela
INF/OF Kristian Campbell
OF Rob Refsnyder
If the Red Sox keep Duran and thus commit to an all-lefty outfield, they'll pretty much have to bring Refsnyder back. The other notable part here is Rafaela on the bench, even after he led all Red Sox position players with 4.8 rWAR. The thinking is that he needs to be made into a super-utility type, as his bat is just not good enough to warrant everyday playing time.
Starting Rotation
LHP Garrett Crochet
RHP Brayan Bello
RHP Kutter Crawford
LHP Patrick Sandoval
LHP Payton Tolle
Giolito and the Red Sox seem likely to part ways, but the team wouldn't necessarily have to fill his shoes if he leaves. Breslow has a ton of options for next year's rotation, including a couple (i.e., Kyle Harrison and Connelly Early) who aren't even listed here.
Bullpen
LHP Aroldis Chapman
RHP Ryan Helsley
RHP Garrett Whitlock
RHP Justin Slaten
RHP Jordan Hicks
RHP Greg Weissert
LHP Chris Murphy
LHP Brennan Bernardino
We're committed to Helsley as a good fit for Boston, and he would provide Cora with a truly elite back end if he were to return to his form of previous seasons. This bullpen is otherwise less lefty-heavy than the current iteration, which is frankly a little too left-heavy for its own good.
Stats courtesy of Baseball Reference, FanGraphs and Baseball Savant.
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