The four weeks since the Red Sox were eliminated from the postseason have been slow, to say the least, with all business on hold until the World Series ends and the offseason begins. Things are about to pick up across baseball, though, and Boston will be forced to make some roster moves in the coming days.
The first key deadline of baseball’s winter calendar comes five days after the conclusion of the World Series, which will come between Monday and Thursday of next week, depending on how long the Blue Jays-Dodgers series goes. If Los Angeles can win back-to-back home games and dispatch Toronto in five games, free agent business might start rolling as soon as this weekend. If the series goes back to Rogers Centre, things will be delayed for a couple days.
The Red Sox, like virtually every team across baseball, are in standby mode. Within five days of the last pitch of the World Series, though, a lot has to get done. Here’s a look at what to expect in the coming days.
Four players will hit free agency immediately after the World Series
The Red Sox have four true free agents with no options or opt-outs attached, and they’ll all become free agents the day after the World Series ends. Veteran lefties Steven Matz and Justin Wilson, starter Dustin May and outfielder Rob Refsnyder are all on expiring contracts and will be free to sign anywhere.
Reunions with Refsnyder, Wilson and Matz on short-term deals are possible but expect all three to have interest elsewhere after strong seasons.
Big opt-out decisions loom, as do easier option decisions
The big storyline to track in the week after the World Series pertains to the left side of Boston’s infield. As has been well-documented, shortstop Trevor Story and third baseman Alex Bregman can both opt out of their contracts and become free agents. Those decisions are due on Day 5 after the World Series.
The Red Sox have not been formally informed Bregman is opting out but sources say all parties are still operating under the assumption that he will, as expected, trigger that clause and hit free agency instead of returning for a (deferred) $40 million salary in 2026. Boston decision makers are — cautiously — quite optimistic that Story will opt in and play out the remaining two years and $55 million on his deal. That choice hasn’t been formalized either.
Beyond Story and Bregman, the Red Sox have some other option-related decisions due soon. One is a formality, as Liam Hendriks’ $12 million mutual option for 2026 will be declined by the club and the Sox will have to pay him a $2 million buyout. He’ll hit free agency. Then there is the matter of Lucas Giolito (more on him in a minute), who has a $19 million mutual option (or $1.5 million buyout). Mutual options, which would need to be exercised by both sides, are usually mechanisms that allow teams to manipulate CBT (competitive balance tax) numbers and are almost never picked up. So the expectation is that will happen with Giolito, making him a free agent.
An unusual decision also looms with Jarren Duran, who is under team control through 2028 but has a club option for 2026 as part of the unique arbitration deal he signed in January. He’s on the roster — barring an eventual trade — whether the Red Sox pick up the option or not. But they can lock in an $8 million salary for him in 2026 by picking up the option the week after the World Series.
Declining Duran’s option would mean the Red Sox would pay him a $100k buyout on that contract, then go back into the arbitration process with him this winter. Again, he’d remain under team control. The sides would then have to come to a new salary for 2026 (or have an arbitration panel decide it). MLBTradeRumors projects Duran to earn $8.4 million through that process.
Will Giolito get the qualifying offer?
Bregman and Story got the qualifying offer before, so they’re not eligible for it again. Matz, Wilson, Refsnyder, May and Hendriks wouldn’t be candidates to be offered a one-year deal valued at $22.025 million.
Giolito, therefore, is the only Red Sox player who might be impacted. Before that Day 5 deadline, the club will have to decide, assuming his mutual option is declined, whether or not to issue the qualifying offer. Giolito would then have until November 18 to either pick it up or decline it. Issuing the QO would mean the Red Sox get draft-pick compensation if Giolito declines and signs elsewhere much like they did last year when Nick Pivetta declined the offer, then later signed with San Diego. There’s also a reasonable chance Giolito, especially after dealing with elbow issues that kept him out of postseason play, would take that deal and return.
40-man roster crunch coming, too
The Red Sox will likely have seven free agents, including Bregman and Giolito, with a slight chance at eight if Story opts out. Right now, they have 38 players on their 40-man roster after jettisoning two pitchers — Isaiah Campbell and José De León were outrighted — earlier this month.
The free agent departures puts the Red Sox at 32 on the 40-man roster (Hendriks, on the 60-day injured list, doesn’t count against it right now). The club then needs to reinstate nine players — Triston Casas, Kutter Crawford, Hunter Dobbins, Luis Guerrero, Tanner Houck, Vaughn Grissom, Marcelo Mayer, Patrick Sandoval and Josh Winckowski — from the 60-day IL, which doesn’t exist in the offseason. That means there will likely be 41 players for 40 spots. The Red Sox will then need to make a cut to fit everyone on.
There are some depth options on the roster who are candidates to be designated for assignment like lefty Jovani Morán and righty Josh Winckowski. Eventually, as winter additions are made, the roster spots of guys like Grissom, Nick Sogard, David Hamilton and others could be become tenuous. The Red Sox do have something of a free space, however, when it comes to first baseman Nathaniel Lowe.
Lowe is not a free agent — yet — because he’s an arbitration-eligible player. But he’s due, after earning $10.3 million last season, to get a raise in the $13.5 million range, according to MLBTR. His performance, of course, is not commensurate with that salary, making him a clear, obvious non-tender candidate. The Red Sox could just cut bait immediately by designating or releasing Lowe and allowing him to hit the open market a little earlier. That would not preclude trying to re-sign him on a lower-dollar deal.
More 40-man moves will be needed ahead of November 18, which is the deadline to protect minor leaguers from Rule 5 eligibility by adding them to the 40-man roster. The most clear Red Sox addition is pitching prospect David Sandlin. Beyond that, there are some players with an outside chance of being added like Shane Drohan. Those decisions are a few weeks away.
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