NEW YORK — The Crimson Sox took an essential step ahead this season, overcoming a litany of accidents to achieve the postseason for the primary time since 2021.
However because the New York Yankees made painfully clear this previous week, the Crimson Sox nonetheless have a methods to go earlier than they are often thought-about true championship contenders.
The offseason got here abruptly for the Crimson Sox, who misplaced the ultimate two video games of the AL Wild Card sequence after initially taking Recreation 1. Defensive miscues, poor situational hitting and a few dangerous breaks doomed the membership, which should now re-tool over the winter to make sure subsequent yr’s group is best geared up to make a deep run.
The Crimson Sox may have the remainder of the postseason to mirror and regroup, however as soon as the World Collection is over Craig Breslow and firm may have an extended to-do listing to deal with over what needs to be a pivotal winter for the franchise.
Will Bregman, Story return?
The primary order of enterprise for the entrance workplace can be determining whether or not or not Alex Bregman and Trevor Story can be again in 2026. Each gamers can choose out of their present offers this offseason, and if neither returns the membership would have an enormous void to fill in each the left facet of the infield and within the clubhouse as a complete.
Final spring Bregman signed with the Crimson Sox on a three-year, $120 million deal that included choose outs after every season. His affect within the clubhouse was past something the membership may have hoped for, however the season didn’t come with out its bumps for the veteran third baseman.
After a pink scorching begin Bregman suffered a quad damage that sidelined him for 43 video games, and upon his return his manufacturing dipped. Previous to the damage the 31-year-old was batting .299 with a .938 OPS, however following his activation he batted .250 with a .724 and slumped badly over the ultimate month.
On condition that, will Bregman cross on the chance to make $40 million in 2026 to attempt to land a longer-term deal as a substitute? If he does will the Crimson Sox play hardball and threat dropping him to a different franchise? If that occurs the membership would have a gaping gap at third base, and there are few choices — inside or exterior — who may come near filling it.
Story’s state of affairs can be fascinating.
Coming off three injury-plagued seasons, Story returned to type in 2025, main the group in residence runs (25), RBI (96) and stolen bases (31). The 32-year-old has two years, $50 million remaining on his contract, so it’s not a stretch to think about he may choose out and attempt to beat that on the open market.
The Crimson Sox may attempt to preempt that by providing an extension, or they may re-sign him in free company, however with Marcelo Mayer ready within the wings and Kristian Campbell presumably nonetheless within the membership’s plans someplace, it’s attainable the Crimson Sox may determine to let Story stroll if he opts out.
Possibly there could be some benefit to that, however Story was one of many membership’s best all-around place gamers this season, and dropping him would create one other huge gap the Crimson Sox must fill.
All opt-out selections are due 5 days after the World Collection ends.
Every other returning free brokers?
Along with Bregman and Story, the Crimson Sox have 4 gamers set to hit free company plus two with mutual choices who’re positive bets to hit the market as nicely.
The free brokers are Steven Matz, Dustin Might, Justin Wilson and Rob Refsnyder, with Lucas Giolito and Liam Hendriks holding the choices.
Matz and Wilson have been each stable lefties out of the bullpen who may conceivably return, and Refsnyder has been one of many membership’s most essential bench gamers and veteran leaders since his arrival in 2022. He has excelled in his position as a lefty killer and fourth outfielder, however with Romy Gonzalez (.331 common, .978 OPS vs. lefties) doubtless returning to a utility position in 2026, Refsnyder’s future in Boston is unsure.
Giolito is a very difficult case.
The appropriate-hander bounced again from a season misplaced to damage and emerged as one in all Boston’s most essential starters. He topped 140 innings and was a key purpose why the Crimson Sox made the playoffs, however his elbow started bothering him once more down the stretch and he finally wasn’t accessible for the playoffs.
Can the Crimson Sox depend on him to carry up in 2026? Will any membership supply him a multi-year deal given his current damage historical past? His well being standing will warrant shut monitoring because the offseason progresses.
Tackle 40-man crunch
Crimson Sox presently have 10 gamers on the 60-day IL, most of whom must be added again to the 40-man inside 5 days of the top of the World Collection.
These are Kutter Crawford, Hunter Dobbins, Luis Guerrero, Tanner Houck, Patrick Sandoval, Josh Winckowski, Triston Casas, Vaughn Grissom, Mayer and Hendriks.
The Crimson Sox additionally want to create space for any Rule 5 eligible prospects they wish to shield from being poached, with right-hander David Sandlin the most definitely addition.
Between the 4 pending free brokers plus Giolito and Hendriks, the Crimson Sox have at the least six spots opening up. From there they must designate a number of gamers for project, with doubtless candidates to start out together with Jose De Leon, Isaiah Campbell, Jovani Moran and Winckowski.
If vital the membership may decline to tender a few of its arbitration-eligible gamers a contract. The most definitely non-tender candidate is Nathaniel Lowe, who’s in line to earn greater than $10 million regardless of an underwhelming season that noticed him launched by the Washington Nationals earlier than touchdown in Boston for the stretch run.

Clear outfield logjam
Past determining if Bregman and Story can be again, the following most pressing matter for Breslow to type out is who will comprise the outfield subsequent season.
At full well being the Crimson Sox have extra beginning caliber outfielders than they’ve spots within the lineup, and whereas the issue sorted itself out organically through the season as soon as Wilber Abreu and Roman Anthony went down with accidents, the state of affairs isn’t sustainable long-term.
Roman Anthony clearly isn’t going wherever, however Breslow will doubtless want to maneuver one in all Jarren Duran, Ceddanne Rafaela or Wilyer Abreu, plus presumably Masataka Yoshida as nicely. Duran was thought-about the most definitely of the group to be moved on the commerce deadline — he’s the oldest of the bunch and has the fewest years of group management remaining — and by shifting him the Crimson Sox may additionally handle a few of their different wants.
Add one other front-line starter
From a depth perspective the Crimson Sox are in nice form. With out making every other strikes the Crimson Sox may go into subsequent season with a projected rotation that features Garrett Crochet, Brayan Bello and a few mixture of Kutter Crawford, Patrick Sandoval, Hunter Dobbins, Richard Fitts, Connelly Early, Kyle Harrison and Payton Tolle.
That’s a whole lot of arms to work with, however as we noticed within the postseason, the membership nonetheless wants a confirmed workhorse to pair with Crochet if it hopes to compete for a championship.
When it comes to free brokers, the highest choices available on the market this winter embrace Framber Valdez, Michael King, Dylan Stop, Ranger Suarez, Zac Gallen and Merrill Kelly, amongst others. None of them will come low-cost, however with a homegrown basis in place and the membership squarely in a aggressive window, there isn’t any purpose why the Crimson Sox ought to shrink back once they may genuinely be one or two gamers away from turning into a title contender.
If not one of the free brokers are interesting, the Crimson Sox may additionally revisit the commerce market.
Boston reportedly made a push for Minnesota ace Joe Ryan on the commerce deadline however couldn’t get a deal over the end line. Maybe the second time could possibly be the appeal?
It labored out nicely for the Crimson Sox with Garrett Crochet final winter, that’s for positive. Touchdown Ryan or one other arm of his caliber needs to be a high precedence for Breslow this offseason.

Discover one other energy bat
When the season started the Crimson Sox anticipated to have Rafael Devers and Triston Casas as the facility threats anchoring the center of the lineup. Casas was misplaced for the yr early on with a devastating knee damage and Devers wound up being traded in June following months of drama and discontent.
Casas may nonetheless return and make an affect in 2026, however even when he does the membership remains to be going to wish extra pop.
This previous week uncovered simply how poor the Crimson Sox offense had turn into from an influence perspective. The place the Yankees had guys up and down the lineup who may plausibly hit one out on any given pitch, the Crimson Sox needed to string two or three hits collectively in the event that they needed any shot, which isn’t going to work while you’re dealing with one of the best of one of the best in a playoff recreation.
Fortuitously there are two free brokers who’d match the invoice completely.
The primary is Mets slugger Pete Alonso, who is predicted to choose out of his deal and take a look at his luck in free company once more this winter. Alonso is coming off a season wherein he hit 38 residence runs with 126 RBI, and thru his first six 162-game seasons he’s by no means hit fewer than 34 homers.
The opposite is Kyle Schwarber.
Letting Schwarber stroll after the 2021 season has confirmed to be a expensive misstep for the Crimson Sox, who spent three years rebuilding whereas Schwarber helped lead the Phillies to a brand new period of playoff glory. The slugger has hit 187 residence runs in 4 years with the Phillies, together with a career-high 56 this previous season.
He’ll in all probability end among the many high vote-getters for Nationwide League MVP.
The Crimson Sox may simply accommodate Casas and one in all Alonso or Schwarber — one may play first base and the opposite DH — however piecing the puzzle collectively could be simpler if the membership additionally moved on from Yoshida. The 32-year-old got here on robust on the finish of the yr and was the membership’s finest hitter down the stretch, however even at full power he’s nonetheless a DH who doesn’t hit for energy.
Possibly Casas gained’t be prepared for Opening Day, and perhaps at full well being Yoshida’s finest days in Boston may nonetheless be in entrance of him. Both approach the Crimson Sox can’t stand pat, and if the Opening Day lineup subsequent March isn’t meaningfully improved, the Crimson Sox will threat squandering the progress they made this season.