The World Series is over, which means the offseason is about to begin for real for the Red Sox and those in their orbit.
With free agency starting — and trade possibilities opening — now that the games are over, here are seven questions that will guide, perhaps dominate, the Sox’ months to come:
1. Where will Alex Bregman land?
This will be the biggest offseason story line, hovering over everything the Sox do or might do until it is resolved, one way or another.
Bregman really liked being with the Red Sox. The Red Sox really liked having Bregman. The most likely outcome, therefore, should be a continued relationship.
But Bregman, who opted out of the three-year contract he signed in February, and his agent, Scott Boras, will play the free agency game. Bregman will be 32 in March; this is his best/last shot to get a career-defining payday.
The Tigers were in on him last offseason and could be again (though the possibility that they trade Tarik Skubal raises questions about whether they plan to contend in 2026 and why Bregman would want to join them). The Blue Jays, maybe fortified financially by a World Series run, don’t have a long-term answer at third base. The Yankees, who acquired defensively inclined Ryan McMahon at the trade deadline, are always capable of jumping in on these things. The Mariners are sending Eugenio Suárez into free agency. The Phillies are considering all sorts of changes, and adding a big-time third baseman isn’t out of the realm of possibility.
So the Sox will have competition, which inevitably will push the market beyond the $120 million guarantee that Bregman signed for last time.
One point of reference: The Giants gave Matt Chapman, the same age then that Bregman is now, $151 million over six years. Expect Bregman to aim higher than that. 1. He will be on the open market, whereas Chapman was getting an extension late in the 2024 season, and 2. He has a better offensive track record and more leadership intangibles.
2. Are the Red Sox willing to pay up for Pete Alonso (or another big bat)?
Alonso is in a spot similar to Bregman’s: reached free agency last year, didn’t have much of a market, took a short-term deal, is opting out, and will try again without a qualifying offer dragging him down.
For the Red Sox, Alonso is this offseason what Bregman was last offseason: the natural fit to what they need (a righthanded slugger at first base/DH) at this moment (post-rebuild, the start of what should be a lengthy competitive phase, with an inexpensive homegrown core).
Alonso, who turns 31 in December, reportedly is looking for a contract of seven years. That would take him through his age-37 season.
As always, we shall see what the market bears. J.D. Martinez reportedly wanted seven years (and $210 million) at the start of his free agency, too. He ended up with five years (and $110 million). So don’t get too caught up in the numbers that get floated at this stage.
3. Will waiting on Bregman put a pause on the rest of the to-do list?
This ties together the Bregman question with, primarily, the big-bat question. And the answer depends on what the Red Sox are comfortable spending.
In theory, any new Bregman deal is already baked into 2026 (and 2027) payroll projections. Without opting out, he would have counted as a $31.7 million annual hit, as calculated for the luxury tax (because much of his $40 million salary is deferred). So if they re-sign him for an average number in that range, it comes out about even near-term. Through that lens, the Sox should have room for another big-ticket player.
But if they are not eager to, say, commit nine-figure contracts to multiple players in their 30s, waiting on Bregman could complicate any pursuit of Alonso or lefthanded DH Kyle Schwarber (and maybe outfielder Kyle Tucker, who will be 29 next season). Boras represents Bregman, Alonso, and Tucker.
The Sox probably will need to walk parallel paths, beginning with yes and no answers on Bregman, possibilities splintering from there. That is the tricky, if routine, nature of front-office work.
4. How will the Red Sox get a No. 2 pitcher?
This assumes, perhaps dangerously, that the Red Sox indeed will bring in a starter to slot between Garrett Crochet and Brayan Bello. But it is an obvious need, so let’s figure that the Red Sox go ahead and fill it.
The free agent pool features Dylan Cease, Framber Valdez, and Ranger Suárez — as well as Rhode Islander and Boston College product Michael King, who doesn’t have the same track record but showed elite potential in 2024 before an injury-marred 2025. It’s a fine group.
Those potentially available via trade include Skubal (perhaps a pie-in-the-sky option), the Twins’ Joe Ryan and Pablo López, the Marlins’ Sandy Alcantara, and the Reds’ Hunter Greene. There are some fun names there, most coming with multiple years of team control.
Maybe the best bet is for the Red Sox to put their productive farm system to use again and package prospects for a big arm, like last year with Crochet. That would save dollars to bolster the lineup, too.
5. What will the trade market for Jarren Duran look like?
Of the four starting outfielders, Duran, who signed a one-year, $7.7 million deal with the Sox on Tuesday, appears most likely to get squeezed out. Roman Anthony is considered a franchise cornerstone, Ceddanne Rafaela is probably the best defensive center fielder in the majors (and on a team-friendly contract), and Wilyer Abreu is a Gold Glove right fielder and one of their most powerful hitters.
Expect the Sox to research several scenarios, but especially those that feature dealing Duran, a game-changing dynamo when at his best. His trade value isn’t as high as a year ago, when he finished eighth in American League MVP voting, but he should still bring back a valuable piece(s).
The return need not take the form of immediate roster supplements. If they include him to get that No. 2 starter, great. But if they pick off a prospect or two from somebody else’s farm system, that can be worthwhile, too, especially if the Sox find themselves trading minor leaguers to fill major league needs.
6. What is the deal with Masataka Yoshida?
Barring major interest from another team, the Red Sox can take a wait-and-see approach here. His role in 2026 will be shaped by what happens on the DH front. Yoshida coming to camp in some sort of part-time, bench-bat, outfielder-once-in-a-while role makes sense.
Given Yoshida’s weird couple of years — playing through an injured shoulder, finally having surgery, eventually returning midseason in 2025 — it is worth seeing what he looks like after a normal offseason and spring training. Maybe he becomes a more productive version of what he was in the second half this past season. Maybe his trade value gets a bump. Either way, it’s not a pressing matter.
7. How will the Red Sox replace Paul Toboni?
It’s not a forward-facing piece of the organization, but it’s a big deal.
Before being hired by the Nationals as president of baseball operations, Toboni, an assistant general manager, was a key part of chief baseball officer Craig Breslow’s inner circle. He oversaw the fundamental and physical development domain, which included all areas of the game — hitting, pitching, defense, base running, and strength and conditioning — in the majors and minors.
Last year, amid a larger restructuring, the Sox plucked Taylor Smith away from the Rays to run their analytics department. Another senior-level outside addition wouldn’t be a surprise.
Tim Healey can be reached at timothy.healey@globe.com. Follow him @timbhealey.