Going in, they face one big question (and plenty of smaller ones): Which big bat(s) will they add to a lineup that needs help?
The hitter market has barely budged. Other than Josh Naylor — whose five-year, $90 million contract was more of a one-off, with the Mariners seeking to retain a trade-deadline acquisition they loved — the best free-agent batters remain available.
Get Starting Point
A guide through the most important stories of the morning, delivered Monday through Friday.
That includes third baseman Alex Bregman, who made his presence felt on and off the field in his debut and potentially only season in Boston; first baseman Pete Alonso, a practically perfect roster fit for the Red Sox who isn’t weighed down by a qualifying offer; Kyle Schwarber, a DH-only slugger whom the Red Sox enjoyed having on the team during his 2021 cameo; shortstop Bo Bichette, who has been linked to the Sox in recent reports and likely would shift to second base if he joined them; and outfielder Kyle Tucker, who doesn’t appear to be a target given their surplus there (and his cost).
Working in the Red Sox’ favor: flexibility in the form of trade chips and financial capability. They are free to go in a bunch of directions.
Consider, for example, the state of the infield. For now, the depth chart looks like Marcelo Mayer as the top option at third base, Romy Gonzalez and David Hamilton at second, and Gonzalez and Triston Casas at first. Trevor Story, at shortstop, is about the only certainty. If they add a star at one position, the incumbents can move around to others.
In his relatively short tenure as the Red Sox’ baseball boss, Breslow has developed a history of deal-making during the Winter Meetings.
In 2023, his first go-around, he traded Alex Verdugo to the Yankees, then acquired Tyler O’Neill from the Cardinals shortly after the event ended. Last year, he pursued but lost out on Max Fried and pivoted decisively to get Garrett Crochet from the White Sox (as well as picking up Carlos Narváez in a minor-at-the-time deal with the Yankees).
The Red Sox’ roster lends itself to trade possibilities. They can deal Jarren Duran or Wilyer Abreu without creating a hole for the 2026 squad. Also, their recent additions of starting pitchers Sonny Gray and Johan Oviedo makes for a full rotation, raising questions about whether they would deal from their pool of pitchers.
The Sox’ major league trade pieces make them intriguing partners for teams who likewise have players to deal but want to contend for the playoffs next season. For example, the Diamondbacks, who are dangling second baseman Ketel Marte, need pitching and could use an outfielder. Alternatively, where would Duran or Abreu plus Brayan Bello get the Red Sox with the Royals on Cole Ragans?
Among the other goings-on at the Winter Meetings:
* Breslow is scheduled to speak to the Boston media on Monday, Tuesday, and Wednesday. Alex Cora will take his turn during manager interviews at 1 p.m. Tuesday.
* The MLB Draft lottery, determining the order for the 2026 draft, is at 5:30 p.m. Tuesday. Since the Red Sox qualified for the playoffs, they are not eligible for a top-six pick, but the results could tweak their first-round position (in the 20s).
* The Rule 5 draft is scheduled for 2 p.m. Wednesday. Unless the Sox open a spot on their 40-man roster, they won’t be selecting a player. But they may lose a minor leaguer or two.
Tim Healey can be reached at timothy.healey@globe.com. Follow him @timbhealey.