Sunday, December 28

BOSTON -- When he arrived at last year’s Winter Meetings, chief baseball officer Craig Breslow’s mission was to put the Red Sox back in the conversation of contenders, and he succeeded by making a blockbuster trade for Garrett Crochet. That move, plus a few others, helped push Boston back into the playoffs for the first time since 2021.  

A year later, as Breslow and his baseball operations staff get ready to head to Orlando, Fla., for this year’s Meetings, the goal is to push the club a step further and make an already strong roster a World Series-caliber one. 

• Winter Meetings presented by CohnReznick: Complete coverage

The Red Sox -- bolstered by a young crop of solid position players (Roman Anthony, Wilyer Abreu, Ceddanne Rafaela, etc.) and elite lefties at ace (Crochet) and closer (Aroldis Chapman) -- aren’t far off. 

Breslow’s first strike of the offseason took place two days before Thanksgiving when he acquired veteran righty Sonny Gray in a trade with the Cardinals. That move was clearly just a starting point. 

“It’s early in the offseason,” Breslow said. “There are still opportunities that I anticipate materializing. Exactly what they look like, I’m not sure. But we’re not going to close off any chance to make the team better.” 

Here is a primer heading into the Winter Meetings, which run from Monday through Wednesday.  

Club needs 

A big bat for the third or fourth spot in the lineup

The Red Sox had that guy for years, and his name was Rafael Devers. The star slugger was dealt to the Giants for a multitude of reasons on June 15, and Boston knows it is vital to replace his production to go deep into October. Keep an eye on Pete Alonso and Kyle Schwarber, the two biggest bats on the free-agent market. Only Aaron Judge has hit more homers than those two sluggers over the past seven seasons. 

Another arm to slot into the top third of the rotation 

The 36-year-old Gray is a nice piece to have. But Breslow will likely seek a clearer No. 2 to slot behind Crochet. A trade could happen to fill this need. While Tarik Skubal seems like a pipe dream, you can be sure Breslow will monitor that situation with the Tigers. Boston already made a run at Minnesota’s Joe Ryan at the Trade Deadline in July, and those talks could be rekindled. If the Royals make Cole Ragans available, the Sox will be interested. There is also a lot of starting pitching available via free agency, including Framber Valdez, Ranger Suárez, Michael King, Zac Gallen and Merrill Kelly. 

Potential trade candidates 

Jarren Duran is someone the Red Sox could definitely deal this winter, but through no fault of his own. The club has a logjam of talent in the outfield in Anthony, Rafaela and Abreu. Power hitter and plus defender Jhostynxon Garcia (ranked by MLB Pipeline as the club’s No. 3 prospect) might have a chance to make the team in Spring Training, while Masataka Yoshida still has two more years under contract.  

Duran has the type of skill set (power, speed, athleticism) and contract situation (not eligible for free agency until 2029) that could make him a compelling part of a package in which the Red Sox could acquire a front-line starter. Another option would be to trade Abreu, but he is coming off back-to-back Gold Glove Awards while covering arguably MLB’s toughest right field at Fenway Park.  

Yoshida is also a candidate to be on the move, but the Red Sox would have to throw in a significant amount of cash to cover the $37.2 million he is owed over the next two seasons. 

Prospect(s) to know 

The prospects you’ve heard about for years -- Anthony, Marcelo Mayer and Kristian Campbell -- graduated beyond prospect status. The next group to keep an eye on is heavy on pitching, particularly lefties Payton Tolle (Boston’s No. 2 prospect) and Connelly Early (No. 5), who both made their regular season and postseason debuts last season but are still classified as prospects.  

Rule 5 Draft 

The Sox have several pitchers who could get selected in next Wednesday’s Rule 5 Draft, including right-hander Noah Song and lefties Jeremy Wu-Yelland and Hayden Mullins (Boston’s No. 17 prospect). On the position-player side, outfielder Miguel Bleis, once one of the organization’s top five prospects, has slipped to No. 14 in MLB Pipeline’s latest rankings. Though he hasn’t produced in the Minors as much as the Red Sox hoped so far, an organization could take a chance on his raw talent. Given that Boston has had good fortune with Rule 5 picks in recent years in relievers Garrett Whitlock and Justin Slaten, it wouldn’t be stunning if the club took another flier on a hard-throwing pitcher. 

Burning question 

How aggressively will the Red Sox engage with agent Scott Boras on the possibility of bringing Alex Bregman back in the fold? There was enormous enthusiasm in February when the Sox signed the veteran leader to a three-year, $120 million contract that included deferrals. However, the contract also included opt-out clauses after the first two seasons, and Bregman took advantage of that by opting out right after the World Series. There has been radio silence from the Sox about Bregman since that day, with Breslow unwilling to tip his hand on the club’s level of interest in exploring a long-term deal with the three-time All-Star. Boston’s clubhouse would certainly be thrilled to have Bregman back. He became the team’s leader instantly upon arrival. 

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