Early every December, executives from all 30 MLB clubs, along with free agents and potential trade candidates, all meet in one place. The execs chat with prospective players and other front office officials to lay the groundwork for signings and trades, and maybe even finish off some deals.
This year's Winter Meetings will run from December 7-10 in Orlando, Florida. The Boston Red Sox were one of the most active teams at last year's Winter Meetings, as Craig Breslow traded for Garrett Crochet and Carlos Narváez at the event. He could make some more trades this time to address one or more of the Sox's pressing needs.
Since the Red Sox's needs are so clear, they're expected to be one of the most active teams in both the free agent and trade markets this winter. These five players who have been linked to the Red Sox could be moved or signed at this year's Winter Meetings — if Boston is serious about any of them, it will have to act quickly.
5 Red Sox targets likely to come off the board fast at 2025 Winter Meetings
Joe Ryan
Links between the Red Sox and Minnesota Twins pitcher Joe Ryan began before the 2025 trade deadline, and Boston fans haven't been able to let them go. Breslow told reporters that he planned to address the top of the rotation this winter (which he's arguably already done with the Sonny Gray trade) and Ryan would be an excellent No. 2 behind Crochet.
The 29-year-old posted a 3.42 ERA, 1.035 WHIP, 125 ERA+, 194 strikeouts and 39 walks over 171 innings for the Twins last season. His body of work earned him his first All-Star nomination. Ryan has three years of control remaining on his contract, and the Red Sox are up against some stiff competition for his services. It'll take a haul of players to entice Minnesota into a deal, but Boston should make the push.
Freddy Peralta
The Milwaukee Brewers have a history of trading their star players before they reach free agency, and it seems Freddy Peralta will be no exception. The righty has been so dominant over his eight-year career that it'd be hard to consider him a No. 2 starter behind anybody, but he and Crochet could become the deadliest one-two punch in the league.
Peralta posted a 2.70 ERA, 1.075 WHIP, 154 ERA+, 205 strikeouts and 66 walks over 176.2 innings, and earned an All-Star nomination and Cy Young Award votes last season. Unlike Ryan, he only has one year remaining on his contract, but he'll still cost a fair few top prospects, and maybe even some big league talent.
Kyle Schwarber
After the Gray trade, Boston's front office said it would turn its attention to adding bats to the roster. After their 2021 playoff run, the Red Sox fumbled hard by letting Kyle Schawrber — a second-half hero and immediate fan favorite — walk in free agency, and now could be their chance to right a wrong and bring him back. Recent reporting has suggested Schwarber's market has picked up, and e could find a suitor at the Winter Meetings.
Sox fans saw Schwarber's home run hitting prowess during his short tenure in Boston, but he's only improved with age. He batted .240/.365/.563 with a .928 OPS, 23 doubles, two triples, a National League-leading 56 homers and an MLB-best 132 RBI over 162 games. Schwarber is a strange fit with the Red Sox given their DH situation, but any shuffling they'd need to do to accommodate him would be worth it — who could say no to 56 homers?
Pete Alonso
Boston has been linked to Pete Alonso for many of the same reasons it's been tied to Schwarber. However, unlike Schwarber, Alonso fills a position of need at first base. His righty power and hallmark durability would both be ideal additions to the Sox's lineup.
Alonso is highly decorated, having collected five All-Star nods, a Silver Slugger award, Rookie of the Year and four years of MVP votes over his seven years in the big leagues. He slashed .272/.347/.524 with an .871 OPS, 41 doubles, a triple, 38 home runs and 126 RBI over 162 games with the Mets last season.
Ketel Marte
The Diamondbacks are listening on their star second baseman — arguably one of the best in the league — Ketel Marte. The 11-year veteran would bring World Series experience, home run power and solid defense to a long-term position of need in Boston's infield.
Marte slashed .283/.376/.517 with an .893 OPS, 28 doubles, 28 homers and 72 RBI over 126 games. He posted above league-average defense and his range ranked in the 74th percentile among second basemen. Marte has five years of control on his contract after signing an extension with Arizona last year, so he'll cost quite a few players to bring to Boston, but he'd be a long-term solution at the revolving door that has been second base.