Bold takeaway: Boston’s window for a blockbuster move is opening at the Winter Meetings, and a significant swap could unfold even before the conference concludes. The Red Sox have already made one strategic addition, but the sense across MLB chatter is that something bigger could be lurking on the horizon, perhaps even a deal that reshapes Boston’s outfield or rotation.
Craig Breslow’s first major executive move could arrive as soon as Sunday when the 2026 MLB Winter Meetings begin in Orlando. The full event runs December 7–10, giving Boston a few days to canvass the market, explore options, and target the deals that fit best. If the latest reporting from Kiley McDaniel and Jeff Passan at ESPN.com is any guide, a second trade could be on the table during the Meetings.
Passan and McDaniel’s piece prioritizes the biggest MLB trade candidates for the offseason, with Tarik Skubal of the Tigers—an ace who has captured consecutive Cy Young awards—ranked at the top. While Boston is mentioned as a potential fit for Skubal, the idea feels like a long shot for now. A more tangible target sits at No. 6: Minnesota right-hander Joe Ryan. Earlier in the offseason, there were whispers that Ryan could have been bound for Boston at the trade deadline, and Breslow and Twins GM Derek Shelton didn’t close the deal then. Orlando could provide another chance to revisit that pairing.
If Boston lands Ryan, he would function as a true No. 2 starter behind a frontrunner like Garrett Crochet, presenting a 3.42 ERA, 194 strikeouts, and 171 innings over 31 appearances (30 starts) in 2025. To pull off a deal, Boston might need to part with a major-league asset that appears on ESPN’s trade-candidate list. The names on that list aren’t surprising for Red Sox followers: Jarren Duran sits at No. 7, and Wilyer Abreu at No. 13.
Interestingly, the Twins aren’t listed as a likely suitor for either outfielder in ESPN’s rundown. Instead, the teams circled as possible trading partners for the Red Sox include the Tigers, Royals, Giants, Pirates, Phillies, Mets, Reds, Diamondbacks, and Astros.
In any scenario, Boston remains in the conversation as a destination for a high-impact player, while also facing the real possibility of shipping out one of its outfield pieces. The Winter Meetings could be precisely the opportunity needed to execute both goals in a single, decisive trade.
Next: Red Sox stay busy with 3 trades in 1 day (https://985thesportshub.com/2025/11/19/red-sox-complete-3-trades-white-sox-mariners-rockies/)
