Bold claim: the Red Sox are not done reshaping their roster, and a blockbuster move could be brewing as the Winter Meetings approach. Boston has already made one trade to strengthen its roster, but everything suggests there’s more ahead—perhaps even bigger than a Sonny Gray deal.
The team’s new front office chief, Craig Breslow, could launch his most consequential maneuver as soon as the Winter Meetings begin in Orlando. The event runs December 7–10, giving Breslow and the Sox a few days to explore options and lock in deals. If recent reporting from ESPN’s Kiley McDaniel and Jeff Passan is any guide, a second major trade could surface during the gathering.
Passan’s overview outlines prime trade targets for the coming weeks, with Tarik Skubal of the Detroit Tigers sitting at the top as a premier, two-time Cy Young winner—yet Boston fans should view this as a long shot at best. A more plausible target sits at No. 6: Twins right-hander Joe Ryan. Earlier talk in August suggested Boston and Minnesota came close to a deal at the trade deadline, but the package couldn’t be finalized. Orlando could serve as the stage to rekindle those conversations and potentially seal a swap.
Joe Ryan would slot in as a true No. 2 starter behind Garrett Crochet for Boston, after posting a 3.42 ERA with 194 strikeouts across 171 innings in 2025 (31 appearances, 30 starts). It’s not hard to imagine that to land him, Boston might have to part with a major-league asset who also featured on ESPN’s trade candidate list. Among the Sox faithful, a familiar trio appears: Jarren Duran sits at No. 7 on the list, while Wilyer Abreu lands at No. 13—names fans recognize from ongoing chatter.
Yet the Twins aren’t singled out as a likely match for either outfielder, according to ESPN’s compilation. Instead, the report points to a broader field of potential trading partners for Boston: the Tigers, Royals, Giants, Pirates, Phillies, Mets, Reds, Diamondbacks, and Astros are the clubs to watch for a significant deal involving the Red Sox.
Whatever happens, Boston remains in the conversation for a high-impact acquisition, and the outlook suggests the team could achieve two major objectives in a single move: acquire a marquee talent and alleviate outfield turnover. The Winter Meetings might be the best opportunity to accomplish both goals in one transaction.
Next up: Red Sox stay busy with three trades in one day (linked coverage).
