The Boston Red Sox are gearing up for a significant trade ahead of the 2026 MLB Winter Meetings, which kick off in Orlando on Sunday. With the goal of enhancing their roster, the team is reportedly eyeing a substantial move, potentially involving a top-tier player. According to Kiley McDaniel and Jeff Passan at ESPN.com, the Tigers' Tarik Skubal, a two-time Cy Young Award winner, is a prime candidate for trade, though it may be a challenging pursuit for the Red Sox at this stage. However, a more realistic option emerges in the form of Joe Ryan, a right-handed pitcher from the Minnesota Twins, who was rumored to be close to a trade with the Red Sox at the deadline. The Twins' GM, Derek Shelton, and Breslow couldn't finalize a deal, but the Winter Meetings provide an opportunity to revisit these talks.
Ryan, with a 3.42 ERA and 194 strikeouts in 171 innings over 31 appearances (30 starts) in 2025, would be a valuable addition as a No. 2 starter behind Garrett Crochet. The Red Sox might need to part with one of their major-league players on the ESPN trade list, which includes Jarren Duran at No. 7 and Wilyer Abreu at No. 13. Interestingly, the Twins are not mentioned as suitors for either outfielder. The potential trade partners for the Red Sox, according to the ESPN list, include the Tigers, Royals, Giants, Pirates, Phillies, Mets, Reds, Diamondbacks, and Astros.
The Red Sox are expected to make a significant move, and the Winter Meetings offer a unique opportunity to address both their need for a big-name player and the need to trade an outfielder. This could be a pivotal moment in the team's strategy for the upcoming season, with the potential to reshape their roster significantly.
