The Boston Red Sox are on the brink of something big, and fans are buzzing with anticipation. But here's where it gets controversial: is their recent trade for Sonny Gray just the tip of the iceberg, or the biggest splash they'll make this offseason? With the 2026 MLB Winter Meetings set to ignite in Orlando from December 7-10, all eyes are on new Chief Baseball Officer Craig Breslow to pull off a blockbuster deal. And this is the part most people miss—Breslow might already have his sights set on a game-changing move as early as Sunday.
ESPN insiders Kiley McDaniel and Jeff Passan have dropped a bombshell list of major league players who could be on the move this winter, and the Red Sox are right in the thick of it. At the top of the list? Tigers ace and two-time Cy Young Award winner Tarik Skubal. While landing Skubal feels like a long shot for Boston, the real intrigue lies in the more attainable options. Enter Twins right-hander Joe Ryan, ranked No. 6 on the list, who nearly became a Red Sox player at the trade deadline. Talks between Breslow and Twins GM Derek Shelton fell apart then, but Orlando could be the perfect stage for a second act.
Ryan’s 2025 stats—a 3.42 ERA and 194 strikeouts over 171 innings—make him a solid No. 2 starter behind Garrett Crochet. But here’s the catch: to secure Ryan, the Red Sox might have to part ways with one of their own trade-bait outfielders. Jarren Duran (No. 7) and Wilyer Abreu (No. 13) are both on the ESPN trade candidate list, though the Twins aren’t rumored to be interested. Instead, teams like the Tigers, Royals, Giants, and Astros are lurking as potential trade partners.
Here’s the bold question: Should the Red Sox prioritize upgrading their rotation with a player like Ryan, even if it means trading away a promising outfielder? Or is there another move brewing that could reshape their lineup entirely? The Winter Meetings are their golden opportunity to address both needs in one fell swoop. With three trades already under their belt this offseason, Boston is clearly in deal-making mode. But will they land a star, or settle for a supporting role in this winter’s trade drama?
One thing’s for sure—the Red Sox aren’t done yet. And neither are the debates. What’s your take? Let us know in the comments below!
