The Boston Red Sox have already made one trade to improve their roster, but there’s got to be something bigger than Sonny Gray on the horizon.

And Craig Breslow’s first really big move could come as soon as Sunday, when the 2026 MLB Winter Meetings kick off in Orlando. The full meeting runs Dec. 7-10, so Breslow and the Red Sox will have a few days to shop around and figure out the deals they want to make. That could very well include another trade, if the latest from Kiley McDaniel and Jeff Passan at ESPN.com is any indication.

The piece ranks the major league players that could be traded over the rest of the winter, and as soon as during the Winter Meetings. Topping the list is Tigers ace and reigning two-time Cy Young Award winner Tarik Skubal, and the Red Sox are mentioned as a fit for him, but he feels like a pipe dream for Boston at this stage. At No. 6 is a more realistic option, Twins righty Joe Ryan, who was rumored to be close to going to the Red Sox at the trade deadline. Breslow and Minnesota GM Derek Shelton couldn’t quite land on the right package to send Ryan to Boston, so perhaps they reopen talks in Orlando and work something out.

Ryan would qualify as a true No. 2 starter behind Garrett Crochet for the Red Sox, after posting a 3.42 ERA and striking out 194 in 171 innings over 31 appearances (30 starts) in 2025. And it’s possible that, in order to land him in a swap, the Red Sox would have to part with one of their major-league players that made the ESPN list of trade candidates. The names aren’t all that surprising for any Sox fan who’s followed the trade rumors: Jarren Duran clocked in at No. 7 on the list, while Wilyer Abreu landed at No. 13.

However, the Twins aren’t mentioned as a suitor for either outfielder. Based on the ESPN list, teams to watch for in a potential deal with the Red Sox are the Tigers, Royals, Giants, Pirates, Phillies, Mets, Reds, Diamondbacks, and Astros.

Regardless, the Red Sox continue to be mentioned as a candidate for a big name, while they’re overdue to ship someone out of their own outfield. The Winter Meetings could be their best chance to accomplish both in one trade.

Matt, a North Andover, Massachusetts native, has been with The Sports Hub since 2010. Growing up the son of Boston University All-American and Melrose High School hall-of-fame hockey player Steve Dolloff, sports was always a part of his life. After attending Northeastern University, Matt focused his love of sports on writing, extensively writing about all four major Boston teams. He also is a co-host of the Sports Hub Underground podcast and is a regular on-air contributor on the Sports Hub. Matt writes about all New England sports from Patriots football to Boston Celtics and Boston Bruins.