Reporters, analysts and fans have big plans for the Boston Red Sox's 2025-26 offseason. Boston's return to the playoffs after three seasons watching from the couch has revealed some clear needs it must address before becoming a postseason regular again, and many of those additions could come at the Winter Meetings.
Starting on December 10, executives from around MLB, as well as potential trade and free agent candidates will convene in Orlando, Florida to start and finish off some negotiations. Red Sox chief baseball officer made his presence known at last year's meetings when he made the blockbuster of the week by trading for Garrett Crochet.