MLB’s hot stove is about to get cranked up this week, as the 2025 winter meetings begin Monday in Orlando, Fla., where executives from all 30 teams will gather. And with executives, managers and player agents in the same room, the proverbial engines of the free agent and trade markets are being revved up. Some of the offseason’s biggest deals often go down at the winter meetings. This year could be no different.
The best available position player on the market, Kyle Tucker, met with the reigning American League champion Blue Jays, perhaps a precursor to his market picking up speed this week. Arguably the next best free agent hitter, National League home run king Kyle Schwarber, is a candidate to be the first free agent domino to fall in Orlando. And then there’s the trade market. Will back-to-back AL Cy Young Award winner Tarik Skubal be dealt by the Tigers? All these questions—and more—will be answered in the coming days, making for an exciting time for baseball fans. That said, here are the biggest questions in MLB heading into the winter meetings.
