Chicago Cubs Winter Meetings Preview
Tonight in Orlando, members of Major League Baseball’s front offices and various other decision-makers will gather for the 2025 Winter Meetings. The meetings are taking place at Walt Disney World, so there’s a non-zero chance that we’ll get pictures of Jed Hoyer and the Cubs front office on TRON Lightcycle/Run (my personal favorite ride there, for what it’s worth). It would be even better to catch them all singing along on It’s a Small World.
Perhaps they’d prefer to indulge in the Country Bear Jamboree, or even Pirates of the Caribbean?
Jokes aside, they’ll likely be too busy to visit Mickey and his friends. This week should be busy for the Cubs, who will look to strengthen their roster in hopes of returning to the postseason and dethroning the division-champion Brewers. Hoyer has been very open about the fact that pitching will be the focus. Whether through a trade or free agent signing, the Cubs will hope to leave the Sunshine State with a bolstered starting rotation.
They can spend big money on arms such as Tatsuya Imai and Michael King or make a deal for one of the many pitchers available on the trade block.
Kyle Tucker left a void that will need filling, although having Seiya Suzuki at designated hitter gives Hoyer more leeway when it comes to finding a slugger for the upcoming season. Old friend Kyle Schwarber is a free agent, although he may be out of the team’s budget. Alex Bregman, whom the Cubs tried to sign last winter, is on the market once again. Signing Bregman and trading for someone like Edward Cabrera may be the most productive way to add talent without completely emptying out the farm system.
Spending a lot of money on the bullpen likely isn’t in the blueprint for the winter, but Tommy Hottovy and Tyler Zombro did well last offseason with their pitching projects and will look to do the same thing this year. Departing pitchers Brad Keller, Drew Pomeranz, and Caleb Thielbar still need homes for 2026. There’s a very good chance that Keller will be too expensive, but bringing back one of the southpaws for one more year makes a lot of sense.
Last year in Dallas, the Cubs kept busy during the Winter Meetings by signing Carson Kelly and selecting Gage Workman in the Rule 5 Draft. After laying a foundation for the trade in Dallas, Hoyer acquired Tucker in one of the biggest moves the league saw last winter. The pressure for Hoyer to produce a winner feels more intense after losing to the rival Brewers in the NLDS, although he has the security of a multiyear extension.
The bottom line is that winning 92 games still wasn’t enough to win the division, and the Cubs have a lot of work to do just to get the roster back to at least that same level. Cubs Insider will have coverage from the Winter Meetings all week long, so make sure to stay tuned on social media for the latest updates.
