MLB offseason pressure: Yankees, Cubs, Tigers among the teams feeling the heat at winter meetings

The MLB winter meetings are fast approaching, and this major offseason event often triggers a flurry of trades and free-agent signings. As teams gather next week in Orlando, Florida, some franchises are under more pressure than others to make significant moves or risk being left behind.

Chicago Cubs

The Cubs are facing uncertainty about their identity as a team. Just last year, they were reportedly aiming to acquire Kyle Tucker, who emerged as a top free agent this season. Following a strong season with Tucker, which included capturing the NLs top wild-card spot before falling to the Brewers in the NLDS, it appears his time in Chicago may be ending.

If Tucker departs, the Cubs will return to last years positionfacing more questions than answers in their lineup. Their pitching rotation also requires reinforcement. Adding to the pressure, the organizations willingness to spend has been questioned in recent seasons as payroll has not remained among the leagues highest. After finally returning to the NLDS in 2025, fans are eager to see decisive moves from GM Jed Hoyer and his team at the winter meetings.

New York Yankees

Last winter, after losing Juan Soto to the Mets, the Yankees signed Cody Bellinger, who performed strongly in 2025, providing both defensive skill and lineup support for AL MVP Aaron Judge. This offseason, Bellinger is once again a key factor, as he is among the top free-agent position players available.

Beyond Bellinger, New York needs to address the first base position and strengthen the back end of its bullpen, especially after losing reliever Devin Williams to the Mets and with Luke Weaver entering free agency. While the Yankees havent made major moves yet, GM Brian Cashman has a history of aggressive activity at winter meetings, suggesting potential action this year.

Detroit Tigers

The Tigers face a critical decision regarding two-time AL Cy Young winner Tarik Skubal. While trading their star pitcher seems unlikely, there have been discussions and interest from other teams. Skubal will be a free agent after next season, raising questions about how to obtain sufficient value if Detroit opts to move him.

After a long rebuild, the Tigers reached the postseason in consecutive years, hinting at a bright future. Extending Skubal would maintain that momentum, but negotiations reportedly remain over $100 million apart. If an extension proves impossible, exploring trade options may be the pragmatic choice, though it is far from an ideal scenario.

Philadelphia Phillies

On paper, the Phillies might not appear under pressure, thanks to a successful recent track record that includes postseason appearances over the past four years. However, three key contributorsKyle Schwarber, left-hander Ranger Surez, and catcher J.T. Realmutoare free agents, forcing the team to make critical roster decisions.

Schwarber, in particular, has been a clubhouse leader and delivered the best season of his career in 2025, making his retention a top priority. Even if he returns, the Phillies will need to address additional needs in both the lineup and bullpen quickly, as their window of opportunity could be closing amid an increasingly competitive National League.

Author: Noah Whitman