The winter meetings are just days away, and the tentpole event of the MLB offseason usually provides plenty of movement via trades and free-agent signings.
Going into next week’s events in Orlando, Florida, some teams are under more pressure than others to make a significant move or risk being left on the outside looking in at the offseason action.
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Here are the four teams under the most pressure at this year’s winter meetings.
Chicago Cubs
No one seems to know what the Cubs want to be, including the Cubs themselves. Around this time last year, they were preparing to put a package together to acquire this year’s biggest free agent, Kyle Tucker. Now, after a successful season with Tucker that included winning the NL’s top wild-card before being bounced by the Brewers in the NLDS, the expectation is that the outfielder’s time in Chicago is over.
If that’s the case, the Cubs are back to where they were last year, with more questions in their lineup than answers. And it’s not just their lineup that needs some reinforcements; their rotation needs help as well.
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But beyond the need to add, the pressure on Chicago comes from the fact that the organization’s desire to spend has come into question in recent years, as the ownership group has pulled back from being near the top of the league in payroll. This fall, Cubs fans finally saw their team get back to the NLDS for the first time since 2018, and they’re tired of hearing about the players the team almost signed.
Next week, GM Jed Hoyer and Co. will have all eyes on them, waiting for a big move at the winter meetings.
Bryce Harper’s Phillies and Aaron Judge’s Yankees are among the teams under the most pressure this winter.
(Jonathan Castro/Yahoo Sports)
New York Yankees
Last winter, after losing Juan Soto to the crosstown rival New York Mets, the Yankees pivoted to Cody Bellinger, who filled the void admirably with a strong 2025 campaign. The former MVP’s impact on New York’s season was significant, as he was not only strong defensively but also provided lineup protection for AL MVP Aaron Judge. This winter, the Yankees could once again lose a pivotal part of their lineup, as Bellinger is one of the best position players available in free agency.
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Beyond the question of bringing back Bellinger, the Yankees need to add a first baseman and reinforcements in the back end of their bullpen. Right-hander Devin Williams signed a three-year, $51 million deal with the Mets earlier this week, and mainstay Luke Weaver is currently a free agent.
The Yankees haven’t made any significant moves yet this offseason. GM Brian Cashman was extremely active at the winter meetings in 2024, and it wouldn’t be shocking to see his team making moves again this year.
Detroit Tigers
The clock is ticking on the Tigers and their time with two-time AL Cy Young Award winner Tarik Skubal. It seems impossible to think Detroit would trade the best pitcher in the world, but reports have indicated that could happen, as they’ve at the very least entertained calls on their ace, who will be a free agent after next season. In that case, the biggest question is how do you get enough value in return for a player of Skubal’s caliber, even with just one year of club control remaining?
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After a long rebuild, the Tigers reached the postseason in back-to-back seasons and seem to have a promising future ahead of them. So after all it took to get here, why not extend Skubal? There has been no better pitcher in baseball over the past two years than the Tigers’ ace, and no matter the return, you will not be able to replace the type of pitcher Skubal is and the impact he can have on a playoff series. The problem, of course, is money, as the two sides are reportedly more than $100 million apart in extension talks.
If the Tigers know they’re not going to find common ground with Skubal, it would be good business to shop him around and see what other teams might offer. Still, that doesn’t feel like the ending either side was hoping for in this situation.
Philadelphia Phillies
On the surface, the Phillies might not seem like a team under a lot of pressure. Over the past five years, they’ve been one of the most aggressive and successful teams in baseball, building a core of talented players on long-term deals and reaching the postseason the past four Octobers. But the Phillies haven’t been able to get to the mountaintop, despite advancing to the World Series in 2022 and the NLCS in ‘23.
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Now Philadelphia has real decisions to make regarding the future of its roster, as three major contributors to the team’s recent success are free agents: NL MVP runner-up Kyle Schwarber, left-hander Ranger Suárez and catcher J.T. Realmuto.
The priority for the Phillies this offseason is undoubtedly Schwarber, who is coming off the best season of his career and has been a leader in the Philadelphia clubhouse since he arrived in 2022. It would be devastating for the franchise to lose a guy like that, one of the most respected players in baseball and a fan favorite.
Outside of Schwarber, what moves does president of baseball operations Dave Dombrowski have up his sleeve? Even if the Phillies re-sign Schwarber, their roster has some other needs in the lineup and bullpen. The front office has the resources to address them, but they’ll need to work quickly. With the roster getting older and the National League only getting better, Philly’s window could be closing.
