The Winter Meetings are just around the corner, marking the most significant event of the MLB offseason that often sees a flurry of trades and free-agent signings. Some teams face more pressure than others as they head to next week’s event in Orlando, Florida, with the risk of missing out on major offseason moves if they don’t act decisively.
Here are the four teams under the greatest pressure at this year’s Winter Meetings:
Chicago Cubs
The Cubs seem uncertain about their direction, even internally. Last year around this time, they were preparing a trade package for Kyle Tucker, their top offseason target. After a strong season with Tucker that included winning the National League’s highest Wild Card and falling to the Brewers in the NLDS, it’s expected Tucker’s tenure in Chicago might be ending. If so, the Cubs will face the same challenges as last year, with questions surrounding their lineup and a rotation in need of improvement. Adding to the pressure is the team’s reduced spending willingness, as ownership has pulled back from maintaining one of the league’s highest payrolls. Cubs fans, eager for more postseason success beyond their recent NLDS appearance—the first since 2018—are hoping GM Jed Hoyer makes a big splash.
New York Yankees
After losing Juan Soto to the Mets last winter, the Yankees pivoted to signing Cody Bellinger, who played a key role in their 2025 campaign, supporting AL MVP Aaron Judge with stellar defense and offensive contributions. However, Bellinger is a top free-agent target again this winter, and the Yankees risk losing another crucial player. Beyond Bellinger’s uncertain future, the team needs reinforcements at first base and bullpen depth, especially after the Mets signed closer Devin Williams and Luke Weaver is still a free agent. GM Brian Cashman has been proactive during past Winter Meetings, so a significant move from the Yankees is expected.
Detroit Tigers
The Tigers face a ticking clock with star pitcher Tarik Skubal, a two-time AL Cy Young Award winner. While trading Skubal seems unlikely, the team is reportedly open to offers given his free agency status after next season. The challenge lies in securing adequate returns for a player of his caliber, despite having only one year left under team control. Following a long rebuild, the Tigers made consecutive postseason appearances and seem poised for a bright future. Skubal has been the best pitcher in baseball over the last two years, and his potential departure would leave a significant void. The sticking point remains money, with extension talks stalled over a $100 million gap. If negotiations fail, the Tigers must consider trading him, although neither party likely desires this outcome.
Philadelphia Phillies
At first glance, the Phillies may not appear to be under significant pressure, given their offensive prowess and postseason consistency over the last five years, including a 2022 World Series appearance and 2023 NLCS run. However, real decisions must be made as three key players—NL MVP runner-up Kyle Schwarber, lefty Ranger Suarez, and catcher JT Realmuto—are upcoming free agents. Schwarber, a clubhouse leader and fan favorite who just had his best season, ranks as a high priority for Philadelphia to re-sign. Even with Schwarber back, the Phillies must address other needs in their lineup and bullpen swiftly. With an aging roster and a more competitive National League landscape, their championship window may be closing.
Fan Take:
These Winter Meetings are critical for shaping the course of several high-profile MLB teams heading into the next season. How these key franchises navigate their offseason pressures will not only impact their competitiveness but could also influence league dynamics and fan excitement for years to come.
