As the holiday season approaches, Major League Baseball executives and agents are set to gather in Orlando, Florida, for the Winter Meetings, which officially commence on March 4, 2024. The New York Yankees enter this crucial period facing significant decisions, particularly regarding the future of outfielder Cody Bellinger and potential enhancements to their pitching rotation.
The Yankees are keen to retain Bellinger, who enjoyed a successful season with the team after being acquired from the Chicago Cubs. General Manager Brian Cashman has openly expressed his desire to keep the 30-year-old, stating that the Yankees would be “better served” if Bellinger remains in the lineup. Following the Yankees’ postseason exit in the American League Division Series, Bellinger himself indicated he is “absolutely” interested in a reunion.
However, Bellinger’s potential departure could leave the Yankees without a crucial impact bat. His free agency poses challenges, as multiple contenders are likely vying for his services, and he is expected to seek a substantial long-term contract. The Yankees could also explore other options, with Kyle Tucker, a promising young outfielder, available but likely at a higher cost.
The question of Bellinger’s return ties into the future of young outfielders Jasson Domínguez and Spencer Jones. If Bellinger stays, the duo may find themselves available for trade. Conversely, if he signs elsewhere, Domínguez and Jones could compete for a roster spot during spring training.
Potential Rotation Improvements
The Yankees face a challenging situation in their starting rotation. While they have several pitchers on the roster, injuries to key players like Gerrit Cole, Clarke Schmidt, and Carlos Rodón raise concerns. With Cole and Schmidt recovering from Tommy John surgery, and other pitchers like Max Fried and Cam Schlittler coming off heavy workloads, the Yankees may need to pursue additional starting pitching options.
One potential target is Japanese free agent Tatsuya Imai, although competition could drive up his price. The free agent market for starting pitchers has already seen significant contracts, including Dylan Cease who signed a seven-year, $210 million deal with the Toronto Blue Jays. The Yankees might find a trade more appealing; names like Joe Ryan from Minnesota and Sandy Alcantara from Miami are expected to be considered.
Addressing Bullpen Needs
The Yankees also need to bolster their bullpen. Currently, they have a reliable closer in David Bednar, but with Devin Williams signing with the Mets and Luke Weaver entering free agency, gaps need to be filled. The team is looking for pitchers with both velocity and command, qualities that were lacking in the previous season.
Free agent options such as Kyle Finnegan, Brad Keller, and Hunter Harvey are intriguing. Alternatively, the Yankees may consider trading for relief help or elevating one of their younger pitchers, such as Will Warren or Luis Gil, to fill a bullpen role if they make additions to their starting rotation.
Financial Considerations
Ultimately, the Yankees’ spending capacity will shape their offseason strategy. Owner Hal Steinbrenner refrained from specifying a budget for the 2026 season but indicated that maintaining payroll under the previous year’s total of $319 million would be “ideal.” Currently, the Yankees’ projected competitive balance tax payroll stands at $283.6 million, just below the second-highest penalty threshold of $284 million.
Balancing the need to improve the roster while adhering to financial constraints presents a significant challenge. The Yankees must address multiple holes in their lineup, including the bench, while striving to construct a championship-caliber team.
As the Winter Meetings unfold, the decisions made by the Yankees will not only impact their 2024 season but also set the tone for their future direction. With key players and critical needs at stake, the coming days will be pivotal for the storied franchise.
