The 2025 MLB Winter Meetings are set to take place soon.
The Yankees have had a quiet offseason so far, with many fans anxiously awaiting news about a new general manager. Following a near two-decade title drought and a failure to return to the World Series in 2025, the team is gearing up to make significant roster improvements.
Brian Cashman, known for his low-profile approach during the offseason, could have a productive winter meeting this year. With several gaps to fill and pressing questions to answer, here are five key issues that veteran GMs need to tackle this week.
First, how much is the Yankees’ spending going to be? This question arises every year for Cashman, especially after Hal Steinbrenner’s remarks suggesting that the 2026 payroll should ideally be lower, sparking concerns that the team’s budget might be tight this offseason. While offers to players like Trent Grisham might influence spending, it shouldn’t drastically limit the budget. Securing Cody Bellinger appears to be Cashman’s top priority, and the team’s payroll is expected to surpass $300 million. The current salary stands at around $283.6 million, so signing a major player could put any doubts regarding the 2026 payroll to rest.
Next, how far will the Yankees go to re-sign Cody Bellinger? Besides managing payroll, Cashman must decide how aggressively the organization will pursue Bellinger. With free agency bringing various options and Kyle Tucker added to the roster, the left field position remains a concern. Reports suggest the Yankees are making a strong effort to bring Bellinger back, but whether they’re fully committed or holding back remains uncertain. Unlike the past with Soto, when the Mets outbid them, Cashman may need to decide how much he’s willing to risk, especially given prospects like Jason Dominguez and Spencer Jones may not be ready for the starting lineup.
The departure of Devin Williams from the bullpen is another issue. Williams started as the team’s closer for 2025 but has now signed with another team, leaving a gap for Cashman to fill. Williams had shown promise, and his absence means the Yankees need to look at other late-inning options, possibly targeting free agents like Luke Weaver, Pete Fairbanks, or Robert Suarez.
Spencer Jones, a top batting prospect, is generating buzz, but the current roster lacks an opening for an outfielder. If Bellinger and Tucker depart, Jones’ chances may improve, though whether he can find a spot at DH or elsewhere remains unclear. Cashman has hinted that Jones could make the opening roster in 2026, but that plan may face challenges.
Finally, the question remains if the trade market holds better opportunities than free agency for Cashman. While free agency offers bidding wars, trades might open doors to acquiring impactful players like Sandy Alcantara, Edward Cabrera, or Tariq Skubal. With uncertainty surrounding deals for Bellinger or Tucker, Cashman’s willingness to engage in trade talks could be crucial to strengthening the roster.
Though Cashman tends to keep his cards close, these are vital areas for the Yankees’ offseason strategy.
Fan Take: This offseason’s moves will be critical in shaping the Yankees’ chances of ending their championship drought, with major implications for competitive balance in MLB. Fans should watch closely as these decisions could not only reshape the Yankees’ lineup but also influence broader league dynamics through trades and signings.
