The 2025 season ended with a thud for the New York Yankees, their playoff hopes erased by the Toronto Blue Jays in the ALDS. For general manager Brian Cashman, it was a wake-up call. The roster that once looked championship-ready now faces an offseason filled with tough decisions and open questions about the team’s identity heading into 2026.
Yankees face key free agent departures
The Yankees are set to lose several key players this winter, including Cody Bellinger, Trent Grisham, Devin Williams, and Luke Weaver. Veteran first baseman Paul Goldschmidt is also likely gone, paving the way for Ben Rice to take over the position full-time next season.
While the team could bring back a few of their departing players, there are no guarantees. Bellinger is expected to test the market after a strong year, and Williams, who rebounded late in the season to rediscover his elite form, might earn himself a qualifying offer or even a multi-year extension. Cashman will have to weigh value against volatility in what could be one of his most important offseasons in years.
Shortstop could become a major competition
Among the Yankees’ biggest questions is what to do at shortstop. The free-agent market features a tempting name in Bo Bichette, one of baseball’s most productive offensive shortstops. The issue is that Bichette’s defense has been among the worst at his position, and that’s a trade-off the Yankees can’t afford after watching their infield defense crumble late in the season.
That likely means an in-house competition between Anthony Volpe and Jose Caballero. Volpe, 24, battled through a partially torn labrum this year, which tanked his production. He hit .212/.272/.391 with 19 home runs and 72 RBIs, posting an 83 wRC+. In the postseason, his struggles only deepened — his 61.5% strikeout rate was among the worst in baseball, and his timing at the plate looked completely off.
Normally, Volpe’s defense can compensate for a cold bat, but this season, that part of his game also regressed. He finished with -7 outs above average, far from what the Yankees expected from their supposed cornerstone infielder.
Caballero’s surge changes the equation
Jose Caballero may not have been the Yankees’ plan at shortstop when he arrived from Tampa Bay, but his performance made it impossible to ignore him. Over 40 games with the Yankees, Caballero hit .266/.372/.456 with three homers, nine RBIs, and 15 stolen bases, good for a 134 wRC+.
Even if those numbers come back down to earth, his defensive value and speed give him a strong case to start. Caballero posted a .976 fielding percentage with four defensive runs saved and five outs above average in only 339 innings at shortstop. He’s one of the league’s best base-running utility players, and his energy often gave the Yankees a spark when the lineup went flat.
If he can replicate even 75% of that production while maintaining steady defense, the Yankees would gladly take it. It’s exactly the type of balanced, gritty play the team needs more of — reliable contact, sharp defense, and smart baserunning.
Looking to the future
Behind Volpe and Caballero looms top infield prospect George Lombard Jr., who is climbing quickly through the farm system. The organization views him as a potential cornerstone for the infield, but his timeline still points toward 2027.
Until then, the Yankees must decide whether to double down on Volpe’s development or give Caballero a legitimate shot at winning the job outright. After a season defined by injuries and inconsistency, New York’s path back to dominance may start with something simple: competition at shortstop.