The Yankees are selling optimism heading into 2025, but there’s a lot more going on beneath the surface. Aaron Boone called this year’s roster the most talented yet during the Winter Meetings – a statement that feels more like expectation management than genuine confidence.
Brian Cashman isn’t sugarcoating the market reality. He’s calling it “glacial” and promising an opportunistic approach rather than aggressive bidding. Translation: they’re not looking to get into spending wars for big-name players.
That pullback makes sense when you consider Hal Steinbrenner’s recent comments about reducing payroll. The Yankees dropped $319 million last season and got hit with $18.7 million in luxury tax penalties for their trouble. Revenue’s still strong, but with CBA talks on the horizon and potential salary cap discussions, some financial restraint seems smart.
What makes this different is the Yankees are betting internal development can offset external spending. That’s a risky strategy in an AL East where everyone else is opening their wallets.
Shortstop Problems Keep Growing
Anthony Volpe’s regression has become a real headache for the organization. After posting a .604 OPS as a rookie in 2024, he took another step back in 2025. Now MLB.com reports he’ll need surgery on his left shoulder labrum, keeping him out until at least May 2026.
That’s a huge problem.
Boone keeps pointing to Volpe’s age, work ethic, and potential as reasons for optimism. But he’s also acknowledged the obvious – Volpe needs to get better at getting on base. The team-friendly deal they signed him to in 2023 looks less appealing when your everyday shortstop can’t hit.
The free agent market doesn’t offer much help. Bo Bichette is the only realistic everyday option, with Ha-Seong Kim as another possibility. Cashman’s been exploring reinforcements, but nothing materialized by late December.
This traces back to their 2025 ALDS loss, where defensive miscues at shortstop hurt them. Without a move, they’re looking at starting 2026 with unproven prospects like Jorbit Vivas or trade fillers.
The Soto Departure Changes Everything
Juan Soto’s move to the Mets after just one season in pinstripes creates both lineup and payroll complications. His $765 million deal – complete with a February 2025 opt-out – shows how luxury tax considerations have impacted roster construction.
The immediate gap in left field puts enormous pressure on Jasson Domínguez. His .240 average and limited power in 2025 raised questions about whether he’s ready for that responsibility. Analysts are emphasizing he needs to improve both offensively and defensively to justify Boone’s youth-focused approach.
Cody Bellinger represents the biggest name available in free agency, but Cashman’s cautious approach is slowing things down. The bigger issue is structural – losing Soto exposes how financial decisions can create competitive vulnerabilities.
In a loaded AL East, they can’t afford to go into the season without a reliable outfield option.
Rotation Crisis Looming Large
The Yankees’ starting rotation is facing it’s biggest challenge heading into 2026. Gerrit Cole is recovering from Tommy John surgery he underwent in March 2025 and won’t be ready for Opening Day. Carlos Rodón is dealing with elbow issues that could delay his return as well.
Injuries to JT Brubaker and Scott Effross make the pitching depth look thin – reminiscent of the struggles they faced in 2025. Boone’s trying to stay positive, highlighting Rodón’s potential comeback and Luis Gil’s return, but banking on injury recoveries is never ideal.
Cashman defended the rotation’s core but admitted staying healthy will be crucial. With Dylan Cease no longer available and no significant trades completed, they’re relying heavily on Nestor Cortes and Marcus Stroman – an uncertain foundation.
That’s where the Yankees find themselves. Optimism mixed with financial reality, health questions throughout the roster, and competitors who aren’t standing still. Without some outside help, they could be looking at another injury-plagued collapse when the games start mattering.
