The Yankees find themselves in a familiar yet uncomfortable position as the offseason drags on. General Manager Brian Cashman is staring at a starting pitching market that has thinned out rapidly, leaving him with two distinct, high-stakes paths to bolster the rotation. He can either open the checkbook to the tune of over $150 million for Japanese ace Tatsuya Imai, or he can pivot to the trade market, sacrificing top-tier prospect capital to land a proven arm like Freddy Peralta or Sandy Alcantara.
The decision is complicated by the Yankees’ financial reality. While reports suggest the Yankees are sitting on a $40 million treasure chest, it is not enough to comfortably win a bidding war for Imai without pushing the payroll into uncomfortable territory. With the market depressed and top arms flying off the board, Imai’s price tag is inflating by the day, potentially forcing the Yankees to pay a premium for a pitcher who has yet to throw a pitch in Major League Baseball.
The Trade Route: High Risk, High Reward
If the financial commitment to Imai proves too rich, Cashman will almost certainly look to the trade market, a strategy he has favored in recent years to avoid paying the “free agent tax.” This path, however, requires parting with significant talent. The Yankees would likely have to dangle headline names like Jasson Dominguez or Spencer Jones, alongside young arms like Will Warren or even Luis Gil, to get a deal done.
The prize at the end of that trade negotiation could be Freddy Peralta, a move that analysts believe changes the landscape of the American League.
There is a strong argument for how acquiring Freddy Peralta turns the Yankees’ rotation into a World Series juggernaut, specifically because of his dominance in 2025. Peralta posted a stellar 17-6 record with a 2.70 ERA and 204 strikeouts. His underlying metrics are elite, ranking in the 97th percentile for pitching run value and the 96th percentile for offspeed run value. He is a finished product who provides immediate ace-level production.
Buying Low on Upside?
On the other hand, the Yankees could target Sandy Alcantara, who represents a quintessential “Cashman reclamation” target with elite upside.
Alcantara struggled mightily in 2025, posting a 5.36 ERA and an 11-12 record over 174.2 innings. However, the raw stuff is still tantalizing; his fastball velocity remains in the 91st percentile, averaging 97.4 mph. The Yankees might view his down year as an opportunity to acquire a former Cy Young winner at a discount, banking on their pitching lab to fix the mechanical issues that led to his high hard-hit rate.
The Cost of Business
Regardless of the target, the cost will be painful. Trading Jasson Dominguez might seem unthinkable to some, but his 2025 struggles have made him a potential trade chip rather than an untouchable piece.
The “Martian” slashed just .257/.327/.397 with 10 home runs and poor defensive metrics, ranking in the 2nd percentile for range (Outs Above Average). If the Yankees believe his development has stalled, flipping him for a rotation anchor like Peralta or Alcantara becomes a justifiable gamble.
Cashman has a history of opting for trades over overpaying in weak free-agent markets, but this winter’s decision might define the next half-decade of Yankees baseball. Whether it is $150 million for Imai or a package of top prospects for a veteran ace, the Yankees have to pay up eventually.