COLUMN: Brian Cashman’s Trent Grisham Mistake Burns the Yankees

New York’s qualifying offer gamble backfires and complicates an already crowded outfield picture

The Yankees thought they were making a smart play. General manager Brian Cashman extended a qualifying offer to Trent Grisham and banked on the outfielder turning it down. The front office expected him to chase a multi-year deal elsewhere, which would have given New York a compensatory draft pick and some needed flexibility. Instead, Grisham accepted the offer. The Yankees now carry a salary they did not plan to pay and face a crowded outfield that limits their options in a pivotal offseason.

Cashman has made risky bets before. This one feels careless. The qualifying offer is supposed to be used on players with clear market value above the one-year salary. Grisham had a career year in 2025, but his jump in production stuck out against the rest of his track record. He put together strong defense and timely power, but his earlier seasons showed wide swings in contact quality and inconsistent on-base numbers. The Yankees treated his breakout like a stable trend instead of what it likely was: an outlier season at the perfect contract moment.

The misread matters. By assuming Grisham would decline, the Yankees built an offseason plan around added resources that never arrived. His salary now sits on the books and squeezes their flexibility before any major moves can begin. For a team trying to balance star power with internal development, that pressure changes the shape of the winter.

The move also affects two players who represent the future and the present. Cody Bellinger remains a top priority, and the Yankees hope to re-sign him after his strong 2025 season. They see him as a stabilizing force in the lineup and a fit for both the short and long term. But Grisham’s acceptance clouds that picture. His salary tightens a payroll that was already under pressure, and it puts ownership in a tougher spot when weighing another major commitment. Every dollar matters in a chase like this, and the Yankees now face a more complicated path to keeping Bellinger in the Bronx.

Then there is Jasson Dominguez. The organization needs him in the lineup. His power, speed and feel for the strike zone give the Yankees a young outfielder with real upside. Every plate appearance matters for his development and confidence. Grisham’s presence blocks those chances. If the Yankees try to rotate the outfield, someone will lose rhythm. Dominguez should not be the player pushed into sporadic at bats to fit the roster puzzle created by a miscalculated qualifying offer.

The long term impact stretches even farther. Kyle Tucker, one of the most complete outfielders in baseball, will reach the free agent market. The Yankees were expected to pursue him if they missed on other top players. Carrying Grisham at his qualifying offer number complicates that pursuit. Big ticket stars require financial preparation. New York now enters that conversation from a weaker position.

The Yankees did not need to be in this spot. They aimed for a draft pick. They ended up with an inflexible roster piece that limits their options in an offseason that calls for bold moves, not forced compromises. Cashman can still maneuver around the mistake, but the margin for error is slimmer and the stakes remain high.

Grisham earned his contract by accepting it. The Yankees must live with why he said yes.

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James O'Donnell