The New York Yankees entered the 2025 season with an outfield that seemed built for October. When healthy, Aaron Judge, Cody Bellinger, Trent Grisham, Jasson Dominguez, and Giancarlo Stanton offered both power and balance. The bench wasn’t short on support either, with deadline additions Austin Slater, Jose Caballero, and Amed Rosario filling in wherever needed.

But as 2026 looms, the landscape is shifting. Bellinger, Grisham, Slater, and Rosario are all set to test free agency, and the Yankees face some difficult choices. Bellinger feels like the most realistic returnee. Grisham, however, presents a tougher call — one that could define how New York approaches its roster construction this winter.

Trent Grisham’s transformation

Few expected Grisham to explode offensively the way he did i

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