It’s not often that free agency starts with a twist, but the Yankees managed to get one before the market even heated up. Trent Grisham accepting the $22 million qualifying offer wasn’t the outcome most in the organization expected, but it instantly reshaped their winter and forced a quicker look at how they want their outfield to look in 2026.
And if you take Brian Cashman at his word, the Yankees aren’t panicking about it.
Cashman’s confidence in Grisham isn’t just lip service
Ryan Garcia of Empire Sports Media and Fireside Yankees caught up with Cashman at the Covenant House sleepout event, and the Yankees’ GM made one thing clear: they believe Grisham’s 2025 season wasn’t a flash in the pan.
That’s not a small statement. Grisham hit .235/.348/.464 with 34 homers, 74 RBIs, and a 129 wRC+. For a player long defined by elite defense and streaky offense, that’s a full-on breakout. It was also his most complete year at the plate, highlighted by improved plate discipline and a better feel for pitches he used to roll over on.
Cashman’s belief is that the swing changes hold up, and if they do, the Yankees have a legitimate power threat who can live at the top or bottom of the order.
The question, of course, is what happens in center field.
Defense is still the elephant in the room
For all of Grisham’s offensive progress, his defense presented a different story. He finished with -11 defensive runs saved and -2 outs above average, an unexpected downturn for someone who once looked like one of baseball’s most reliable glovemen.
Trimming weight and improving his athleticism should get him closer to the player he once was, but that could impact his power negatively. The Yankees aren’t naive about it. They know they need better play in center. But they clearly think the tools are still there. Being in a contract year and more mass probably contributed to the added power, but regaining some athleticism could do him well.
It’s a bet, but with Grisham under contract for $22 million, it’s a bet they’re now committed to.
Two “vacancies,” and what that says about the Yankees’ real plan
Cashman also made a comment that turned heads: the Yankees had “two vacancies” in the outfield.
That phrasing says a lot—mainly that Jasson Dominguez may not be penciled in as an everyday starter, at least not to open 2026. It could be caution after his injury setbacks. It could be a desire to ease him into a full-time role. It could simply be that the Yankees want more certainty around him.
Either way, it tells you who they really want back.
Cody Bellinger. And not quietly.
The Yankees have been open about valuing his versatility, his makeup, and the steadiness he brought to the lineup last season. Bringing Grisham back doesn’t block anything; it just solidifies the floor. The goal remains a Bellinger return, and Cashman’s wording strongly suggests he views him as part of the 2026 plan.
If New York runs it back with Bellinger, Grisham, and Aaron Judge, they’ll again field one of the most productive outfield groups in baseball.
But they can’t ignore the other holes
The Yankees like this outfield, but familiarity isn’t enough. They need another starting pitcher. They need another high-leverage reliever. They need an infielder who can provide insurance if Anthony Volpe stagnates or forces a defensive shift.
Some of those things require big spending — and the Grisham decision added complexity to a budget already tighter than expected.
Still, the path is there. The Yankees believe in the players they already have. They want their stars back. They know their weak spots and have the means to patch them.
Now the winter becomes a question of how far they’re willing to push to make 2026 feel like something more than a rerun.