This impending New York Yankees' free agent is definitely a complicated case.

Even though the New York Yankees are currently in the heat of a pennant race, it's never too early to start thinking about the offseason.

The Yankees have numerous players preparing to hit the free-agent market this winter, and perhaps none are more complicated than Trent Grisham.

Grisham has been a revelation for New York this year. The previously light-hitting outfielder is slashing .237/.346/.461 with 30 home runs and 64 RBI this season. This from a player who registered OPSes of under .700 the preceding three campaigns and was actually a non-tender candidate following his Bronx debut last season.

On the flip side, the 28-year-old's defense has slipped tremendously in 2025, as he owns a minus-9 DRS. The two-time Gold Glover has had a pretty steep defensive decline over the last couple of years, which is something teams will definitely keep in mind during the hot stove. And don't think for a second the Yankees won't take that into serious consideration.

Here's the real rub: who is to say that Grisham's offensive breakout is for real? He hit .190 last year. Actually, he batted under .200 three years in a row between 2022 and 2024. Sure, batting average is obsolete as an elite stat, but when you're hitting under .200 on a consistent basis, there is a problem.

Another odd thing about Grisham's sudden outburst is that he only has nine doubles this season. Thirty of his 40 extra-base hits have come via the long ball, and considering that Grisham never even hit 20 homers prior to 2025, alarm bells should be sounding.

A former first-round pick of the Milwaukee Brewers, Grisham stands to land a very lucrative contract this coming offseason. It would not be shocking if rival squads ponied up four or five-year offers worth in excess of $100 million for the Burleson, Tx. native.

But will the Yankees be one of them? Probably not. New York will surely be more concerned with retaining fellow outfielder Cody Bellinger, who is almost guaranteed to opt out of his deal. Plus, New York has Jasson Domiguez already on the roster, and you have to figure that top prospect Spencer Jones will be up at some point in 2026, as well.

Taking all of those things into account, it seems rather likely that the Yankees will play it safe and allow Grisham to walk via free agency rather than paying through the nose to keep him.

Unless New York trades one of Dominguez or Jones (which cannot be ruled out) or fails to re-sign Bellinger, chances are that Grisham will be playing in a different uniform come next spring.