Aug 29, 2025; Chicago, Illinois, USA; New York Yankees center fielder Trent Grisham (12) watches his grand slam against the Chicago White Sox during the fourth inning at Rate Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images Kamil Krzaczynski-Imagn Images

Retaining Rising Star Isn't Complicated for Yankees

Originally posted on New York Yankees on SI
By Joseph Randazzo | Last updated Aug 30, 2025 5:00 PM ET

Trent Grisham's future will be a point of debate between now and the moment he signs his next deal. Every time he gets a big hit, like the grand slam he had against the Chicago White Sox, the question of what the New York Yankees should do with him will come up. The man known as Swaggy T or the Big Sleep, depending on which circles you hang around in, has undoubtedly opened up his options. The conversation may not be as complex as it will be made out to be, though, because there's a simple solution. The Yankees should extend a qualifying offer to Grisham and wait for his decision.

If the Yankees are intent on keeping Grisham but don't want to give him a multi-year deal, the qualifying offer is a relatively easy commitment. Last year's qualifying offer was $21 million. That's an easy risk to assume, and if Grisham peters out, looking more like the version of himself who was a below-average hitter for most of his career, they can move on without eating much money. Either that or use him for defense. He'll always have his glove as a calling card, whether he hits or not.

Trent Grisham in 2025:

407 AB
.248/.354/.482
.836 OPS
28 HR
133 wRC+

It’s been a career year for Swaggy T. pic.twitter.com/1XwuFotAnI
— Rod (@theyanksonly) August 30, 2025

Another reason to give Grisham the qualifying offer is that he becomes less attractive on the open market. If he rejects the qualifying offer, the team that does sign him will owe the Yankees a compensatory draft pick. Not only is there a risk in paying a player who has not ever hit like this before this year, but they'll also lose a pick in the process. If Grisham is still available later in free agency, they can offer him a deal then as well.

Teams are generally more conservative in signing players who have rejected qualifying offers. The most extreme example was Dallas Keuchel's free agency before the 2019 season. Keuchel rejected the Houston Astros' qualifying offer, and he didn't sign until after the MLB draft. In that instance, the Atlanta Braves finally signed him in June.

The last time this benefitted the Yankees, they ended up drafting the current captain of the team. Nick Swisher left in free agency after rejecting the qualifying offer, opting instead to sign a four-year deal with the Cleveland Indians. The Yankees used that compensatory pick on Aaron Judge.

Unless either the Yankees or Grisham is dead set on this union coming to an end in 2025, there's no reason he can't return—at least for one more year. It's hard to imagine where the Yankees would be without Grisham. Giving this one more shot wouldn't hurt. He may never hit this many home runs again, but there's value in an average to slightly above league-average bat if they bring elite centerfield defense to the table.

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