Inside The Pinstripes

Insider Predicts Yankees' Trent Grisham Decision

New York Yankees outfielder Trent Grisham will be a free agent following the season. His walk year includes a career-high 30 home runs.
Sep 2, 2025; Houston, Texas, USA; New York Yankees center fielder Trent Grisham (12) hits a single during the second inning against the Houston Astros at Daikin Park. Mandatory Credit: Troy Taormina-Imagn Images
Sep 2, 2025; Houston, Texas, USA; New York Yankees center fielder Trent Grisham (12) hits a single during the second inning against the Houston Astros at Daikin Park. Mandatory Credit: Troy Taormina-Imagn Images | Troy Taormina-Imagn Images

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New York Yankees outfielder Trent Grisham is having the best season of his big-league career at the best time and will cash in as a free agent following the season. But will he be staying in the Bronx?

On the latest "Pinstripe Post" podcast, the New York Post's Joel Sherman looked into his crystal ball.

"The Yankees lost Juan Soto and if they don't have a successful season this year, I don't think it's going to be about the loss of Juan Soto. Again, I, because I know what Yankee fans think, they're like, '(Brian) Cashman sucks at everything.'

"Cody Bellinger and Trent Grisham are on Cashman's ledger also," Sherman continued. "Cashman got Grisham included in the trade. And there was a real tough decision, I think for me in the offseason, whether they even tendered him a contract coming off a bad year, and they tendered him and they got Bellinger and those two guys together, and even independently, their numbers stand up.

"You know, it's like their numbers clearly stand up to Kyle Tucker, who would've cost them Luis Gil in a trade. Grisham is the kind of player, he's a Yankee in a lot of ways. He is really talented. There's a smoothness, obviously, to his game. He is not one of those guys who blinks under pressure. We saw that, right? He played great against the Mets as a Padre in their playoff series a couple of years ago.

New York Yankees outfielders Cody Bellinger and Trent Grisham
Jul 19, 2025; Atlanta, Georgia, USA; New York Yankees left fielder Cody Bellinger (35) and center fielder Trent Grisham (12) celebrate after a victory over the Atlanta Braves in the ninth inning at Truist Park. Mandatory Credit: Brett Davis-Imagn Images | Brett Davis-Imagn Images

"If you know you're keeping Bellinger, you don't have to keep Grisham. If you don't know, do you have to keep Grisham? If you really believe in Spencer Jones, do you have to keep Grisham? I think there's a media question. The qualifying offer will probably be about $22 million. I think if the Yankees put the qualifying offer, I think there's a fairly good chance he might take it," Sherman continued.

Grisham hit his career-high 30th home run in Thursday's 8-4 win over the Houston Astros, giving him five home runs and 14 RBIs in his last eight games. His 30 home runs are second-best on the Yankees, trailing only Aaron Judge (43 home runs).

The 28-year-old Grisham, two-time Gold Glove Award winner, is on track for personal bests in on-base percentage (.355), slugging percentage (.485) and OPS (.840).

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Michael Rosenstein
MICHAEL ROSENSTEIN

Professor and award-winning multimedia journalist with three decades of success leading newsrooms, control rooms and classrooms.