Inside The Pinstripes

Yankees Breakout Star Likely Leaving In Free Agency

New York Yankees general manager Brian Cashman will have several tough decisions to make in free agency following the 2025 World Series.
Aug 28, 2025; Chicago, Illinois, USA;  New York Yankees outfielder Trent Grisham (12) hits a two run home run against the Chicago White Sox during the eighth inning at Rate Field. Mandatory Credit: Matt Marton-Imagn Images
Aug 28, 2025; Chicago, Illinois, USA; New York Yankees outfielder Trent Grisham (12) hits a two run home run against the Chicago White Sox during the eighth inning at Rate Field. Mandatory Credit: Matt Marton-Imagn Images | Matt Marton-Imagn Images

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"See ya." The catchphrase of New York Yankees broadcaster Michael Kay could be what the club says to outfielder Trent Grisham this winter.

Grisham, a two-time Gold Glove winner, is enjoying a breakout year, slamming a career-high 27 home runs with more than a month left in the regular season. His .476 slugging percentage and .830 OPS also are personal bests.

As a result. Grisham won't be hurting for suitors when free agency begins after the 2025 World Series. But New York Post Yankees beat writer Greg Joyce explained why the outfielder's return to the Bronx is unlikely.

"Aaron Judge will presumably — barring his elbow injury turning into something that needs surgery — be back in right field next season," Joyce wrote. "Jasson Domínguez has lost his grip on everyday playing time this month, but he is still likely to be back in left field next year.

"Cody Bellinger is playing well enough that he is expected to exercise his opt-out and join Grisham on the free-agent market, though it would not be surprising to see the Yankees try to make a bid to retain him.

"And then there is the wild card of Spencer Jones, whom the Yankees hung on to at the trade deadline last month with the center fielder on an absolute heater at Triple-A, though there are still questions about exactly what they have in him," Joyce added.

Look, there are clearly several variables in the mix here. Yes, it's likely that Bellinger opts out. And yes, it's possible the Yankees prioritize the former MVP over Grisham.

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

But it's also possible another team (possibly the Mets) outbids the Yankees for Bellinger. Or maybe the Yankees trade Dominguez. Or general manager Brian Cashman uses Jones as trade bait.

However it's hard to ignore the looming possibility that the 28-year-old Grisham could be gone after the season.

"Even if the Yankees believe this version of Grisham is sustainable for the next few years, he still seems like a long shot to return given the money he has made himself this season," Joyce added.

The seven-year MLB veteran joined the Yankees in December of 2023 as part of the blockbuster Juan Soto trade with the San Diego Padres.

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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.