Inside The Pinstripes

Aaron Judge May Have Helped Yankees Keep Trent Grisham

The New York Yankees' center fielder chose to bet on himself by accepting the Yankees' qualifying offer, and it looks like something Aaron Judge did just a few years ago.
Oct 2, 2025; Bronx, New York, USA; New York Yankee outfielders Cody Bellinger (35), Trent Grisham (12) and Aaron Judge (99) react  following game three of the Wildcard round for the 2025 MLB playoffs against the Boston Red Sox at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images
Oct 2, 2025; Bronx, New York, USA; New York Yankee outfielders Cody Bellinger (35), Trent Grisham (12) and Aaron Judge (99) react following game three of the Wildcard round for the 2025 MLB playoffs against the Boston Red Sox at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

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New York Yankees center fielder Trent Grisham just accepted the team's $22 million qualifying offer, finalizing most of the Yankees' 2026 outfield leading to mixed reactions from fans and commentators. Grisham is still under-proven, and his 2025 season looks like a fluke to some, but there are plenty of reasons to believe Grisham will make the most of this opportunity after taking a commendable chance on himself.

Chief among them might be playing alongside Aaron Judge, who made a similar contract decision ahead of the 2022 season. Grisham, who has now played two seasons with the Yankees, may be shooting for the same fate (or trying, at least, to get even close). Writing for The Athletic, Brendan Kuty pointed to the similarities between the players' decisions, and how it might pan out for Grisham if he can ride this inspiration.

"There’s reason to believe Grisham might be reaching his offensive peak — especially in getting another chance to hit in front of Aaron Judge on a winning team with a home ballpark fit for his approach," Kuty wrote. "And wouldn’t he be even more motivated going into 2026 with a big contract and a shot at another one next offseason (when he can’t receive another qualifying offer)?"

New York Yankees outfielder Aaron Judge (99) celebrates with outfielder Trent Grisha
Oct 7, 2025; Bronx, New York, USA; New York Yankees outfielder Aaron Judge (99) celebrates at home plate after hitting a three-run home run in the fourth inning against the Toronto Blue Jays during game three of the ALDS round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | Vincent Carchietta-Imagn Images

"Don’t forget: Grisham is close with Judge, who was one of the best bet-on-yourself cases in recent memory. In 2022, Judge turned down the Yankees’ extension offer and turned it into an American League home run record and a $360 million payday that winter. Maybe Grisham hopes to follow a similar path."

Having Judge at his side and batting behind him may be motivation enough for Grisham to shoot for the moon again, and if he can build on his 2025 breakout, he'll be looking at a very different market next offseason.

Grisham in New York Again

New York Yankees outfielder Trent Grisham
Aug 28, 2025; Chicago, Illinois, USA; New York Yankees outfielder Trent Grisham (12) celebrates in the dugout after he hit 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

Grisham's second season in the Bronx was his best since 2021 in terms of overall offense, and his best ever for home runs (34) and RBIs (74). In homers and on-base percentage, he was second only to Judge on the Yankees roster, and he may well be coming into his own — at least the Yankees' organization and Grisham seem to both think so. In a recent interview to talk about his annual Sleep Out for homeless youth, Yankees general manager Brian Cashman described him as an "important piece taken care of off last year's team,"

The fan concerns seemed to stem from Grisham's poor postseason performance, which was certainly concerning, and concerns that the QO would prevent the Yankees from going after free agent outfielder Cody Bellinger, who the Yankees want a reunion with this offseason. At least in the case of the budget, Cashman has made it clear that the QO will not affect their pursuit of Bellinger. The same outfield as last season would likely be a good thing, if not very exciting.

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Published
Erin Shapland
ERIN SHAPLAND

Erin covers the New York Yankees for On SI, reporting on all aspects of the championship chase that comes with a storied franchise. A fan of all storylines, who's looking to bring the latest news and updates to one of professional sports' greatest fanbases.