Yankees Breakout Star Perfect Match for Phillies?

New York Yankees center fielder Trent Grisham had a breakout first season in pinstripes, and as he enters free agency, he'll be a desirable outfielder with an impressive track record. Though he sometimes paled in comparison to the titans around him, Grisham proved his worth at the plate and as a defender, and he's likely to be worth approximately $48 million for a four-year contract as he navigates free agency.

Yankees Outfield Gaps

Fellow outfielder Cody Bellinger has been the subject of much more debate in the offseason so far, with commentators weighing in on whether the Yankees should sign Bellinger or Chicago Cubs right fielder Kyle Tucker for the outfield. Grisham may not be as likely to return given his underwhelming performance in the postseason, and in his piece anticipating MLB stars who could break out with new teams in 2026, Zachary D. Rymer of Bleacher Report named Grisham as an ideal fit for the Philadelphia Phillies if he does end up moving on.

New York Yankees outfielders Cody Bellinger (35), Trent Grisham (12) and Aaron Judge (99) — 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

"The Phillies have to switch things up with their roster, and they would do well to start with an outfield that produced only 2.1 rWAR this year," Rymer wrote. "With Harrison Bader looking at free agency and Nick Castellanos likely on the outs, they certainly have a window to do so."

"Grisham would fit nicely in center field in Philadelphia, and Citizens Bank Park needs no introduction as a hitter's haven. For lefties in particular, it's the best home run park in the league."

Nicknamed "the Big Sleep" because of his calm demeanor paired with an ability to hit homers, Grisham slashed .235/ .348/ .464 in the regular season with 34 home runs and 74 RBIs. Grisham rounded out an outfield that consisted of Aaron Judge (and at times, Giancarlo Stanton) and Cody Bellinger, as well as Jasson Dominguez and deadline acquisition Austin Slater. With Bellinger and Grisham posing questions for the Yankees at the moment, the question of how to build an outfield and a batting lineup around Aaron Judge will be challenging.

Yankees Facing Outfield Dilemma

Sep 17, 2025; Minneapolis, Minnesota, USA; New York Yankees outfielder Trent Grisham (12) flies out against the Minnesota Twins during the sixth inning at Target Field. Mandatory Credit: Nick Wosika-Imagn Image | Nick Wosika-Imagn Images

The Yankees have some under-proven young options in Dominguez and up-and-comer Spencer Jones, who could be called up from Triple-A this season, but Grisham and Bellinger would be leaving a serious experience and performance gap, and the Yankees would need to make up for it somehow. Their offseason priorities should be strong starting pitchers and outfielders, given the gaps. If that means a reunion with Grisham, so be it. If not, he may be a good match in Philadelphia.

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