The New York Yankees are heading into another pivotal offseason, one that will define how close they are to finally getting back to the World Series. They had the roster to make a deep playoff run in 2025, but too many missed chances and unreliable pitching in key moments cut their journey short.
Now, attention shifts to free agency and one of the most pressing questions surrounding the team: what to do with Trent Grisham.
Grisham’s breakout year raises questions, not answers
On paper, Grisham put together the best season of his career. The 28-year-old outfielder hit .235 with a .348 on-base percentage and a .464 slugging rate. His 34 home runs and 74 RBIs marked career highs, a massive leap from his previous best of 17 homers back in 2022.
Those power numbers made him look like a legitimate force in the Yankees’ lineup, but the front office will have to decide how much of that was sustainable and how much was simply a hot stretch in a contract year. Grisham’s approach at the plate still showed inconsistency, and outside of the home runs, his overall production was modest.
His postseason struggles didn’t help his case either. After an electric regular season, he faded when the games mattered most. That’s a red flag for a team trying to build a roster built on reliability under pressure.
Decline in defense changes the equation
For much of his career, Grisham’s defensive play was his calling card. He had built a reputation as one of the most dependable center fielders in baseball, a player who could change the outcome of a game with his glove as easily as his bat. But that wasn’t the case in 2025.
Across 1,133 innings, Grisham posted -11 defensive runs saved and -2 outs above average. Those were career-worst marks and a sharp contrast from his previous seasons as a Gold Glove-caliber defender. Whether it was positioning, reaction time, or just fatigue, the drop-off was noticeable — and it matters.
For a Yankees front office that values defense as much as power, that regression makes a long-term investment in Grisham a far riskier move.
Younger options and bigger targets
The Yankees also have to look ahead. With top prospect Spencer Jones waiting in the wings and nearly ready for a full-time role, the front office may view Grisham as expendable. Jones, a left-handed slugger with elite size and athleticism, could slide into the outfield and bring both upside and cost control.
Meanwhile, the Yankees are expected to be aggressive in free agency. Kyle Tucker of the Chicago Cubs is a name already being linked to them, and he would bring both consistency and star-level production that Grisham hasn’t proven capable of sustaining.
Given the choice between paying Grisham after one breakout season or investing heavily in a proven elite player, the Yankees will almost certainly lean toward the latter.
A short-term spark or long-term solution?
Grisham’s story this year was one of redemption. He bounced back from underwhelming seasons and became an unlikely hero at the top of the lineup. But the Yankees are a franchise built on long-term success, not short-term surprises.
His combination of streaky offense and declining defense makes it difficult to justify a major contract extension, especially for a team with both young talent coming and big-money ambitions in free agency.
The Yankees will thank him for a season that exceeded expectations, but when the front office looks at the bigger picture, it’s hard to see Trent Grisham as part of their future plans.
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