The New York Yankees are ready to move on from two players they once built around. After another postseason disappointment, the Bombers face uncomfortable roster questions, and this time, two players who once seemed central to the Yankees’ future are now expendable.
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Trent Grisham’s power surge in 2025 briefly softened the blow of losing Juan Soto, while Jazz Chisholm Jr.’s outspoken personality and unconventional style made him a polarizing figure in pinstripes.
But with both players now approaching free agency, their time in New York could be nearing its end. And if insider Jorge Castillo’s report is any indication, the Yankees may already be ready to move on from both.
“Jazz Chisholm Jr. and Trent Grisham are as good as gone. So they’ll need to figure out center field and second base. But there are internal options for all those uncertainties,” SleeperMLB quoted Castillo.
Back in 2024, Grisham took no time to burst into the scene for the Yankees. When Juan Soto sat out a game due to minor forearm inflammation, Grisham drew the start. Facing the Dodgers, brutalized by New York fans chanting “We Want Soto!” right at him, Grisham famously slammed a go-ahead, three-run home run off Tyler Glasnow on the very next pitch.
It prompted the Bleacher Creatures to immediately switch to an apologetic, tongue-in-cheek chant of “We Want Grisham!”, instantly turning him into a cult favorite. Even Aaron Judge was left stunned. “Soto’s going to heal up and be fine, but, man, Grish is a heck of a ballplayer,” Judge said back then.
In 2025, Grisham emerged as the perfect alternative to Soto. He experienced a massive statistical surge, altering his swing mechanics to unlock raw, pull-side power tailored perfectly for Yankee Stadium. In the first 40 games of 2025, Grisham had actually offered similar Wins Above Replacement value at a fraction of the cost ($5 million vs. Soto’s $765 million deal).
Riding the high of his 34-homer season, the Yankees made an aggressive bet on Grisham by offering him a $22.025 million qualifying offer for the 2026 season, which he accepted. Unfortunately, the bet failed to pay off.
This year, he hit just .211 with 18 home runs over 121 games. Enough for the Yankees to probably no longer offer an extension.
While Grisham’s decline was gradual, Chisholm’s collapse was immediate and public.
Chisholm entered the 2026 season vocal about his goals to hit 50 home runs and steal 50 bases. Instead, he endured a massive offensive decline, hitting just .231 with 19 home runs, 55 RBIs, and a below-average 97 OPS+. His postseason was even worse, as he turned in a brutal .561 OPS over 25 playoff games with the team.
Moreover, Chisholm’s inappropriate on-field moves have gotten worse. “They have some guys who act like fools. I saw Jazz Chisholm playing with a lollipop. He’s a disgrace to the Yankees. He’s a clown,” Yankees legend Goose Gossage said about Chisholm entering the field with a lollipop sticking out of his mouth.
During the ALDS against the Tampa Bay Rays, Chisholm committed costly defensive errors. When asked about a repeated throwing mistake, he baffled the Yankees by saying he would make the same play again rather than taking accountability. He was subsequently benched in critical games for Anthony Volpe.
The final straw: Chisholm’s $35M annual ask was more than the Yankees were willing to spend on a declining player.
Reportedly, Chisholm was seeking a long-term contract averaging roughly $35 million annually for 8 to 10 seasons. But the Yankees’ internal depth could withstand his absence. Anthony Volpe took reps at second base toward the end of the year, and with other infield options like José Caballero and top prospects rising, New York preferred to allocate those resources toward more pressing needs like relief pitching or a dedicated third baseman.
The Yankees are moving on. Both Chisholm and Grisham will test free agency elsewhere. Results were not on their way last season after running it back. Even a partial overhaul could make a difference in 2027.