The Yankees’ front office playbook is famously unpredictable sometimes in the script and sometimes off it. A decade of Cashman moves reads like a thriller when he let Robinson Canó leave in 2013 instead of matching Seattle’s massive offer. Even he allowed top bullpen pieces to walk when risks looked too large. So, the annual guessing game officially begins in New York over who will stay and who will go as the 2025 season is about to end.

So, let’s dive into one of this year’s most intriguing stories: outfielder Trent Grisham. He had a fantastic season, hitting a career-high 33 home runs and posting a .239/.347/.473 slash across 135 games. All of this comes with a modest $5 million salary. But Spotrac projected that Grisham’s market value is going to be around $48M a four-year deal, with an AAV of $12 million. That all comes after his 130 wRC+ and nearly 3.0 WAR breakthrough season.

Still, critics consider Grisham a “streaky” star, and in a recent Fansided article, Henry Palattella bluntly advises the team to move on. Palattella writes, “Grisham is a quality player who is in the midst of a solid bounce-back year… But this season has shined a new light on how streaky he can be even when he’s at his best, which should lead to Brian Cashman and Co. letting him walk in free agency.”

Palattella explains that Grisham’s “season numbers are going to look a lot better thanks to a strong August where he slugged 10 home runs.” However, that hot streak was followed by a slump, as he “started September just 6-for-42 (.143) before saving the team’s bacon in Minnesota.” While Grisham boasts a 14.6% barrel rate and a .380 xwOBA — numbers that suggest his power comes from genuine contact improvements rather than pure luck — these very stats highlight both the potential reward and the risk for any team considering a big contract offer.

Palattella also highlighted that he “has struck out 122 times this year,” despite his power, and more alarmingly for a player with two Gold Gloves on his resume, he “has been worth -1 Outs Above Average on defense this year.” And he suggested the Yankees have a much better option. “A qualifying offer? Absolutely. A long-term deal? Stick with Cody Bellinger,” Palattella advised. Bellinger, who roughly hit .272/.331/.489 in 2025 and finished with a higher WAR than Grisham, posted an .820 OPS with 29 homers and offers far more defensive versatility at multiple positions.

But Grisham isn’t the only player whose future in pinstripes is cloudy

Several other players may have worn out their welcome in the Bronx. Reliever Luke Weaver, a hero last year, had a disastrous 2025 campaign, and his ERA ballooned to 3.97, and he unraveled late in the season.  Fellow bullpen arm Mark Leiter Jr. has been defined by blowups and big innings, and it would not be surprising to see the Yankees wash their hands of both as they seek more reliable relief arms for 2026.

Then there’s the curious case of Devin Williams, whom the Yankees acquired in a one-year “prove-it” deal. Unfortunately for both sides, that deal “crashed and burned.” His overall perfromance is so disappointing that even a strong run in October probably won’t be enough to earn him another contract.

Perhaps the biggest name on the list is shortstop Anthony Volpe. Just two years ago, he was a Gold Glove winner with endless hype. But now, with 19 errors, he leads the American League, and with an OPS+ stuck in the 80s for three straight seasons, moving on from him might be the right move for the franchise’s future.

If the Yankees move away from Grisham, who fills his spot? Internally, Jasson Domínguez and Spencer Jones are waiting in the wings, and both are expected to be ready for big-league roles in 2026. The free-agent market also offers Kyle Tucker and options like Kyle Schwarber, who offers immense power but little defensive value.

And contexts like Robinson Canó show that no player is guaranteed a future in the Bronx even after a career year if the risk is too high. So, which side will the Yankees choose? What do you think?