With the way the New York Yankees have been playing lately, many fans are already looking ahead to 2026 and beyond.
While that may be an overreaction, the upcoming offseason is an intriguing one for the Yankees. The front office will have a few key opportunities to shape the franchise’s future via contract extensions. On the other hand, the Yankees should also make sure not to retain expiring assets that don’t make sense.
Here’s a look at three current Yankees worthy of contract extensions and two guys New York should avoid bringing back.
Bellinger’s .182 batting average in April had fans worried, but he bounced back in May (.302) and, on the whole, has been as good or better than the Yankees expected him to be when they traded for him in December.
Entering Sunday, the former National League MVP was slashing .267/.322/.485/ with 22 home runs, 69 RBI and 10 stolen bases on the season. It’s been one of the better years of Bellinger’s career; he’s only surpassed an .810 OPS in one season (2023) since his 2019 MVP campaign.
Bellinger’s first six seasons in Major League Baseball — all with the Los Angeles Dodgers — were a rollercoaster of highs (Rookie of the Year and MVP seasons) and lows (.193 combined batting average in 2021 and 2022). Bellinger’s two-year Chicago Cubs stint may have been a “bridge” to his ultimate destiny with the Yankees; that is, if New York decides to invest in him long-term.
Beyond his offensive production and positional versatility (which would benefit any club), Bellinger’s value to this team is franchise-specific — he just feels like a classic Yankees player. Maybe it’s in his genes. Bellinger’s father, Clay, won two World Series rings in pinstripes, of course. There have been moments this season when the younger Bellinger embraced the Yankee way in a manner that looked effortless. His three-homer game on July 11 at Yankee Stadium — against the Cubs, no less — felt like an iconic Yankees moment, curtain call and all.
Bellinger, 30, looks comfortable in a Yankees uniform, and it’s not outlandish to assume, based on his career arc, that he’d be content playing out the rest of his career in the Bronx. On the other hand, he’s not an irreplaceable player, and Yankees general manager Brian Cashman would be forgiven for moving on from Bellinger if other productive bats were brought in to fill the void. Still, if Cashman is interested in continuity and culture-building (as he should be), extending Bellinger is an obvious move.
Chisholm hasn’t done anything to suggest that he’s not the viable second baseman of the future for the Yankees. He has an entirely superior slash line so far in 137 games with the Yankees — .240/.334/ .477 — than he did with the Miami Marlins (.246/.309/.440 in 403 games), which makes Cashman look good.
A 2025 All-Star, Chisholm entered Saturday with an .811 OPS this season to go along with 21 home runs, 54 RBI and 18 stolen bases. With 43 games left on the schedule, Chisholm has a chance to top his single-season home run mark (24) from last year.
No matter how you evaluate players, Chisholm is one of the better infielders in MLB. He’s entering his prime at 27 years old, and he’s got the magnanimous personality that fits well in the Big Apple. An extension makes sense, although with Chisholm still having another year of arbitration coming in 2026, Cashman, per usual, might hold off on finalizing a long-term deal until necessary.
Whether it’s this winter or next, Chisholm should be in line for a new contract that keeps him in pinstripes for many years to come. Let’s just make sure to limit his in-game interviews moving forward.
It didn’t take long at all for Bednar to make himself indispensable in the Yankees’ clubhouse. Within a week of being acquired, Bednar snatched up the team’s closer job, which has been a calamity for most of the season (more on this below).
Like Chisholm, Bednar has another year of arbitration ahead, but based on the urgency and importance of Bednar’s role, Cashman might jump the gun and lock in the right-hander to a new deal this offseason.
A two-time All-Star and the National League saves leader in 2023, Bednar is still relatively young at 30. The sample size is still small in New York for Bednar, but if the Yankees have indeed found their closer, they should look to extend him as soon as possible.
Williams has done loads of damage to his professional reputation in 2025 by consistently being one of the worst relievers in baseball. For whatever reason, Yankees manager Aaron Boone was still placing Williams in high-leverage situations up until about two weeks ago, which doesn’t help anyone in the world other than the batters facing Williams.
New York’s trade for Williams back in December would be viewed as a disaster even if Cashman had given up close to nothing to acquire the closer. The emergence of Caleb Durbin has only added insult to injury in that regard.
To Cashman’s credit, he went out and got Bednar before the deadline, a move which has already begun to heal the trauma of Williams’ ongoing Yankees stint.
An extension for Williams would be the most surprising front office move in the history of Major League Baseball. Unless Cashman wants to etch his name in the record books while getting fired, he won’t be planning anything this winter for the soon-to-be free agent Williams.
The Yankees likely aren’t going to offer extensions to both Bellinger and Grisham, which makes Grisham the odd man out in New York’s outfield. There’s also Spencer Jones’ recent production to consider, which foreshadows a 2026 MLB debut.
Grisham has excelled this year, and he’ll be paid handsomely by someone this winter because of it. Entering Saturday, the former No. 15 overall pick carried a .798 OPS with 21 home runs and 46 RBI.
Some assumed the Yankees would leverage Grisham’s hot season and trade him at the deadline for more pressing roster needs. Instead, the 28-year-old remains in New York for at least a couple more months, and he’ll be a crucial bat for the Yankees down the stretch if they decide to start playing winning baseball again and make the playoffs.
Grisham not receiving an extension has nothing to do with his performance — the Yankees just have too many outfielders and probably can’t pay close to top dollar for someone entering their age-29 season given the presence of so many other veterans.
