There's an obvious reason Yankees can't open Jazz Chisholm Jr. contract extension talks

Contract extensions are like walking a tightrope. Commit too early, and what seems like a great deal at the time can tie you to a player whom you'd rather let go of. Take a run at it too late, and you lose the value of what an extension would bring and end up paying market rates anyway. The latter is pretty much where the Yankees find themselves with Jazz Chisholm Jr.

The Yankees had their shot to keep Chisholm Jr. in the fold long-term and get a deal, but their inaction has cost them. After a historic 30-30 season, any hope of the Yankees locking the electric second baseman up long-term at a discount is gone.

No matter how much he claims to love playing in New York, the only way Chisholm Jr. signs an extension while coming off a career year is if the Yankees pay what he'd expect to get in free agency, and even then, it would behoove him to test the open market.

The Yankees can't extend Jazz Chisholm Jr. now

Even if Chisholm Jr. were amenable to an extension, the Yankees can't do it now. Doing so would only present them with risk.

First, Chisholm Jr. has been an injury-prone player throughout his career. He missed time this season with a torn oblique, yet the 130 games he played were the second-highest tally of his career. Prior to 2024, he had managed more than 97 games in a season just once, playing 124 in 2021.

Second, there's the chance of regression. As good as he was in 2025, his .813 OPS is 50 points better than any mark he's put up previously, with the exception of 2022, when he was limited to just 60 games.

Much of what fueled Chisholm Jr.'s breakout was an improved walk rate. The 27-year-old's 10.9% rate of free passes in 2025 was substantially higher than the 8.4% mark he's posted for his career.

Therefore, it would behoove the Yankees to make sure that he can continue his success with his newfound discipline, while also hoping that he can put up a relatively healthy 2026 campaign, before committing long-term money to him.

That doesn't mean they should do something foolish like trade him. They're a better team with him than without him. Simply put, the Yankees missed the window where signing Chisholm Jr. to an extension would've been advantageous, and as such, their best course of action now is to have him play it out and prove that he truly is the player they saw in 2025. Then, this time next year, they'll be able to throw him an offer to keep him in the Bronx for the long haul.