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.