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Five Moves the Yankees Must Make Before Judge’s Window Slams Shut

Originally posted on Athlon Sports | By Kristie Ackert | Last updated Oct 8, 2025 10:45 PM ET

Highlights

Trent Grisham, Luke Weaver, Paul Goldschmidt, and Amed Rosario are among the Yankees’ free agents.
Cody Bellinger and Jonathan Loaisiga hold option decisions that will shape the roster.
Prospects Spencer Jones and George Lombard Jr. are close to forcing their way into the picture.

The New York Yankees watched another team celebrate ending their season on the field in the Bronx once again. The Toronto Blue Jays beat them and move on to the American League Division Series, while the Yankees are left to try and figure out what went wrong and what is next.

That disappointment leaves no time for gradual decisions. This winter is about urgency. New York has payroll concerns, critical roster holes, and players ready to move on.

Here are the five things the Yankees must do immediately.

1. Decide on Free Agents

The list is long: Trent Grisham, Luke Weaver, Paul Goldschmidt, and Amed Rosario all hit free agency. Grisham’s 34-homer breakout season will draw offers, Weaver could find closing jobs elsewhere, and Goldschmidt was always a one-year rental. Rosario, acquired at the deadline, is a depth decision. The Yankees need to determine now who gets qualifying offers, who walks, and whether they can keep any of these players at a price that doesn’t block their younger talent.

2. Make the Option Calls

Cody Bellinger has a $25 million player option for 2026. If he opts out, as expected, the Yankees must decide whether to extend him long term or turn to Spencer Jones and Jasson Dominguez in center. Jonathan Loaisiga has a $5 million club option, but health questions could make the decision easy. Tim Hill also has a club option after his two-year deal. These decisions can’t drag.

The Yankees’ roster puzzle depends on clarity in October, not January.

New York Yankees center fielder Cody Bellinger. Credit: Jerome Miron-Imagn Images© Jerome Miron-Imagn Images

3. Clarify the Infield

Jazz Chisholm Jr. is the everyday second baseman -- and the Yankees should decide if he will be in the future as well.

That steadies one spot, but questions remain around third base and shortstop depth. Ryan McMahon is guaranteed $16 million in 2026, but his bat is a question at third. Anthony Volpe’s struggles have many dreaming of when George Lombard Jr. comes in to take the job. Do the Yankees want to wait and see how Volpe rebounds from this season? They could use another bat in the infield.

4. Fix the Bullpen

The rotation is set with Max Fried, Carlos Rodon, Will Warren, Cam Schlittler, and Luis Gil. The bullpen, however, is not. Luke Weaver’s free agency, Loaisiga’s uncertain health, and Hill’s option decision leave Aaron Boone without enough late-inning stability. The Yankees must add at least one proven high-leverage reliever and a multi-inning bridge arm. With the rotation strong, the bullpen becomes the area where a single miss could cost them another postseason.

5. Manage the Payroll

The Yankees’ 2026 commitments already hover between $215–230 million, and if Bellinger opts in, they’re effectively at the $244 million luxury tax threshold. Judge, Stanton, Rodon, Fried, and McMahon are all locked in, while Gerrit Cole’s $36 million salary hits the books even as he recovers from Tommy John. Brian Cashman must trim dead money, structure new deals carefully, and lean on cost-controlled prospects like Spencer Jones and Lombard Jr. Without that discipline, even the Yankees’ spending power won’t save them.

Outlook

The Yankees have not won a World Series in over a quarter of a century. Maybe this roster does not need an overhaul, but it feels like something has to give. The noise to fire Aaron Boone and Brian Cashman will peak in the aftermath of the loss, but that’s not happening.

They have some heavy lifting this winter if they are going to get Aaron Judge a World Series ring.

Deciding quickly on their free agents, clearing up the option calls, and building a bullpen that can hold a lead will go a long way. The payroll is heavy, but there’s enough young talent close to the majors to balance the books. Get these five decisions right, and the Yankees will be back in the fight in 2026. Get them wrong, and well, October heartbreak has already become routine for young Yankees fans.

This article first appeared on Athlon Sports and was syndicated with permission.

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