ST PETERSBURG, FLORIDA - OCTOBER 05: Jonathan Aranda #8 of the Tampa Bay Rays is out at second base as Jazz Chisholm Jr. #13 of the New York Yankees attempts to turn a double play during the first inning in game two of the American League Division Series at Tropicana Field on October 05, 2026 in St Petersburg, Florida. Chisholm was given an error on the throw on this play. (Photo by Julio Aguilar/Getty Images) | Getty Images

The Athletic | Chris Kirschner ($): The Yankees have ten men that will be free agents after the World Series, including one of the starting infielders and the established closer. They also face a winter

of deep labor uncertainty, potential changes to compensation as underlined by a new CBA, and a possibility of lower revenue for 2027 if there are lost games. All those factors come together, along with what can reasonably be expected out of those ten guys going forwards, to set out the players the Yankees should try and retain, and who gets to test the market on their own.

New York Post | Greg Joyce: Speaking of free agents, David Bednar represents perhaps the most interesting question for the Yankees. Over the past few years the club has avoided long-term, big money contracts for closers, while routinely churning out excellent bullpen units. Still, Bednar seems extremely comfortable in New York, and though his velo was down a tick this season, sure has the numbers to back up investing in him long term.

New York Daily News | Gary Phillips: It seems likely Aaron Boone will return for his last year under contract as manager, but there’s no guarantee in continuity across the entire coaching staff. Matt Blake is also a free agent, and the talented pitching coach will likely have several offers from other MLB teams if the Yankees don’t return his services. Austin Wells’ failed triple wasn’t Luis Rojas’ fault, but the Yankee third base coach has drawn ire in his tenure before and could also be on a hot seat.