As the Yankees head into a winter of discontent following their ALCS sweep at the hands of the rival Astros, they face the challenge of trying to put together a World Series contender that can win eight more playoff games in 2023.

But who will be a part of that effort? On the office side, general manager Brian Cashman is nearing the end of his contract. Aaron Boone has two years remaining on his deal, but his future appeared less than secure after some postseason missteps.

Then there’s the roster. Aaron Judge heads to free agency coming off of one of the best offensive seasons in Yankees history, and a mega-dollars negotiation awaits. The team holds an option on Luis Severino; Anthony Rizzo has a player option. Other free agents include: Jameson Taillon, Andrew Benintendi, Matt Carpenter and Aroldis Chapman (yeah, right). The team could look to shed the contracts belonging to Josh Donaldson or Aaron Hicks. Gleyber Torres is another potential trade candidate.

So, to be blunt: Who should stay and who should go? Sound off below.

Comments
anonymous profile image
Powered by RoundtableBuilt on infrastructure designed for real-time media. Learn more at RTB.io.© Roundtable 2026. By using this site you agree to the Terms of Use and Privacy Policy