The 2025 MLB season is fully in the books, the Dodgers repeating as champions and burnishing their case as one of the great dynasties in league history. Though the champagne in the clubhouse has hardly dried, the rest of the league, the Yankees included, has been glancing ahead at the offseason for some time, and we can now turn our attention to the offseason calendar.

Below you’ll find all the important dates for the winter. Stay with us as we chart the course through what will hopefully be another busy offseason for the Yankees.

November 2nd – Free agents file

Eligible players file for free agency a day after the World Series ends. Teams have a five-day window to negotiate with their internal free agents, to tender qualifying offers— set at $22.02 million for this year —to any of thei

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