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Rundown of important offseason dates for Pirates fans to know and hold organization accountable

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The upcoming 2025-26 offseason represents an important opportunity window for the Pittsburgh Pirates to demonstrate a commitment to contention. Over the next several weeks, the front office will have to show that they’ve filled major holes or risk entering the season under-prepared.

For a team like Pittsburgh, which relies on smart drafting, development and affordable assets, having efficient offseason execution is especially critical. If the front office fails to show meaningful action by the mid-December and early-January marks, it may foreshadow a slower rebuild or missed window.

Important dates for Pirates fans to know in the 2025-26 MLB offseason

Non-tender deadline (Nov.