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

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. 21)

This year's non-tender deadline falls on Nov. 21, immediately following the MLB Owners Meetings in New York City. This is the date by which teams must decline to offer an arbitration-eligible player a contract for the upcoming season, making that player a free agent. Non-tendered players can then negotiate with any of the 30 teams, including the one that non-tendered them.

The Pirates have nine arbitration eligible players – Dennis Santana, Johan Oviedo, Joey Bart, Justin Lawrence, Yohan Ramirez, Oneil Cruz, Colin Holderman, Dauri Moreta and Jack Suwinski. Of these, Cruz ($3.6 million) and Santana ($3.4 million) are estimated to receive the biggest pay raises, while Ramirez, Holderman and Suwinski seem like the most obvious non-tender candidates.

MLB Winter Meetings (December 8-11)

This year's Winter Meetings take place from Dec. 8-11 in Orlando. The Pirates should show up here with clarity: Are they trading to upgrade, or standing still? How aggressive is the front office?

The Pirates' biggest trade of the 2024 offseason, which netted them Spencer Horwitz, took place during last year's Winter Meetings, so perhaps fans can expect them to do some more wheeling and dealing at this year's event when executives from all 30 MLB teams are in one place.

The 2025 MLB Draft Lottery also takes place during the Winter Meetings, set for Dec. 9 at 4 p.m. ET. The 2025 MLB Rule 5 Draft takes place on Dec. 10 from 2-4 p.m. ET.

Pitchers and catchers report to spring training (February 2026)

Pitchers and catchers will report to the Pirates' spring training complex in Bradenton, Fla., in mid- to late-February. Pittsburgh's Grapefruit League schedule will likely be released sometime this fall.