Pittsburgh Pirates: 2023-2024 Key Off-Season Key Dates

The World Series will conclude in early November, kicking off several important offseason deadlines for the Pittsburgh Pirates front office.

One of the first key dates is five days after the World Series ends, when free agents can officially sign with new teams. The Pirates are not expected to be major buyers, but GM Ben Cherington could look to add some complementary pieces to the roster.

Later in November comes the roster protection and non-tender deadlines. Pittsburgh will need to add prospects like catcher Endy Rodriguez and infielder Maikol Escotto to the 40-man roster by November 15th to protect them from the Rule 5 draft. Additional prospects beyond just the top names are likely to be protected, as Cherington has shown a tendency to take an aggressive approach there.

The non-tender deadline on November 17th could see the Pirates part ways with arbitration-eligible players deemed too expensive, like catcher Roberto Perez, infielder Kevin Newman or pitcher Mitch Keller. This deadline often coincides with tough roster protection decisions.

In early December, Cherington and his staff will head to the Winter Meetings in Nashville. While blockbuster moves are unlikely, the meetings provide an opportunity to lay groundwork for the future. The Pirates could also look to bolster their talent pipeline in the Rule 5 draft concluding the meetings.

Later in the offseason comes the arbitration process, where eligible players like Miguel Andujar and JT Brubaker will exchange proposed salaries with the team. If no agreement is reached, an arbitration hearing will take place in February.

International prospects will also be a focus, as the Pirates have bonus pool money to spend when the signing period opens on January 15th. The team has acquired bonus money towards the time period so they are close to the top in terms of bonus money to spend. The majority of signings will be amateur teenagers from Latin America.

The offseason priorities for the Pirates remain focused on acquiring and developing young talent to complement the emerging core already on the big league roster.

For GM Ben Cherington, manager Derek Shelton, and the front office, it will be a busy winter shaping the roster and finding the right supporting pieces to put around that youthful foundation.

In a perfect world, the Pittsburgh Pirates will be able to acquire some controllable players under 30 through trades or free agency to fit their timeline. If those options don't materialize as hoped, expect Pittsburgh to pursue short-term veteran deals to fill gaps until the next wave of prospects is ready. The overarching goal is finding players whose timelines align with the team's emerging young core, be it through controllable acquisitions or stopgap veterans on short-term deals.

The offseason priorities for the Pittsburgh Pirates remain focused on acquiring and developing young talent. More specifically, the team will likely look to add organizational depth at starting pitcher, first base, and outfield. For GM Ben Cherington, Manager Derek Shelton, and the front office, it will be a busy winter shaping the roster and building for the future, especially in those positions of need. The Pirates will aim to make the most of each offseason deadline and transaction period to continue strengthening the ballclub as they progress through their rebuilding process.