Pirates Offseason Primer: Everything You Need to Know
An unbelievably entertaining World Series ended in a dramatic game seven on Saturday night in which the Los Angeles Dodgers defeated the Toronto Blue Jays 5-4 in 11 innings.
The bad news is that there will not be a meaningful baseball game again until March. But the good news is that the offseason is underway.
Relatively speaking, it should be an aggressive offseason for the Pittsburgh Pirates, who are facing mounting pressure to try and put a competitive team together behind ace Paul Skenes and return to the postseason for the first time since 2015.
There’s a lot that needs to be done between now and the start of spring training. Ben Cherington, back for a seventh season, is on the hot seat. Team president Travis Williams is too.
With the 2025 season in the rearview mirror, let us all get ready for the offseason and the buildup for 2026.
Key Dates
- November 6: Free agency opens and players are permitted to negotiate and sign with any of the 30 teams. This is also the deadline for teams to extend eligible players a qualifying offer. (The Pirates won’t have anyone receiving a QO).
- November 10-13: The General mangers meetings take place. This is where a lot of the groundwork is laid out for the rest of the offseason.
- November 12: Award announcements start on Monday, but the Cy Young Winners get announced on Wednesday of that week. Pirates right-hander Paul Skenes is the favorite to win the National League honor.
- November 18: Teams have to protect eligible players from the Rule 5 Draft by adding them to their 40-man roster. The Pirates have some decisions to make. Esmerlyn Valdez will need to be added. Brandan Bidois is among a handful of others worth considering.
- November 21: The non-tender deadline. Teams must decided whether or not they will tender contracts to arbitration-eligible players and pre-arbitration players. Those who don’t get tendered a contract will become free agents.
- December 7-10: The Winter Meetings! The busiest week of the offseason. All 30 teams will meet in Orlando. Expect plenty of free agent signings and trades.
- December 9: Draft Lottery. The Pirates are once again in the running for the first pick.
- December 10: Rule 5 Draft.
- January 8: Arbitration exchange deadline.
Early Housekeeping
The first order of business for the Pirates will be to reinstate players who ended the season on the 60-day injured list. Those players are — RHP Dugan Darnell, RHP Jared Jones, C/1B Endy RodrÃguez, INF/OF Ronny Simon and INF Enmanuel Valdez. Pittsburgh will have to clear spots on their 40-man roster or remove any of the players listed from the roster in one way or another — DFA, trade, etc.
Additionally, manager Don Kelly has to round out his coaching staff by hiring a bench coach, a third base coach and perhaps an assistant pitching coach.
Pirates Free Agents
The Pirates have only two players who are free agents. Designated hitter Andrew McCutchen is back on the market after signing consecutive one-year deals with the Pirates each of the last three offseasons. He’s stated he wants to continue playing, but there’s at least a chance he does so for a team other than Pittsburgh in 2026.
Outfielder Tommy Pham, who the Pirates signed as a free agent last offseason, is the other.
Arbitration-Eligible Players
- C Joey Bart, OF Oneil Cruz, RHP Colin Holderman, RHP Justin Lawrence, RHP Dauri Moreta, RHP Yohan RamÃrez, RHP Johan Oviedo, RHP Dennis Santana, OF Jack Suwinski
Needs
The biggest need for the Pirates is offense. Specifically, the Pirates will be on the hunt for a corner outfielder and someone who can play on the left side of the infield — whether at shortstop or third base — until top prospect Konnor Griffin is ready.
The Pirates could also look for upgrades at catcher, second base and designated hitter depending on Andrew McCutchen’s decision.
While offense will be the focus for the Pirates, they also need reinforcements in the bullpen. A left-handed option should be the priority, but the Pirates should also look to add a higher-leverage option with Dennis Santana in the back-end.
Starting pitching depth should also be addressed. It’s a real possibility the Pirates trade Mitch Keller this offseason for two reasons. Trading Keller could net the Pirates a bat to boost the lineup and would shed nearly $17 million from next year’s payroll.
While the Pirates have plenty of young starting pitching options, adding a veteran as they have done each of the last six offseasons under Cherington would be wise. Especially if they tap into their depth in potential trades.
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