Pittsburgh Pirates general manager Ben Cherington listens to a question from the media after signing third baseman Ke’Bryan Hayes to an eight-year contract extension through the 2029 season with a club option for 2030, before the home season opening baseball game against the Chicago Cubs in Pittsburgh, April 12, 2022. (AP Photo/Gene J. Puskar)
The 2026 MLB season is over and the Brewers are World Series champions. Milwaukee bested Tampa Bay in five games to win its first World Series in franchise history.
The Pirates, who saw their National League Central rivals hoist the trophy, had their first winning season since 2018. An 82-80 finish was an improvement, but not one that was good enough to break the league’s second-longest playoff drought.
With the season now over, the offseason begins. Teams are once again allowed to make trades and free agency will officially open early next week.
This offseason will be a unique one as MLB’s collective bargaining agreement expires in just over a month. The consensus is that a lockout looms. There’s no telling how long it will drag out or when the 2027 season will start. But for now, it’s business as usual.
Here’s everything you need to know about the Pirates’ offseason.
Key Dates
November 1: Gold Glove winners are announced. The Pirates have two finalists — Brandon Lowe (second base) and Jared Triolo (utility).
November 2: Free agency begins at 5 p.m. ET. MLB free agents are permitted to negotiate with any of the 30 teams in the league.
November 9-12: Awards week. MVPs, Cy Youngs, Rookies of the Year and Managers of the Year will be announced.
November 10-12: GM Meetings in Las Vegas. It’s typically not as active as the Winter Meetings. But uncertainty looming this winter could lead to early action. Either way, a lot of the groundwork for future deals is laid here.
November 17: Qualifying offer decision deadline. The Pirates will have an answer from Lowe, assuming he indeed gets a QO as expected. Silver Sluggers are also announced on this day. Lowe looks to be in position to win the first of his career. Additionally, teams need to protect prospects eligible for the Rule 5 Draft by adding them to the 40-man roster. Busy day.
November 20: 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 1: The current CBA expires at 11:59 p.m. ET. If no deal is agreed to before this date, MLB will enter a lockout. *Note: All the subsequent dates listed are contingent on a new CBA being implemented. The expectation is that a lockout will take place.
December 7-10: The Winter Meetings in Orlando. The busiest week of the winter but unlikely to take place this offseason. The draft lottery is set for Dec. 8. The Rule 5 Draft is the following day.
January 8: Arbitration exchange deadline. Players and teams must exchange salary figures by this date.
First Order of Business
One of the first orders of business for the Pirates will be to issue a $23.15 million qualifying offer to second baseman Brandon Lowe. Lowe can either accept the one-year offer or decline it (which he will) and opt for free agency. Should he leave the Pirates, Pittsburgh will receive a compensation draft pick.
Pirates Free Agents
The Pirates only have two players scheduled to hit free agency this offseason. The first is a big one in Lowe, who will be a free agent for the first time after a stellar first — and perhaps only — season in the black and gold. Lowe is considered one of the top free agents available this offseason and is expected to land a three or four-year deal.
The other soon-to-be free agent is left-handed reliever Gregory Soto. Like Lowe, the 2027 season was Soto’s first in Pittsburgh. Overall, it was a solid season for the 31-year-old, who signed with the Pirates as a free agent last offseason.
*Right-handed reliever Kirby Yates would’ve been a third Pirates free agent but retired after the season.
Arbitration-Eligible Players
CF Oneil Cruz, C Henry Davis, INF Nick Gonzales, 1B Spencer Horwitz, RHP Jared Jones, RHP Carmen Mlodzinski, RHP Yohan Ramírez, C/1B Endy Rodríguez, RHP Paul Skenes, INF Jared Triolo
Biggest Needs
The biggest need for the Pirates this offseason is attempting to re-sign second baseman Brandon Lowe. In order to bring him back, they’ll have to shatter their franchise free agent contract record.
If they are unable to bring Lowe back to Pittsburgh in 2027, the Pirates will need to pivot to add offense elsewhere. Turning to another second baseman not named Lowe is a possibility. Adding a third baseman and moving Nick Gonzales back to his natural position at second base is another.
But the Pirates need to add a bat somewhere. It will be nearly impossible to make up for all of Lowe’s production should he land elsewhere, but an external upgrade will be needed.
The second biggest need for the Pirates this winter is in the bullpen. They’ll need to add at least one left-handed option to pair with Mason Montgomery, who presumably will be the team’s closer in 2027. They would be wise to add another high-leverage option to go along with Montgomery and Like Weaver.
Other areas the Pirates could look to address are adding a right-handed bat capable of hitting left-handed pitching. Pittsburgh had its struggled against lefty starters in 2026. Rotation depth — and potentially adding a left-handed starter — should also be on the agenda.
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