The Pirates’ offseason is already loaded with dates that could shape the next stage of the franchise’s push forward.
Pittsburgh comes into the winter fresh off its first winning season since 2018, an 82-80 finish in 2026 that still left the club outside the playoffs for the 11th straight year. There’s also the sting of watching division rival Milwaukee, another small-market club, win the World Series for the first time in Brewers history.
Now the calendar starts moving fast.
Brandon Lowe and Gregory Soto became free agents at 9:00 a.m. on Oct. 29, and the Pirates have five days of exclusive negotiating rights with both players. After that window closes, Lowe and Soto can talk with other teams. Even so, a return for either player looks unlikely, with both expected to test the market.
The Pirates also regain the ability to deal with any team, something they have not been able to do since the Aug. 3 trade deadline. At the same time, the front office can begin looking around at outside free agents of its own and start working toward signings.
One of Pittsburgh’s first major decisions is looming on Lowe. The Pirates will most likely extend him a qualifying offer, which has to be made by Nov.
- That one-year deal is worth $23.15 million for 2027.
If Lowe gets the offer, he has until 4 p.m. (EST) on Nov. 17 to accept or reject it.
If he turns it down and signs elsewhere, Pittsburgh would receive a compensatory pick in the 2027 MLB Draft, and teams can also gain more international signing bonus money when that happens.
There’s another roster crunch coming soon, too. The Pirates must add any players they want to shield from the Rule 5 Draft to the 40-man roster by Nov.
- Anyone left off is exposed to the other 29 MLB teams.
Clubs that select a player in the Rule 5 Draft have to keep him on the 26-man roster and cannot simply stash him in the minors.
The eligible group includes players who were 18 or younger on June 5 when they signed and are now in the fifth Rule 5 draft after that, or players who were 19 or older on June 5 when they signed and are in the fourth Rule 5 draft after that. In practical terms, that means players from the 2022 International Signing Period and high school draftees from 2022, or college draftees from 2023.
Pittsburgh has several names to weigh, including right-handed pitcher Derek Diamond, outfielders Mitch Jebb and Lonnie White Jr., catcher Axiel Plaz, third baseman Jhonny Severino and shortstop Yordanny De Los Santos. The Pirates currently have 38 players on the 40-man roster, so they can add two players without creating a problem. Any additions beyond that would require designating someone for assignment.
Nov. 20 brings another key deadline: tendering contracts to all arbitration-eligible and pre-arbitration-eligible players. Pittsburgh has 10 arbitration-eligible players and 22 pre-arbitration-eligible players.
If the Pirates choose not to tender a contract, that player becomes a free agent. They do not have to finalize a deal by then, but they do have to offer one if they want to keep the player for 2027.
There’s also award season to track. Lowe and utility man Jared Triolo are up for National League Gold Glove honors in 2026.
Lowe is competing with Milwaukee’s Brice Turang and St. Louis rookie JJ Wetherholt, while Triolo is matched against Atlanta’s Mauricio Dubón and Arizona’s Ildemaro Vargas.
The league will roll out major awards this week, though the Pirates will not have finalists for Rookie of the Year, Manager of the Year, Cy Young or MVP when those are announced on Nov. 2.
Pittsburgh does, however, have five players in the mix for All-MLB teams: right-handed starters Paul Skenes and Braxton Ashcraft, left-handed reliever and closer Mason Montgomery, third baseman Nick Gonzales and Lowe. The All-MLB teams, Reliever of the Year and Comeback Player of the Year will be announced on Nov.
- Silver Slugger finalists are also set for Nov. 2, giving the Pirates another possible award winner to watch.
Beyond the roster decisions and award announcements, November also brings two big league gatherings. The general manager meetings run in Las Vegas from Nov. 10-12, a time when front offices begin working the market, even if deals don’t always follow immediately. The owner meetings in New York City take place Nov. 17-19 and are usually more about league business, but they also give ownership a final chance to discuss how to approach a possible lockout.
That threat is very real. The current collective bargaining agreement between the owners and the MLBPA expires at midnight on Dec. 2, or rather, on Dec.
- If there is no new agreement in place, the owners will lock out the players and all transactions and communication stop - no trades, no free-agent signings, no 40-man roster moves.
Both sides could avoid that by striking a new deal, but they’ve been at odds for more than a year and are expected to push the fight deep into the offseason. Skenes sits on the MLBPA eight-player executive subcommittee, and catcher Henry Davis is the Pirates’ MLBPA representative.
If there is no new CBA, several standard winter events would be wiped out. The Winter Meetings would not happen in the usual way, which would stall the signings and trades that normally start there.
There would also be no Rule 5 Draft or Draft Lottery, which would leave the Pirates ineligible for a top-six pick after getting one in each of the past two seasons. Arbitration hearings and moves would be affected as well, and the opening of the International Signing Period could be impacted, too.
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