After a disappointing 2025 campaign, the bar is being raised for the Pirates in '26, setting the stage for a potentially busy offseason.
"Our expectations are that we win and that we make the playoffs. In order to do that, we knew we had to be aggressive in the offseason,” Pirates president Travis Williams said last week.
" … We know we have a really good opportunity with the team we have in place,” Williams continued. “We know that there are some great additions on the offensive side that we can really add to this team and achieve our goals of winning and making the playoffs.”
The Winter Meetings are a prime opportunity to accomplish that. Taking place this coming Monday-Wednesday, Dec. 8-10, in Orlando, the Pirates and the rest of the league will come together to talk to agents and each other about trades and signings. While transactions may not always be completed during the meetings, discussions to get the ball rolling will definitely happen.
Here’s what you need to know ahead of the busiest three days of the offseason calendar:
WHAT DO THEY NEED?
Bats. Emphasis on plural.
Last year’s Pirates team finished last in baseball in runs, home runs and OPS. They are going to need bounce-back seasons from players like Bryan Reynolds and Oneil Cruz, but they also need to add to the lineup. The Pirates have been connected to some big free agents, most notably Kyle Schwarber, and they have some financial flexibility to add.
In terms of specific positions, their most pressing needs are a corner outfielder and an infielder on the left side of the infield. They could use a true No. 1 catcher, another infielder, or even just a big bat to be a DH. They also gave themselves a need for a third baseman when they traded Ke’Bryan Hayes to the Reds in July, while the outfield has needed help for years. It’s hard to see this being a successful offseason without upgrading at least one of those two positions (DH and third base).
WHO ARE THEIR TRADE CANDIDATES?
The most obvious is Mitch Keller. The 2023 All-Star has been at the center of trade rumors for about a year now, and given the Pirates’ starting rotation depth and need for offensive firepower, he could be dealt.
If the Pirates keep Keller, they could deal from their starting pitching depth to acquire a bat. No, it won’t be Paul Skenes, but someone like Johan Oviedo or Thomas Harrington could fetch a nice return. Outside of pitching, Joey Bart is part of an already crowded catchers' room that the Pirates could look to upgrade this winter.
WHICH PROSPECTS SHOULD WE KEEP OUR EYE ON?
The most obvious answer here is Konnor Griffin. MLB Pipeline's No. 1 prospect in the game could very well crack the Majors in 2026, which has to be taken into account as the Pirates build this team this winter. They need more production out of the shortstop spot, but are they better off acquiring middle infield help or trusting their internal options?
WHO IS ELIGIBLE FOR THE RULE 5 DRAFT?
The Pirates didn’t leave much up to chance this year, adding seven prospects to the 40 man roster this winter to protect them from the Rule 5 Draft or free agency. There are still two prospects on MLB Pipeline’s Top 30 list that were left unprotected: catcher Omar Alfonzo (No. 19) and left-hander Anthony Solometo (No. 25). Given that Alfonzo had a bumpy start with Double-A Altoona and Solometo spent most of 2025 rehabbing a left shoulder injury, neither seems like a prime candidate to be poached by another team.
The Pirates’ roster is currently full at 40 players, so unless they clear a spot, they will not be able to take a play in the Major League portion of the Rule 5 Draft.
ONE BURNING QUESTION
We’ve seen rumors of the Pirates being connected to some high-profile free agents. They have some money to spend, a few obvious needs and a sense of urgency to return to the postseason in 2026.
They also tried to add the last couple winters but didn’t accomplish much. Will this offseason be different?
The Pirates’ core has some talented players, but they’re going to need external additions to get over the hump. They’re talking the talk this winter. Now they have to follow through.