ORLANDO, Fla. — As reports continue to emerge about the Pittsburgh Pirates’ interest in free agents typically well beyond their price range, the club has certainly captured the curiosity of those milling the hallways at the Signia by Hilton, the site of this year’s Winter Meetings. All that talk has put the Pirates in a position they rarely occupy at the annual event: relevant players for big names.
The Athletic’s Ken Rosenthal reported Sunday that the Pirates had a four-year offer out to slugger Kyle Schwarber. On Monday, general manager Ben Cherington and manager Don Kelly declined to discuss specific free agent pursuits but underscored the importance of improving the lineup this offseason.
“Just looking to seize an opportunity,” Cherington said. “We believe we have the foundation. We’ve got to add to it. We believe we can win in 2026 if we do the necessary work to do that. Part of that’s going to be roster building. Part of that’s going to be building the culture of the team and executing well. We’re pursuing a whole host of free agent and trade options as part of that strategy. Some stuff gets out, and some stuff doesn’t.
“We’ve just got to stay on it and be in position to land the ones we can land.”
The Pirates have finished under .500 in nine of the past 10 seasons. They have not exceeded 76 wins in the six seasons since Cherington took the reins. Yet the Pirates have now begun to act more aggressively to build around Cy Young Award winner Paul Skenes. Their primary focus is to strengthen a lineup that has been among the worst in the majors in recent years.
Cherington said he would prefer to add power and left-handed bats — Schwarber, Jorge Polanco and Ryan O’Hearn are three lefties linked to the Pirates — but he’s open to a variety of hitting traits.
“In a sort of perverse, good way, our bar is such that we can improve in any number (of ways): more on base, more power, more contact,” Cherington said. “You name it. We need all of it.”
The Pirates recently swapped starter Johan Oviedo for outfield prospect Jhostynxon García in a five-player trade with the Boston Red Sox. Cherington indicated the Pirates could trade further from their starting depth, but it would likely need to be for an immediate lineup upgrade. Cherington also wants to improve the bullpen: leverage arms and arms to face lefty hitters.
There’s a lot left on the to-do list at this point in the offseason, and many in the industry are understandably dubious of the Pirates’ appetite to spend significantly to address their needs. However, with a farm system flush with talent and additional spending capacity this offseason — due to both Cherington’s trade-deadline maneuvering and ownership’s reported willingness to push payroll — Cherington appears to have a few ways to go forward.
“We’re not short on things we could do,” Cherington said. “What we’re still pushing toward is the thing we want to do at the price we think makes sense.”
A diverted flight kept Kelly from landing in Orlando until the early hours of Monday morning, so the Pirates manager, who assumed the job midseason this year, was working on short rest at his first Winter Meetings media availability. But Kelly’s enthusiasm was evident as he discussed the club’s direction this offseason. Kelly, a Pittsburgh native, echoed Skenes’ thoughts on how rewarding it would be to build a winning ballclub at PNC Park.
“I get chills thinking about it, honestly,” Kelly said. “Pittsburgh is a special place. It’s a tough town, it’s a gritty town, and that’s the attitude and the identity that we want to bring as a ballclub to the city.”
That sentiment is part of Cherington’s pitch to free agents this winter: It’s an opportunity to do something special.
“That means it’s not for everybody,” Cherington said. “But it’s a chance to be a part of something different, and be a part of changing the story, which I think for certain players can be compelling.”
If they are to become contenders in 2026, the Pirates will also rely upon internal improvement. No player represents a greater potential upgrade than shortstop prospect Konnor Griffin, who The Athletic’s Keith Law ranked as baseball’s 10th best prospect in his midseason update. The Pirates drafted Griffin No. 9 overall in 2024, and last season he hit .333/.415/.527 with 21 home runs and 65 steals across three levels of the minors.
“The sky’s the limit for him — the talent that you see, the wiring, the way he goes about it,” Kelly said. “He’s really, really impressive.”
Though Griffin has played just 21 games at Double A, ESPN reported last month that the Pirates are “strongly considering” giving Griffin a chance to win the starting shortstop job this spring.
On Monday, Cherington and Kelly pumped the brakes, saying it was too early to say. Cherington said they’ll “get to that” as spring training gets closer. He also said the Pirates “haven’t engaged” Griffin’s camp on contract extension talks at this point. For now, the front office’s focus is elsewhere, like turning all this talk into actual transactions.
“You chase down 100 things, and three, four or five land,” Cherington said. “That’s just the way it works. That’s still the stage we’re at.”