Bucs' 3-part pitch to free agents includes 'opportunity to do something different'

ORLANDO -- There are plenty of factors that go into courting a free agent. What are the terms of a potential contract? What does the playing opportunity look like? Is this the best fit?

All of that can vary from player to player, and given how busy the Winter Meetings are, the Pirates are having plenty of conversations with free agents to try to improve the 2026 club. The specifics will change, but Pirates general manager Ben Cherington’s pitch has centered on three points.

1. “We aren’t that far away.” Yes, they went 71-91 in 2025, but they boast one of the best young rotations in baseball. They have the NL Cy Young Award winner, Paul Skenes, anchoring that rotation. There is a foundation to potentially build upon.

“We truly believe and think we can share evidence for the fact that we aren’t that far away,” Cherington said at the Winter Meetings in Orlando Monday. “We have a chance. Our pitching gives us a chance. The roster foundation gives us a chance. We need to add to it, no question. We need to improve. We need to do a lot of things well. We can win in 2026. It’s attainable. We’re able to share information that supports that.”

2. “It’s a fantastic place to be as a baseball person,” says Cherington. That’s his experience, and he feels players that do “due diligence" usually feel the same.

3. “It is an opportunity to do something different.” It’s no secret the last three decades have been mostly rough for the Pirates. The exception is that run of three straight playoff berths from 2013-15, with the 2013 NL Wild Card Game being the highlight. The city and its team had a special connection during that run, and with a stated goal of returning to the postseason in ’26, it is a chance to potentially be part of another club that has a deeper connection with Pittsburgh.

“Maybe that means it’s not for everybody,” Cherington said, “but it’s a chance to be part of something that’s actually different, be a part of changing a story, which I think for certain players can be really compelling.”

That selling point might not be for everyone, but it certainly is for the team’s manager and its star player.

Manager Don Kelly is a Pittsburgh kid, raised in the Mt. Lebanon suburb. He remembers watching that 2013 Wild Card Game when he was still playing with the Tigers. He’s suited up at every level of baseball in Pittsburgh -- high school, collegiate, the Majors -- and knows what it would mean to bring the winner.

“I get chills when I talk about it,” Kelly said Monday. “Pittsburgh is a special place. It's a tough town. It's a gritty town. That's the attitude and the identity that we want to bring as a ball club to the city.”

Then there is Skenes. Pittsburgh is an adopted home, but he has become involved in the community and established himself as the face of the franchise and a leader in the clubhouse, so much so that on the night he won the Cy Young Award, his focus was on winning a World Series.

“The focus needs to be winning a World Series in Pittsburgh,” Skenes said on Nov. 12. “We haven't done it since 1979. That's 46 years. It's not the longest drought in Major League Baseball, but that's something we're working to change from within the clubhouse. I know the organization is doing the same thing.

“That's why I'm throwing and lifting and doing all that right now. That's the goal. I have the Cy Young now. What else do I have to accomplish in this game? A World Series championship.”

Free-agent life is a pitch. The Pirates are looking to add and have financial flexibility to do so, and they have taken a big swing by making an offer to Kyle Schwarber these Winter Meetings. Now they’ll see if their pitch, especially bringing a winner back to Pittsburgh, is good enough.

“When we're here at the Winter Meetings and we're up in the suite talking about things, talking about the adjustments, talking about the offense, talking about how to continue to build the pitching foundation, that's what excites me,” Kelly said. “That's what we expect. That's what the fans expect, and that's what we want to bring to Pittsburgh in 2026.

“Certainly it's not about me. It's about the players. It's about the city. It's about the fans. And it's about bringing winning baseball back to Pittsburgh.”