The Pittsburgh Pirates have had four winning seasons in the last 33 years. They haven’t been to the playoffs since 2015, haven’t won a division title since 1992, and haven’t won a postseason series since beating the Baltimore Orioles in the 1979 World Series.
The Pirates have shown interest in two high-profile free agent sluggers this offseason in Josh Naylor and Kyle Schwarber. Naylor re-signed with the Seattle Mariners, and Schwarber followed suit with the Philadelphia Phillies. So, the Pirates have missed on two players who could have greatly improved an offense that was last in MLB in runs scored, home runs, and OPS this past season.
General manager Ben Cherington says the Pirates continue to be active in the free agent market. They agreed to terms with left-handed reliever Gregory Soto on a one-year, $7.75-million contract earlier this week.
So, how does Cherington sell free agents on signing with the Pirates? The job can’t be easy.
Cherington says he takes a three-step approach. The first part is that the Pirates have a promising young pitching staff led by reigning National League Cy Young Award winner Paul Skenes.
“We truly believe and think we can share evidence for the fact that we aren’t that far away (from being a contender),” Cherington said. “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.”
Part two is the city of Pittsburgh. Though it has deservedly earned the reputation of being a football and hockey town, Cherington has learned in the six seasons he has been with the Pirates that interest in baseball is high. While they may lag in attendance, the Pirates have solid television ratings.
“I really do believe this, once you get to Pittsburgh and you play in Pittsburgh or you work in Pittsburgh or whatever, it’s a fantastic place to be as a baseball person. Whether you’re a player or not,” Cherington said. “That’s been my experience. I think that’s the experience of most players once they’re here. I think we can share that honestly. When players do their due diligence, I think they mostly hear that.”
The third part of Cherington’s pitch is that players who could help turn the franchise around would emblazon their names in Pirates’ lore. Case in point is the folk-hero status pitcher A.J. Burnett and catcher Russell Martin achieved in helping the Pirates end a 20-game losing streak in 2013, the longest skid in major North American professional team sports history.
“It is an opportunity to do something different,” Cherington said. “Maybe that means it’s not for everybody. 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.”