Ben Cherington Reveals Pirates’ Exciting Pitch To Free Agents

After not doing much in free agency over the last decade, the Pittsburgh Pirates are ready to change that. They’ve entered this offseason with a more aggressive mindset and money to spend as they look to improve their team around Paul Skenes.

The Pirates have already proven they’re serious by offering Kyle Schwarber a four-year, $125 million deal. While he re-signed with the Philadelphia Phillies instead, Pittsburgh still sent a message by pursuing the reigning NL home run champ.

With Pirates GM Ben Cherington at the Winter Meetings in Orlando this week, he explained his three-part pitch to free agents to MLB.com’s Alex Stumpf.

Cherington’s message is that “We aren’t that far away,” “It’s a fantastic place to be as a baseball person” and “It is an opportunity to do something different.”

On the night he won the Cy Young, Paul Skenes talked about how much it would mean to win in Pittsburgh. Don Kelly, a Pittsburgh kid, talked yesterday about what it would mean to win in here.

And that is a big part of Ben Cherington’s pitch to free agents.https://t.co/mVdyKt66cF

— Alex Stumpf (@AlexJStumpf) December 9, 2025

Regarding the first part, Pittsburgh has one of the best pitching staffs in baseball, not to mention the reigning NL Cy Young winner in Skenes. The Pirates ranked seventh in MLB in ERA last season, so if they get some bats, they can definitely contend in the NL Central. They also have a bright future with several talented prospects like Konnor Griffin, Bubba Chandler and Jhostynxon Garcia.

Pittsburgh also boasts a great, passionate fanbase and one of MLB’s best ballparks in PNC Park, making it an attractive destination for free agents.

Lastly, the Pirates have a chance to do something special. The franchise hasn’t won a multi-game playoff series or a championship since 1979, so the fans and city are hungry for a title. Pittsburgh’s become a perennial underdog, and winning there would mean more than winning another title for a spoiled fanbase like Boston or Los Angeles.

It’s a good pitch, especially if it’s combined with a competitive offer. Time will tell who, if anyone, is ready to accept Cherington’s challenge and bring their talents to the Pirates.

More Pirates: Paul Skenes Taking On New Leadership Role For Pirates This Offseason