PITTSBURGH — Pittsburgh Pirates general manager Ben Cherington has a huge offseason ahead of him and will change how he and the team operate in free agency.
Pirates Aiming for Change in Free Agency Dealings
The Pirates have rarely spent much money in free agency, which has put them towards the bottom of payroll for most of the tenure of Bob Nutting’s ownership of the franchise since 2007.
Their free agent deals last season didn’t impress anyone, signing outfielder Tommy Pham for $4.025 million, left-handed pitcher Andrew Heaney for $5.25 million and re-signing former player Adam Frazier for $1.525 million, all for one year.
Pittsburgh hasn’t signed a free agent to a multi-year deal in almost a decade, but general manager Ben Cherington is ready for a change towards how they approach a crucial part of the offseason.
“It’s bound to happen,” Cherington said to Alex Stumpf of MLB.com.“We have tried. It’s bound to happen. The odds have increased a little bit each offseason with the combination of the strength of our pitching — and the opportunity to win with that pitching foundation — and a little bit more flexibility. I think a combination of those two things gives it a better chance, but we’ll find out.
Recent History of Pirates Free Agency Dealings
The Pirates haven’t signed a free agent to a multi-year deal since starting pitcher Iván Nova on Dec. 27, 2016 for three years, $26 million. Their last position player they signed was outfielder John Jaso for two years, $8 million on Dec. 23, 2015.
Their recent deals have been just for one-year, including Andrew McCutchen‘s second stint being three straight seasons of one-year, $5 million deals.
Sep 3, 2025; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates designated hitter Andrew McCutchen (22) circles the bases on a solo home run against the Los Angeles Dodgers during the second inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images
Most of their signings were either at first base, which they couldn’t replace full time following the trade of Josh Bell, plus numerous left-handed starting pitchers and relief pitchers as well.
Pittsburgh’s biggest free agent signing is bringing back Francisco Liriano for three years, $39 million on Dec. 9, 2014.
Pirates Reportedly Pushing For Best Talent in Free Agency
Cherington previously talked about the Pirates having more flexibility when it comes to free agency and trades and that they will act more “aggressively” than years past at the general manager meetings in Las Vegas last week.
The Pirates have a great pitching staff, led by National League Cy Young Award winner Paul Skenes, but were one of the worst hitting teams in baseball last season, leading to a 71-91 finish.
Jeff Passan of ESPN released a recent report, which showed that the Pirates are acting with more urgency this free agency period, especially around signing position playres.
Passan reported that the Pirates were willing to sign first baseman Josh Naylor for more than twice the amount of money they offered Liriano, around $78 million, who re-signed with the Seattle Mariners for five years, $92 million.
Oct 19, 2025; Toronto, Ontario, CAN; Seattle Mariners first baseman Josh Naylor (12) singles in the fourth inning against the Toronto Blue Jays during game six of the ALCS round for the 2025 MLB playoffs at Rogers Centre. Mandatory Credit: Nick Turchiaro-Imagn Images | Nick Turchiaro-Imagn Images
He also reported that they are interested in signing NL MVP finalist Kyle Schwarber and Japanese sluggers in Muneta Murakami and Kazuma Okamoto.
Pirates fans won’t pay much attention to this news until they finally make a signing, but these recent reports suggest that the front office is working towards finding those players to get closer to playoff contention.