The Pirates enter this winter on a quest to augment their offense in a way that could allow them to contend while superstar hurler Paul Skenes is still in town. Skenes is backed by a solid group of pitching options, including veteran Mitch Keller as well as young arms like Braxton Ashcraft and Bubba Chandler in the rotation along with closer Dennis Santana in the bullpen. That deep array of pitching options has virtually no support from the offense, however; while Bryan Reynolds and Oneil Cruz certainly have the capability of being quality regulars in the lineup, only Spencer Horwitz (119 wRC+) and Joey Bart (101 wRC+) were actually above average hitters for Pittsburgh this year.
That leaves the team in need of help in the lineup, and they appear to be unusually willing to dip into free agency to get it. The team had interest in Josh Naylor before he re-upped with the Mariners and has even shown interest in star slugger Kyle Schwarber. A deal at or approaching $100MM would be virtually unheard of for the Pirates in their team history. Reynolds’ $100MM extension is the only nine-figure deal in history, and their next two richest deals (the $70MM range for Mitch Keller and Ke’Bryan Hayes) were both extensions as well. Francisco Liriano’s three-year, $39MM deal from the 2014-15 offseason remains the largest free agent expenditure in team history more than a decade later.
While the Pirates have indicated they have more financial flexibility than previous offseasons and their interest in Schwarber indicates at least some willingness to spend, it would be understandable for fans in Pittsburgh to take the stance that they’ll believe ownership would greenlight that sort of financial outlay when they see it. Adding a top-ten free agent in this year’s class isn’t the only way the Pirates could improve this winter, however. Ken Rosenthal and Evan Drellich of The Athletic reported yesterday that Pittsburgh is also looking at players like Ryan O’Hearn, Jorge Polanco, and Kazuma Okamoto as “perhaps more realistic options” to bolster their lineup via free agency.
All three clock in well below Schwarber’s five-year, $135MM prediction from MLBTR’s Top 50 MLB Free Agents list. Okamoto is predicted for a four-year, $64MM deal, while Polanco is predicted for three years and $42MM and O’Hearn is predicted for two years and $26MM. Of that trio, only O’Hearn wouldn’t represent a new record in free agency for the Pirates, and given the fact that the Pirates entered 2025 with three $70MM+ contracts on their books it’s hardly out of the realm of possibility that they could stomach a deal on one of those levels. Any of those hitters would substantially improve the Pittsburgh lineup as well and could combine with Horwitz, Bart, Reynolds, and Bart to create a much more competent offense than the team had this season.
With that said, Rosenthal and Drellich caution that it could be difficult for the Pirates to convince even mid-level free agents like those to sign on in Pittsburgh if they get similar offers from teams with clearer paths towards contention. MLBTR’s Top 40 Offseason Trade Candidates list holds intriguing names like Brendan Donovan, Jarren Duran, Brandon Lowe, and Alec Bohm, all of whom would substantially improve the Pirates’ offense in their own right and allow them to do so without spending significant dollars or the player having the opportunity to turn them down. Of course, a trade wouldn’t necessarily preclude a free agent signing; in fact, if they were to acquire an affordable piece like Donovan, it might actually make them more likely to sign a free agent if players begin to view their path to contention in 2026 as more credible.
How do MLBTR readers view the hints of spending in Pittsburgh this winter? Will they make a splash in free agency this winter? Or, if not, will they at least sign a credible enough free agent to break the record held by Liriano’s deal from more than a decade ago? Will they go high enough to surpass the $70MM range of the Hayes and Keller deals? Have your say in the poll below:



