Pirates General Manager Ben Cherington expressed a newfound financial flexibility for the team this offseason, indicating that the organization is prepared to spend more than in previous years. Recent reports suggest that the Pittsburgh Pirates could approach a $40 million spending limit this winter. This willingness to invest has generated early interest in some prominent free agents, particularly Kyle Schwarber, with previous interest in Josh Naylor before he re-signed with the Seattle Mariners.
While specific details of the Pirates’ talks with Naylor remain unclear, reports indicated that Pittsburgh was ready to offer him more than $78 million, which would have set a franchise record for a free agent signing. The current record is held by Francisco Liriano, who signed a three-year, $39 million deal back in December 2014. Naylor ultimately chose to remain with the Mariners for five years and $92.5 million, highlighting his preference for a team that appears to be on a consistent path to contention, contrasting the Pirates’ struggles with seven consecutive losing seasons.
Schwarber, expected to attract multiple offers from larger-market teams, particularly from the Philadelphia Phillies, is projected by MLB Trade Rumors to secure a five-year contract worth approximately $135 million. Although he is transitioning into a designated hitter role at the age of 33, Schwarber’s potent power and established value as a clubhouse leader make him an appealing target for teams looking to enhance their offensive output.
The mere fact that Schwarber and Naylor are being linked to the Pirates signals a potential shift in the team’s strategy towards a more aggressive approach in reinforcing its roster. Historically, Cherington has tended to distribute limited spending across various players rather than pursuing standout free agents. However, this offseason might see a change as the Pirates could consider adding a key player to their lineup, stepping outside their usual budget constraints. While the most elite free agents, such as Kyle Tucker or Bo Bichette, may still be out of reach, the rumors surrounding Schwarber and Naylor suggest that other impactful players, including Cody Bellinger, Pete Alonso, and Eugenio Suarez, may now be plausible targets.
Pirates fans might understandably adopt a skeptical viewpoint regarding the team’s interest in major league free agents, but the recent arrival of Paul Skenes, who is being hailed as one of baseball’s best pitchers, adds urgency for the organization to enhance its competitive position while Skenes is still under team control. The Pirates faced a significant challenge with a lackluster offense in the previous season and prioritizing the addition of hitting talent is essential for their offseason strategy.
There was speculation that the Pirates might trade from their depth of young pitchers to acquire much-needed hitting help. Although Cherington has dismissed the notion of trading Skenes, other less-experienced arms might still be used to facilitate trades for promising young position players. Furthermore, veteran pitchers such as Johan Oviedo and Mitch Keller have garnered trade interest, providing additional avenues for the Pirates to free up payroll for new acquisitions.
The interest in Naylor does not necessarily imply dissatisfaction with first baseman Spencer Horwitz, who could transition into the designated hitter position if a new first baseman is brought in. Alternatively, the Pirates’ search for a standout bat may reflect a broader strategy of seeking any available top talent rather than focusing on a specific positional need at this stage.
One area the Pirates are unlikely to invest much in during this offseason is shortstop, as top prospect Konnor Griffin is anticipated to make his major league debut, potentially as early as Opening Day in 2026. Griffin, regarded as one of baseball’s top prospects, has impressed with limited pro experience, suggesting that the organization is optimistic about his future impact. Should he thrive at the major league level, especially during his pre-arbitration years, the Pirates stand to benefit from potential draft incentives, adding further excitement to their rebuilding efforts.