The Pittsburgh Pirates are demonstrating an unexpected willingness to invest in their team this offseason. After showing interest in designated hitter/outfielder Kyle Schwarber and first baseman Josh Naylor, who both signed contracts with other teams, the Pirates recently secured first baseman Ryan O’Hearn with a two-year, $29 million deal. This marks the first multiyear contract the franchise has offered since Ivan Nova was signed in 2016 for three years and $36 million.
The Pirates are not stopping with O’Hearn. Reports indicate they are also pursuing pitcher Framber Valdez to further bolster their roster. While these moves reflect a positive trend for the franchise, they bring to light another important consideration: the future of star pitcher Paul Skenes.
At just 23 years old, Skenes is poised to enter arbitration after the 2026 season, which is likely to result in a significant salary increase. Since making his debut in 2024, Skenes has arguably been the best starter in baseball. He earned the 2024 NL Rookie of the Year title and was named an All-Star twice. In 2025, he won the NL Cy Young Award and finished sixth in the National League MVP voting. Over his career, Skenes has maintained an impressive 1.96 ERA and 0.948 WHIP across 320.2 innings, striking out 386 batters while issuing just 74 walks.
Given Skenes’ dominance on the mound, securing his future with the organization should be a priority for the Pirates. According to Dan Zangrilli of 93.7 FM The Fan, discussions regarding a contract extension began in August. However, aside from this report, there have been few updates about ongoing negotiations between Skenes and the Pirates.
Securing a long-term deal with Skenes would signal the Pirates’ commitment to building a competitive team. His presence on the roster makes the Pirates a formidable opponent each time he pitches. Additionally, locking him in could attract other top free agents, similar to how the Toronto Blue Jays became a more appealing destination after Vladimir Guerrero signed a long-term contract.
The Pirates’ recent spending habits are a welcome change for fans who have long awaited a more aggressive approach in free agency. However, the organization must not overlook its most valuable asset. Ensuring Paul Skenes remains in Pittsburgh could establish a foundation for sustained success and ultimately transform the team into a serious contender in the league.
