For nearly a decade, the Pittsburgh Pirates have been known more for patience than ambition. But this winter, something feels different.
According to ESPN’s Jeff Passan, the Pirates are exploring an aggressive move in free agency, one that would signal a major shift in how the franchise approaches winning.
Their top target is Kyle Schwarber, the power-hitting lefty who crushed 56 home runs last season and hit 187 over four years in Philadelphia before entering free agency.
Bringing him to Pittsburgh would be a stunning move for an organization that has spent years avoiding big-ticket contracts.
The rumor, which surfaced this week, has already sent a jolt through the fan base and the broader baseball world.
Breaking from old habits
Owner Bob Nutting has long been a target of frustration in Pittsburgh, accused of pocketing profits while the team languished in the standings. The Pirates‘ last meaningful free-agent signing came back in 2016 with pitcher Iván Nova, a drought that symbolized their hesitancy to spend even as young talent flashed potential.
But that model is no longer sustainable. Despite having one of baseball’s most electric pitching staffs, anchored by Paul Skenes and Mitch Keller, the Pirates couldn’t generate enough offense to contend in 2025. Skenes finished the year with a dominant 1.97 ERA and 216 strikeouts, Cy Young-level production that went largely unrewarded because of inconsistent run support.
With the team’s window beginning to open and Skenes‘ prime years ahead, there’s a growing belief inside the organization that now is the time to invest.
“We need to win more games and believe we have some flexibility to pursue some things in free agency and trades,” general manager Ben Cherington said recently, hinting that the front office is finally ready to shift gears.
A new tone in the clubhouse
Skenes, who has become the face of the franchise faster than anyone expected, has made his priorities clear. “I’m on the Pirates. My goal is to win with the Pirates,” he said earlier this fall.
That declaration struck a chord in Pittsburgh, a rare instance of a young star committing publicly to the team’s long-term vision. But for that loyalty to last, management must match his competitiveness with real reinforcements.
Schwarber would fit that need perfectly. His left-handed bat, postseason experience, and leadership would provide instant credibility to a young lineup that struggled to generate consistent power. Slotting him into the heart of the order alongside Bryan Reynolds and Ke’Bryan Hayes would transform a once-anemic offense into one capable of supporting an elite pitching staff.
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