PITTSBURGH - The Pittsburgh Pirates have spent too many seasons stuck in the same place, and the fix isn’t just about talent. It’s about finally playing without the hesitation that has too often shaped this franchise.
The numbers tell the story of how far the Pirates have fallen: five World Series titles, but none since 1979, which was also the last time they won a postseason series. Since then, Pittsburgh has made only six playoff trips, including three-year runs from 1990-92 and 2013-15. In the past 34 years, the club has managed just five winning seasons, with a brutal stretch of 20 straight losing seasons from 1993 to 2012.
That history is hard to ignore, but the Pirates did at least give themselves a fresh point of reference in 2026 with a winning season. Now the question is whether they can turn that into something lasting.
One of the biggest obstacles has been fear. It shows up in the way decisions get made, in how quickly a team adjusts, and in whether a front office is willing to take a real swing when the moment calls for it. For the Pirates, that hesitation has too often meant playing it safe instead of pushing for real progress.
That mindset showed up in the 2025 offseason, when Pittsburgh did not make serious additions. The result was a 71-91 record, the firing of Derek Shelton and a wasted Cy Young campaign from Paul Skenes. Whether that quiet offseason was driven by fear or not, the end result was the same: the Pirates didn’t show enough ambition to make 2025 a success.
The club did bring in Brandon Lowe and Ryan O’Hearn before 2026, and those moves helped, but they still couldn’t cover for a bullpen that became one of the team’s biggest problems. Pittsburgh’s relief corps regressed in key spots and gave away too many games that could have changed the shape of the season.
The Pirates did get more aggressive at the trade deadline, but by then the damage had already piled up. A 7-16 slump from late July to mid-August left them trying to dig out of a hole they had already let get too deep.
Manager Don Kelly took heat along the way, sometimes unfairly, and bullpen management was a major reason why. One moment that summed up the frustration came on Sept. 12 at Wrigley Field against the Chicago Cubs, when left-hander Gregory Soto was struggling in the eighth inning and Kelly stayed with him. Two runs crossed, the lead disappeared, and Pittsburgh lost 4-3.
Still, this wasn’t just on the dugout. When the Pirates were in position to make their postseason chase matter down the stretch, the players didn’t capitalize. That made the collapse feel collective, not isolated.
The encouraging part is that this doesn’t look like a team starting from scratch. The Pirates bring back most of their roster from 2026, along with the experience of being in a race that actually mattered. They have a young rotation that looks strong, a lineup that can produce runs, and a bullpen that should be better than it was a year ago.
Kelly also has a full season of lessons behind him now, which should matter when the game tightens up. He’ll have a better feel for lineup construction, rotation usage and bullpen decisions after living through those moments once already.
General manager Ben Cherington also deserves credit for some of the moves he made last offseason and at the trade deadline, but the job isn’t done. The Pirates need that same kind of follow-through again this winter.
There is a real path here: a strong group of players, a manager determined to bring winning baseball to his hometown, and a front office that knows it has to deliver. If Pittsburgh can move past the fear and failure that have lingered for years, 2027 could be the season that changes the conversation.
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