In the theater of a 162-game season, some losses are more revealing than others. Getting swept at home by the Chicago White Sox, a team with an even worse record, was not just a bad series. For the 2025 Pittsburgh Pirates, it was a symbolic nadir. The team is lifeless, the trade deadline looms, and the architect of it all has already turned his attention to 2026.
This is the inevitable, damning result of a flawed organizational philosophy that has reached its breaking point.
Waving the White Flag
The final confirmation of this failure came directly from General Manager Ben Cherington. On Sunday, he delivered a masterclass in capitulation.
“Obviously, we’re in a situation that we don’t want to be in,” Cherington stated. “We need to find ways… to put ourselves in a better situation going forward… to increase the chances of the Pirates being a winning team in 2026 and beyond. That’s our only focus.”
This is a public surrender after another failed season. Before the calendar had even flipped to July, the season was a lost cause. So now the focus is on surviving the future, a future that will be shaped by more trades from Ben Cherington. And we’ve all seen how those have turned out so far.
The Anatomy of a Failure
This admission of failure was not precipitated by bad luck, but by a cascading series of underperformances and a roster that was never built to withstand them. Key players expected to produce more on offense have regressed or stagnated. Bryan Reynolds, Ke’Bryan Hayes, and Joey Bart have not provided the necessary impact. Henry Davis has struggled in his limited opportunities, while Spencer Horwitz’s season was derailed before it even started by a wrist injury. Jack Suwinski was sent down early on and upon being called back up has yet to provide much. Outside of Oneil Cruz, Nick Gonzales (who was injured the first 2 months of the season), and Andrew McCutchen, production from the daily lineup has been a black hole. Part-time players have fared no better, either regressing or failing to find a rhythm amidst inconsistent playing time.
The consequence is a predictable pre-deadline yard sale. Expiring contracts like Andrew Heaney, Isiah Kiner-Falefa, Caleb Ferguson, and Tommy Pham are all but gone. Even more foundational pieces are reportedly on the table. The idea that Mitch Keller, Ke’Bryan Hayes, or David Bednar could be moved is no longer unthinkable.
The Cherington Doctrine
The mid-season firing of Derek Shelton and the hiring of Don Kelly was a cosmetic fix. Kelly’s initial fire has been extinguished by a team that simply cannot perform. The manager is irrelevant when the organizational philosophy itself is broken.
And that is the central issue. Ben Cherington’s hitting philosophy has been an abject failure.
While the organization has shown a commendable ability to develop pitching, its approach to hitting has been catastrophic. The results are a damning indictment. The Pirates offense is last in runs scored. Last in home runs. Last in OPS. This is not a statistical anomaly. The offense has been bottom five bad for Ben Cherington’s entire tenure as GM. It is the direct outcome of an offensive approach that prizes passivity over aggression, leaving players hesitant and unable to do damage.
This is Ben Cherington’s legacy. It’s a philosophy that has produced a lifeless, ineffective offense and a team that is, once again, looking up from the bottom of the standings. The time for excuses has passed. It is time to move on from both the philosophy and its architect.