Ben Cherington appears headed back for an eighth season as Pirates general manager, and by now that news lands with a shrug more than a jolt.
Cherington said his conversations with team chairman Bob Nutting have left him expecting to return in 2027, and that should surprise no one who has watched how the Pirates have operated. The more striking point is how long Pittsburgh has already had to make a different call - and never did.
If Nutting was going to decide Cherington wasn’t the right executive to finish the rebuild, the time to do it was years ago. It could have happened after another 100-loss season.
It could have happened while the Pirates kept living near the bottom of the National League despite all those high draft picks. It could have happened during yet another offseason when the major-league roster had obvious holes and little urgency to fill them.
Those were the clean break points. Instead, ownership kept choosing continuity.
That matters because once Cherington was allowed to keep steering the ship through the development of Paul Skenes, Jared Jones, Oneil Cruz, Konnor Griffin, Bubba Chandler and the rest of the organization’s young core, it became hard to picture Nutting suddenly changing direction right as the team began to show signs of life. That doesn’t mean the patience was justified. It just means the decision point came and went.
The Pirates’ 82-80 finish and first winning season since 2018 counts as progress. It also remains a pretty modest milestone for a general manager hired in 2019. Seven seasons into Cherington’s tenure, Pittsburgh still hasn’t made the postseason, and that’s the part that matters more than finally getting above .500.
The whole point of hiring Cherington was to build a sustainable contender. The losing, the roster churn, the patience - all of it was supposed to lead somewhere better. Seven years later, the destination still hasn’t arrived.
The Pirates already made their choice on Cherington when they kept him through the long stretch of rebuilding. They made it when they let him continue handling draft picks, trades and free-agent decisions after the club kept failing to move forward in any meaningful way. They made it again every time a disappointing season ended without a real shakeup at the top.
At this stage, firing him now would almost be more surprising than moving on from him years ago would have been. That’s the bind ownership created by waiting too long.
None of that gives Cherington a free pass. If Nutting really has decided this is still Cherington’s team, then 2027 cannot become another year where progress is measured by scraping out 84 wins or treating September baseball like a breakthrough. There’s no reason for celebration if October is still watched from home.
The Pirates have the pitching. They have young talent coming. They have enough established major leaguers that the conversation should no longer be about whether the rebuild is moving in the right direction.
The only question that matters now is whether it produces a playoff team.
Cherington may not be going anywhere. But after seven years, that’s no longer the main story.
The story is whether the organization that spent all that time avoiding accountability will finally demand the result the rebuild was supposed to deliver.
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Pirates Offense Suddenly Has A 2027 Decision Fans Can Feel Coming
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What makes that stretch matter now is the broader question it creates for the front office. Pittsburgh has spent years trying to find a sustainable offensive core, and the way those three produced in September gave the organization a new kind of window to think about as it looks ahead. There is a decision coming for the Pirates, and if that late-season progress is real, the club may soon have to sort out which bats are part of the long-term plan. [Read more 🡒]