Pirates already missed the window to make Ben Cherington decision that mattered

Ben Cherington expects to be back for an eighth season as general manager of the Pittsburgh Pirates.

At this point, does it really matter?

Cherington said that every conversation he has had with team chairman Bob Nutting has given him the impression that he will return in 2027. Given everything we know about how the Pirates operate, that should surprise absolutely no one.

But the more revealing part of the situation isn’t that Cherington appears safe. It’s that Pittsburgh passed on far more logical opportunities to make a change long ago.

If Nutting was ever going to decide Cherington wasn’t the executive capable of finishing this rebuild, that decision should have come two or three years ago. It could have come after another 100-loss season. It could have come when the Pirates continued finishing near the bottom of the National League despite years of accumulating high draft picks. It could have come when Pittsburgh entered another offseason with obvious holes on the major-league roster and little urgency to fill them.

Those were clean exit points. Instead, ownership repeatedly chose continuity. And once the Pirates allowed Cherington to oversee the development of Paul Skenes, Jared Jones, Oneil Cruz, Konnor Griffin, Bubba Chandler and the rest of what has become the organization’s core, it became increasingly difficult to imagine Nutting suddenly handing the operation to somebody else right as the team finally started showing signs of progress. That doesn’t mean the patience was justified, though.

The Pirates finishing 82-80 and posting their first winning season since 2018 is progress. It is also an extraordinarily low bar for an executive who was hired in 2019. Seven seasons into Cherington’s tenure, Pittsburgh still hasn’t reached the postseason — and that matters far more than finally sneaking above .500.

The Pirates hired Cherington to construct a sustainable contender. The entire justification for years of losing, roster churn and patience was supposed to be that something much better was waiting on the other side. Seven years later, we're still waiting — and that's why another offseason debate about Cherington's job status feels almost pointless.

Ben Cherington's expected return to Pirates barely matters, because ownership missed its chance to move on years ago

The Pirates already made their decision on Cherington.

They made it when they retained him after the rebuild dragged deeper into his tenure. They made it when they let him continue making draft picks, trades and free-agent decisions after the organization failed to take meaningful steps forward. And they made it again every time another disappointing season ended without a substantial change at the top.

Firing Cherington now, after Pittsburgh finally reached 82 wins and has assembled perhaps its most talented young core in years, would almost be stranger than firing him several seasons ago would have been. That's precisely the problem. Ownership waited so long that the logical accountability window passed.

None of that should earn Cherington unlimited runway, though. Quite the opposite.

If Nutting has decided this is still Cherington's team, then 2027 can't become another season in which progress is measured by clearing some modest benchmark. There can be no celebration of 84 wins, meaningful September baseball or another incremental improvement if Pittsburgh is once again watching October from home.

The Pirates have the pitching. They have young talent arriving. They have enough established major leaguers that the conversation should no longer revolve around whether the rebuild is "headed in the right direction." The only meaningful question left is whether it produces a playoff team.

Cherington apparently isn't going anywhere. Fine. But after seven years, his continued employment isn't really the story anymore.

The story is whether the organization that spent all those years refusing to hold him accountable will finally demand the result the entire rebuild was supposed to produce.

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