Pirates’ late-season surge could save Ben Cherington but it should also raise expectations for him

The Pittsburgh Pirates' 2026 season appeared to be unraveling in August. A team that reached the All-Star break firmly in the National League Wild Card conversation watched its offense collapse, losing six consecutive series at one point and eventually falling six games under .500 on Aug. 28.

For a franchise that entered the season publicly talking about making the playoffs, it looked like another promising year was about to end with the familiar explanation that the Pirates were still building toward something.

Then, suddenly, they started winning again.

The Pirates clawed their way back to .500 in September, winning five consecutive series during one stretch and forcing themselves back onto the outskirts of the Wild Card race. Their postseason odds remained microscopic because of how much damage had already been done, but the turnaround offered another glimpse of what this roster can look like when its young core is healthy and producing.

That could matter significantly for general manager Ben Cherington. He's under contract through 2027, and Pittsburgh's strong finish gives ownership a fairly easy argument for maintaining continuity rather than making a front-office change entering what could already be a complicated offseason.

But keeping Cherington absolutely cannot mean giving him another development year. If anything, the Pirates finishing 2026 strongly should raise expectations for him.

If Pirates are committed to Ben Cherington as GM, expectations should be even higher in 2027

Paul Skenes is already one of baseball’s premier starting pitchers. Bubba Chandler, Braxton Ashcraft and Jared Jones have increasingly looked capable of becoming another frontline arm. Konnor Griffin, Oneil Cruz and Esmerlyn Valdez give Pittsburgh legitimate offensive building blocks, while players such as Ryan O’Hearn have demonstrated just how much competent veteran offense can change the complexion of this lineup.

In other words, the foundation isn't hypothetical anymore. That means Cherington’s responsibility this winter should be to aggressively improve it.

Pittsburgh still has glaring questions at multiple positions, needs more reliable offense surrounding its young hitters and cannot enter another season hoping everything goes perfectly with its existing roster. The August collapse demonstrated exactly how thin the margin for error remains when injuries strike or several hitters slump simultaneously.

Seven years into Cherington's tenure, development can no longer be the destination. If the Pirates believe this September surge is evidence that they're finally close, then they need to act like it this winter.

Cherington may have done enough to earn one more season. Now he has to build a roster good enough that reaching the postseason isn't considered a pleasant surprise.

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