Pirates' farm system decline exposes a problem Ben Cherington can't keep ignoring

There is an aspect of rebuilding a baseball franchise that holds some excitement. High draft picks, promising prospects, and anticipation all keep the fans’ attention while the on-field performance limps along.

When those prospects finally reach the Majors en masse, the team reaches a make or break moment. That’s where the Pirates are right now, and it may be the defining moment of Ben Cherington’s career.

The latest MLB Pipeline prospect rankings, which came out in August, are a testament to the Pirates turning a corner. Before the 2026 season, the farm system ranked No. 3. By August, the graduation of Konnor Griffin and Bubba Chandler knocked the team down to No. 13. Sure, Seth Hernandez, Edward Florentino, and Derek Curiel are waiting in the wings, but they likely won’t hit the big leagues until 2028.

The Pirates have officially been rebuilt… and they still didn’t make the postseason.

The Pirates’ rebuild timeline has shifted from anticipation to anxiety

Granted, it was an unusually competitive year in the NL, and ace Paul Skenes had a down season. But even in the best of conditions, the retooled Pirates roster doesn’t seem able to compete with the perennial powerhouses. There simply aren’t enough quality internal options, especially among the position players, and Cherington has no willingness to bring in high-profile free agents or trade targets.

When Cherington has spent some big bucks, his strategy has failed. Marcell Ozuna was one of the biggest flops not only in Pittsburgh, but across baseball this season. It also seems likely that the Pirates will lose their most valuable player in 2026, Brandon Lowe, to free agency.

Without veteran leadership (and, more importantly, veteran production), all of the pressure falls on the youngsters who were in the Minors just a few years or even months ago. The White Sox saw the flaws of this approach as they folded against the Guardians in the ALDS. Chicago even had the advantage of several veteran bit players like Randal Grichuk and Andrew Benintendi who have postseason experience.

The Pirates’ rebuild, then, has fallen short of its objective. Cherington seems to have proven that you can’t just draft your way to a competitive franchise. The uncertainty of prospect development necessitates other approaches to roster construction, and Cherington just doesn’t seem willing to go there.

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