Pirates Rebuild Debate Is Starting To Turn On Ben Cherington

As General Manager Ben Cherington faces tough decisions, the decline of the Pirates' once-promising farm system spotlights a critical issue that could affect the franchise's future success.

The Pirates have reached the part of a rebuild that usually decides everything. The prospect buzz has mostly done its job, the young talent has arrived, and now the organization is left with a much tougher question: is there actually enough around that wave of youth to win?

According to the latest MLB Pipeline prospect rankings released in August, Pittsburgh’s farm system has taken a noticeable step back. Before the 2026 season, it was ranked No.

  1. By August, the graduations of Konnor Griffin and Bubba Chandler dropped the Pirates to No.
  2. Seth Hernandez, Edward Florentino, and Derek Curiel are still in the pipeline, but they are not expected to reach the big leagues until 2028.

The big picture is blunt: the Pirates have officially been rebuilt, and they still missed the postseason.

That reality has shifted the rebuild from hopeful to uneasy. Yes, the NL was unusually competitive, and ace Paul Skenes had a down season.

But even with better fortune, this roster does not look built to keep pace with the league’s perennial heavyweights. The issue goes deeper than one rough year.

There just are not enough strong internal options, especially among the position players, and Ben Cherington has shown no appetite for the kind of high-profile free-agent additions or major trade swings that could change that.

When he has opened the wallet, the results haven’t helped much. Marcell Ozuna turned into one of the biggest disappointments not just in Pittsburgh, but across baseball this season. And it also appears likely the Pirates will lose their most valuable player in 2026, Brandon Lowe, to free agency.

That leaves a lot on the shoulders of players who were in the minors only a short time ago. It is a fragile way to build, and the White Sox offered a reminder of how that can unravel when they fell to the Guardians in the ALDS. Even Chicago had a handful of veteran depth pieces such as Randal Grichuk and Andrew Benintendi, both of whom brought postseason experience.

So far, the Pirates’ rebuild has not delivered on its promise. Cherington has shown that a franchise cannot be built on draft picks alone. Prospect development is always uncertain, and if there is no willingness to supplement it with other roster-building moves, the whole plan starts to look shaky.

In Other News...

Esmerlyn Valdez Is Raising A Familiar Pirates Concern

Esmerlyn Valdez gave the Pirates exactly the kind of early jolt they hope a young bat can provide, reaching the majors in May 2026 and quickly looking like a rare developmental win. By July, he had been named National League Rookie of the Month, and for a while it seemed as if Pittsburgh might have found a young hitter whose approach and power would translate right away.

But the second half has brought a more familiar concern for a club that has seen this movie before. Valdezs swing decisions and contact issues have started to look a lot like the path Jack Suwinski once took, which puts the Pirates back at a familiar crossroads: keep trusting the same developmental formula, or rethink how they handle a prospect whose early success has already started to bend the wrong way. [Read more 🡒]

Pirates Prospect Pipeline Suddenly Has A Problem Fans Can't Ignore

The Pirates still have plenty to point to in the lower minors, with Seth Hernandez, Edward Florentino and Murf Gray all giving the system some needed optimism. But the organizations pipeline has taken on a more uneasy feel in 2026, because some of the names that were supposed to bridge the gap to Pittsburgh did not take the expected step forward. Termarr Johnson endured a rough season in Triple-A, and Thomas Harrington also had trouble finding traction at that level.

Zander Mueths path has become even harder to chart. Injuries have interrupted his development and limited the innings he has been able to stack, which matters in a system that needs help from more than just its headliners. When a prospect group starts losing momentum in both performance and availability, it changes the conversation quickly, and for the Pirates, that leaves one of the more important questions in the organization still hanging over the rest of the season. [Read more 🡒]

Pirates May Have Found The Buy-Low Bullpen Arm They Need

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Erceg still offers traits Pittsburgh would value, even with some recent rough patches clouding the picture. The real question is whether the Royals would even entertain moving him, because if they do, the Pirates could see a reliever with upside and team control as a fit for a bullpen that needs more reliable late-inning answers. [Read more 🡒]