Revealed Ben Cherington contract details mean Pirates fans might be stuck

Pittsburgh Pirates fans collectively groaned last weekend when general manager Ben Cherington said that he expected to return to the role in 2026. Those groans grew even louder when The Athletic's Ken Rosenthal reported that Cherington's contract isn't even up for two more years.

In six years under Cherington, the Pirates have a record of 363-504 and have finished 4th or 5th in the National League Central in every season. They stagnated in 2023-24, posting identical 76-86 records in back-to-back seasons, before regressing in 2025, where their maximum win total now sits at 72. Put simply, these results are unacceptable.

Giving credit where it's due, Cherington has assembled an elite collection of young arms during his tenure in Pittsburgh. In addition to 2024 National League Rookie of the Year Paul Skenes, Cherington also drafted the likes of Bubba Chandler and Hunter Barco, both of whom made their MLB debuts this season. Pitchers like Mike Burrows and Braxton Ashcraft were drafted before Cherington's arrival in Pittsburgh, but they have also developed into strong, middle-of-the-rotation arms under his watch.

But impressive as their pitching has been, the Cherington's Pirates have had far too many misses on offense. Henry Davis and his sub-.200 batting average are turning into one of the biggest flops at No. 1 overall in MLB Draft history. Doubts are already surfacing about Termarr Johnson, the No. 4 pick in 2022, and his ceiling as a power hitter.

Nick Gonzales has developed into a solid Major League infielder, and Konnor Griffin sure looks like the real deal. But after six years, the Pirates should at least have a far more robust farm system under Cherington to offer any kind of hope that their draft-and-develop strategy is going to work.

Ben Cherington contract details devastate Pirates fans, but hope remains

Cherington's contract terms may guarantee him money over the next two years, but there is still reason to believe that the 2025 season could be his last in Pittsburgh. The last time Bob Nutting cleaned house following the 2019 season, then-GM Neal Huntington still had three years left on his deal. If he did choose to dismiss Cherington, therefore, it wouldn't be without precedent.

Huntington was also fired after a winning season (remember those?!) in 2018, when the Pirates went 82-79. That was also the last time Pittsburgh finished a season above .500.

Cherington has already been given six years' worth of chances, and he's hardly deserving of any more. The financial cost of dismissing him with two years remaining on his contract would be more than worth it if it saves the Pirates organization from being run further into the ground.