Uncertainty around Ben Cherington’s return gives Pirates fans reason to believe

It's been six years since the Pittsburgh Pirates hired Ben Cherington to oversee a rebuild in 2019, and they are even further away from contention than they were when he arrived. They lack any kind of clear identity beyond "waiting for prospects," and the prospects who have arrived under Cherington have largely disappointed at the big league level.

The Pirates have never had a winning season in six years under Cherington. Most recently, they put up back-to-back 86-loss campaigns in 2023 and 2024, and they are about to follow it up with an even worse record in 2025.

Pittsburgh has one of the worst offenses in baseball and currently ranks 28th out of 30 teams in batting average (.231) and hits (1,195), while sitting dead last in slugging percentage (.350), OPS (.655), home runs (112) and runs scored (561). 

Simply put, after six years, those kinds of numbers are unacceptable. So, too, is the fact that the Pirates have shown no sense of urgency under Cherington to improve by surrounding young talent with adequate veterans or making any kind of bold moves in free agency to accelerate the rebuild – one that has already taken far too long as it is.

Ben Cherington’s uncertain future could be a turning point for Pirates

Cherington was asked, point-blank, during a media availability on Saturday whether he had received any assurance from principal owner Bob Nutting that he would be returning as GM of the Pirates in 2026.

“I'm certainly doing the job that way,” Cherington responded (via Noah Hiles of the Pittsburgh Post-Gazette). “We talk all the time. Haven't heard anything to the contrary. I don't know if any of us in this room ever have full assurance of anything, but I want to help the Pirates win more games."

So, Cherington thinks he'll be back next year. But that wasn't the question. The question was, specifically, whether Nutting had given him any assurance of his job status – and Cherington's failure to answer that question may have told us everything we need to know.

If Cherington really wants to help the Pirates win more games, he'll resign. But since that's highly unlikely, we'll have to hope that his job isn't as safe as he thinks it is.