MLB Insider Predicts Pirates Keep GM Ben Cherington

The Pirates have improved under Don Kelly 52-55 overall, but have a 64-81 record and are headed towards their seventh consecutive losing season. They have 24.5 games back from the Milwaukee Brewers, who lead the NL Central, 12.0 games back from the last NL Wild Card spot and have the fourth worst record in the MLB.

Pirates fans have become disgruntled with the results, particularly as the team has one of, if not the, best pitchers in baseball in right-handed starter Paul Skenes, who has had an historic start to his MLB career and will likely win the NL Cy Young Award.

The Pirates have a strong pitching staff, with the right-handers in veteran Mitch Keller, Johan Oviedo, rookies in Braxton Ashcraft, Mike Burrows and Bubba Chandler, plus relievers in Isaac Mattson and Dennis Santana.

They also have served as one the worst hitting teams in baseball in 2025, with the lowest slugging percentage (.350) and OPS (.656), the third lowest batting average (.232) and the seventh lowest on-base percentage (.306).

Buster Olney of ESPN looked at potential changes at both the managerial and front office levels in the MLB and looked at the Pirates situation.

Olney gave plaudits to Kelly for his performance since taking over and also notices the fan dislike for Cherington. He notes that with owner Bob Nutting and his low payrolls, it's unlikely that Cherington will lose his job at the end of the season.

"Manager Don Kelly, a Pennsylvania native, is well-liked and well-respected, and his stock is rising after taking over in early May following the firing of Shelton," Olney wrote. "Cherington, who oversees Pittsburgh's operations, has drawn fan scrutiny, on the other hand. But as one rival official said: "When is the owner [Bob Nutting] going to spend more money? He's probably too cheap to fire Ben, if he wanted to make a change."