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Ben Cherington Explains Why He Should Stay With Pirates

The Pittsburgh Pirates general manager spoke on his future with the team.
Apr 19, 2025; Pittsburgh, Pennsylvania, USA;  Pittsburgh Pirates general manager Ben Cherington observes batting practice before the game against the Cleveland Guardians   at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
Apr 19, 2025; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington observes batting practice before the game against the Cleveland Guardians at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | IMAGN IMAGES via Reuters Connect

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DETROIT — Ben Cherington is nearing the end of his seventh season as Pittsburgh Pirates general manager and he's still trying to build a winning baseball culture.

The Pirates will miss the playoffs for the 12th straight season in 2026, but did make improvements, ending their seven-year losing season streak, and are 81-79 with two games remaining.

Cherington didn't confirm whether he would stay as general manager, but said his conversations with Pirates owner Bob Nutting have focused on improving the team and that they are working towards making the postseason.

"Every conversation I’ve had with Bob was just about that," Cherington said. "How do we keep getting better? How do we assess this season? What do we need to learn from it? The progress, the things that need to get better and what can we do about that going forward?

"Everything we’ve done over time is building toward October. Every decision we’ve made, and certainly every decision we’ve made over the last 12 months, was all aimed toward that. I don’t think that changes. It can’t change. We have to go into this offseason focused on that."

Cherington Believes He is Right For GM Role

Nutting made Cherington his general manager ahead of the 2020 season, and the Pirates have not had much success during that time.

The Pirates had the worst record in baseball in 2020, back-to-back seasons with 100 losses in 2021 and 2022, then two seasons in 2023 and 2024 with strong starts, but slumps and collpases that ended any postseason hopes.

Pittsburgh Pirates general manager Ben Cherington
May 12, 2026; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington looks on during batting practice before the game against the Colorado Rockies at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | IMAGN IMAGES via Reuters Connect

Cherington stayed on as general manager after an abysmal 2025 campaign, 71-91, which saw the dismissal of manager Derek Shelton, and vowed to improve the team.

The Pirates were in the National League Wild Card race for most of 2026, but a 7-16 stretch from late July to mid-August, featuring seven straight series defeats, put them six games below .500 and too far out of it to make up ground.

Pittsburgh will retain most of its players for next season, so there is hope from the team and front office that they can make the postseason next year.

Cherington also has faith in that happening and that he can be the general manager to give Pirates fans winning baseball once again.

"I don't want to...I have a lot of respect for all of you and fans, and I don't think it's my job to tell people how they should or shouldn't feel," Cherington said.

"I know what we're focused on. I know the progress we've made. I know the talent that exists in this organization on the field and in baseball operations and in the staff believe we have shown that we're able to make good decisions in all areas of baseball operations and push this thing forward.

"Believe we owe our fans better. Certainly, I know I've said that before. That's the job: deliver better to our fans. I know I'm entirely focused on that. Believe I can be a part of that. It's just about the work, then. You know, it's not... It's just about the work to do that. I don't spend energy on anything else."

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Dominic Campbell
DOMINIC CAMPBELL

Dominic writes for Pittsburgh Pirates On SI, Pittsburgh Panthers Pn SI and also, Pittsburgh Steelers On SI. A Pittsburgh native, Dominic grew up watching Pittsburgh Sports and wrote for The Pitt News as an undergraduate at the University of Pittsburgh, covering Pitt Athletics. He would write for Pittsburgh Sports Now after college and has years of experience covering sports across Pittsburgh.