May 12, 2024; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington looks on before the Pirates host the Chicago Cubs against at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images Charles LeClaire-Imagn Images

Pirates GM Ben Cherington's Contract Length Revealed

Originally posted on Pittsburgh Pirates on SI
By Dominic Campbell | Last updated Sep 26, 2025 11:00 AM ET

PITTSBURGH — Pittsburgh Pirates general manager Ben Cherington has spent this entire decade in the same role, but many fans wonder how long he'll stay in the job going forward.

Cherington took over as the general manager after the 2019 season and the Pirates have a 363-504 record (.419) in his sixth season in charge.

The Pirates have seven straight losing seasons, 10 consecutive seasons without a postseason appearance and have served as one of the worst teams in baseball in the 2020s.

They are 69-90 overall this season, with the fourth worst record in baseball, and saw Cherington fire manager Derek Shelton after a 12-26 start on May 8.

Cherington has helped the Pirates build a strong pitching staff, including ace Paul Skenes, veterans in Mitch Keller and Johan Oviedo, rookies in Braxton Ashcraft, Hunter Barco, Mike Burrows and Bubba Chandler, plus relief pitchers in Justin Lawrence, Isaac Mattson, Carmen Mlodzinski and Dennis Santana.

He has struggled building a competent offense, as the Pirates rank amongst the worst metrics in the MLB, including the lowest slugging percentage (.349) and OPS (.653), plus the least runs (570), RBIs (549) and home runs (113).

The biggest juxtaposition for this is that the Pirates have the most shutouts at 19, but have also suffered the most shutout defeats, 16, in 2025.

Ken Rosenthal of The Athletic wrote about Cherington in his article about 15 MLB teams who could make managerial and front office changes.

Rosenthal reported that Cherington still has two seasons left under his contract, through the 2027 campaign, but that doesn't necessarily mean they'll keep him around.

"Cherington, according to sources briefed on his status, is under contract for two additional years, through 2027. But after six straight losing seasons, that doesn’t necessarily make him secure. The division rival Milwaukee Brewers play in an even smaller media market, and have made the playoffs seven of the last eight years.

"The last time owner Bob Nutting cleaned house, after the 2019 season, GM Neal Huntington had three years left on his deal and manager Clint Hurdle two. Nutting got stuck paying more than $10 million to people who no longer worked for him, according to a source. The cost of dismissing Cherington would be less.

"Cherington drafted NL Cy Young Award favorite Paul Skenes and the game’s No. 1 prospect, shortstop Konnor Griffin. Around Skenes, he has assembled an enviable collection of young arms. If Nutting trusts Cherington to balance the team’s roster by trading pitching for hitting, the GM could end up leading the Pirates back to prominence. If not, the executive who replaces him could end up benefiting from the foundation Cherington put in place."

This article first appeared on Pittsburgh Pirates on SI and was syndicated with permission.

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