Pirates Bringing Back GM Ben Cherington in 2026
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PITTSBURGH — The Pittsburgh Pirates will likely make changes this offseason, but the general manager will remain the same heading into 2026.
Pirates general manager Ben Cherington spoke to the media on Sept. 29 and confirmed that he would remain in his position for the 2026 season, with a simple, "Yes."
Fans and national media wondered whether they would bring back Cherington after another poor season in 2025 and he will stay in the role for the foreseeable future.
Ken Rosenthal of The Athletic reported that Cherington has two years left on his contract through the 2027 season, likely playing a role in him coming back.
Cherington spoke to the media after announcing that they signed manager Don Kelly to an extension, making him the future leader of the Pirates after taking over in the role on May 8, following the firing of manager Derek Shelton after a 12-26 start.
The Pirates finished 71-91 overall, last in the National League Central Division and the fifth worst record in baseball.
Cherington took over as the general manager of the Pirates on Nov. 18, 2019, after previously serving as the vice president of baseball operations for the Toronto Blue Jays.
He also served as the general manager of the Boston Red Sox ahead of the 2012 season and won the 2013 World Series before resigning from the position on Aug. 18, 2015 with the team at 47-58 overall.
The Pirates haven't had success under Cherington, with a 365-505 record, a .420 winning percentage. Only the Washington Nationals, 354-416 (.407) and the Colorado Rockies, 331-538 (.381) having worse records than them.
This includes the worst record in baseball in 2020 at 19-41 overall, a shortened season due to the COVID-19 pandemic, back-to-back 100-loss seasons in 2021 and 2022, collapses after a great start in 2023 and being in National League Wild Card contention after the trade deadline in 2024 and then another poor season this year.
The Pirates have had seven consecutive losing seasons and 10 seasons outside of the playoffs, with only the Los Angeles Angels having longer streaks that them in both categories.
Cherington hasn't had much success on the field, but the Pirates have finally started getting more prospects up at the MLB level.
This is especially true on their pitching staff, with Paul Skenes, the first overall pick in the 2023 MLB Draft, Bubba Chandler, a third round pick in the 2021 MLB Draft, Hunter Barco, a second round pick in the 2022 MLB Draft, both Carmen Mlodzinski and Jared Jones, Competitive Balance Round pick and the second round pick in the 2025 MLB Draft.
Pittsburgh also has both Braxton Ashcraft and Mike Burrows, who joined the team in the 2018 and 2019 MLB Drafts, respectively, under previous general manager Neal Huntington, who had strong seasons in 2025 after dealing with long-term injuries.
The Pirates also have the top prospect in baseball in Konnor Griffin, who they took ninth overall in the 2024 MLB Draft, that many expect will make the MLB roster at some point in 2026.
Cherington will have the offseason to improve the Pirates, who ranked towards the bottom of most offensive metrics, and fans are desperate to see a team competing for the postseason in October 2026.
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.