Insider 'Fully Expects' Pirates to Make This Ben Cherington Decision
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PITTSBURGH — The Pittsburgh Pirates are heading towards another disappointing season and questions on general manager Ben Cherington's tenure are starting to arise.
Cherington is in his seventh season, and the Pirates are headed towards missing out on the playoffs and potentially another losing season as well.
Buster Olney of ESPN wrote in his latest article that he would be surprised if the Pirates make a change at general manager this offseason, and Jason Mackey of Pirates.com shared the same sentiments on 93.7 The Fan.
"It is. Yep. I would be surprised if they do anything at this point," Mackey said. "I am fully expecting Ben Cherington to be back, barring something that none of us see coming."
Why the Pirates May Keep Cherington
Cherington and the front office made some strong moves this offseason, like trading right-handed starting pitcher Mike Burrows for second baseman Brandon Lowe, left-handed relief pitcher Mason Montgomery and outfielder Jake Mangum.
Lowe became the first Pirates player to hit 30 home runs since Josh Bell in 2019 and has the most home runs in a season for a Pirates second baseman. Montgomery turned into an elite closer and Mangum has filled in all three outfield spots and found different ways to get on base.
The Pirates also signed free agent Ryan O'Hearn to a two-year, $29 million contract, making him their first multi-year free-agent signing since 2016.
O'Hearn has had a strong season, batting .266/.330/.452 for an OPS of .782 with a career-high 18 home runs, and is an important voice in the clubhouse.
Cherington and the Pirates also secured the future of rookie shortstop Konnor Griffin, signing him to a record nine-year, $140 million contract extension on April 8, five days after making his debut.
The Pirates have also dealt with serious injuries all season to their star players, including center fielder Oneil Cruz, Griffin, O'Hearn, first baseman Spencer Horwitz and catcher Endy Rodríguez, plus both starting pitcher Braxton Ashcraft and rookie right fielder Esmerlyn Valdez most recently.
Pittsburgh is likely in a much better spot without their injuries, with one of the National League Wild Card spots.
Why the Pirates Could Move On From Cherington
The Pirates underwent a massive rebuild starting in 2020, but they haven't had success during Cherington's tenure, 426-570 (.428), with no winning seasons or postseason appearances.
Cherington took over as general manager after a terrible 2019 season for the Pirates, where they finished 63-93 and both manager Clint Hurdle and general manager Neal Huntington lost their jobs.
Pittsburgh last had a season above .500 in 2018 and made the postseason in 2015, the second-longest streak to only the Los Angeles Angels.
The Pirates are 75-76 with 11 games remaining and seven games back in the NL Wild Card race, needing a lot of luck to even come close to making the postseason.
Pirates team president Travis Williams said at the start of the 2025 offseason that the goal was the playoffs: "Period. Full Stop."
Cherington also made some poor decisions, such as signing Marcell Ozuna to a one-year, $12 million deal, neglecting the bullpen and not adding starting pitching depth.
Ozuna was terrible for the Pirates and they cut ties with him in early August, the bullpen was poor and blew numerous games until they fixed it at the trade deadline and the Pirates have two starting pitchers out injured in Mitch Keller and Ashcraft.
Cherington will also become one of just three general managers that stayed on for an eighth season after not having a season above .500 since 1950 (non-expansion team), Cam Bonifay of the Pirates (1994-2001) and Rick Hahn of the Chicago White Sox (2013-20), if the Pirates keep him.
The Pirates could move on from Cherington to another general manager, who will get them to the postseason and establish a winning culture.
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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.