Pirates GM Ben Cherington’s contract runs through the 2027 season, according to Ken Rosenthal of the Athletic. Cherington has been at the helm of Pittsburgh’s front office since November 2019. While it was previously unknown if his contract ran through 2026 or ’27, this latest update gives him at least two more years worth of guaranteed salary.
Dating back to Cherington’s first season at the helm – the COVID-shortened 2020 season – the Pirates have a record of 363-504 and have finished 4th or 5th in the NL Central in every season. The club’s last winning season was in 2018 under then-GM Neal Huntington. They lost 93 games the following season. Owner Bob Nutting fired Huntington and brought in Cherington after the following season, even though Huntington had multiple years remaining on his contract at the time.
That same offseason saw the Bucs fire manager Clint Hurdle, whom they replaced with Derek Shelton. Pittsburgh stuck with the Cherington-Shelton pairing for five full seasons, maxing out with 76-86 seasons in both 2023 and ’24. A 12-26 start to year six led them to fire Shelton in early May. They’ve been better under interim skipper Don Kelly, yet their 57-64 record in that time has them playing at the same 76-win pace of the previous two seasons. Some growing pains are always expected at the beginning of a rebuild, but the record has plateaued even as the Bucs have put together a talented collection of young arms.
Under Cherington, Pittsburgh has had much more success drafting and developing pitching than they’ve had on the position player side. The Pirates drafted Paul Skenes No. 1 overall in 2023, and the righty is now the favorite to win the NL Cy Young Award. He gives the club their first bona fide ace since Gerrit Cole and should anchor the rotation for the next few years.
Braxton Ashcraft and Mike Burrows were drafted before Cherington’s arrival but have developed into promising pitchers this season. Closer Dennis Santana has broken out since being claimed off waivers last June. There’s more pitching talent in the pipeline. Five of MLB.com’s Top 100 prospects are in the Pirates organization, and two of them – RHP Bubba Chandler (No. 7) and LHP Hunter Barco (No. 82) – have recently made their big-league debuts. They added another potential impact arm with RHP Seth Hernandez, the sixth overall pick this summer.
Impressive as the pitching group has been, they’ve had too many misses on offense. Henry Davis, the first overall pick in 2021, is a career .178/.260/.288 hitter. Nick Gonzales, selected seventh overall in 2020, has a .259/.302/.378 line in more than 900 plate appearances. While it’s too early to close the book on 2022 fourth overall pick Termarr Johnson, he’s not as highly regarded as he was at draft time because of questions about his power ceiling and defense at second base.
Last year’s first-round pick looks much more successful. Konnor Griffin, the #9 pick in 2024, had a phenomenal minor league season. He’s a potential franchise shortstop and arguably the #1 prospect in the game. Griffin has a chance to become the dynamic position player talent that the club has lacked, but they’ll need a lot more production throughout the lineup. Spencer Horwitz and Joey Bart are their only two hitters who have been even slightly above-average at the plate this season, as measured by wRC+. No team has scored fewer runs.
Cherington said over the weekend that he hasn’t received any indication from ownership that he won’t remain in the position going into 2026. If that proves to be the case, he’ll first need to decide whether to retain Kelly as the permanent manager. The focus will again be on building even a league average offense. Skenes, Chandler, and Mitch Keller form a strong front of the rotation, with all three under control through at least 2028. The team’s payroll annually ranks in the bottom 10 of the league, likely leaving the front office looking in the third or fourth tiers of free agency to acquire some complementary pieces to strengthen the lineup in hopes of getting above .500 and challenging for a Wild Card spot.
This is an outrage! The Pirates are never going to reach the playoffs with Cherington and Nutting still around.
My belief has always been that Cherington must be the lowest paid GM in the league and that’s the only reason why he’s still there
The losses will continue until morale improves
People seem to forget that a GM/POBO’s primary job is to make the owner money.
Apparently, Nutting is making money hand over fist because he has kept Cherington on the job while the team has continued to lose and lose bad.
During Cherington’s tenure including 2025 the Pirates have not finished better than 4th place in the central, have 4 last place finishes, have a .418 win %, and have not had a winning season.
I know it’s hard for him to win with nutting giving him zero payroll but in the years he’s been at the helm, he hasn’t found a way to make the front office run on no money
Cleveland, Milwaukee, Tampa, etc all find ways to win but cherington isnt smart enough to do the same
Exactly he was given 30 million to spend on free agents and decided to sign 5 non impact players
Keep in mind that in terms of fWAR, Joey Bart and Jack Suwinski are his most productive players he has acquired himself (either through draft, trade, etc.).
Don’t forget mccutchen but he has acquired literally no offense year in and year out
I’d argue that if the pirates didnt get Paul skenes there’s a chance he would’ve been fired by now
Forgot to mention Oneil Cruz is a disappointment too.
He can still be fired at anytime so there is always hope.
I can almost hear Bob Nutting sounding like a penny pinching dad:
“We are not buying a new GM. We have a perfectly fine one already, and its only a couple years old!”
Gonna need a lot of fireworks and bobbleheads to get people out when Skenes isn’t pitching.
Skenes old news. They came out early 2024 for him. By late 2024 they didn’t really care. Sure if you are going to buy a random ticket might as well see Skenes but it’s not a drastic attendance boost.
Okay.
Bob Nutting, you absolute buffon, if you see this as a reason to bring him back, so help me god. For the love of everything holy in this world, just make one right decision.
There are a lot more, harsher words I would like to use right now that would likely get my account banned.