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.