The Pittsburgh Pirates are staring down another lost season, and the biggest question around the franchise is no longer about the roster. It’s about Ben Cherington.
After seven years on the job, the general manager’s future is getting dragged into the spotlight as Pittsburgh heads toward missing the playoffs again and possibly finishing with another losing record. Still, the sense around the team is that a change at the top is not coming this offseason.
Buster Olney of ESPN said he would be surprised if the Pirates made a general manager move, and Jason Mackey of Pirates.com echoed that view 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."
That’s not to say Cherington hasn’t had some wins this year. Pittsburgh’s front office landed a strong return when it traded right-handed starter Mike Burrows for second baseman Brandon Lowe, left-handed reliever Mason Montgomery and outfielder Jake Mangum.
Lowe has given the Pirates something they haven’t had in a while, becoming the first Pittsburgh player to reach 30 home runs since Josh Bell in 2019 and setting the franchise mark for a Pirates second baseman. Montgomery has emerged as an elite closer, while Mangum has become a useful all-around outfielder who can handle all three spots and reach base in different ways.
The Pirates also made a notable move in free agency by signing Ryan O'Hearn to a two-year, $29 million deal, their first multi-year free-agent signing since 2016. O'Hearn has delivered with a .266/.330/.452 line, an .782 OPS and a career-high 18 home runs, and he’s also become a key voice in the clubhouse.
There was another major commitment, too. On April 8, just five days after his debut, Pittsburgh locked up rookie shortstop Konnor Griffin on a record nine-year, $140 million extension.
But the year has also been defined by injuries, and plenty of them. The Pirates have been without center fielder Oneil Cruz, Griffin, O'Hearn, first baseman Spencer Horwitz and catcher Endy Rodríguez at different points, and more recently have lost both starting pitcher Braxton Ashcraft and rookie right fielder Esmerlyn Valdez.
Without all of that damage, Pittsburgh would likely be sitting in a much stronger place, even in the mix for one of the National League Wild Card spots.
Instead, the numbers under Cherington paint a bleak picture. Since taking over after the Pirates’ awful 2019 season, when they went 63-93 and both Clint Hurdle and Neal Huntington were fired, Cherington has overseen a 426-570 (.428) stretch with no winning seasons and no playoff trips.
The franchise’s drought is now stretching into familiar territory. Pittsburgh hasn’t finished above .500 since 2018 and hasn’t made the postseason since 2015, the second-longest active stretch behind only the Los Angeles Angels.
The Pirates are 75-76 with 11 games left and sit seven games out in the NL Wild Card race, so even a late surge would require a heavy dose of help.
Team president Travis Williams made the goal plain at the start of the 2025 offseason: "Period. Full Stop."
And there have been misses along the way this year, too. Cherington signed Marcell Ozuna to a one-year, $12 million contract, but that move went sideways quickly and Pittsburgh cut ties with him in early August. The bullpen was a problem for much of the season before being addressed at the trade deadline, and the rotation has taken hits with Mitch Keller and Ashcraft both out injured.
If the Pirates do stick with Cherington, he would join a very short list of general managers to last into an eighth season without producing a winning record since 1950 among non-expansion teams, alongside Cam Bonifay of the Pirates from 1994-2001 and Rick Hahn of the Chicago White Sox from 2013-20.
The alternative is obvious: move on and give someone else a chance to push the Pirates back to the postseason and build a winning culture.
In Other News...
Pirates Own Up To A Costly Mistake Fans Wont Forget
A quiet but damaging moment in the Pirates game against the Brewers came on the bases, where a chance to add to the board vanished because of a routing mistake involving Nick Gonzales and Ryan OHearn. Third base coach Tony Beasley later took responsibility, saying he did not see the ball clearly and told Gonzales to hold at third, turning what should have been a live scoring opportunity into an avoidable pause in the action.
For a Pirates club that has spent plenty of time searching for clean execution, these are the kinds of plays that linger because they are so fixable. Gonzales said he simply followed the instruction he was given, which puts the focus squarely on the coaching box and leaves the larger question hanging around a team that cannot afford to give away chances like that, especially in a tight game against Milwaukee. [Read more 🡒]
Pirates Had No Margin For Error Against Milwaukee After One Costly Mistake
Jacob Misiorowski kept the Pirates off balance for five scoreless innings, and the margin for Pittsburgh never really got any wider after that. Milwaukees starter lowered his season ERA to 1.89 and picked up his 15th win of the year, while the Pirates scratched out just five hits and spent most of the night trying to recover from a game that slipped further away in the fourth inning.
Pittsburgh finally got on the board in the eighth, but by then the damage was done. A baserunning error earlier in the game helped stall any early momentum, and against a Brewers club that kept adding pressure, the Pirates were left with too little room to work with in a 5-1 loss. [Read more 🡒]
Pirates Face A Real Brandon Lowe Test They Usually Avoid
Brandon Lowe has given the Pirates exactly the kind of midseason jolt they hoped for when they brought him in through last offseasons three-team trade. He has been one of the most productive hitters on the roster, piling up 30 home runs and carrying an .803 OPS while giving Pittsburgh a proven presence in the middle of the lineup.
Now the question is what comes after the season, because Lowe is headed for free agency and the Pirates may have to decide whether to extend a qualifying offer. Even if they do, he is widely expected to pass on it, and the bigger issue may be whether the sides can bridge a gap in contract philosophy, with Lowe reportedly looking for a multi-year deal while Pittsburgh usually prefers shorter commitments. [Read more 🡒]