If the Pirates were hoping 2026 would finally settle the Ben Cherington question once and for all, the latest read on his future probably won’t thrill the fan base.
FanSided MLB insider Robert Murray said this week he is leaning toward Cherington sticking around in Pittsburgh beyond this season. His reasoning comes down to two things: Cherington is already signed through 2027, and the possibility of an MLB lockout could make the Pirates hesitant to shake up their baseball operations department right now.
That would amount to a major reprieve for a general manager who has been in charge since November 2019 and still hasn’t produced a winning season. His contract runs through 2027, but letting the final guaranteed year of a deal drive a baseball decision would be a tough sell after seven seasons.
The numbers tell the story plainly enough. The high point of the Cherington era is 76 wins.
Pittsburgh is 63-68 with 31 games left, meaning the club would need to go 14-17 just to top that mark, 18-13 to finish at .500, and 19-12 to get to a winning record. As Eric Bowser put it on August 23, 2026: “It is year seven, yet there's silence from 115 Federal.”
The frustrating part for Pirates supporters is that this season was supposed to be different. Pittsburgh entered 2026 believing it could contend.
The club spent more aggressively, extended Konnor Griffin and approached the trade deadline as buyers instead of tearing things down again. Cherington said around the deadline that the Pirates believed in their roster and wanted to give it every chance to make the postseason.
Instead, another late-season slide has left the same old questions hanging over the organization. The issues now are the ones Pittsburgh keeps circling back to: roster construction, player development and whether Cherington should still be the one steering the ship.
The looming labor fight only adds another layer of complication. MLB’s current collective bargaining agreement expires Dec. 1, and talks have already touched on major ideas like a salary cap and floor. MLB has also proposed changes to the offseason transaction calendar, including possible quiet and frozen periods.
All of that would make a front-office change more cumbersome than usual. A new baseball operations leader could be dropped into a system facing a roster, payroll structure and offseason landscape unlike anything under the current setup.
Still, that uncertainty shouldn’t become a shield from accountability. Teams make executive changes in messy situations all the time. For Pittsburgh, the real question is whether ownership believes Cherington is the right person to maximize a core built around Griffin, Paul Skenes, Oneil Cruz, Bubba Chandler and the rest of the young talent.
If the answer is yes, the Pirates need to say it directly and stand behind it. If the answer is no, a potential lockout shouldn’t be enough to hand Cherington another year.
For fans who have spent most of this decade waiting for his plan to finally produce sustained winning, using labor uncertainty as another reason to wait until 2027 would feel an awful lot like the finish line getting moved again.
In Other News...
Paul Skenes Just Made This Pirates Win Feel Even Bigger
Paul Skenes kept the Pirates latest win from feeling like just another tidy one-run result. In his first career start against the Angels at PNC Park, the rookie right-hander worked 5 1/3 scoreless innings, allowed four hits and struck out two, giving Pittsburgh exactly the kind of steady night it needed in a game decided 1-0. He mixed in a sinker that got him outs and twice reached better than 98 mph, adding the sort of power look that keeps a lineup honest even when the strikeout total stays modest.
For Skenes, there was a little extra layer to the matchup, too. He grew up as an Angels fan, which made facing Los Angeles in Pittsburgh a notable backdrop for one of his sharper outings of the season. The Pirates needed every clean frame he could supply, and he delivered them with enough command and velocity to make the win feel more meaningful than the final score alone might suggest. [Read more 🡒]
Pirates Just Created A New Opportunity Fans Will Want To Watch
The Pirates made a late roster tweak ahead of their series finale against the Angels, recalling outfielder Ronny Simon from Triple-A Indianapolis and sending utility man Nick Yorke back down. It is the kind of move that can look minor on paper but carries a bit more intrigue for a club still sorting out how to make the most of its bench and daily lineup.
Simon brings the sort of flexibility managers tend to value in September-style roster churn, with the ability to handle multiple outfield spots and serve as a switch-hitting option at designated hitter. Yorke had only recently gotten a look with Pittsburgh, but the decision to option him opened the door for Simon to get more playing time with the current group, giving fans another name to watch as the Pirates mix and match their way through the final game of the set. [Read more 🡒]
Oneil Cruz Is Giving Pirates Fans Hope With One Big Concern
Oneil Cruz has given Pirates fans plenty to like this season, especially with the way his bat has played against left-handed pitching. He has been much more productive in that matchup, hitting .294/.349/.471 with four home runs over 102 at-bats, a meaningful step forward for a player the Pirates need to anchor the middle of the order as their offense keeps inching ahead.
Still, the larger picture comes with a familiar caution sign. Cruz is also striking out at a 40.6% clip, and that kind of swing-and-miss can quickly blunt even a real improvement at the plate. Pittsburgh has made progress offensively this year, but left-handed pitching remains an area where the lineup still needs more answers, which leaves Cruz as both a reason for optimism and a reminder of how much more stable his production has to become. [Read more 🡒]