Why Pirates Could Have Hard Time Finding Manager if Don Kelly is Replaced
The Pittsburgh Pirates face a big decision early in the offseason. OK, they actually face several, but one of the biggest will be who will be the club’s manager in 2026?
The Pirates foolishly brought Derek Shelton back for the 2025 season only to fire him six weeks into the season amidst a 12-26 start.
Pittsburgh promoted Don Kelly to manager at the time it was announced that Shelton was dismissed. Instead of naming him interim manager, the Pirates announced that Kelly would be manager for the remainder of the 2025 season, still leaving his future up in the air.
Under Kelly’s leadership, the Pirates played better. They went 59-65 in the 124 games Kelly was the head of the bench. Good enough? No. But better? Absolutely.
Pirates’ players enjoyed playing for Kelly, a genuinely good person with a mild-mannered personality – other than a few entertaining spats with umpires – and a good baseball mind. He’s someone that’s been widely-respected around the league going back to his days as a utility player for the Detroit Tigers under Jim Leyland.
But during a late-season scrum with the media, general manager Ben Cherington wouldn’t take a firm stance on Kelly’s future.
“It’s so important that I would never be satisfied with where we are culturally,” Cherington said. “I also think the end of a very difficult season is a difficult time to assess culture. I think we have a massive opportunity going into 2026 with the group we will have, no matter what happens, some new form of leadership from the beginning of 2025 to really make that what we want to make it.”
If Kelly does not return and Cherington does, the Pirates might have trouble landing a top candidate to take the reins.
To be fair, it’s not certain that Cherington will return. However, in the aforementioned media availability late in the season, the Pirates’ general manager said he’s operating under the assumption the 2025 season was not his last.
“I’m certainly doing the job that way,” Cherington said when asked if he was told he will return as GM. “We talk all the time. Haven’t heard anything to the contrary. I don’t know if any of us in this room ever have full assurance of anything, but I want to help the Pirates win more games. That’s it.”
Letting Cherington continue to serve as general manager would be an odd choice considering the team’s consistent lack of success during his tenure. Cherington’s best seasons were 76-86 finishes from 2023-24. Somehow, in year six of a rebuild, Pittsburgh regressed and finished 71-91 this year.
If Cherington does continue in his role, it’s hard to envision him doing so beyond next year if the Pirates don’t have a postseason game on the schedule this time next year, or at least ending the regular season with a winning record.
Knowing that the current general manager could have one year left at most, why would any serious managerial candidate consider attaching himself to what looks like a sinking ship?
If the Pirates go in a direction other than Kelly, the new manager could potentially have one year in the role before a new general manager takes over and has their own say in who they want to lead the team.
It gives the Pirates a dilemma and a choice of three options. Keep Cherington and Kelly and hope for the best. Keep Cherington and take your chances bringing in a new manager, hoping the appeal of working with a promising young pitching staff led by the best starter in baseball is enough to land a top option. Or fire Cherington and leave the choice up to the new GM.
We should have some clarity on the futures of both Cherington and Kelly in the coming days.
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