Cherington talks progress, 2027 outlook at end-of-year conference

DETROIT -- With two games left to play, 2026 has already featured the best season of Ben Cherington’s tenure as general manager. The Pirates have secured a non-losing season and improved by double-digit wins since a year ago.

Cherington addressed the media pregame on Saturday in the visitors’ dugout at Comerica Park as his end-of-season news conference.

“Our goal was to play games in October. That's not happening, so we fell short of that goal. We made real progress. We've got to stay laser-focused on the work necessary to put ourselves in that position next year that we'll be playing games in October,” Cherington said.

“I do believe that the seeds of that are being laid. You see that in the culture that's being set, see that in the core of this roster that's developing and the strength you can see across the roster. Clearly, there's more really important work to do, and we've got to stay laser-focused on that.”

Here are the key takeaways from Cherington’s news conference Saturday:

Coaching, front office changes

Cherington made it clear he doesn’t feel it’s his job to tell fans, or the media, how they should feel out of respect. Though he sees the progress that has been made, and the talent that exists in the organization. Cherington said he believes the baseball operations department has proven they’re able to make good decisions.

“Every conversation I've had with [owner] Bob [Nutting] is just about that. 'How do we keep getting better?' 'How do we assess this season when we need to learn from it?' The progress, the things that need to get better and what can we do about that going forward?” Cherington said.

“Everything we've done, really over time, is building toward October, and every decision we've made -- and certainly every decision we made over the last 12 months -- was all aimed towards that. I don't think that changes. That can't change. We got to go into this offseason focused on that and beat the other teams.”

Cherington also noted he believes they, as a front office, owe the fans better. He believes he can be a part of that.

Another part of delivering for the fans is with the scouting department, and how the club selects their players. Assistant general manager Kevan Graves ran the 2026 MLB Draft temporarily after the departure of Justin Horowitz, and Cherington hopes to fill that role more permanently going forward.

The Pirates have begun a search process for a domestic director position, led by Graves. Cherington also expects natural change in the baseball operations department, which could include promotions internally or additions externally.

As for manager Don Kelly (who is wrapping his first full season as manager after he replaced Derek Shelton on May 8 last season), Cherington has been impressed with his “pursuit of holding a cultural standard.” Cherington believes the Pirates' coaching staff will be largely the same group in 2027, led by Kelly.

“We see our performance in close games improving over the course of the season,” Cherington said. “We're finishing a lot of one-run games and doing small things, and we can still get better at that. So he's clearly the right person to manage this team. He's someone I love coming to work with every day, and our goals are the same: Do the work necessary to be playing games in October.”

Needed improvements

Cherington’s offseason entering 2026 featured a remarkably successful trade for Brandon Lowe, Mason Montgomery and Ben Cherington. Though it also featured a signing of Marcell Ozuna that didn’t go as planned. The team improved, but there are always moves that might not go the team’s way.

“We need to get more right than not. And the ones that we don't get right, we've got to look at clearly and learn from,” Cherington said. “So, in whatever particular case this year that happened, we've done that.

"Bottom line, our approach isn't going to change. Our goal is to get better, and we've got to be willing to take some risks to do that. And when you take risks, you need to win your fair share, and every once in a while, you're going to find one you don't.”

Cherington pointed to run prevention as an area to improve on going forward, specifically defensively. Offensively, he looked at more consistency in scoring, though is proud of the offensive improvements already made, which turned in the most homers in a single season in team history.

Lowe is set to become a free agent after a great first season with the Pirates. Cherington described Lowe as “everything we could have hoped for” as a player and in the clubhouse.

“It would be a great outcome if he's a Pirate next year,” Cherington said. “We'll have some things to talk about and plenty of time in October to have more conversation with him about that. We just need to learn more about what opportunities are out there for us, and he's put himself in a strong position, too.

"So more to learn on that front, but would be a great outcome if he's a Pirate and think the world of him and the job he's done.”

Heading into 2027, Cherington said the Pirates are a team that needs to beat expectations by playing smart baseball and progressing. He sees tangible progress, and a postseason berth in 2027 could be next.

“In Pittsburgh, we've got to build the best, strongest, deepest roster we can, knowing roughly what the resources are,” Cherington said. “And we believe we'll have those resources. We can win, and it's just about execution inside that.”