Pirates GM Cherington On Trade Deadline: Taking Risks, Demand for Keller, Bednar
Preparing for his sixth trade deadline at the helm of the Pirates front office, general manager Ben Cherington and his staff are once again looking to the future instead of the present.
That’s no surprise. Nearly two-thirds of the way through the 2025 season, the Pirates sit 18.5 games out of first place with a 43-62 record. Firmly out of the playoff picture, their earliest chance to end their decade long postseason drought will come in 2026.
Cherington stressed that the Pirates don’t have to force moves now in preparing for 2026, as they also have the offseason to look forward to. Even so, he doesn’t want the team to exercise caution, citing a need to make aggressive moves in order to keep up with the rest of the pack in a league with as much talent disparity as MLB.
“I don’t think we can be risk averse. I don’t think that’s going to work in Pittsburgh. We want to win, we’re going to have to assume risk. With risk comes downside to that, obviously. If that doesn’t work out, we get criticized. That’s ok. I don’t think we can win without assuming that,” Cherington said.
“It’s case by case, right? We’re not going to assume — need to or will assume — massive risk on every decision. We’re going to have to be willing to assume risk, I believe, to win. That risks can come in different forms. Sometimes that’s going to come in the form of a player that we believe in that hasn’t done anything in the big leagues yet. Until they do, there’s no proof that they will.”
Preparing for the Deadline
Two Pirates floated repeatedly in trade rumors are starting pitcher Mitch Keller and closer David Bednar. They’ve both put on excellent performances in 2025, with Keller posting a 3.53 ERA that ranks No. 31 in all of baseball, borderline staff ace material. Bednar hasn’t allowed a run in his last 23 appearances on the mound (22.1 innings), converting 16 straight save opportunities.
Keller and Bednar don’t just help the Pirates win games on the field. They’re also two veteran leaders on a young team in need of those sorts of voices. Cherington described what type of trade offers he’d entertain for players of their caliber.
“Yeah I think the leadership certainly and just the proven performance. If we’re going to be better in 2026, we need more of that, not less,” Cherington said. “We would only contemplate giving up something that’s seemingly more proven if we really believe that they give us a better chance to be better by next year.”
Quality Teams Don’t Trade Quality Bats
Most of the Pirates’ struggles this season result from their offense. While Pittsburgh’s 3.75 team ERA places them as the No. 9 team in baseball, their .638 team OPS ranks worst in baseball by a full 20 points.
Cherington underlined one of the Pirates obstacles in improving their offense, namely that most good bats play for good teams, ones not looking to part with a player who could help them in pursuit of a championship run. As such, the Pirates need to look for trades involving less proven bats.
“We also know in Pittsburgh, and in a lot of cases, we’re going to be acquiring players who are not fully proven yet, who we believe can contribute, whether it’s on the pitching side or position player side in the near-term, but aren’t fully proven yet,” Cherington said.
“Part of this, of getting better, is really doing that really well, is acquiring those less proven players and bringing them into an environment where they can thrive and are getting better. We’ve seen some examples of that happening, maybe a little bit more on the pitching side. We’ve got to do that really well too. So that’s part of it, given that often, it’s going to be the case that the players that were acquired are not fully mature or fully certain players.”
Build Like the Rays
What, then, can the Pirates do in order to acquire top flight position players? Anyone who’s followed the team for any length of time knows they aren’t going to do so through free agency.
Cherington cited the blueprint other small market teams have placed for success — he didn’t mention them specifically, but the Tampa Bay Rays are one such example — as a route forward. Over the course of six Julys in Pittsburgh, however, Cherington knows that that’s easier said than done.
“It’s very clear to me over time, you’re not going to score 1.000, you’re not going to bat 1.000 on these things and be 100%. That’s really not the goal. The goal is to put the Pirates in a stronger position,” Cherington said.
”I believe trades have to be something [you’re] willing to do… because if you look at teams that are succeeding that are most similar to us, they’re getting a lot of value through trades. And they don’t win every one of them, they don’t get every one of them right, but they get enough over time that it adds up and we have to be ready to do the same thing.”
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