Pirates GM: To win, 'we're going to have to assume some risk' in trade deadline deals

Ben Cherington is approaching Thursday’s MLB trade deadline with the intent to build a team that is going to be better in 2026, so the Pittsburgh Pirates general manager is preparing to strike on deals that can do that.

Although the Pirates are expected to be sellers, Cherington emphasized that it is not a fire sale. He expressed a willingness to wait if the Pirates can’t find desirable deals but isn’t afraid to take a gamble.

“I don’t think we can be risk averse,” Cherington told reporters Sunday morning at PNC Park. “I don’t think that’s going to work in Pittsburgh. (If) 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 emphasized that “the exercise is not to move payroll” but to get better, saying that the Pirates are communicating that to potential trade partners while remaining open-minded about moves.

The Pirates are looking to add bats, most likely in the form of top-100 prospects or players on the cusp of making it to the major leagues. They are expected to trade some, if not all, of their players on expiring contracts — left-handers Caleb Ferguson and Andrew Heaney, shortstop Isiah Kiner-Falefa and outfielder Tommy Pham — but the bigger trade chips are All-Star right-handed starter Mitch Keller, Gold Glove third baseman Ke’Bryan Hayes and two-time All-Star closer David Bednar, as well as high-leverage reliever Dennis Santana.

Word in baseball circles is that everyone but two-time All-Star right-hander Paul Skenes is available, but it would take quite the return package for the Pirates to part with center fielder Oneil Cruz or minor leaguers shortstop/outfielder Konnor Griffin and right-hander Bubba Chandler, who are ranked among the game’s top five prospects.

“Part of it is not forcing it,” Cherington said. “We need to score more runs to win more games. That’s clear, and that’s a goal going into 2026. We’re still learning. Obviously, working long hours right now to find out what those opportunities are between now and Thursday. And we can’t force it. We’ve got to stay disciplined and not do something that we don’t believe in just because it brings back a position player that might look a little bit better on the roster. So we’ve got to stay disciplined.

“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. And that’s just as important. 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.”

If Cherington is on the fence about trading anyone, it’s Bednar. The Mars alum earned his 100th career save Saturday night in the 2-0 win over the Arizona Diamondbacks and got emotional afterward.

A three-time Roberto Clemente Award nominee for his community service, Bednar cherishes playing for his hometown team and battled back from the adversity of a demotion to the minors to make 23 consecutive appearances without allowing an earned run.

With Bednar making $5.9 million this season and one year of arbitration eligibility remaining, he’s aware that this might be the optimum time to trade him to a contender. Bednar took photos of the city skyline on his way out of the ballpark after the game, knowing it might be the last time he pitches a night game at PNC Park.

“I think I’ve said something like this before but I do mean it: I’m not sure I can recall a single player who has been as strong on the field and off the field and who happens to be from that city as David has been,” Cherington said. “The sort of trifecta of those things is not lost on any of us. So much respect for him for who he is, the performer on the field, the person off the field, the willingness to fight through adversity, which he has done here also not too recently.

“I don’t know what’s going to happen. He’s a really valuable pitcher, a really important person. I think we should take that very seriously. Any conversations I have with him I’ll keep between him and I, but I have a huge amount of respect for him.”

Cherington also addressed the news that second-round draft pick Angel Cervantes announced on social media that he would attend UCLA instead of signing with the Pirates. He was selected 50th overall, so the team will receive the No. 51 pick as compensation in the 2026 MLB Draft.

“I do expect he’s going to attend UCLA. We respect that decision,” Cherington said. “As a group, we spent a lot of time over the past several months getting to know Angel and his family, and, obviously, we really like him. We wouldn’t have taken him where we did if we didn’t and he’s a really talented young high school pitcher. Believe he should flourish at UCLA.”

Cervantes, a 17-year-old right-hander from Downey, Calif., was ranked the No. 49 prospect by MLB Pipeline and No. 51 by Baseball America. The Pirates picked Cervantes even after taking a prep right-hander with the No. 6 overall pick: Seth Hernandez, who signed Tuesday for a $7.25 million bonus. Slot value for the No. 50 pick was $1,934,700.

When Cervantes chose not to sign, Cherington said the Pirates “were able to pivot” and sign 15th-rounder McLane Moody, a 6-foot-7 right-hander from Northside (Ark.) who was committed to Arkansas, and 17th-rounder Carter Gwost, an outfielder from Little Falls (Minn.) who was committed to Nebraska.

“As we got closer to that pick in the draft, we wanted to honor our board as much as we possible can, and he was the player we believed was the best player on our board at the time we selected,” Cherington said. “We understood when we selected him that there was a risk. We understood enough about the situation, what we were hearing about him and his representatives that there was some risk that he would not sign.

“We took him knowing that. We planned for that in the later rounds and after the 10th round and we did, I believe, made a very aggressive and fair offer for him, which he ultimately chose to turn down, and I respect that. Respect that decision, wish him well. … We’re excited to have the pick back next year in what looks like a really strong draft.”