Pirates GM Hints At Possibility Of Bold Trade Deadline Moves

The Pittsburgh Pirates aren’t where they want to be…yet.

Despite winning five of six games last week, they’re still last in the National League Central and 18 games below .500, putting them on pace for a seventh straight losing season. With a playoff appearance unlikely for 2025, they’re already looking ahead to 2026.

While the Pirates seem stuck, they have a chance to alter their trajectory this week with the MLB Trade Deadline coming up on July 31. With the right moves, Pittsburgh has a chance to accelerate its rebuild and potentially return to contention next year.

In order for that to happen, however, Pirates general manager Ben Cherington believes his team can improve through trades and must be willing to take on risk, indicating he may be open to making some bold, aggressive moves this week.

“I don’t think we can be risk-averse. I don’t think that’s going to work in Pittsburgh,” Cherington said during his media availability session on Sunday. “We want to win, we’re going to have to assume risk…I don’t think we can win without assuming that.”

Ben Cherington spoke with the media this morning. A lot was discussed. For me, this was his most notable quote from the availability: pic.twitter.com/E1NGSYJ8tS

— Noah Hiles (@_NoahHiles) July 27, 2025

Cherington added how that includes taking risks on prospects and unproven players who haven’t “done anything in the big leagues yet.”

He also noted how trading well and often is key for helping smaller-market teams like Pittsburgh compete.

“I believe trades have to be something that we’re willing to do, and probably a lot over time,” Cherington said. “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 we have to be ready to do the same thing.”

Based on that, Cherington appears to be gearing up to potentially trade veterans for prospects and younger players who can help his team win down the line.

While the Pirates have improved considerably over the last several years compared to where they were at the beginning of the decade, their rebuild seems to have stalled. They have a promising core emerging with Paul Skenes, Oneil Cruz and Bryan Reynolds, but they’ve yet to put the right pieces around them to build a contender.

This week will be another opportunity for Cherington to change that. It’s clear that if he wants to help Pittsburgh reach the next level, he has to be willing to take some big swings.

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