Ben Cherington's latest trade deadline world salad feels hopeless for Pirates

Pittsburgh Pirates general manager Ben Cherington addressed the media on Sunday to outline where the club stands ahead of Thursday's MLB trade deadline. Unfortunately – and yet, unsurprisingly – he said exactly zero things that should instill confidence in Pirates fans regarding his ability to guide this franchise through yet another critical deadline.

Cherington reiterated his deadline goal of looking beyond this season to improve the Pirates for 2026. He addressed the Pirates' need to add offense but acknowledged that the club will need to take on risks in order to do so.

“I don’t think we can be risk-averse,” Cherington said. “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."

On a basic level, Cherington's not wrong. Teams often have to take big risks to reap the big rewards. But the kinds of risks Cherington appeared to predict the Pirates taking sound completely misguided – again, unsurprisingly – and unlikely to produce the kinds of rewards that will actually move the needle enough to break the franchise out of the cycle of perpetual mediocrity.

Ben Cherington's latest trade deadline world salad feels hopeless for Pirates

Sometimes, Cherington said, risk is going to come in the form of "a player that we believe in that hasn't done anything in the big leagues yet."

Oh, so kind of like how the Pirates took a "risk" and dramatically overpaid for Spencer Horwitz – an injured, 26-year-old rookie who played for the one team whose offense was worse than the Pirates' last year – to be their savior at first base? Yeah, no thanks.

The types of risks the Pirates should be open to taking include a willingness to part with controllable assets like Mitch Keller, David Bednar, Dennis Santana and others in order to acquire high-level, MLB-ready offense that can actually help this team get better now. That's not to say that they should force trades of those controllable assets when they don't make sense, but they have to be willing to get a little weaker in one area to get stronger in another.

"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," Cherington said. "So we’ve got to stay disciplined.”

So... Cherington wants to make the Pirates better in 2026, but not if it means giving up any of the tradable assets that would actually net an impactful return. Got it. In other words, this team has no hope of improving as long as this man is at the head of the front office.

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