Pirates GM adds insult to injury with truly baffling trade deadline explanation

They might not be the biggest losers of Thursday's MLB trade deadline — they've got the Boston Red Sox and Chicago Cubs to thank for that, at the very least — but the Pittsburgh Pirates are certainly a loser. Ben Cherington's team had a chance to take a meaningful step towards contention this week; instead, they sold pieces for pennies on the dollar ... or, in some cases, refused to sell at all.

By far Pittsburgh's most valuable trade chip was closer David Bednar, who's in the midst of a resurgent season and comes with one more year of team control in 2026. Given how much that impact, controllable relievers were going for in the midst of a red-hot market — Jhoan Duran fetched two top-100 prospects for the Minnesota Twins, while the A's turned Mason Miller into arguably the most enticing talent currently in the Minors — you'd think this would be a golden opportunity for the Pirates to acquire at least one player who could help this offense as soon as 2026.

Instead, the Pirates traded Bednar to the New York Yankees for a three-player package that included precisely zero prospects currently ranked in MLB Pipeline's top 100. It was a truly baffling return, even if there's reason to feel pretty good about centerpiece catcher Rafael Flores. So, what gives? Did Cherington know something everybody else didn't? Was there some reason why Bednar's market didn't materialize in the same way that other star relievers' had?

No, none of that. It turns out that Cherington just ... decided not to acquire more highly regarded players. Seriously: He said as much in his post-deadline press conference, and a recent report suggests he could've gotten Eduardo Tait instead — MLB Pipeline's No. 56 overall prospect, who the Phillies included in their package to get Duran.

Somehow, that might not have been the most confusing decision he made in the span of a few hours on Thursday. Prospect evaluations are notoriously more art than science; maybe Cherington will be vindicated for prioritizing the players he got. But there's simply no justification for not finding trades for Isiah Kiner-Falefa, Andrew Heaney and Tommy Pham, three pending free agents who the team almost certainly won't be re-signing this winter.

Cherington's response? The Pirates simply "didn't feel like they had to trade anybody". Okay then.

Meaningless platitudes to the contrary, it beggars belief that a rebuilding team like Pittsburgh would fully pass on the chance to get controllable talent in return for players that will play zero part in the team's future. It doesn't matter if you don't find what you think is commensurate value; literally anything is better than holding on to them and getting nothing.

Unless, that is, you're an embattled GM who's looking to save some face down the stretch of another losing season. Because the real common denominator amid all the baffling things that Cherington did and said on Thursday is an overriding desire to save his own job at the expense of the organization he works for.

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Ben Cherington was only worried about saving his own skin, not helping the Pirates

Really, how else are we supposed to make sense of all of this? Why would the Pirates not trade three rentals who will be cycled out come the offseason, if not Cherington's desire to keep the team from totally bottoming out over the next two months? Why would he turn down a chance at acquiring a more highly regarded talent like Tait, if not a desire to find a player closer to the Majors in Flores?

Flores is hitting well in Triple-A right now, and figures to be ready for the Majors as soon as Opening Day of 2026. Tait, meanwhile, is an 18-year-old in High-A. If you were in Cherington's shoes, and you were in desperate need of some sort of tangible progress to show your bosses next season, which one would you choose? Not that that should be of any comfort to Pirates fans, who would hope that their lead executive would care mostly about securing as much talent for their team as possible.

It's very possible that Pittsburgh takes a leap next year, with a homegrown rotation that could feature Paul Skenes, Jared Jones, Bubba Chandler, Mitch Keller and Hunter Barco. But there are still holes that need to be field, and a moribund offense that needs to be flipped. The Pirates let Cherington bungle a prime chance at doing so, and in the process exposed just how far away they really are.