It's sounding more and more like Ben Cherington is going to botch Pirates trade deadline

But there may be a silver lining...
May 19, 2025; Pittsburgh, Pennsylvania, USA;  Pittsburgh Pirates general manager Ben Cherington (left) and special advisor Gene Lamont (right) talk on the field before the game against the Cincinnati Reds at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
May 19, 2025; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington (left) and special advisor Gene Lamont (right) talk on the field before the game against the Cincinnati Reds at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

With the Pittsburgh Pirates projected to be sellers at this year's trade deadline, two names have emerged above the rest at the forefront of the rumor mill: starting pitcher Mitch Keller and closer David Bednar.

Trading either (or both) of these assets would immediately move the Pirates into the "aggressive seller" category, and many believe that's exactly where they should be. However, the latest reports out of Pittsburgh seem to indicate a high likelihood of general manager Ben Cherington getting in his own way at the deadline.

The Detroit Tigers, Philadelphia Phillies and Texas Rangers are just three of what is likely a long list of clubs that have contacted the Pirates about Bednar. But according to Noah Hiles of the Pittsburgh Post-Gazette, general manager Ben Cherington is looking to "sell high on his blue chip bullpen asset."

According to Hiles, the Pirates' asking price for Bednar is sky high and includes, at minimum, an organization’s top-five prospect. On the surface, such a price might sounds unreasonable, but a two-time All-Star with an additional year of team control remaining could – and should – demand a hefty return on what is otherwise a thin relief market.

Here’s why the Pirates holding onto their pitchers at the trade deadline may actually be a good thing

With Emmanuel Clase off the market and Jhoan Duran and Ryan Helsley already getting traded on Wednesday, Bednar is by far the most valuable reliever remaining on the trade block. Keller also has value as a consistent, high-end starter with multiple years of team control remaining, so many are of the belief that the Pirates should strike while the iron's hot and trade both while their value is at its highest.

Cherington has stated that his main focus is to improve the team in 2026, but none of the moves he's made so far have addressed the 2026 Pirates in any significant way. At this rate, given Cherington's horrendous track record with trades, there's no reason to believe that he would net more value in a deadline deal than Bednar and Keller are already providing.

The most efficient way for the Pirates to improve next season is to limit Cherington's ability to make franchise-altering moves. Perhaps, after six long years, principal owner Bob Nutting is beginning to realize that.

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