Pittsburgh Pirates general manager Ben Cherington is a dead man walking, a sitting duck, on the chopping block. However you want to use to describe the situation, his time running the franchise into the ground is nearing the end; everyone knows it. Recent intel from Bob Nightengale of USA Today only confirmed the inevitable, but it also raised a concerning and strange question worth addressing.
Per Nightengale, chatter about Cherington's looming dismissal arose "less than six hours" after the 2025 MLB trade deadline passed. "No one in baseball has less job security" than Pittsburgh's top decision-maker (and Colorado Rockies executive Bill Schmidt). That's not exactly surprising news. Nonetheless, the fact that it's such common knowledge and Pirates chairman Bob Nutting still signed off on him selling off talented players is jarring.
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Pirates letting GM Ben Cherington make trade deadline moves despite scorching hot seat is fittingly baffling
The Pirates rerouted a pair of valuable relievers in fan favorite David Bednar and southpaw Caleb Ferguson. They parted ways with a former top prospect and elite defender with five years of club control, third baseman Ke'Bryan Hayes. If rival front offices were this sure Cherington is on the outs, why does he have the green light to gut Pittsburgh's roster?
Just because Cherington won't stick around to see things through in Pittsburgh doesn't mean his successor should step into a full rebuild. Ferguson is a pending free agent, so sending him to the Seattle Mariners for 19-year-old minor league right-hander Jeter Martinez made sense. But Bednar and Hayes are worthwhile pieces with strong ties to the organization that could've helped the next person in charge.
Cherington and presumably much of the Pirates' brass are counting their days until the pink slip comes. The writing has been on the wall for a while, and the official announcement will merely be a formality. To make matters worse, Nutting is giving him free rein to wreak havoc and leave a mess on the way out. We'd call that bad business, to say the least.
It's incredibly shocking that Cherington is given the leeway to continue wheeling and dealing ... until you remember this is the Pirates we're talking about. This is quite on brand for a squad that hasn't sniffed the postseason in a decade and has no sight of ending said drought.