Former MLB exec says this trade deadline could cost (or save) Ben Cherington his job

Ben Cherington has had nearly six years to rebuild the Pittsburgh Pirates, and all he has are five (going on six) losing seasons to show for it.

The Pirates have done nothing but stockpile pitching depth under Cherington's watch, all while failing to assemble an offense that even remotely resembles a Major League batting order. Even the arrival of generational pitching talent, back-to-back All-Star starter and 2024 National League Rookie of the Year Paul Skenes appears to have done nothing to light a fire under Cherington to build a competitive team around him.

With the Pirates barreling toward yet another last-place finish in the NL Central division and the July 31 trade deadline quickly approaching, Cherington's seat isn't just warm; it should be sizzling.

That fact should be obvious, as it has been for at least the last couple of years now, but former MLB general manager Jim Bowden said recently in an article for The Athletic that Cherington is one of the six MLB GMs under the most pressure to deliver difference-making results at this year's trade deadline.

Former MLB exec says this trade deadline could cost (or save) Ben Cherington his job

Cherington comes in at No. 2 in Bowden's GM trade deadline pressure rankings, behind only Mike Elias of the Baltimore Orioles. Based on recent history, though, it's hard to believe that Cherington will show any sense of urgency to save his job this year.

All of the pitching that Cherington has been stockpiling over the last six years should come in handy this trade deadline season, including starters Mitch Keller and Andrew Heaney and relievers David Bednar and Dennis Santana. All four have appeared in numerous trade rumors, as have other players including infielders Ke'Bryan Hayes and Isiah Kiner-Falefa.

Even if they trade multiple starters, the Pirates can backfill those roles with relative ease. They still have top prospect Bubba Chandler waiting to be promoted from Triple-A, and they will be getting Jared Jones back from his Tommy John recovery at some point next year.

If Cherington can make trades at the deadline that turn his pitching depth into legitimate Major League (or close to MLB-ready) bats, it might just save his job in Pittsburgh for at least another year. If he can't, he could (and should) be out the door by the end of the season.

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