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Ben Cherington's latest offense surfaces as Pirates-Cubs trade details are finalized

How does this guy still have a job?
ByEmma Lingan|
Aug 25, 2021; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington looks on during batting practice before the game against the Arizona Diamondbacks at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
Aug 25, 2021; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington looks on during batting practice before the game against the Arizona Diamondbacks at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

In a rather unsurprising move, the Pittsburgh Pirates flipped one of the assets they acquired in Wednesday's Ke'Bryan Hayes trade in the final hours leading up to Thursday's trade deadline.

After spending roughly 24 hours as a member of the Pirates organization, veteran southpaw reliever Taylor Rogers was flipped to the division rival Chicago Cubs – his third National League Central team in the last two days – in exchange for minor league outfielder Ivan Brethrowr.

On the surface, it makes sense; Rogers is 34 years old and on an expiring contract, so he isn't going to be of any use to a Pirates team that has already punted to next year (or, realistically, beyond). He can, however be useful to the Cubs, who are in second place in their division and currently in possession of the first NL Wild Card spot.

It seemed like a fine bit of business for general manager Ben Cherington and the Pirates – a wash, if nothing else. But when the full details of the trade were revealed more than an hour after the 6 p.m. ET deadline, it was another excruciating reminder of Cherington's ineptitude when it comes to making even the most straightforward of deals.

Ben Cherington's latest offense surfaces as Cubs trade details become finalized

According to the final terms of the deal, the Pirates acquired Brethowr from the Cubs in exchange for Rogers ... and cash considerations.

Yes, you read that correctly. The Pirates actually paid the Cubs to take an asset that was barely even theirs to offer in the first place – and one that already had value at the deadline.

At that point, why not just keep Rogers? He's still not going to help the Pirates in 2026; but neither is Brethowr, an unranked, High-A outfielder who is still years away from the Majors (if he makes it there at all). At least Rogers could have helped the Pirates win a few games this season or given them a relief option to possible reunite with in the offseason.

But alas, such is life when an organization's leadership doesn't prioritize winning – either now or in the future.

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