Pressure on Pirates' Ben Cherington is enormous whether ESPN sees it or not

Ben Cherington is feeling the heat with under two months until the MLB trade deadline. Cherington's plan for the Pirates when he took over back in 2019 was to make the organization competitive at the major-league level by 2025 and 2026. Last season was a wash, and Bob Nutting opted to give his front office another season to prove itself.

So far, Cherington's received mixed reviews. Yes, some of his prospects and draft picks are starting to make an impact. Yet, the team is hovering around .500, still not in possession of a coveted NL Wild Card spot. For a team like the Pirates, the right trade deadline additions could be the difference between making the postseason and watching October baseball from afar for the 11th straight season. If the latter becomes the reality, Cherington's job could be in jeopardy.

ESPN missed mark on Ben Cherington's status with Pirates

Earlier this week, ESPN's Buster Olney ranked the executives under the most pressure at the MLB trade deadline. That list included obvious candidates like Cubs president of baseball operations Jed Hoyer and Red Sox executive Craig Breslow.

Cherington was a notable absence from this list. While Pittsburgh may be a smaller market than Boston and Chicago, no executive is facing the same level of pressure than Cherington, whose job could and should be on the line if the Pirates fail to take advantage of their current standing. At the 2025 trade deadline, for example, Cherington spoke of the necessity to contend in 2026. Even he seemed to understand the expectation of a team built around young talent like Paul Skenes and Konnor Griffin.

“The leadership certainly and just the proven performance [is weighed in trade discussions],” Cherington said. “If we’re going to be better in 2026, we need more of that, not less. We would only contemplate giving up something that’s seemingly more proven if we really believe that they give us a better chance to be better by next year.”

How Ben Cherington can save his job with the right Pirates trade deadline

Cherington's done a tremendous job building up the Pirates farm system and trading expiring assets for that very purpose. That, plus making the right draft picks and using Pittsburgh's international bonus pool money to his advantage, has completed the Pirates rebuild. Now, for this first time in Cherington's career, he'll need the fruits of his labor to come full circle and reach their full potential.

So far, this Pirates team has shown more promise than any in Cherington's tenure. That is the good news. The bad news is he'll have to trade from the prospect cupboard he's helped stock for the right deadline additions. That means a back-end bullpen arm (or two), and perhaps adding another bat to make up for the $12 million Cherington wasted on Marcell Ozuna.

Cherington's had seven years to turn his vision for the Pirates into results. Pittsburgh baseball fans have waited long enough on this fantasy.

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