As the Pittsburgh Pirates once again fall out of contention in the National League, all eyes are on GM Ben Cherington. Few MLB executives are under more pressure, if not from ownership, then from the fanbase. We know Bob Nutting and the Pirates' brass does not particularly care about winning relative to profits. But for Cherington, whose job it is to build a winner despite financial limitations, his lack of success is damning.
We can point to plenty of issues with this Pirates roster. There aren't enough bats. The bullpen lacks depth. Even the starting rotation, while top-heavy, is not bulletproof beyond Paul Skenes. And yes, the Skenes factor looms large here. Pittsburgh only has so much time under Skenes is on to greener pastures, A.K.A. a bigger contract. Wasting time in mediocrity with a potentially all-time great pitcher on your roster is criminal.
And yet, perhaps the best example of Cherington's incompetence — his pervasive inability to evaluate talent and develop from within — is current Milwaukee Brewers ace Quinn Priester, who's coming into his own as a bankable rotation option. Just last season, he was making his bones in a Pirates uniform.
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Pirates quit way too soon on Quinn Priester
Pittsburgh dealt Priester to Boston midway through the 2024 campaign in exchange for IF/OF Nick Yorke, now the Pirates' No. 6 prospect, per MLB Pipeline. Yorke, 23, is close to his big-league debut and could, in theory, help address the Pirates' ongoing offensive shortage. He has a .726 OPS, six home runs and 39 RBI in 74 games with Triple-A Indiana this season.
At the time, it was at least justifiable. Pittsburgh long needed to trade pitching for hitting, especially with Skenes on the rise and fellow rookie Jared Jones throwing gas. The Pirates' farm system is much deeper in terms of arms than bats, with another top pitching prospect nearing his MLB debut in Bubba Chandler.
In hindsight, however, it feels like a gross miscalculation. Either the Pirates needed more than a potential utility bat in Yorke, or Pittsburgh should have simply doubled down on a strength and kept Priester in the rotation.
Quinn Priester is on the rise for Brewers
The Red Sox flipped Priester to the Brewers in the offseason, where he is now thriving. At least in Boston's case, the Red Sox received several quality assets — a top-10 prospect, a recent MLB Draft pick, and a compensatory first-round pick in 2025. Far more than Pittsburgh got for him, and that's after Priester barely saw an MLB field for half a season in the Red Sox system. His value was down, not up, but Craig Breslow still sold for a much higher return than Cherington.
With 18 appearances (13 starts) under his belt for Milwaukee, Priester boasts a 3.33 ERA and 1.204 WHIP. He's not a great swing-and-miss pitcher, but Priester's sinker yields a lot of groundballs and tends to keep the offense limited to dinky singles, rather than explosive extra-base hits. He looks poised and proficient on the mound, peaking with six scoreless innings in Friday night's win over the Dodgers. He allowed only three hits and notched 10 strikeouts.
You and everyone you know should be talking about Quinn Priester pic.twitter.com/myUFWobqmW
— Milwaukee Brewers (@Brewers) July 19, 2025
Pittsburgh got pennies on the dollar for Priester, who could've given them another bankable starter behind the headliners of Skenes and Mitch Keller. Instead, we wait to see if Yorke can actually boost the Pirates' offense down the line, or if he's just more of the same.
Right now, it feels like Ben Cherington and the Pirates front office will live to regret this one.