Pirates fans can't believe Craig Breslow is making Ben Cherington look like executive of the year

It takes a lot for Ben Cherington to win over the Pittsburgh Pirates fan base.

For most of the past six years, he’s been the face of frustration — the architect of a rebuild that dragged, a roster that felt perpetually incomplete, and a development pipeline that didn’t always translate to wins at the big-league level. If you asked Pirates fans a year ago to describe Cherington, “competent” wouldn’t have cracked the top 100 responses.

And yet, here we are. Because somehow, some way, Craig Breslow is making Cherington look like a genius.

Interestingly enough, Cherington traded for Breslow — now the Red Sox chief baseball officer — back in 2012, when Breslow was a pitcher and Cherington was the general manager in Boston. The pair went on to win a World Series with the Red Sox the following year.

Now, more than a decade later, the implosion in Boston Red Sox leadership isn’t just about manager Alex Cora getting fired. It’s the full teardown — the hitting infrastructure, the bench, even longtime voices like Jason Varitek being reassigned. That’s not a reset. That’s an admission — and it’s one Breslow now owns entirely.

Pirates fans have a new appreciation for Ben Cherington as Craig Breslow saga unfolds in Boston

Pirates fans know what it looks like when leadership runs out of places to point the finger. They lived it. Cherington spent years operating under the shadow of payroll limitations, development criticism, and failed trades. But here’s the difference: when the pressure peaked, he didn’t burn the house down — he adjusted.

This offseason was the clearest example yet. Instead of doubling down on caution, Cherington got aggressive. He added legitimate middle-of-the-order production in Marcell Ozuna, Brandon Lowe, and Ryan O'Hearn. He took a swing on upside with Jake Mangum. He supplemented the pitching staff with arms like Mason Montgomery and Gregory Soto.

Perhaps most importantly, Cherington secured the future. Locking up Konnor Griffin to a long-term extension wasn’t just a baseball move — it was a statement. It told fans, for once, that a superstar wouldn’t just pass through Pittsburgh. That this time, the plan might actually stick.

Meanwhile in Boston, Breslow is still searching for his plan. He mishandled the Rafael Devers situation. He failed to stabilize the offense. He built a pitching staff that gives up too many home runs. And now, by gutting the coaching staff, he’s removed any remaining buffer between himself and the results. There’s no one left to blame.

That’s the part Pirates fans recognize most — and maybe even appreciate now. For all the criticism Cherington has taken, he never positioned himself this squarely in the line of fire without at least offering a counterpunch. Breslow just did.

And in doing so, he’s created an unlikely reality: Pirates fans are looking at their own front office… and feeling something close to confidence. Not because Cherington suddenly became perfect. But because compared to what’s unfolding in Boston, he looks — dare we say it — steady. Calculated. Even competent.

Sometimes, perception shifts not because you change everything, but because someone else shows you what worse really looks like. Right now, that someone is Breslow. And in Pittsburgh, that’s making all the difference.

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