If you’ve followed the Pittsburgh Pirates long enough, you’ve learned the rules: stay skeptical, expect nothing, and be pleasantly surprised by anything more. But this offseason feels… different. And for once, it isn’t just the usual whispers from Pittsburgh or the fan-driven optimism we all talk ourselves into every winter. National writers — national writers — are openly wondering whether the Pirates might finally make a real push to improve the roster. Ken Rosenthal. Jeff Passan. Jesse Rogers. All hinting the same thing.
But then comes the counterweight: reality.
During a recent episode of North Shore Nine LIVE, Ryan and Tyler spent nearly two hours unpacking the mixed signals coming out of Federal Street. The front office is saying the right things. Executives around baseball are suggesting the Pirates might actually spend. Yet everyone inside Pittsburgh knows the truth — until the Pirates actually write the checks, nobody is buying it. “Until I see them do it, they’re not doing it,” Tyler said bluntly. And honestly? He’s right. Could This Be the Most Active P…
Names like Jorge Polanco, Ryan O’Hearn, and Eugenio Suárez get tossed around. All would instantly become one of the Pirates’ best hitters — which speaks less to their ceilings and more to the holes still sitting in this lineup. Add in the Mitch Keller trade rumors, the uncertainty with Andrew McCutchen, and the desperation for real Major League bats, and the Pirates find themselves at a crossroads.
If there was ever a moment to push forward — with Paul Skenes in-house and a controllable young rotation — this is the window.
The question now: do they finally act like it?
One way or another, this offseason will reveal exactly who the Pirates really want to be.

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