Cubs-Brewers playoff showdown just evoked a nightmare Pirates trade reminder

If you’re a Pittsburgh Pirates fan, Game 3 of Cubs–Brewers doesn’t just feel like October baseball — it feels like rubbing salt in an old wound. On one side, a former first-rounder who blossomed the second he left town. On the other, a pitcher Pittsburgh once developed, endured, believed in, then moved on only to watch him settle into a dependable October arm someplace else. You don’t need a history book to feel the sting; you just need a box score and a memory.

This is the kind of matchup that turns a neutral series into a Pittsburgh think piece. Quinn Priester vs. Jameson Taillon isn’t merely Brewers vs. Cubs. It’s a reminder of how the Pirates’ margin for error in pitching trades remains razor thin, despite an embarrassment of riches, and how often the organization has watched innings, value, and narrative pay off somewhere with a different skyline behind the mound.

As Cubs face Brewers, Pirates fans get a painful reminder of deals past

For Milwaukee, Priester (13–3, 3.32 ERA) has been the reveal of the year. An innings-eater with teeth who looks fresher, sharper, and more self-assured every turn. That’s a tough mirror to stare into for Pittsburgh, considering Priester is the kind of young arm who should have been part of the Pirates’ next wave.

Instead, he’s the “what if” in a rival’s rotation. Ever since he left at the 2024 deadline, dealt to Boston for infielder Nick Yorke, Priester has pretty much done nothing but validate those pre-draft hopes. He made one crisp Red Sox start (5 innings, 1 earned), and by April 2025 the Brewers pounced, betting there was more ceiling to mine. They were right. 24 starts and 29 total appearances later, he’s the guy stepping on the gas in a series that can send the Cubs home.

Across the diamond, Taillon (11–7, 3.68 ERA) is chasing a different kind of confirmation. He’s the testimony that development scars can still yield a steady veteran who knows how to pitch under playoff lights. Outside of a choppy 2023 in Chicago, Taillon has been exactly that for both the Yankees and Cubs from 2021–25. Reliable, resilient, and good enough to tilt a short series when the margin turns razor-thin. Pirates fans remember the high-water mark, 2018’s 14–10 with a 3.20 ERA, two complete games and a shutout. And they remember the trade, too. Pittsburgh sent Taillon to New York in 2021 for Roansy Contreras, Maikol Escotto, Canaan Smith, and Miguel Yajure; fair to say the return hasn’t come close to matching the accumulated value Taillon’s logged since.

That’s the gut punch of tonight: it compresses two eras of second-guessing into nine innings. Priester is the breakout who slipped through the fingers. Taillon is the steady postseason adult in the room who had to become that somewhere else.

And it’s not a one-off pattern. This has been the tension line for years — an organization that keeps promising the next wave of arms while providing rival highlight reels when those arms finally ripen. Even with legitimate pitching talent moving through the system now, nights like this stir the doubt: will the Pirates develop and keep the right ones this time?

The history lesson only sharpens the edge, from Gerrit Cole’s post-Pittsburgh ascension to names like John Candelaria, Joe Musgrove and Taillon himself — arms that either found new chapters elsewhere or, worse, reminded everyone what the Pirates once had. Pittsburgh’s pitching timeline is littered with reminders that the evaluation-and-retention part of the puzzle matters as much as drafting and dreaming.

So, yes, Cubs–Brewers is a great October watch on its own. But inside Pittsburgh, it’s something else: a referendum on process. If Priester buries Chicago, the “how did this happen?” chorus gets louder. If Taillon shoves to extend the series, the “why couldn’t that be us again?” whispers return. Either way, the lesson is the same for the Pirates’ front office as the next wave arrives: identify correctly, develop relentlessly, and when you finally get the good ones, hold on tight.