If you’re the Milwaukee Brewers, you’ve gotten pretty used to penciling the Pittsburgh Pirates in as “annoying, but beatable” on the NL Central bingo card. Young arms, a couple of dangerous bats, but never quite enough spending or star power to really tilt the balance of power. That’s why the noise coming out of Pittsburgh this winter should have Milwaukee’s attention.
The Pirates aren’t just talking about being more aggressive; they’re reportedly “in on” Kyle Schwarber and seriously considering handing the Opening Day shortstop job to the No. 1 prospect in baseball, 19-year-old Konnor Griffin. For a franchise that has made frugality a personality trait, even flirting with moves like that is a pretty loud change of tone.
Brewers can’t ignore how serious the Pirates suddenly look about Kyle Schwarber
From a Brewers perspective, this is exactly the kind of rival behavior that can quietly reshape a division if you’re not careful. Milwaukee has made a living exploiting the middle — drafting and developing at a high level, threading the needle on trades, and trusting their pitching infrastructure while other clubs waffled between rebuilding and contending. If the Pirates actually follow through on this new script, they stop being the patient, step-by-step project and start looking a lot more like a team trying to step on the gas at the same time the Brewers are juggling their own payroll questions.
The Schwarber piece is where the alarm bells really start to ring. According to ESPN’s Jeff Passan, the Pirates are legitimately in the Kyle Schwarber conversation, at least enough to register as a real suitor. On paper, it makes all the sense in the world for them: Pittsburgh finished dead last in MLB in runs, home runs, and RBIs in 2025. Schwarber just put up an NL MVP runner-up season, mashing 56 homers and driving in 132 runs. Dropping that kind of left-handed thunder into the heart of their order would instantly give Paul Skenes and that young rotation something they’ve barely had: margin for error.
The catch — and the reason Brewers fans are allowed a little skepticism — is the checkbook. This is still the Pirates, whose largest free-agent deal ever remains the three-year, $39 million contract they gave Francisco Liriano a decade ago. Schwarber is living in a completely different zip code financially, likely needing a five-year commitment well north of $100 million. He has obvious suitors in place already, led by a Philadelphia Phillies team that would love to keep him, plus big-market threats like the Boston Red Sox and New York Mets lurking around the bidding. History says the Pirates don’t win those kinds of auctions, and a lot of people in Pittsburgh assume “in on” means “called the agent, heard the price, and hung up.”
But even if Schwarber ultimately lands somewhere else, the intent coming out of Pittsburgh is what should have Milwaukee paying attention. Ben Cherington has been clear that there’s new financial flexibility and that the priority is upgrading an anemic offense. The Pirates reportedly took a real swing at first baseman Josh Naylor before he chose the Mariners and are now hanging around the Schwarber sweepstakes.
Then there’s the Griffin factor, which is easy to dismiss as prospect hype until you look at the profile. Pittsburgh is strongly considering giving the 19-year-old the chance to win the Opening Day shortstop job in 2026 after he rocketed to consensus No. 1 prospect status in his first full pro season. If they actually roll into the year with Skenes fronting the rotation, Griffin headlining the infield, Oneil Cruz roaming the outfield, and a serious attempt to add a bat like Schwarber, the Pirates stop being a “cute upstart” and start looking like a real problem in the same neighborhood Milwaukee is trying to defend.
For the Brewers, this doesn’t mean panic. It does, however, underline how quickly the NL Central can tilt if one of the long-dormant clubs wakes up and starts acting on its upside. Schwarber to Pittsburgh remains a long shot, but the fact the Pirates are even playing in that part of the market — while fast-tracking their top prospect and building around an ace — is a clear sign they’re done treating contention like a someday conversation. If they hit on even half of this plan, Milwaukee’s margin for error in the division gets a lot thinner, and the Brewers’ own brand of quiet aggression may have to keep pace.
