The Milwaukee Brewers are one win from the NLCS, and the Pittsburgh Pirates ought to be studying how they got there.
Milwaukee didn’t reach 103 wins by stacking the league with headline names. The Brewers did it the harder way: depth, development, versatility and a roster with very few soft spots. That’s the model Pittsburgh should be chasing as it looks ahead to the offseason.
The part that should jump out first for the Pirates is that they already have the kind of pitching foundation Milwaukee would love to start with. Paul Skenes, Jared Jones, Bubba Chandler and Braxton Ashcraft give Pittsburgh a young rotation core that most teams would gladly build around, and there is more pitching depth behind them as well.
That’s the advantage. The question is what comes next. Can the Pirates build enough offense around that group to make the most of the years before elite, inexpensive pitching starts getting a lot more expensive?
Pittsburgh can enter 2027 with Skenes, Jones, Chandler and Ashcraft as the backbone of its rotation. That is a rare place to be. But a staff like that only goes so far if the lineup keeps handing out easy outs.
Milwaukee has shown a cleaner path. The Brewers built around Jackson Chourio, one of baseball’s brightest young stars, and then added established production from Christian Yelich and William Contreras, plus a deep mix of contributors like Brice Turang, Sal Frelick, Garrett Mitchell and others.
That gives manager Pat Murphy options. Different handedness.
Defensive versatility. Speed.
Enough bats that the lineup doesn’t depend on one or two hitters to rescue the whole night.
Pittsburgh, by contrast, has spent too many seasons with too many lineup spots built on hope. A young player needed to break out right away.
A reclamation project needed to find his swing again. A glove-first player had to become usable with the bat.
Someone coming off a bad year had to bounce back.
One of those bets is fine. Four or five becomes a roster problem.
That matters even more now because the Pirates finally have a pitching staff good enough to support an offense that is merely solid instead of overwhelming. They do not need to chase one splashy fix. They need depth.
Brandon Lowe’s free agency is part of that conversation. If Pittsburgh can’t keep one of its most productive hitters, it has to replace that production, not just move everyone else up a rung and hope the math works out.
The catching situation needs more clarity. The outfield needs more offense.
The Pirates also need a much better answer against left-handed pitching after finishing near the bottom of virtually every meaningful offensive category against southpaws this season. And if Konnor Griffin and Rafael Flores Jr. are part of the future, the Pirates need them to add to a functional lineup, not be asked to save one.
Milwaukee hasn’t erased uncertainty from roster building. No team does. But the Brewers have enough quality throughout the group that one injury, one slump or one missed projection doesn’t drag the whole offense down.
Pittsburgh is trying to get there.
The Pirates have already handled the hardest part: developing high-end starting pitching. Skenes is the centerpiece, but Jones, Chandler and Ashcraft give them something even more valuable than one ace - a chance to control a strong rotation for years.
That window won’t stay open forever. As those arms get older, arbitration costs rise and free agency gets closer, the bill gets bigger. The best advantage is right now, while so much of that group is still young and affordable.
So Milwaukee’s postseason run should feel less like something to envy and more like a lesson. The Brewers have built a roster with competence across the board, enough depth to survive the grind and enough offense that their pitching doesn’t have to be flawless every night.
Pittsburgh already has the rotation piece. This winter is about building the rest.
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Still, when McCutchen was asked to sort through all of it, he pointed to the Roberto Clemente Award in 2015 as the moment that meant the most. For a player whose Pirates legacy is built on both production and presence, that choice says plenty about how he has always viewed the game, and why his time in Pittsburgh has resonated well beyond the box score. [Read more 🡒]