Pirates should be embarrassed watching MLB’s smallest markets dominate October

The Pittsburgh Pirates have spent years explaining all the ways baseball's economic system makes their job harder. Then October arrives, and teams facing many of the same disadvantages keep making those explanations sound less convincing.

Look around the Division Series field. The Milwaukee Brewers finished with the best record in Major League Baseball. The Tampa Bay Rays finished with the best record in the American League. The Cleveland Guardians won the AL Central while carrying the lowest payroll in the sport.

All three are still playing. The Pirates are watching from home.

Milwaukee went 103-59, finishing three games ahead of the $300-million-plus machine in Los Angeles for MLB's best record. The Brewers won the NL Central by 14 games and finished a staggering 21 games ahead of Pittsburgh.

Milwaukee has become exactly what Pittsburgh has spent the Ben Cherington era claiming it wants to become: a sustainable small-market organization that drafts well, develops pitching, makes smart trades and continually finds useful major-league players without shopping at the very top of free agency.

The Brewers aren't operating with Dodgers money, either. Their Opening Day payroll ranked 19th in MLB at roughly $125.5 million. That is more than Pittsburgh spent, but it isn't another economic universe.

The Rays went 98-64, the best record in the American League, despite once again operating near the bottom of MLB's payroll rankings. They won the AL East over the Yankees, then opened their ALDS against New York with Drew Rasmussen carrying a no-hitter into the eighth inning of a 1-0 victory. By Monday night, Tampa Bay had taken the first two games of the series and moved within one victory of the ALCS.

The Rays' payroll entering the season was approximately $89.6 million — lower than Pittsburgh's roughly $102.1 million figure.

One of the Pirates' favorite implied defenses — that they simply cannot be expected to compete against organizations with greater financial resources — doesn't work very well when a team spending less money wins 16 more games and captures the best record in its league.

Pirates can’t blame payroll while Brewers, Rays and Guardians keep winning

Cleveland might be the most uncomfortable comparison of all. The Guardians finished the season with baseball's lowest payroll at approximately $74.2 million. They still went 85-77, won the AL Central and earned a first-round bye into the Division Series.

That doesn't mean Pirates fans should want Bob Nutting to look at Cleveland and decide spending less is suddenly the answer. Quite the opposite. The lesson is that limited resources make organizational competence even more important.

Milwaukee, Tampa Bay and Cleveland routinely identify players other clubs miss, develop pitchers, maximize depth and make difficult roster decisions before those decisions become obvious. When one star becomes too expensive, there is usually another player coming. When a weakness develops, they don't spend three seasons talking about how difficult that weakness is to fix. And when their competitive windows open, they actually take advantage of them.

The Pirates finally finished above .500 in 2026, going 82-80 for their first winning season since 2018. That's progress. It just isn't remotely enough to declare the rebuild successful, especially when the organization possesses a young pitching core built around Paul Skenes, Jared Jones, Bubba Chandler and Braxton Ashcraft.

The Pirates already have the part that small-market teams usually spend years desperately trying to build. Now they have to prove they know what to do with it.

Watching Milwaukee win 103 games should destroy the notion that an NL Central title is unrealistic. Watching Tampa Bay dominate the American League on an even smaller payroll should destroy the idea that Pittsburgh's financial limitations make contention impossible. Watching Cleveland reach October with MLB's lowest payroll should eliminate whatever remains of the belief that market size alone explains why the Pirates keep falling short.

There are legitimate structural problems in Major League Baseball. The Pirates operate under constraints the Dodgers, Mets and Yankees will never understand. But Pittsburgh isn't being judged against the Dodgers right now.

Organizations like Milwaukee, Tampa Bay and Cleveland face versions of the same problem and keep finding solutions. The Pirates keep finding excuses.

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