MLBSep 25
Brewers Lead October Pressure Watch as Dodgers Chase History
Milwaukee's breakthrough bid, Cleveland's title drought and Philadelphia's aging roster add urgency to the postseason, while Los Angeles faces a different burden.
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Milwaukee seeks the missing championship
The Brewers enter October with a franchise-best regular season behind them and their biggest ambition still unfulfilled: winning the World Series. Sustained contention has raised expectations without delivering a championship, and their 2025 NLCS loss to the Dodgers adds another layer of frustration. Los Angeles again represents the obstacle Milwaukee needs to overcome. San Diego faces a similar challenge, with the Padres also pursuing their first championship after years of waiting for a postseason run that ends with a parade. Cleveland's urgency comes from an even longer history. The Guardians have baseball's longest active championship drought, dating to 1948. Their 2016 American League pennant offered a breakthrough, but not the ultimate relief.
Veteran contenders feel the clock
Philadelphia's pressure is increasingly tied to its roster's age. The Phillies have the oldest team in MLB, making another October opportunity particularly valuable after several seasons of contention. Keeping Kyle Schwarber and J.T. Realmuto provided continuity, while Ranger Suarez departed. The central question now is how much longer this group can keep its championship window open. The Yankees carry a different kind of weight. A 34-year run of winning seasons and a recent American League pennant have not satisfied a franchise measured against championship expectations. For the Cubs, meanwhile, 10 years have passed since their drought-breaking title, and the current roster has a chance to create its own postseason identity.
Winning brings its own burden
Recent championships ease the historical pressure on the Dodgers, but they do not lower expectations. Payroll investment and an established standard of success leave little room for anything short of another title. Los Angeles also has history within reach: becoming the first National League team to win three consecutive World Series. Other contenders can approach October with fewer expectations. The White Sox have already exceeded forecasts by reaching the postseason, while Boston's recovery from a deep midseason hole gives its run a more celebratory feel.
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