MLBSep 30
World Series possibilities offer drought breakers and a Chicago reunion
The 2026 playoff field could produce a small-market showcase, a long-awaited championship or a crosstown matchup not seen since 1906.
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Milwaukee and Tampa Bay offer a different style
With 12 clubs entering the postseason, the World Series has 36 possible matchups. For fans without a team to follow, the appeal could lie in how a series is played as much as who wins it. The Brewers and Rays would bring speed, defense and contact to the championship stage. Both finished in the bottom third in home runs but ranked among the top five in stolen bases. Tampa Bay also led the majors in sacrifice bunts and bunt hits. Milwaukee reached 100 wins for the first time despite relying heavily on rookie starters. A meeting with the Rays would pair the top regular-season clubs from each league, something that has happened just five times in the wild-card era.
Cleveland and San Diego chase relief
A Guardians-Padres matchup would guarantee an end to a lengthy championship wait. Cleveland last won the World Series in 1948, while San Diego has never claimed the title since entering the National League in 1969. Cleveland rookie Parker Messick would offer a compelling test for Fernando Tatis Jr. And Manny Machado. Messick posted a 2.55 ERA, while Tatis recovered from an extended early home run drought to become a major offensive force. Machado endured his weakest offensive season but still delivered 29 homers.
Chicago could revisit a distant rivalry
The Cubs and White Sox have not met in the World Series since 1906, when the White Sox upset a Cubs club that had won 116 games. Another meeting would spotlight an extraordinary White Sox turnaround after 121 losses in 2024 and 102 in 2025. The Cubs, meanwhile, would bring Pete Crow-Armstrong and his 40/40 season into the matchup. Crow-Armstrong already troubled the crosstown pitching staff during the regular season, batting.304 with four home runs across six games against the White Sox.
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