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Shocktober: The Biggest Upsets in World Series History

2025

Synopsis

Baseball’s October showcase has provided some high drama over the years. Willie Mays’s spectacular catch in 1954, Bill Mazeroski’s walk-off homer in 1960, and Kirk Gibson’s pinch-hit blast in 1988 are just a few of the memorable moments that have dominated highlight reels. The outcome of the Series has not always been terribly surprising—especially during the late 1940s and early 1950s when the Yankees captured five consecutive championships, breaking their previous record of four straight titles from 1936 to 1939. But in spite of its predictability at times, the Fall Classic has taken many unexpected turns. The 1906 Cubs lost to the weak-hitting White Sox after establishing a new regular season record for wins. The 1955 Dodgers avenged seven prior October failures with an improbable victory over the seemingly invincible Yankees. And in 1969, the Mets finally shed their image as “loveable losers,” dethroning the powerful Orioles. In more than a century of World Series plays, a number of similar scenarios have emerged. Twenty-two of those stories are told in Shocktober.

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