Last Updated: June 17th, 2026 by Michael Schatz
Baseball history is filled with dramatic moments that changed the course of games, careers, and even the sport itself. From crucial fielding errors to questionable managerial decisions, these ten moments represent the most significant blunders that have left an indelible mark on America’s pastime.
Don't lose this article. Enter your email below, and I'll send it to you right now. Plus, we'll send you other unbelievable stories from baseball's past.
Bill Buckner’s Fatal World Series Fumble (1986)
In Game 6 of the 1986 World Series, Boston Red Sox first baseman Bill Buckner committed one of baseball’s most infamous errors. With two outs in the tenth inning and the Red Sox one out away from their first championship since 1918, Mookie Wilson’s routine ground ball rolled through Buckner’s legs, allowing the winning run to score. The error became a symbol of the “Curse of the Bambino” as the Mets went on to win Game 7 and the Series.
Fred Merkle’s Boneheaded Baserunning (1908)
Nineteen-year-old Fred Merkle’s infamous baserunning error cost the New York Giants the 1908 pennant. In a crucial game against the Cubs, Merkle failed to touch second base on what should have been a game-winning hit. The Cubs noticed, forced him out, and won the replayed game and eventually the pennant by a single game. The play became known as “Merkle’s Boner” and haunted the young player for the rest of his career.
Mickey Owen’s Dropped Third Strike (1941)
Brooklyn Dodgers catcher Mickey Owen’s dropped third strike in Game 4 of the 1941 World Series changed everything. The Yankees’ Tommy Henrich reached first safely on what should have been the final out, sparking a four-run rally. The Yankees won the game and took the Series the next day, transforming what should have been a Series-tying Dodgers win into a devastating loss that changed baseball history.
Don Denkinger’s World Series Call (1985)
Umpire Don Denkinger’s controversial call in Game 6 of the 1985 World Series altered the series outcome. He ruled Kansas City’s Jorge Orta safe at first base when replays showed he was clearly out. This ninth-inning call sparked a Royals comeback victory, and they went on to win Game 7. The Cardinals never recovered from this controversial decision, which remains one of baseball’s most disputed calls.
Steve Bartman Incident (2003)
The infamous Steve Bartman incident occurred during Game 6 of the 2003 NLCS when the Cubs fan deflected a foul ball that left fielder Moises Alou might have caught. The Cubs, leading 3-0 and just five outs from their first World Series since 1945, completely unraveled afterward, allowing 8 runs in the inning. This moment became a symbol of the Cubs’ century-long championship drought.
Babe Ruth’s World Series Baserunning Blunder (1926)
In one of baseball’s most bizarre World Series endings, Babe Ruth was caught stealing second base for the final out of the 1926 World Series. The Yankees were trailing the Cardinals by one run, with Bob Meusel (.315 hitter) at the plate and Lou Gehrig on deck. Ruth’s inexplicable decision to attempt stealing ended the Yankees’ chances and handed the Cardinals the championship.
Grady Little’s Pedro Martinez Decision (2003)
Red Sox manager Grady Little’s fateful decision to leave a tired Pedro Martinez in Game 7 of the 2003 ALCS against the Yankees proved disastrous. Despite having closer Alan Embree ready in the bullpen, Little stuck with Martinez, leading to a Yankees comeback victory. This managerial blunder cost Little his job and became a defining moment in the intense Red Sox-Yankees rivalry.
Jim Joyce’s Perfect Game Mistake (2010)
Umpire Jim Joyce’s incorrect call at first base cost Detroit Tigers pitcher Armando Galarraga a perfect game with two outs in the ninth inning. Joyce called Cleveland’s Jason Donald safe when replays showed he was clearly out. While Joyce admirably admitted his mistake afterward, this error became a catalyst for implementing expanded replay review in baseball.
Fred Snodgrass’s World Series Drop (1912)
Giants outfielder Fred Snodgrass’s dropped fly ball in Game 8 of the 1912 World Series led to the Red Sox scoring the winning run and claiming the championship. Known as “Snodgrass’s Muff,” this error demonstrated how a single moment could define a player’s entire career, similar to Merkle’s infamous play, and became one of baseball’s most memorable World Series blunders.