Last Updated: June 17th, 2026 by Matthew Brown
Baseball history often hangs by a thread—a single pitch, a split-second decision, or a bounce of the ball that goes one way instead of another. These moments, frozen in time, tantalize us with their possibilities. What if things had gone differently? How would the story of baseball have changed? Let’s explore some of the game’s most pivotal crossroads.
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What If Merkle Had Touched Second Base in 1908?
One forgotten base touch changed baseball forever. If 19-year-old Fred Merkle had simply completed his run to second base, the Giants, not the Cubs, would have won the 1908 pennant. Instead, it became baseball’s most infamous mental error, and the Cubs’ last championship for 108 years came gift-wrapped in controversy.
What If Willie McCovey’s Line Drive Was Two Feet Higher?
With two outs in the ninth inning of Game 7 of the 1962 World Series, runners on second and third, McCovey’s screaming liner found Bobby Richardson’s glove instead of right field. If that ball had been just slightly higher, the Giants would have won their first San Francisco championship, and the Yankees’ dynasty might have ended differently.
What If Gibson Had Been Too Injured to Bat?
Kirk Gibson could barely walk that night in 1988, and by all logic, should have stayed in the clubhouse. If Tommy Lasorda hadn’t sent him to bat, Dennis Eckersley closes out Game 1, the A’s likely win the Series, and one of baseball’s most magical moments never happens. Instead, a hobbled hero gave us an impossible ending.
What If Bevacqua Had Caught Buckner’s Ball?
Few remember that Dave Stapleton usually replaced Bill Buckner for defense late in games. If manager John McNamara had made that routine substitution in Game 6 of the ’86 Series, the Red Sox curse might have ended that night. Instead, Buckner’s error extended Boston’s heartbreak for another 18 years.
What If Lonnie Smith Hadn’t Been Deked in ’91?
Chuck Knoblauch’s phantom double-play fake in Game 7 of the ’91 Series kept Lonnie Smith from scoring on Terry Pendleton’s double. Without that masterful deke, the Braves likely win their first Atlanta championship, and the Twins’ miracle season ends in heartbreak instead of jubilation.
What If Jeffrey Maier Hadn’t Reached for That Ball?
A 12-year-old’s reach in the 1996 ALCS changed the course of two franchises. If young Jeffrey Maier hadn’t interfered with Derek Jeter’s fly ball, the Orioles might have won that series, preventing the start of the Yankees’ dynasty. One fan’s hand altered the balance of power in the American League for years to come.
What If Grady Little Had Pulled Pedro?
The fateful conversation on the mound in Game 7 of the 2003 ALCS haunted Boston for years. If Grady Little had gone to his bullpen instead of leaving an exhausted Pedro Martinez in to face the Yankees, the Red Sox might have broken the curse a year earlier. Instead, Aaron Boone wrote another chapter in the rivalry’s lopsided history.
What If Don Denkinger Had Called Orta Out?
One missed call in Game 6 of the 1985 World Series changed everything. If Denkinger had correctly called Jorge Orta out at first base, the Cardinals likely win their second title in four years. Instead, the Royals rallied for their first championship, and Denkinger’s name became forever linked to baseball’s human element.
What If Bucky Dent Had Faced a Different Pitcher?
Mike Torrez had been the Red Sox’s World Series hero just a year earlier. If manager Don Zimmer had gone to his bullpen in that 1978 playoff game, Bucky Dent might have remained just another light-hitting shortstop. Instead, one unlikely swing created a nickname that still makes Boston fans cringe.
What If Steve Bartman Had Stayed Home?
Five outs away from their first World Series since 1945, the Cubs watched it all unravel after a foul ball interference. If Bartman hadn’t reached for that ball, Moises Alou might have made the catch, and the Cubs’ curse might have ended eleven years earlier. Instead, one fan’s instinctive reach became Chicago’s newest curse.
What If Fred Snodgrass Hadn’t Dropped the Ball?
A routine fly ball in the 1912 World Series turned into baseball’s first famous error. If Snodgrass had caught that simple pop-up in Game 8, the Giants would have won the Series. Instead, his “million-dollar muff” gave the Red Sox new life and changed both franchises’ trajectories.
What If Carlton Fisk’s Ball Had Gone Foul?
The most famous body-english in baseball history kept that ball fair in Game 6 of the ’75 Series. If Fisk’s dramatic homer had hooked foul, we’d have lost one of baseball’s most iconic images. Instead, his midnight wave created the template for every dramatic home run celebration that followed.