Last Updated: June 17th, 2026 by Michael Griffin
When it comes to sports, there are always victors and those who suffer defeat. It’s important to remember that while these moments made some fans giddy, they also brought heartbreak to others. Also, in many of these instances, the moments recalled weren’t the final dagger (like Joe Carter’s home run off Mitch Williams) but only served as a wound that would be fatal to their championship hopes a game or two later.
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 Grounder (1986 World Series)
One slow roller through the legs, and 68 years of Red Sox frustration found its defining moment. With Boston one out away from their first championship since 1918, Mookie Wilson’s routine grounder somehow escaped Bill Buckner’s glove, allowing Ray Knight to score the winning run. The cruel irony? Buckner, one of baseball’s most reliable first basemen, had been routinely replaced for defense late in games. Still, manager John McNamara left him in to “be on the field for the celebration.” The Sox would see another lead crumble in Game 7 as Shea rocked with delirious Mets fans.
Cubs Fan Steve Bartman’s Foul Ball Nightmare (2003 NLCS)
Five outs from their first World Series since 1945, the Cubs watched their dreams unravel after a fan named Steve Bartman reached for a foul ball, preventing Moises Alou from making the catch. What followed was an eight-run Marlins rally that seemed to confirm every curse ever whispered about the Cubs. The image of Bartman being escorted from Wrigley Field, wearing his green turtleneck and headphones, became an unfair symbol of 95 years of Cubs futility.
Red Sox’s Bucky “Bleeping” Dent Disaster (1978)
The light-hitting Yankees shortstop with just 40 career homers chose Game 163 to break Boston’s heart. With the Red Sox leading 2-0 in the seventh, Dent’s three-run shot barely cleared the Green Monster, silencing Fenway Park and completing New York’s improbable comeback from a 14-game deficit. The homer earned Dent a permanent middle name in New England that can’t be printed in family newspapers.
The Angels’ Tragic 9th Inning Collapse (1986 ALCS)
One strike away from their first World Series, the Angels watched their dreams dissolve in a nightmare ninth inning. Dave Henderson’s home run off Donnie Moore turned certain victory into devastating defeat, launching a Red Sox comeback from a 3-1 series deficit. The moment haunted Moore, whose tragic death three years later gave this baseball story a heartbreaking human dimension.
Cleveland’s Jose Mesa Meltdown (1997 World Series)
Cleveland was three outs away from their first title since 1948 when closer Jose Mesa couldn’t hold a one-run lead in Game 7. The Marlins tied it in the ninth and won it in the 11th, extending Cleveland’s championship drought. The moment sparked a bitter feud between Mesa and teammate Omar Vizquel that lasted years after their playing days.
Yankees’ 2004 ALCS Implosion: The Stolen Sox Revenge
No team had ever blown a 3-0 playoff series lead until the mighty Yankees made history in the worst way possible. After Dave Roberts’ steal sparked an extra-inning comeback in Game 4, the unthinkable happened: Boston won four straight, including a Game 7 victory in the Bronx that silenced 86 years of “1918” chants forever.
Grady Little’s Pedro Martinez Gamble (2003 ALCS)
With a fresh bullpen and Pedro Martinez clearly running on fumes, Red Sox manager Grady Little made a visit to the mound in the eighth inning of Game 7. What followed – leaving Pedro in despite his obvious fatigue – became one of baseball’s most second-guessed decisions. The Yankees rallied to tie, won it on Aaron Boone’s homer in the tenth, and Little never managed another game in Boston.
Pirates’ Sid Bream Heartbreak (1992 NLCS)
The slowest runner in baseball somehow beat Barry Bonds’ throw home, ending Pittsburgh’s season in gut-wrenching fashion. Sid Bream’s slide represented more than just a Game 7 loss – it marked the end of the Pirates’ competitive era and the beginning of a 20-year losing streak that would become the longest in North American sports history.
Giants’ Epic Collapse to Angels (2002 World Series)
Eight outs away from their first San Francisco title, with a 5-0 lead and Barry Bonds crushing everything in sight, the Giants watched it all slip away. The Angels’ comeback denied Bonds his only real shot at a ring and kept the Giants’ championship drought alive for another eight years. The sight of manager Dusty Baker’s son being pulled from home plate by J.T. Snow became the lasting image of a series that got away.
Phillies’ Dynasty-Ending Stunner (2011 NLDS)
The 102-win Phillies watched their golden era end in cruel fashion, as Ryan Howard crumpled to the ground with a torn Achilles on the final out. Roy Halladay’s gem went to waste in a 1-0 loss to Chris Carpenter and the Cardinals, marking the last playoff appearance for one of the greatest Phillies teams ever assembled. The dynasty died as Howard lay in the dirt, unable to rise.
Bobby Thomson’s “Shot Heard ‘Round the World” (1951)
The Brooklyn Dodgers led the Giants by 13½ games in August, only to watch it vanish in a playoff game that ended with baseball’s most famous home run. Ralph Branca’s pitch to Bobby Thomson became the stuff of legend, while Brooklyn’s collapse represented the darkest moment in the borough’s baseball history until the team left for Los Angeles six years later.
Oakland’s Kirk Gibson Nightmare (1988 World Series)
The mighty Oakland A’s watched helplessly as Kirk Gibson, barely able to walk, somehow launched Dennis Eckersley’s backdoor slider into the right field seats. The hobbled hero’s home run in Game 1 deflated the heavily favored A’s, who never recovered and lost the Series in five games. Eck’s gesture of disbelief as the ball cleared the fence became an eternal symbol of October’s unpredictability.
Wohlers’ World Series Nightmare to Leyritz (1996)
The Braves were six outs from taking a commanding 3-1 World Series lead when Jim Leyritz turned the baseball world upside down. His three-run homer off Mark Wohlers not only erased Atlanta’s lead but sparked a Yankees dynasty. The moment marked the beginning of the end for the Braves’ dominance of the National League and haunted Wohlers for the rest of his career.
Cardinals’ Denkinger Call and Clark’s Cruel Twist (1985 World Series)
Don Denkinger’s missed call at first base in Game 6 sparked a Cardinals collapse that included a cruel twist of fate for Jack Clark. Just days after his heroic home run knocked out the Dodgers in the NLCS, Clark’s dropped pop-up contributed to the Cards’ unraveling. The championship ring that seemed destined for St. Louis ended up in Kansas City, where they still toast to Denkinger’s vision.
The Dodgers’ Jack Clark Catastrophe (1985 NLCS)
Tom Niedenfuer’s fateful fastball to Jack Clark with first base open became the stuff of Dodger nightmares. Clark’s towering home run into the left field seats at Dodger Stadium silenced the crowd and ended LA’s season in shocking fashion. Manager Tommy Lasorda’s decision to pitch to Clark rather than walk him with first base open remained a topic of debate in Southern California for decades.