⚾ The Worst-of-Seven: Baseball’s Biggest Postseason Blunders

Baseball in October is usually about heroes, clutch hits, and storybook endings.
But sometimes, it’s about the opposite — moments that live forever for all the wrong reasons.

Mistakes. Miscues. Total meltdowns.
They happen to everyone, but when they happen in the postseason — especially with a season on the line — they become part of baseball legend.

That brings us to Orion Kerkering and the Philadelphia Phillies, whose 2025 NLDS ended on one of those nightmare moments.
The hard-throwing reliever’s error in Game 4 handed the Dodgers a walk-off win — and the Phillies, a stunning elimination.

Stat guru Jayson Stark called it the first walk-off error to end a playoff series — until fans reminded him of the 2016 “Donaldson Dash”, when Toronto swept Texas in similar fashion. Either way, it’s an extremely rare way to lose.

So, how does Kerkering’s mistake stack up among the most infamous October errors in MLB history?
Here’s our Worst-of-Seven ranking — where each game is unforgettable for all the wrong reasons.

7. Willie Davis — 1966 World Series, Game 2 (Dodgers vs. Orioles)

Think today’s outfield shadows at Dodger Stadium are bad? In 1966, the sun completely swallowed up Willie Davis.

In a 0–0 game, Baltimore’s Paul Blair lifted a routine fly ball to center. Davis lost it in the sunlight. Moments later, he misplayed another fly ball — and then launched an overthrow past third base. Three errors in six pitches.

The Dodgers never recovered, getting shut out for the rest of the series in what remains their only World Series sweep.

6. Orion Kerkering — 2025 NLDS, Game 4 (Phillies vs. Dodgers)

To be fair, comebackers to the mound can be trickier than they look.

But Orion Kerkering’s slow roller in a tied elimination game went from harmless to disastrous in seconds. He appeared to rush the play, bobbled the ball, then threw wildly to home — where Ha-Seong Kim scored the winning run anyway.

It didn’t blow a late lead or decide a Game 7, but it did end the season of a World Series favorite — and instantly entered the postseason blooper reel.

5. Daniel Murphy — 2015 World Series, Game 4 (Mets vs. Royals)

For much of that postseason, Daniel Murphy was the Mets’ hero. Then, his glove betrayed him.

With New York up 3–2 in the eighth, Eric Hosmer hit a routine grounder that slipped under Murphy’s glove, allowing the tying run to score. The Royals pounced, took the lead, and never looked back.

A night later, Murphy made another costly misplay as Kansas City clinched the title. From October legend to tragic figure in 24 hours.

4. Aaron Judge — 2024 World Series, Game 5 (Yankees vs. Dodgers)

When a superstar stumbles, it hits harder.

Aaron Judge, the Yankees’ MVP and usually sure-handed outfielder, had gone 57 postseason games without an error. That streak ended on a routine line drive to center.

Judge appeared distracted by a baserunner at first, dropped the ball, and opened the floodgates for a five-run Dodgers rally. The inning that should’ve ended quietly instead turned into a disaster — and New York never recovered.

3. Alex Gonzalez — 2003 NLCS, Game 6 (Cubs vs. Marlins)

Poor Steve Bartman will always be remembered for reaching into the stands — but Alex Gonzalez’s error was what truly doomed Chicago.

With the Cubs up 3–1 and a double-play ball rolling right to him, Gonzalez booted it. Instead of escaping the inning, Chicago melted down completely, allowing eight runs and losing the game — and the series the next night.

A World Series drought that had lasted 95 years would continue for another 13.

2. Tony Fernández — 1997 World Series, Game 7 (Cleveland vs. Marlins)

Few moments sting like this one.

Game 7. Extra innings. World Series on the line.

With one out in the 11th, Craig Counsell hit a routine grounder to Tony Fernández, a defensive wizard with four Gold Gloves. Somehow, the ball slipped under his glove. Three batters later, Édgar Rentería drove in the winning run — and Cleveland’s title drought lived on.

It’s one of the rarest heartbreaks imaginable: an error in extra innings of Game 7 of the World Series.

1. Bill Buckner — 1986 World Series, Game 6 (Red Sox vs. Mets)

The moment that defines baseball heartbreak.

The Red Sox were one out away from their first championship since 1918. Up 5–3 in the 10th, they watched the Mets tie it — then came the slow roller from Mookie Wilson.

The ball slipped between Bill Buckner’s legs, the Mets walked it off, and Boston’s “Curse of the Bambino” lived on. The Mets went on to win Game 7, while Buckner became the face of Red Sox pain for a generation.

Time eventually healed the wound — and Buckner received a standing ovation when he returned to Fenway in 2008 after Boston finally broke its curse.

⚾ The Fine Line Between Fame and Infamy

Baseball is a game of inches — and sometimes, those inches separate glory from disaster.
Each of these moments reminds us that even the greatest players are human, and that October baseball has a cruel way of turning routine plays into lifelong memories.

Maybe someday, Orion Kerkering will get his redemption story in red and white — just like Buckner finally did in Boston