For the White Sox, the Jerry Dybzinski baserunning blunder in Game 4 of the 1983 ALCS. The White Sox were trailing in the series (best of 5) two games to one, with Cy Young winner Lamarr Hoyt set to pitch if they could force a fifth game. Dybzinski overran second base to take the White Sox out of a bases-loaded-and-one-out situation in the bottom of the seventh inning of a 0-0 tie. The Sox eventually lost in 10 innings.
As a fan of my football team, there have been many. The worst for me would be “Fake Spike”
“The Drive.”
I’m not actually a football fan any longer, but that one still hurts.
Ahhh, one of my happiest sports “points of pleasure.”
Snatching defeat from the jaws of victory. I was a little young to have that effect me greatly but I do remember.
That was bad but I think the Diamondbacks beating them in 2001 was worse. If we ever needed a win that was the year.
My father was a diehard Brooklyn Dodger fan. It was pretty much all pain. Ending with them ripping his heart out in 1958.
Cleveland Indians: 1997 World Series, losing to the fucking Marlins and Jose Mesa losing his shit. Also there’s the oft-remembered but oft-forgotten The Catch by Willie Mays which was amazing for Willie Mays but not so great for the 1954 Indians in the World Series.
Cleveland Browns: Not only do we have the aforementioned The Drive, but also The Fumble and Red Right 88. Oh and that time our owner packed up and moved to Baltimore in the middle of the night.
Cleveland Cavaliers: The Shot, The Decision
Do other cities have such well-documented tales of woe? 
Hagler destroyed Leonard, no question, split decision my ass flips table, storms out of room
I was a Baltimore sports fan in 1969.
Are you talking about that time when the noted (loudly) devout christian Eugene Robinson went trolling for hookers on the eve of Atlanta’s only Super Bowl appearance?
On a business trip last year, I met someone from Cleveland; since I’m from Denver, it was one of the first things we talked about.
I don’t think he was even born in 1987; “The Drive” wounds him nonetheless.
One of my GREATEST MEMORIES EVER!!! Bottom of the ninth, two on. Line drive to left. Sid Bream rounding third, the best baseball player ever bounces the throw. Braves are going to the World Series.
Brings a tear to my eye.
The original “Hail Mary”
Yes, it’s this for me. I mean, what’s worse than losing your entire team?? And then watching that team go on to win Super Bowls while you’re left with a miserable expansion effort that mires in crap for over a decade.
One of those things that tends to come up in baseball oddity highlights, and that I happened to be watching live as it happened: Chan Ho Park surrenders two grand slams…both to Fernando Tatis…in the same inning. Link.
That play actually grows more painful each year.
At the time, it hurt but it wasn’t huge. The Bills had had a great season and made their first Superbowl appearance. Okay, they lost by a single point. But at the time we were confident they would come back and win the championship.
But then they kept losing Superbowls. And then they kept getting knocked out of the playoffs. And then they began not making the playoffs. And then they had a record streak for not making the playoffs.
So now that play stands as being as close as the Bills ever got to winning the championship. It’s all been downhill since then. Our peak was a failed play and we never had our moment of triumph.
Nebraska Cornhusker fan here, but I don’t think there were any catchy nicknames
For the heartbreakers, we lost 2 national championship games:
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1983 Orange Bowl: Rather than tie Miami and gain the national title, Coach Tom Osborne went for 2 to secure the win. They missed.
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1994 Orange Bowl: lost to heavily-favored Florida State, who benefitted from a phantom clip and uncalled fumble on a TD dive. Despite that, we outplayed them enough to have it come down to a missed NU field goal.
For the infamous:
- Lawrence Phillips: possibly the most talented I-back ever at Nebraska. Coed assaulted his fists with her face. Became a gigantic cloud over a perfect 1995 national championship and tarnished Coach Osborne’s legacy.
Hmm, just thought of one “catchy name”, but for Bayard’s sanity, I won’t mention the “Flea-Kicker”.
Kirk Gibson, 1988.
Ask Inter Milan about the 2005 European cup final, 3-0 up at half time against Liverpool and then…oops.
Or Bayern Munich in 1999, same competition. 1-0 up against Man. U. with the 90 minutes already gone…whoops! I’ve rarely seen a bunch of players quite so devastated in such a short time.
To be fair, In neither case was it the only glimpse of glary for either team but it definitely leaves a scar.
Probably worse when it turns out to be the only sniff you get, and you do it under the unforgiving, solo scrutiny of the camera, and the horror takes just long enough to allow grown men to contemplate it, flinch somewhat, then cover their eyes, then go into the next room. The time is just enough for the despair to grow to an acceptable size.
For that you need Jean Van de Velde at Carnoustie in 1999
I had to Google this one to find out what it was about. One of the results was an article quoting an anonymous Michigan player on that team who claimed that several of his fellow players took Appalachian State so lightly that they got stoned out of their gourds right before the game. At least one was involved in a game-affecting error.
Interesting, if true.
I’ll add two more to the NY Giants litany of pain:
The utter collapse in the playoff game vs. the 49ers after the 2002 season. After this one, the name “Trey Junkins” still gives GIants fans PTSD.
And there was that other collapse, this one against the Eagles during the 2010 season, punctuated by the Matt Dodge punt to DeSean Jackson that basically cost Dodge his NFL career. At least that one was followed a year later by the Jints’ crazy Super Bowl win after a 9-7 regular season.