Here is a great article by Michael Wilbon of the Washington Post on the Cleveland Curse. He does a good job talking not only about Cleveland sports misery but how that misery, in some weird metaphysical way, a mirror for the troubles of the city itself.
I have to disagree with the guy Wilbon quotes on "The Fumble" and "The Drive" being the worst sports moments for Cleveland, though. I firmly believe that the Indians losing the '97 World Series was worse. Now, I'll admit that a large part of that sentiment comes from not being alive for The Fumble and The Drive, and for being a massive Indians fan in '97 (back then I was totally obsessed with the Indians--people who knew me in middle school can attest that I wore an Indians hat to school every day, memorized every big stat about the team, and could mimic every player's swing). But we were literally one out away--a couple pitches away--from winning the freaking World Series. It wasn't a semifinal game (which is essentially what the AFC Champion is). Jaret Wright had just thrown an incredible game in the best series of his career. Jose Mesa, Mr. Automatic during those years, was on the mound (I had forgotten just how good this guy was during that stretch--check out his stats from '95 to '97). And, still, we found a way to blow it.
Given the stage and how well things had been going for the Tribe up to that point, it's hard for me to say that anything was worse. This from a guy whose first sports memory is Jordan hitting "The Shot" over Craig Ehlo.
That's why tomorrow night is so exciting for me. Nobody expects the Cavs to beat the Spurs, whereas everyone expected the Indians to beat the Marlins. Hell, even I don't expect us to beat the Spurs. For some reason, I feel strangely zen about the fact that the Cavs are in the NBA Finals--maybe beating Detroit was too satisfying, but I think it comes from the fact that the Cavs are essentially playing with house money. And from the fact that I'd forgotten how exciting it is to have a team in the title hunt. For once, it feels good to be a Cleveland sports fan.