Our city's history of sports tragedy is well documented and likely burned on your mind for all of eternity, and thankfully writer Neil Paine digs up some silver linings.
When I plugged Cleveland teams’ basic championship probabilities (i.e., if a team played in a 30-team league, its chance of winning the championship would be 1 in 30) into the simulation, their expected number of championships since 1903 was 12.4. That’s only 0.4 more than they actually won in real life, even after going nearly a half-century without any titles at all. So, if you take the long view, Cleveland hasn’t been cursed at all. Its teams simply front-loaded their championships, winning 5.2 more than random chance says they should have over the 62 years between 1903 and 1964.
A nice way of looking at things, it would seem. Paine admits he's oversimplifying things there (seasons being variable in terms of individual team/division dynamics and such), which makes the rest of his stats-heavy article well worth the click.
(It's worth noting that he does concede the point that "[e]xactly why Cleveland’s been so bad for so long is beyond the scope of this article.")
But give us the bottom line, good sir! Paine transposes the probability of post-season success in Cleveland against that in New York, which makes for a less than thrilling perspective. Overall, he claims (variables and all) that the odds of city going 49 years without a championship (Cleveland!) clock in around 2.9 percent (about, say, 1-in-34ish).