I've railed for years at people who suggest Cubs and Red Sox fans are/were the most tortured fans in sports. Bullshit, Cleveland wins hands down, sure the Cubs haven't won since since 1908 and the Red Sox hadn't won since 1918 but ya know what? Those cities had other winners. Chicago had the Bulls and the Bears (and recently the White Sox) while Boston fans had the fucking Celtics and more recently the Patriots. Cleveland? Nada.
Papa Cass breaks down the curse a bit more.