1. Chicago Cubs, 107 Seasons
Tribe fans may be hard up, but at least there are living, breathing, people who can still recall the Indians’ win in 1948. The last time the Chicago Cubs won the Series was in 1908. That’s 107 seasons of futility.
Go to any Cubs’ bar in Wrigleyville and you probably won’t hear any 20-somethings reveling in the history of the four Hall of Famers who helped Chicago capture their last crown. The baseball immortals who played on that team included manager/first baseman Frank Chance, second baseman Johnny Evers, shortstop Joe Tinker and pitcher Mordecai Brown.
The Cubs drought is so bad, consider the team hasn’t appeared in the World Series since 1945–three years before the Indians won their last title!
The Cubs haven’t gotten as close to ending their drought as the Indians did in the late 1990s, but the franchise certainly had their opportunity in 2003–until the Bartman game.
Nobody is picking the Cubs in 2015, and that’s a good thing, because a Cleveland/Chicago World Series may signal the end of time.
Next: Longest World Series Droughts