Ask your average sports fan to name the Greater Chicagoland area's most ignominious loser, and he or she will almost certainly offer up the Chicago Cubs. Fair enough. The Cubs last won the World Series in 1908, and 1908 was an extremely long time ago. The lore of their losing is mythical, from the Billy Goat to Steve Bartman, and only adds to their fame.
But this is an incorrect answer. The correct one, as most good college basketball fans -- and any Northwestern alum -- would know, is the Northwestern men's basketball team.