Cicero, Illinois
Cicero was once called Al Capone's "private playground." Naturally, that type of criminal activity did not breed very successful growth in the area. After the crime boom of the 1920s, the city has endlessly tried to retake its name.
Officials desparately wanted the city to lose it's notoriety. In 1999, they even voted to force known gang members to leave the city or face a daily $500 fine. Nothing much has changed since then.