Olean garnered notoriety as a major stop on bootlegging routes during Prohibition in 1920s. Dempsey, the Chief of Police, did not condone these thugs or their illegal activities. He did not aggressively pursue arrests, however, unless he had evidence the violator was responsible for a crime committed in his jurisdiction. As long as you kept your nose clean in the Olean City limits, it was a "safe haven". Local stories relating to this period are numerous. Some are documented and some are legends. Olean, located on a back road route between Chicago and New York City, was often frequented by famous mobsters of the era. Al Capone of Chicago, probably the most famous gang leader of the time, visited Olean in pursuance of his illegal endeavors. Olean was nicknamed "Little Chicago" in the press, due to its connection with mobsters and bootleggers, and Capone was a frequent visitor.