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33. Pearl Elliott
There was no putting a stop to Pearl Elliott. She ran a thriving brothel out of Kokomo, Indiana. Her reputation as a madam alone made local police keep a close eye on her. However, the brothel was just the beginning of Pearl Elliott’s wild career. Perhaps most notably, Elliott played a major role in helping notorious gangsters John Dillinger and Harry Pierpont go about their unsavory business.
Once, she helped oversee a bank robbery committed by Pierpont. Pierpont was caught and interrogated, but he refused to let on that Elliott had anything to do with it. In 1933, Elliott was one of just two women to grace the public enemies list kept by the Chicago Police Department.
