6. Pearl Elliott

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She shared ties with John Dillinger and Harry Pierpont, but Elliott was no hanger-on or gun moll. Instead, she was a notorious madam. She owned a whorehouse in Kokomo, Indiana that boasted police protection. To help keep things at her rural brothel safe, they had a system where she'd shine a flashlight out a window to signal for help should some john get out of hand.

Her establishment also served as a hideout for Pierpont's crew following a 1925 bank robbery. Later, her role as "treasurer" for Dillinger earned her a spot on the 1933 Public Enemies list, which ordered officers to "shoot to kill." Despite her illegal operation and dangerous dealings, Elliott did not die in a hail of gunfire or in prison. She passed away on August 10, 1935, from an illness that may have been cancer. She was 47.

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