Pearl Elliott (nee' McDonald) did not fit the profile of other women of the Dillinger gang. Most women connected to Dillinger acted as wives and girlfriends of his gang members. Pearl differed in that she operated as an independent woman in her activities with Dillinger.
She operated a house of prostitution in Kokomo, Indiana as a madam.
The early 20th Century madams were fiercely independent women. Most were born in the 19th Century, coming of age in under dire economic circumstances. Many madams of the early 20th Century depended upon protection. Pearl operated her house of prostitution under the protection of her uncle, a political appointee. With a tight safety net around her enterprise, she kept her 21 room boarding house going for a decade, from the early 1920s to 1934.
As a rural madam, she used the "flashing light at the window" signal which notified the local police if there was an unruly male "guest" who needed to be thrown out. This method of obtaining police protection was a standard method used by rural madams, and is described in the famous book on prostitution, Polly Adler's "A House is Not a Home." FBI agents observing Pearl's house, would record in their memoranda that there was a "flashing light at the window" observed in Pearl's establishment.
She figured in the 1925 robbery of the South Kokomo, and New Harmony, Indiana bank robberies which were committed by Harry "Pete" Pierpont, Dillinger's closest friend in Michigan City Penetentiary. When arrested for complicity in the bank robbery, he failed to give information that would have incriminated her. He went to prison and she remained indebted to him. By 1933, she agreed to help Dillinger by holding receipts of several key bank robberies committed during the summer and fall of 1933. On September 26, 1933, Pierpont escaped from prison with eight other convicts. Along with Dillinger, John "Red" Hamilton, Charles "Fat Charley" Makley, and Russell Clark, Pierpont formed "The Terror Gang."
Pearl Elliott's husband, Dewey Elliott, shared the friendship with Pierpont. Dewey assisted by getting the gang established in Chicago, where he had connections with the Frank Nitti gang.
Pearl was known to Captain Matthew Leach, the head of the Indiana State Police. Through Leach, Pearl came to the attention of the FBI. By then, in early 1934, Pearl went on the lam with Dewey Elliott. She left her 21 room brothel in the care of another prostitute. Shortly thereafter, she became sick. She died in 1935, of cancer.
From her secret past to her untimely death, Pearl Elliott remained an enigma.