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Born in Bloomington in 1864 to a well-established family in McLean County, Florence Stevens was a teacher for brief time before her marriage to Harris Kaywood, but little is known about her during the years of her marriage. In 1910, she was appointed police matron by the Bloomington City Council, a position she held for the next 16 years. Police matrons were hired to take care of female prisoners and their children, which was by no means easy work. In 1919, she was credited with saving a woman who attempted suicide in her jail cell.