After her father was murdered by his slaves in 1817, Rose O'Neal was invited to move to Washington, D.C., to live at her aunt's stylish boarding house. She became an active member of the society circle there, ultimately meeting and marrying a well respected doctor who eventually left her a widow with seven children.
When the Civil War broke out, even though she lived in Washington, the seat of the Union, she was not secretive about her support for the Confederacy, so in fairly short order, she was recruited to be a spy for the South. Along with pro-Confederacy legislators and sympathetic Union officers, Greenhow passed critical information to the armies of The South and was, in fact, credited by Confederate President Jefferson Davis with the Confederate win at the battle of Manassas.
Even after she was placed on house arrest, military maps and other documents were found in her possession, so Greenhow was ultimately incarcerated in the Old Capitol Prison. Still, in-your-face as ever, she continued to pass information in all manner of creative ways, including in the bun of a woman visitor, and went so far as to fly a Confederate flag from the window of her cell! It's easy to see how she got her childhood nickname of "Wild Rose."
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