Rose O’Neal Greenhow (c. 1815–1864) was the Confederacy’s most celebrated female spy at the start of the Civil War. A popular widow and hostess in Washington, D.C., she moved easily in the social circles of the nation’s capital. When hostilities commenced in the spring of 1861, few were better connected than she. An ardent Southern sympathizer, Greenhow used her ample charms and guile to pass along information on the defenses of Washington and Union troop movements to Confederate officials.
She is credited with alerting Southern rebels just prior to the Battle of Manassas. Her clandestine activities were so successful that noted detective Allan Pinkerton surveilled her. Although he put Greenhow under house arrest and ultimately had her jailed, she was always considered a security risk, given her extensive social connections.
This photograph of Greenhow with her daughter Rose was taken at the Old Capitol Prison by Alexander Gardner for Mathew Brady’s studio.