Throughout the Civil War, many of the spies were slaves who were desperate for the North to win, and thus secure their freedom. These slaves, both men and women, risked their lives passing information on to the Union army. In addition to the slaves, there was also a great deal of spying being done by well-to-do white women. Women spying for either the North or the South used their large hoop skirts to hide weapons, secret documents and other contraband, as well as other means.

Rose O'Neal Greenhow was born in Port Tobacco, Maryland about1817, the orphan of a prosperous planter family. She was rich and attractive, and to the disappointment of her many admirers, she married, yet was widowed in 1854 from her husband Dr. Robert Greenhow, with whom she bore four daughters. She had been very active in the prewar Washington social scene, with such political figures as James Buchanan and John C. Calhoun, one of her closest companions. Because of her contacts, she was able to obtain sensitive, and sometime classified information for the Confederacy.

Being careless concerning her activities, she soon aroused the suspicion of Allan Pinkerton, a police detective and Union informer. Pinkerton arrested Rose in August 1861, and through a search warrant, found detailed maps of Washington fortifications, and numerous notes and letters outlining Union military troop movements. Placed under arrest and housed in local jails, she was finally moved to the Old Capitol Prison in January 1862. Rose's eight-year-old daughter, also named Rose and called Little Rose, was also imprisoned with her at the Old Capitol Prison. From prison she continued her spy activities, and was able to forward this information to the Confederacy. In May 1862, she was released from prison and deported to Richmond, Virginia. For a time in Richmond she was imprisoned in her home, where she still continued her clandestine activities.

In August 1863, she was sent by President Jefferson Davis to England and France on a diplomatic mission to plead the Confederacy's cause. While there she wrote and had published a book titled, "My Imprisonment and the First Year of Abolition Rule in Washington."

On October 1, 1864, Rose was returning to the United States on her blockade runner ship the Condor, when it was spotted by a Union warship off the coast of North Carolina. She reached the mouth of the Cape Fear River, outside of Wilmington, North Carolina when the Union ship gave chase. In the chase, the Condor ran aground on a sandbar in the early morning hours. A storm began, and Rose, fearing that the Condor would be captured, and she would be returned to prison, asked the captain to send her and two companions ashore in a small lifeboat. In the stormy waves, their boat capsized. Rose, who was carrying $2,000 in gold, at some point was forced under the water due to the weight of the gold.

Having drowned, her body was washed ashore and identified two days later. Rose Greenhow was given a military funeral and buried with honors in Washington, D.C. Each year her grave is decorated on Confederate Memorial Day.

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