View Video!
Rose O'Neal Greenhow was a well-known person in Washington, DC, before the Civil War. President James Buchanan was her close friend. She liked to attend sessions of Congress and Supreme Court hearings. Greenhow would eventually write about her decision to support the South "I had a right to my political opinions. I am a Southern woman, born with revolutionary blood in my veins. Freedom of speech and of thought were my birthright, guaranteed, signed and sealed by the blood of our fathers."

Greenhow was recruited into the spy ring headed by Colonel Thomas Jordan. Soon Greenhow was leading a large network of Confederate spies operating in Washington, DC. Her network included dentists, professors, architects and cooks and spanned as far as New Orleans, Boston and across the ocean to London.

Union generals and politicians continued to be charmed by Greenhow, visiting her well into the war. Even Greenhow's own daughter did not suspect her of being a spy.

Greenhow's relaying of information proved invaluable to the Confederacy victories during the early months of the war. Confederate President Jefferson Davis even went so far as to tell Greenhow "but for without you, there would have been no Bull Run."

Greenhow's luck began to change in August, 1861, when she was arrested for spying by famed detective Allan Pinkerton. She recounted her arrest in her book My Imprisonment and the First Year of Abolition Rule at Washington:

On Friday Aug. 23, 1861, as I was entering my own door on returning from a promenade, I was arrested by two men, one in citizens clothes and the other in the dress of an officer of the United States Army. This latter was called Major Allen, and was the chief of the detective police in the city. They followed close upon my footsteps. As I ascended my steps the two men ascended also before I could open the door and asked "Is this Mrs. Greenhow?" I answered "Yes. Who are you and what do you want?" "I come to arrest you." "By what authority?" The man Allen, or Pinkerton (for he had several aliases) said: "By sufficient authority." I said: "Let me see your warrant." He mumbled something about verbal authority from the War and State Department and then they followed me into the house. By this time the house had become filled with men, and men also surrounded it outside like bees from a hive. An indiscriminate search now commenced throughout my house. Men rushed with frantic haste into my chamber. My beds, my wardrobes were all upturned. My library was taken possession of and every scrap of paper was seized.
The evidence gathered at Greenhow's house is still preserved in the National Archives in Washington, DC.

Although Greenhow was able to destroy the secret documents she was hiding on her person before being strip-searched, she was kept prisoner in her own house for six months, and the heavily guarded residence became known as "Fort Greenhow." But house arrest didn't stop Greenhow from relaying messages to Confederate forces. In January, 1862, the decision was made to move Greenhow to the Old Capitol Prison. Greenhow wrote of how she learned of the move in My Imprisonment and the First Year of Abolition Rule at Washington:

On Saturday, January 18th, at two o'clock, I learned incidentally, that I was to be removed from my house to another prison. I was sitting in my library reading. I immediately sent for the officer of the guard to know the facts. He told me he had orders not to communicate with me on the subject, but he would go to the Provost Marshal and obtain further instructions. He returned with orders fixing the hour of my removal. Detective Allen [Pinkerton] had the ordering and regulations of the arrangements. A covered wagon surrounded by a file of soldiers was ordered by Allen to be my conveyance to my prison. Believing that I should feel humiliated by this indignity, Lieutenant Sheldon however positively refused to obey this order.
Life in the Old Capitol Prison was harsh. Greenhow was completely cut off from the outside world. She was confined to a 10 by 12-foot cell with only a straw bed, a wooden table, and a water glass. She ate only soldiers rations, and all of her outgoing letters were subjected to a chemical treatment in an attempt to find treasonous information.

Greenhow still had powerful Union friends, and in June, 1962, she won her release from the Old Capitol Prison, but was exiled from Federal lines. She moved to Richmond, VA, and after meeting with Jefferson Davis, set off for Charleston, SC. She meant to run the Union blockade and set sail for Europe, but the lack of vessels made the trip impossible. Greenhow then traveled to Wilmingon, NC, and made the trip to Bermuda and then to England and France.

While in France, Greenhow met with Napoleon III. In England, she met Queen Victoria and wrote My Imprisonment and the First Year of Abolition Rule at Washington, which was published by Richard Bentley.

On August 10, 1864, Greenhow set sail for a return trip to the Confederacy, secretly carrying gold for the Confederate cause either in a purse around her neck or in a belt around the waist. But the ship encountered rough weather as it was preparing to run the Union blockade on September 30. Greenhow argued with the captain to let her go ashore in a boat. At first the captain refused, but eventually relented.

A few yards from the ship the smaller boat capsized. While others in the boat were saved, Greenhow, weighed down by the gold, drowned. Her body washed up on the shore, and lay in state in Wilmington, North Carolina. She was buried with full military honors in Wilmington's Oakdale Cemetary.

Every year on May 10, which is the Confederate Memorial Day, United Daughters of the Confederacy place flowers upon Greenhow's grave.