Skip to content

Rose O’Neal Greenhow, The Civil War Spy Who Smuggled Secrets To The Confederacy

Rose O’Neal Greenhow, The Civil War Spy Who Smuggled Secrets To The Confederacy

When thinking of influential spies during the Civil War, names like Harriet Tubman and Belle Boyd may come to mind. However, there is another remarkable figure who played a crucial role in the conflict – Rose O’Neal Greenhow. Her contributions to the Confederate cause were so significant that she was buried with full military honors after tragically drowning in 1864.

A Remarkable Journey from Humble Beginnings to High Society

Rose O’Neal Greenhow was born around 1815 on a small farm in Maryland. Her early life was filled with tragedy, as her father was killed by an enslaved man when she was just a girl. Afterward, she and her siblings were separated and placed in the care of various relatives.

At the age of 13 or 14, Greenhow moved to Washington D.C., where she lived with an aunt who ran an elite boarding house. Despite her admiration for the capital’s social scene, Greenhow initially struggled to establish herself within it. However, her life changed when she met and married Dr. Robert Greenhow, a federal librarian and translator, around 1835. With her husband’s support, Rose entered the upper echelons of Washington society, befriending prestigious individuals such as former First Lady Dolley Madison, South Carolina Senator John C. Calhoun, and President James Buchanan.

Choosing Sides: Loyalty to the Confederacy

After briefly living on the West Coast, Rose O’Neal Greenhow returned to Washington D.C. a widow in 1854. The election of President Abraham Lincoln in 1860 divided the nation, and Greenhow, passionate about her southern roots and pro-slavery beliefs, made the fateful choice to support the Confederacy.

Proud of her heritage and determined to aid the South, Greenhow agreed to organize a spy ring for Lieutenant Colonel Thomas Jordan, an assistant to Confederate General P.G.T. Beauregard. Her mission was to gather vital information that could give the Confederate forces an advantage.

A Decisive Contribution to the Confederacy

Rose O’Neal Greenhow’s espionage efforts proved instrumental in the Confederate victory at the First Battle of Bull Run. When she learned of Union forces planning to march on Manassas, Virginia, Greenhow sprang into action. She employed a young woman named Bettie Duvall to deliver a coded message to Beauregard and his headquarters in Fairfax, Virginia.

Thanks to Greenhow’s warning, the Confederate troops were prepared, and to the surprise of many, emerged triumphant in the battle. Confederate President Jefferson Davis attributed their success to her invaluable contribution.

The Capture and Unyielding Dedication

Following the First Battle of Bull Run, Rose O’Neal Greenhow’s spy network continued to operate in Washington D.C., transmitting crucial information to Beauregard and other Confederate forces. However, her activities did not go unnoticed. Allan Pinkerton, Head of the U.S. Intelligence Service, became suspicious of Greenhow and placed her under surveillance.

Pinkerton’s suspicions were confirmed when his agents caught a Union soldier passing battle maps to Greenhow. A subsequent search of her home uncovered a vast trove of sensitive materials, including letters, maps, notes, and her encrypted messages. Despite being placed under house arrest, Greenhow persisted in her espionage activities, even using her daughter to smuggle messages written inside candy wrappers.

Imprisonment and Banishment

Inevitably, Rose O’Neal Greenhow’s activities caught up with her. She was arrested and imprisoned in the Old Capitol Prison alongside her daughter, “Little Rose.” Despite her confinement, her dedication to the Confederacy remained unwavering. Union officials eventually banished her from the North in 1862, and she returned to the South a celebrated hero.

The Tragic End of a Confederate Spy

Rose O’Neal Greenhow’s European diplomatic trip would be her ultimate downfall. While traveling through France and Britain, she met with Emperor Napoleon III of France and Queen Victoria of England, and even became engaged to a British earl. However, disaster struck as she sailed home with $2,000 in gold earned from her book sales and intended for the Confederacy.

Off the coast of Cape Hatteras, North Carolina, the British blockade runner Condor, carrying Greenhow, was confronted by the Union vessel, U.S.S. Niphon. During the encounter, the Condor was run aground, and Greenhow attempted to escape in a lifeboat. Tragically, the boat capsized, and weighed down by the gold she wore, Greenhow drowned.

The Confederate spymaster’s body washed ashore the next day and was laid to rest with full military honors at Oakdale Cemetery in Wilmington, North Carolina, wrapped in a Confederate flag.

The Legacy of Rose O’Neal Greenhow

Rose O’Neal Greenhow’s remarkable story highlights her loyalty, unwavering dedication, and role as a vital Confederate spy during the Civil War. Her influence on the course of the conflict and her tragic end make her a figure worth remembering.

To delve further into the fascinating stories of this era, read about Mary Bowser, the enslaved woman turned Union spy who played a significant role in dismantling the Confederacy. Additionally, explore captivating color photographs depicting the realities of the Civil War.