Rose Greenhow:
A Spy in the Lion’s Den

Born to slaveholding parents in Maryland, Rose Greenhow was a Washington, D.C., socialite and a passionate sympathizer for the Confederate cause who became one of the most infamous Southern spies. A widow, she lived with her young daughter, Little Rose, on 16th Street Northwest near Lafayette Park, in close proximity to the White House, and was among the first Confederate secret agents in the capital.

In the pre-war years, Greenhow became acquainted with people at the highest levels of Washington society, including presidents and members of Congress. She socialized with then-Senator Jefferson Davis, the future President of the Confederacy, and considered Senator John C. Calhoun, the firebrand and ardent defender of slavery from South Carolina, a mentor.

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From top: Confederate President Jefferson Davis; Confederate Brigadier General Thomas Jordan; John C. Calhoun

Born to slaveholding parents in Maryland, Rose Greenhow was a Washington, D.C., socialite and a passionate sympathizer for the Confederate cause who became one of the most infamous Southern spies. A widow, she lived with her young daughter, Little Rose, on 16th Street Northwest near Lafayette Park, in close proximity to the White House, and was among the first Confederate secret agents in the capital.

In the pre-war years, Greenhow became acquainted with people at the highest levels of Washington society, including presidents and members of Congress. She socialized with then-Senator Jefferson Davis, the future President of the Confederacy, and considered Senator John C. Calhoun, the firebrand and ardent defender of slavery from South Carolina, a mentor.

At the outset of the war, Greenhow was asked by Lieutenant Colonel Thomas Jordan, an assistant to General P.G.T. Beauregard, the commanding general of nearby Confederate forces, to organize a spy ring in Washington, D.C., among Southern sympathizers that could provide information on Union military activities. She immediately agreed.

Greenhow became a driven and enthusiastic agent, later described by the Provost Marshal in Washington, D.C. as “formidable,” with “masterly skill.” In the early months of the war, she and her network employed a wide range of tactics to relay intelligence to Confederate forces in Virginia. Couriers carried messages that Rose stitched into tapestries or sewed into silk pouches concealed in garments and hair. Before the Confederates were driven away from the immediate Washington area, she transmitted signals across the Potomac River by placing varying numbers of burning candles in her window and communicated in Morse code using her window blinds.

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Ciphered Greenhow letter

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Ciphered Greenhow letter

In July 1861, Greenhow relayed two ciphered messages to the Confederates about an imminent Union advance planned against Manassas Junction, Virginia, just 30 miles from Washington. Greenhow’s report, combined with other intelligence received, aided the South in its first major victory of the war at the First Battle of Bull Run. Brigadier General P.G.T. Beauregard, commanding the Confederate forces at Manassas Junction, later credited Greenhow’s intelligence as pivotal to the outcome of the battle.

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From left: Map of Bull Run; Ciphered Greenhow letter; Beauregard's headquarters at Bull Run; General P. G. T. Beauregard

Greenhow soon came under suspicion and Union General George McClellan, commander of the Army of the Potomac, ordered his intelligence chief, Allan Pinkerton, to investigate her activities. While personally surveilling Greenhow, Pinkerton witnessed a Union officer visiting her residence and sharing a map of Washington, D.C.’s defenses. Greenhow was arrested, and after searching her home, Pinkerton discovered one of her secret messages written in plain text, as well as sensitive documents and personal letters from well-known dignitaries. These included correspondence from Senator Henry Wilson of Massachusetts, the Chairman of the Senate Military Affairs Committee, who shared with Greenhow information about Union troop dispositions and defenses around the capital.

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From left: Old Capitol Prison, Washington; Little Rose Greenhow; Senator Wilson letter to Rose O'Neal Greenhow; Rose O'Neal Greenhow; Rose O'Neal Greenhow with her daughter; Senator Henry Wilson

Greenhow was undaunted by her house arrest and continued to gather and transmit information to the South through her visitors, even using her young daughter who passed secret messages scrawled on candy wrappers. In January 1862, Greenhow was transferred to the Old Capitol Prison in Washington, D.C., and remained there for four months with her daughter.

After her release, Greenhow was deported to Richmond and welcomed as a hero. When Confederate President Jefferson Davis asked her to serve as a European envoy promoting the Confederate cause abroad, Greenhow departed for England. She published a memoir there and became quite popular with the European social elite, many of whom were sympathetic toward the South, and even had audiences with Queen Victoria and French Emperor Napoleon III.

In 1863, a year later, Greenhow returned to America aboard a British blockade-runner. As the ship neared the North Carolina coast, it was pursued by a Union gunboat and ran aground at the mouth of the Cape Fear River. Greenhow fled in a lifeboat, but drowned when the boat capsized near Fort Fisher, North Carolina, and the weight of the gold she was carrying dragged her underwater.

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From left: Fort Fisher; USS Niphon

In 1863, a year later, Greenhow returned to America aboard a British blockade-runner. As the ship neared the North Carolina coast, it was pursued by a Union gunboat and ran aground at the mouth of the Cape Fear River. Greenhow fled in a lifeboat, but drowned when the boat capsized near Fort Fisher, North Carolina, and the weight of the gold she was carrying dragged her underwater.