Confederate Spies: Rose O’Neal Greenhow

This entry is part 5 of 12 in the series Spies of North and South

Rose O'Neal Greenhow with her daughter RoseOne of the most renowned Confederate spies of the early Civil War years was Rose O’Neal Greenhow of Washington, D.C. Mrs. Greenhow who was 48 or 49 when the war began (her birth year is given as 1813 or 1814), was a Washington socialite who moved in the very highest circles of society.

Rose Greenhow’s early life was not the easiest. She was born at Port Tobacco, Maryland as as Maria Rosetta O’Neal. Both of her parents died by the time that she was a teenager. She was invited to live with her aunt, Maria Ann Hill, who ran a stylish boarding house at the Old Capitol building in Washington.

Through the assistance of her aunt, Rose met a number of personages and frequented capital society. In 1935 she married Dr. Robert Greenhow. He taught her history and gave her access to government documents through his work in the U.S. Department of State.

The Greenhow’s had eight children but only four of them lived beyond infancy. Soon after her namesake last child was born, her husband died. Meanwhile one daughter moved West and another died.

Rose Greenhow’s sympathies were always with the Confederacy due to her friendship with John C. Calhoun. Soon after the war began, she was recruited by then-Union officer Thomas Jordan. He supplied her with a 26-symbol cipher for creating encoded messages. Jordan resigned his U.S. Army commission in May 1861 and received a captain’s commission in the Confederate States Army. He would end the war as a brigadier general after which he joined the Cuban Liberation Army.

On July 9, 1861, and July 16, 1861, Greenhow passed secret messages to Confederate General P.G.T. Beauregard containing critical information regarding military movements for what would be the First Battle of Bull Run, including the plans of Union General Irvin McDowell. Assisting in her conspiracy were pro-Confederate members of Congress, Union officers, and her dentist, Aaron Van Camp. Confederate President Jefferson Davis credited Greenhow’s information with securing victory at Manassas.

Greenhow’s spying career was shortlived. On August 23, 1861 Allan Pinkerton, head of the recently-formed Secret Service, apprehended Greenhow and placed her under house arrest. Leaked information was traced back to Greenhow’s home, and upon searching for further evidence, Pinkerton and his men found maps of Washington fortifications and notes on military movements.

On January 18, 1862, Greenhow was transferred to Old Capitol Prison. Her daughter, “Little Rose”, then eight years old, was permitted to remain with her. Greenhow continued to pass along messages while imprisoned. She was said to have sent one message concealed within a woman visitor’s bun of hair. Passers-by could see Rose’s window from the street. The position of the blinds and number of candles burning in the window had special meaning to the “little birdies” passing by. Greenhow also on one occasion flew the Confederate Flag from her prison window.

Rather than continue her incarceration, the Union government deported her to Richmond, Virginia where she was hailed as a heroine by Southerners. Jefferson Davis welcomed her home and enlisted her as a courier to Europe. From 1863 to 1864, Greenhow traveled through France and Britain on a diplomatic mission for the Confederacy. While in Britain, Greenhow wrote her memoirs, titled My Imprisonment and the First Year of Abolition Rule at Washington, which sold well there.

In September 1864, Greenhow left Europe to return to the Confederate States, carrying dispatches. She traveled on the Condor, a British blockade runner. On October 1, 1864, the Condor ran aground at the mouth of the Cape Fear River near Wilmington, North Carolina, while begin pursued by a Union gunboatUSS Niphon.

Fearing capture and further imprisonment, Greenhow fled the grounded ship by rowboat. A wave capsized the rowboat, and Greenhow, weighed down with $2,000 worth of gold in a bag around her neck from her memoir, royalties intended for the Confederate treasury, drowned.


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