Pinkerton Arrests Confederate Spy Rose Greenhow (23 AUG 1861)

Photo By Lori Stewart | Rose Greenhow and her daughter, Little Rose, at Old Capitol Prison in Washington, 1862.  

UNITED STATES

08.18.2023

Story by Lori Stewart 

U.S. Army Intelligence Center of Excellence

by Lori S. Stewart, USAICoE Command Historian

23 AUGUST 1861
On 23 August 1861, Allan Pinkerton, a counterintelligence agent working with the Union Army, arrested Washington socialite Rose O’Neal Greenhow for spying for the Confederacy. Her actions, some confirmed and others questioned, became the subject of Confederate legend.

Greenhow was born about 1814 in Maryland and grew up around Washington. By the time the Civil War began, the widow with four children was a well-known fixture in Washington society and had friends in high places. In the spring of 1861, U.S. Army officer Thomas Jordan recruited the outspoken, Southern-sympathizing Greenhow as a spy when he vacated his oath and joined the Confederate army. Jordan became adjutant to Brig. Gen. P.G.T. Beauregard, commander of the Confederate Army of the Potomac. Before leaving town, Jordan provided Greenhow with a simple twenty-six symbol cipher. He directed her to collect and forward any militarily useful information to their headquarters at Manassas, Virginia, thirty miles southwest of Washington.

Greenhow, with contacts at all levels of society around the city, “employed every capacity with which God had endowed me” to fulfill her duty for Jordan. She quickly built a network of nearly fifty individuals, primarily women who could move about without suspicion. Her “scouts” monitored military movements around the Capital, eavesdropped, and enticed information out of lovestruck suitors. Greenhow passed enciphered messages stitched into tapestries or pouches her female scouts tied up in their hair. By some accounts, she also communicated in Morse code using her window blinds or by burning varying numbers of candles.

Her most notable feat was supplying information that helped Beauregard identify the location of a pending Union surprise attack. This information allowed the Confederate general to reinforce his army in time to defeat that attack at Bull Run on 21 July 1861.

Overconfidence and carelessness, however, soon led to Greenhow’s downfall. Unusual activity around her home, the high number of rebel visitors, and her own vocal support of the Confederacy drew attention from her social rivals, who may have tipped off Assistant Secretary of War Thomas Scott. Scott requested Pinkerton, a counter-intelligence agent under contract to the Union Army, to surveil Greenhow.

The night of 22 August 1861, Pinkerton followed an Army officer from Greenhow’s home to his quarters. The officer wheeled on the detective, arrested him, and placed him in the guardhouse overnight. Released the next morning, Pinkerton rushed to arrest Greenhow and search her residence. His operatives found copies of several of her reports torn in pieces in the trash or the wood stove. Their key find was two versions of the same report: one in plain language and the other in cipher.

Greenhow was held under arrest for several months in her own home, from which she reportedly continued to pass messages to her contacts. In the following months, however, many of her collaborators, identified by the reports seized from her home, were also arrested. In early 1862, Greenhow was moved to the Old Capitol Prison, where she remained until released and banished to the Confederate capital in Richmond, Virginia. Greenhow then spent a year in Europe on a diplomatic mission for Jefferson Davis, during which time she wrote her highly embroidered memoir, "My Imprisonment and the First Year of Abolition Rule at Washington." She died on 1 October 1864 when the blockade runner she was on ran aground off the coast of North Carolina in sight of Union forces. Desperate to escape, she commandeered a rowboat that subsequently capsized. Weighted down by gold, Greenhow drowned trying to reach shore.

In the months and years following her arrest in 1861, Greenhow became a legend within Confederate circles, but some historians have since questioned the value of her reporting. Her passing of reliable and timely intelligence on the eve of the First Battle of Bull Run was confirmed by Beauregard himself, but much of her other reporting has been described as unconfirmed gossip obtained from undocumented sources.

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• Date Taken: 08.18.2023
• Date Posted: 08.18.2023 16:16
• Story ID: 451677
• Location: US