With Greenhow's help, the Confederacy won an important victory at the First Battle of Bull Run in July 1861

Rose Greenhow, Confederate Spy

InThePastLane.com                                                                                 By Edward T. O’Donnell

Confederate spy, Rose O’Neal Greenhow

On August 23, 1861, Rose O’Neal Greenhow heard a knock at the front door of her fashionable Washington, DC home.  Outside stood several secret service agents bearing papers placing her under house arrest.  The charge was conducting espionage for the Confederacy.  Greenhow became an instant celebrity and, despite her confinement under armed guard, she continued to transmit vital secrets to the Confederate government for another six months.

Rose O’Neal Greenhow was born in 1817 in Montgomery County, Maryland.  Her ancestors, the O’Neals, migrated from Ireland to the Chesapeake region in the late 1600’s.  Her father was a planter, but apparently not a very successful one.  She received only a limited formal education, but by all accounts was very smart.  She was also quite attractive and impetuous, leading many to call her “Wild Rose” when she was young.

As a teenager, Rose O’Neal moved to Washington, DC with her sister and took up residence with an aunt who ran a boarding house.  This arrangement allowed them to befriend many young and ambitious politicians who boarded in the house and by the time they were in their twenties the O’Neal sisters were active in the capital’s elite social scene.  At age 26 Rose married Robert Greenhow, a wealthy and socially prominent Virginian who worked for the State Department.  They had four daughters together before Robert died in the early 1850s.  As a widow Rose had both wealth and powerful friends to rely upon, the latter including some of the most important political figures in the capital.

When the Civil War broke out in the spring of 1861 Greenhow – known for her pro-South sympathies — was recruited into a Confederate spy ring.  As a woman she was, at least initially, above suspicion.  This cover allowed her to ask all sorts of questions of her high placed friends in the Lincoln administration and Congress without raising an eyebrow.  But what appeared to her powerful friends as the excited chatter of an attractive southern belle was in fact the calculated secret gathering of an expert spy.  Perhaps her most indiscreet source of information was Senator Henry Wilson of Massachusetts whom much evidence suggests may have been her lover.

Greenhow not only proved adept at gathering information, she also managed to recruit dozens of additional spies and devised several ingenious methods for transmitting the information gathered to the right people.

With Greenhow’s help, the Confederacy won an important victory at the First Battle of Bull Run in July 1861

Her greatest success came in the weeks leading up to the war’s first major battle, Bull Run.  On July 10, 1861, Greenhow sent one of her recruits, a young woman named Betty Duvall, into Confederate lines.  Carefully hidden in her clothing were coded massages detailing the Union Army’s plan of attack.  These were immediately forwarded to Confederate General P. G. T. Beauregard.  Six days later Greenhow sent additional details to Beauregard outlining, the general later wrote, that “the enemy – 55,000 strong, I believe – would positively commence that day his advance from Arlington Heights and Alexandria on to Manassas [near Bull Run].”  Beauregard sent this information to President Jefferson Davis who responded by ordering Gen. Joseph Johnston to move his army 50 miles to reinforce Beauregard.  On July 21, in what proved to be a confusing clash of inexperienced armies, the Confederacy handed the Union a humiliating defeat.  Days later Greenhow received a note from the head of the spy ring: “Our President and our General direct me to thank you.  We rely upon you for further information.  The Confederacy owes you a debt.”

Despite a mounting counterintelligence effort by the Lincoln administration that increased the likelihood that she would be exposed as a spy, Greenhow continued to gather and transmit information into the summer.  In late July, however, suspicion over her activities began to mount and government agents began surveillance of her home.  Three weeks later, on August 23, 1861, they placed her under house arrest along with her youngest daughter and several suspected spies.  A thorough search of the premises turned up copies of eight intelligence reports concerning Union military strength and plans.  On August 21, for example, Greenhow had written “No more troops have arrived.  Great activity and anxiety here, and the whole [military] strength concentrating around Washington, and the cry ‘The Capital in danger,’ renewed.”  Several of the reports mentioned her high placed sources by name, including Senator Wilson.

News that a major Confederate spy – and a woman at that – had been arrested in the capital soon hit the newspapers.  The novelty of her story made Greenhow a celebrity of sorts and thousands of curiosity seekers filed by her house each day hoping to catch a glimpse of her.

House arrest did not stop Greenhow from continuing her work as a spy.  As she later wrote in her account of her saga, when she discovered that one of her guards was smitten with one of her maids, she quickly took advantage of the situation.  The maid, who was devoted to Greenhow, agreed to lead the guard on and accepted his frequent invitations to take long strolls through the city.  The lovestruck man never suspected that she was using these walks to sneak information in and out of the Greenhow house.

The Lincoln administration decided the best course of action for dealing with a female

Rose O’Neal Greenhow wrote a best-selling account of her exploits in Washington, DC during the first year of the war.

spy was to exile her to the South.  So Greenhow was released in the spring of 1862 and sent to Richmond.  She met President Davis who bestowed upon her $2,500 in gratitude for her services, saying “But for you there would have been no battle of Bull Run.”  One year later she accepted a new assignment and sailed for Europe to lobby the governments of France and England on behalf of the Confederacy.  There she wrote a book about her experiences, My Imprisonment and the First Year of Abolitionist Rule at Washington which became a bestseller. But on the return voyage in September of 1864, Greenhow’s vessel ran aground off the coast of North Carolina and she was drowned when her lifeboat overturned.

Sources and Further reading:

Ann Blackman, Wild Rose: Rose O’Neale Greenhow, Civil War Spy (Random House, 2005).

Larry G. Eggleston, Women in the Civil War: Extraordinary Stories of Soldiers, Spies, Nurses, Doctors, Crusaders, and Others (McFarland, 2009)

Edwin C. Fishel, The Secret War For The Union: The Untold Story of Military Intelligence in the Civil War (Houghton Mifflin, 1996)

Rose O’Neal Greenhow, My Imprisonment and the First Year of Abolition Rule at Washington (1863)

H. Donald Winkler, Stealing Secrets: How a Few Daring Women Deceived Generals, Impacted Battles, and Altered the Course of the Civil War (Cumberland House, 2010)