Pre-War Letter of Jefferson Davis to the Confederacy’s Most Famous Spy, Rose O’Neal Greenhow

Rose O’Neal Greenhow was born into obscurity, but became one of the most powerful women in Washington, D.C. and in time became a famous Confederate spy.  Arriving in Washington at the age of fourteen, she became fascinated with the Washington socialite scene and attempted to gain acceptance by the well-to-do Washingtonians. Even though she was mocked for her low birth, she eventually caught the eye of Dr. Robert Greenhow, a federal librarian and translator with medical and law degrees. The couple married on May 26, 1835 and, with her new husband, Rose gained acceptance into high society and socialized with famous Washingtonians, like First Lady Dolley Madison. She became friendly with South Carolina Senator John C. Calhoun, whose views influenced her. In fact, she nursed Calhoun on his deathbed. She also met and socialized with her future leader, Jefferson Davis. By 1854 she was a widow with a pension from the Federal government; she bought a house four blocks north of the White House and resumed her socialite occupation. She also established and maintained political alliances, including with President James Buchanan.

During the Civil War, Greenhow aligned herself with the Confederacy. She wrote ciphered (secret code) messages to the Confederates and provided information about Union military plans. President Jefferson Davis credited her with helping the South win the First Battle of Bull Run, a key victory. Greenhow did this by providing a message about the Union troop’s movements in time for Brigadier Generals Pierre Beauregard and Joseph Johnston and to meet at Manassas, Virginia. A young woman working with Greenhow named Betty Duvall carried the message wrapped in a tiny black silk purse and wound up in a bun of her hair.

Greenhow’s spy network spanned several states and included 48 woman and two men. Head of the U.S. Intelligence Service Allan Pinkerton observed Greenhow as part of his counterintelligence activities and found sufficient evidence to place her under house arrest. Greenhow claimed she knew she was under surveillance but had defiantly continued her spying activities. Pinkerton and his men searched Greenhow’s home and seized documents including letters, maps, notes, ciphered messages, and burnt papers that Rose had tried to destroy in her stove. After a period under house arrest, Greenhow was transferred to Old Capitol Prison where she continued to send encoded messages and collect secret information. This change in scenery did not stop Rose from being a nuisance and she was able to smuggle in a Confederate flag to her prison cell and wave it from the prison window.   After a hearing, she was deported to Richmond, Virginia in May 1862. There she was hailed as a hero. She met with Jefferson Davis, who sent her on a diplomatic mission to Europe in 1863. On her return trip to the South on October 1, 1864, the blockade runner the Condor encountered Northern forces and ran aground. Rose Greenhow tried to escape in a rowboat, but it turned over and she drowned.

In 1855 Jefferson Davis was Secretary of War under President Pierce. Invited to one of Greenhow’s soirees, he declined, apparently because she would be too preoccupied with other guests to spend time with him.

Autograph letter signed, Washington, December 27th 1855, to Greenhow. “My dear Madam, I regret that it will not be in my power to meet you this evening in the midst of the many friends who always when permitted gather around you. With many thanks for your kind remembrance…”

This is the first letter of Davis to his future spy Greenhow that we have ever seen. Moreover, a search of public sale records going back decades shows no other such letter reaching that marketplace, making this a true rarity.