Despite the James Bond stereotype, some of history’s most effective spies have been women. There may be no nineteenth-century spy who used her many social and political connections to better affect than Rose O’Neal Greenhow.
The Washington, DC, socialite moved in important social and political circles during the period leading up to the Civil War. Her friendships with high-ranking officials, military officers, presidents, and first ladies gave her considerable access to information which proved useful to the Confederate Army. “To this end,” she later wrote, “I employed every capacity with which God had endowed me, and the result was far more successful than my hopes could have flattered me to expect.” Confederate President Jefferson Davis credited her with supplying information which helped to secure the South’s victory at the First Battle of Bull Run.
Greenhow was placed under house arrest by newly appointed Secret Service chief Allan Pinkerton. When she continued to send out dispatches from her home, she was moved to the Old Capitol Prison. After five months she was released, and soon after traveled to England and France on a diplomatic mission representing the Confederacy. It was on the return from this trip that she drowned in the Cape Fear River off Wilmington, NC. She is buried in the city’s Oakdale Cemetery.
Several books and movies have been made about Greenhow. The women’s auxiliary of the Sons of Confederate Veterans honored Greenhow in 1993 by changing their name to Order of the Confederate Rose.
An Accidental Socialite
Greenhow was born in 1813 in Montgomery County, Maryland (although some sources say 1817 in Port Tobacco, Maryland). Named Maria Rosetta O’Neale (the family later dropped the final e), she was the third of five daughters born to planter and slaveholder John O’Neale and Eliza Henrietta Hamilton. They were Roman Catholics. Several years after her father was murdered, Rose and her sister Ellen went to live with their aunt in DC. The aunt ran an upscale boarding house at the Old Capitol Building (later the Old Capitol Prison) where Rose and Ellen met many of the capital’s important citizens. The building, on the site now occupied by the Supreme Court, was constructed as a temporary home for Congress after the original Capitol was burned during the War of 1812.
One of those individuals was Virginian Robert Greenhow Jr, a linguist, doctor, and lawyer. His courtship with Miss Rose O’Neal is reported to have been well received by Washington society, including Dolley Madison. At the same time, Ellen O’Neal was courted by Madison’s nephew James Madison Cutts. Ellen and Cutts were married in 1833. Rose and Greenhow married in 1835.
Recruited to the Cause
Robert Greenhow worked at the US Department of State, further ensuring their position among Washington society. By 1850 Robert’s job took the family to Mexico City, and then to San Francisco. Rose moved her three daughters back to the capital in 1852 and gave birth to her last daughter there. Robert was killed in an accident in San Francisco in 1854.
Rose Greenhow stayed on in Washington, enjoying the life of an educated, well-heeled socialite. Her loyalty to the South was unyielding and perhaps fueled by a strong friendship with US Senator John C. Calhoun of South Carolina. Others noticed, and she was recruited by US Army Captain Thomas Jordan to join a pro-South spy network in Washington. Jordan subsequently left the US Army and headed south where he enlisted as a captain in the Confederate Army. He supplied Greenhow with a 26-symbol code for messages, a piece of which exists today. Jordan is believed to have been Greenhow’s handler throughout the war and for the newly-formed Confederate Secret Service.
In July 1861 Greenhow sent a female courier to Confederate General Pierre G.T. Beauregard at his Fairfax, Virginia, headquarters. The ten-word message, carefully folded into her hair bun, contained Union military movements for what would be the First Battle of Bull Run. The information helped to secure a Confederate victory over the Union Army at Manassas. Beauregard later testified that because of the gained intelligence, he requested extra troops from General Joseph Johnston’s nearby command, helping the Confederates score a dramatic victory in the first major battle of the War.
Realizing her activities may endanger her daughters’ safety, Greenhow sent all but young Rose to live elsewhere. When Pinkerton and his agents traced leaked information to Greenhow’s 16th Street NW home, he placed Greenhow and her courier Lily Mackall under house arrest. Despite her attempts to burn evidence, numerous documents, maps, and letters were found in Greenhow’s house. Some of these are now at the National Archives and Records Administration, and some are available online.
Pinkerton closely supervised Greenhow and moved other suspected spies and sympathizers into the house—so many, in fact, that it was nicknamed Fort Greenhow.
Given her extensive connections, Greenhow was always considered a security risk. In January, 1862, Greenhow and others were ironically moved to Old Capitol Prison where she had lived with her aunt and had later attended Senator Calhoun prior to his death. A two-man commission was set up to review their cases. Eight-year-old Rose remained with her mother in prison. Greenhow continued to provide information to the Confederate Army, even while imprisoned. One account says she flew the Confederate flag from her prison window.
Her imprisonment, more than her messages, made her a martyr in the eyes of the Southern people according to Princeton University’s James McPherson. “The brutal Yankees who would imprison a mother and child provided ammunition for the Confederate propaganda mills,” McPherson said.
Greenhow was never subjected to a trial. After questioning in which she stymied all attempts at gaining a confession, she was released and exiled to the Southern states. She is reported to have left the Old Capitol Prison draped in a Confederate flag.
Representing the South in Europe
Greenhow was welcomed as a hero in Richmond. President Jefferson Davis sent her to Europe as a courier and diplomat for the Southern cause. She ran the blockade, and from 1863 to 1864 she traveled in France and Great Britain. The strong commercial ties between Britain and the South (with cotton, naval stores, tobacco and much more) resulted in sympathetic leanings among the aristocracy. She met with Queen Victoria and Napoleon III, and she met and became engaged to Granville Leveson-Gower, 2nd Earl Granville. She even found time while in London to write a well-received memoir titled My Imprisonment and the First Year of Abolition Rule at Washington.
Rose left Europe on the Condor, a British blockade runner, carrying dispatches for the Confederacy and $2000 in gold from her book sales on August 19, 1864. Pursued by USS Niphon, a Union gunboat, Condor ran aground at the mouth of the Cape Fear River on October 1, 1864. Greenhow took to a rowboat to go ashore, perhaps afraid of capture and imprisonment. When the rowboat capsized, Greenhow was weighed down by the gold sewn into her clothing.
Greenhow was buried with Confederate military honors at Oakdale Cemetery. In 1888 the Ladies Memorial Association marked her grave with a cross that read, “Mrs. Rose O’Neal Greenhow. A Bearer of Dispatches to the Confederate Government.”
Greenhow’s personal diary is held at the North Carolina Archives. Many of her papers are at the Duke University Special Collections Library.