Rose O'Neal Greenhow - Confederate Spy in the US Civil War

She was born in 1817 as Maria Rosetta O'Neal on a small plantation in Montgomery County, Maryland, northwest of Washington, DC.  She was the third of five daughters. Her father John O'Neal, a planter and slaveholder, and his wife Eliza Henrietta (Nee Hamilton), were both Roman Catholics. She was called “Rose” as a child, and was close to her older sister Ellen (Mary Eleanor). Their father was said to have been murdered by 2 of his own slaves.

Rose and her sister Ellen were invited to live with their aunt in Washington, D.C. Their aunt, Mrs. Maria Ann Hill, ran a stylish boarding house at the Old Capitol building, and the girls met many important figures in the Washington area. Her olive skin "delicately flushed with colour" earned her the nickname "Wild Rose." Personable, intelligent, and outgoing, she adapted easily to the social scene of the capital, and people in Washington's highest circles opened their doors to her.

Marriage and family

Rose was regarded as a beautiful, ambitious, seductive woman.  In 1835 at the age of 26, she disappointed an army of suitors by marrying 43-year-old Dr. Robert Greenhow,  a Virginian, who was both wealthy and socially well placed. A prominent doctor, lawyer, and linguist, he was an influential, learned man under whose tutelage she flourished. Robert Greenhow worked at the U.S. Department of State. His step-sister, Mary Greenhow Lee, would visit him and Rose became close friends with her.

Due to Robert's work with the State Department, the family moved with him to Mexico City in 1850 and then to San Francisco, California. In 1852 Rose returned East with her children, a journey which took some months, giving birth to her last daughter in 1853. By the time she was in her mid-thirties, Rose was the mother of four daughters:  Florence, Gertrude, Leila and Rose. Her youngest child was also named Rose O'Neal Greenhow, just like her mother, and was nicknamed "Little Rose".

Living back in the nation’s Capital. Surrounded by the many advantages that her prestigious husband could offer her, Greenhow became well-known for her beauty, her manners, her gift for intrigue, and her determination to accomplish whatever she set her heart upon. However, her life was about to change very drastically. Her husband died in a fatal accident in San Francisco in 1854. A short time later, their oldest child Florence married Seymour Treadwell Moore, a West Point graduate, career army officer and Mexican War veteran.

Confederate spy

After losing her husband, Greenhow became more sympathetic to the Confederate cause. She was strongly influenced by her friendship with U.S. Senator John C. Calhoun from South Carolina. Greenhow's loyalty to the Confederacy was noted by those with similar sympathies in Washington, and she was soon recruited as a spy.  She developed a close association "with Lieutenant Colonel Thomas Jordan (alias Thomas John Rayford) of Virginia, a former quartermaster in the United States Army who was in the process of developing an elaborate Confederate spy network in the federal Capital.  From Jordan, Greenhow learned the use of a 26-symbol cipher, and began to exploit her connections with the prominent Unionists for the purpose of eliciting information that she then transmitted in code to relevant figures in the Confederacy. Over time, Greenhow and Jordan enlisted the regular help of various others, forming an extensive spy ring that included both men and women.

After passing control of the espionage network to Greenhow, Jordan left the US Army, went south, and was commissioned as a captain in the Confederate Army. He continued to receive and evaluate her reports. Jordan appeared to be Greenhow's handler for the Confederate Secret Service during its formative phase.

On July 9 and July 16 of 1861, Greenhow passed secret messages to Confederate General P. G. T. Beauregard containing critical information regarding Union military movements for what would be the First Battle of Bull Run, including the plans of General Irvin McDowell. Assisting in her conspiracy were pro-Confederate members of Congress, Union officers, and her dentist, Aaron Van Camp, and his son and Confederate soldier, Eugene B. Van Camp.

A 1863 letter written by General P.G.T. Beauregard confirms that on July 10, Greenhow sent an attractive young woman named Betty Duvall to Fairfax Court House, just a few miles from Bull Run, bearing – tightly wound in her chignon bun - a message concerning Union commander Irvin McDowell’s preparation to advance on the Confederacy six days later. General Milledge L. Bonham of South Carolina received the message and transmitted it directly to Beauregard, who notified President Davis and then immediately began preparations to undermine McDowell’s advance. On the sixteenth, Greenhow communicated a second time with Beauregard, who was now encamped with the army near Bull Run. With the help of George Donellan, a former Interior Department clerk, Greenhow sent Beauregard an encoded dispatch containing the news that, as Beauregard later wrote, "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), via Fairfax Courthouse and Centerville."

This news Beauregard also forwarded by telegraph to President Davis, who ordered General Johnston, stationed 50 miles away, to bring his troops into the area as reinforcements. While awaiting Johnston’s arrival, Beauregard shifted his own troops to meet the advancing federals, and on July 21, the Union suffered a stunning and humiliating defeat. Confederate President Jefferson Davis credited Greenhow's information with the Confederates securing victory at Manassas over the Union Army on July 21.The following day Greenhow received from Thomas Jordan an expression of  Davis’s gratitude for her loyal service.

"Our President and our General direct me to thank you. We rely upon you for further information. The Confederacy owes you a debt. (Signed) JORDAN, Adjutant-General."   

She then became known as "Rebel Rose" for her work for the South.

Capture and Imprisonment

In I861, knowing she was suspected of spying for the Confederacy, Greenhow feared for her remaining daughters' safety. Leila was sent to Ohio to join her older sister Florence, whose husband Seymour Treadwell Moore had become a captain in the Union Army. Only Little Rose stayed with Greenhow in Washington.

Allan Pinkerton was made head of the recently formed Secret Service and one of his first orders was to watch Greenhow, because of her wide circle of contacts on both sides of the sectional split. He placed her under house arrest at her 16th Street residence, along with one of her couriers, Lily Mackall and stationed guards inside the house.

Pinkerton supervised visitors to Greenhow's house and moved other suspected Southern sympathizers into it, giving rise to the nickname Fort Greenhow. He was pleased to oversee the visitors and messages, as it gave him more control of the Southern flow of information. While messages continued to be sent to Jordan, he discounted them after Pinkerton mounted his control.

His agents traced other leaked information back to Greenhow's home. While searching her house, Pinkerton and his men found extensive intelligence materials left from evidence she tried to burn, including scraps of coded messages, copies of what amounted to eight reports to Jordan over a month's time, and maps of Washington fortifications and notes on military movements.

Although Greenhow was able to destroy a number of papers, enough was uncovered to incriminate her and heap suspicion upon some prominent Unionist figures that came under her influence. One of these was the powerful abolitionist Republican senator from Massachusetts, Henry Wilson, who seems to have been one of Greenhow’s primary sources and her lover, as a stack of love letters found in her home indicated. She considered him her prize source, and said he gave her data on the "number of heavy guns and other artillery in the Washington defences," but he likely knew far more from his work on the Military Affairs Committee.

Word spread quickly that federal agents had captured a major figure in Confederate espionage who was also a woman, and on August 26, both the New York Times and the New York Herald smugly reported Greenhow’s arrest. When a letter from Greenhow  was publicized that complained of her treatment, there was Northern criticism for what was perceived as too lenient treatment of a spy.

Greenhow remained under house arrest until she was transferred, along with her daughter, to the Old Capitol Prison, on January 18, 1862. So many political prisoners were detained that a two-man commission was set up to review their cases at what were called espionage hearings.  Greenhow was never subjected to trial. "Little Rose", then eight years old, was imprisoned with her.

For five months, she and her daughter remained locked up in the very same place where as a teenager Greenhow had acquired her first taste of social life in Washington. However, even being jailed did not deter her from continuing to provide information to Southern loyalists.

Passers-by could see Rose's window from the street. Historians believe that the position of the blinds and number of candles burning in the window had special meaning to the "little birdies" passing by. Another account lists her prison room facing the prison yard so that she could not see or be seen and every effort was made to keep Mrs. Greenhow away from the windows. Greenhow also on one occasion flew the Confederate Flag from her prison window. News of her activities brought publicity and tremendous popularity among Southern sympathizers.

International acclaim

The Federal authorities wanted to banish her south, where they presumed she could do less harm. On May 31, 1862, Greenhow was released without trial (along with her daughter), on condition she stay within Confederate boundaries. On June 2, the New York Times recorded her release and removal under close custody. After they were escorted to Fortress Monroe at Hampton Roads, she and her daughter went on to Richmond, Virginia, where Greenhow was hailed by Southerners as a heroine.

President Jefferson Davis welcomed her return and enlisted her as a courier to Europe. Greenhow ran the blockade and, from 1863 to 1864, travelled through France and Britain on a diplomatic mission building support for the Confederacy with the aristocrats.

Many European aristocrats had sympathy for the South's elite; there were also strong commercial ties between Britain and the South. While in France, Greenhow was received in the court of Napoleon III at the Tuileries. In Britain, she had an audience with Queen Victoria. Greenhow met and in 1864 became engaged to Granville Leveson-Gower, 2nd Earl Granville.  

The details of her mission to Europe are recorded in her personal diaries, dated August 5, 1863, to August 10, 1864, when she wrote, "A sad sick feeling crept over me, of parting perhaps forever, from many dear to me...A few months before I had landed a stranger--I will not say in a foreign land--for it was the land of my ancestors--and many memories twined around my heart when my feet touched the shores of Merry England--but I was literally a stranger in the land of my fathers and a feeling of cold isolation was upon me."

Two months after arriving in London, Greenhow wrote her memoir, titled My Imprisonment and the First Year of Abolition Rule at Washington. She published it that year in London and it sold well in Britain. After some time, Greenhow yearned to return to America where she owned property.

Death

On August 19, 1864, she boarded the Condor, a British blockade-runner which was to take her home.  On October 1, 1864, the Condor ran aground at the mouth of the Cape Fear River near Wilmington, North Carolina, while being pursued by a Union gunboat, USS Niphon.

Against the captain’s wishes and advice, Greenhow and two other passengers attempted to make it to shore in a rowboat. A wave capsized the  boat, and Greenhow drowned. She was dragged down by the weight of the $2,000 worth of gold sewn into her underclothes which she had received in royalty payments for her book. When Greenhow's body was recovered from the water near Wilmington, searchers found a small notebook and a copy of her book also hidden inside her clothes inside the book was a note meant for her daughter, Little Rose.

She was buried on October 1, 1864 and was honoured with a military funeral in Wilmington, North Carolina. Her coffin was wrapped in the Confederate flag and carried by Confederate troops. Her body was carried in a long funeral procession through the streets of Wilmington, a guard of honour accompanying her horse-drawn casket. Thousands of soldiers marched behind it, led by Admiral Hampden and many other Confederate officers, to Oakdale Cemetery. A squad of Confederate soldiers fired their muskets over her grave as the guns of Fort Fisher boomed in her honour. The Ladies Memorial Association, in 1888, marked her grave with a cross that read "Mrs. Rose O'Neal Greenhow - A Bearer of Dispatches to the Confederate Government."

Legacy

In 1993 the women's auxiliary of the Sons of Confederate Veterans changed its name to the Order of the Confederate Rose in Greenhow's honour.

Since the mid-20th century, two separate biographies have been published about Greenhow, and her work was also included in a 1996 book about the role of military intelligence during the war.

Greenhow was a featured character played by Nina Foch in an episode of the 1961 NBC TV series The Americans, The Rebellious Rose. Greenhow's exploits were also dramatized in the 1992 television film The Rose and the Jackal, in which she was played by Madolyn Smith Osborne opposite actor Christopher Reeve.