Rose O ' Neal Greenhow Rose O ' Neal Greenhow ( 1813 or 1814 – October 1 , 1864 ) was a renowned Confederate spy during the American Civil War . A socialite in Washington , D . C . during the period before the war , she traveled in important political circles and cultivated friendships with presidents , generals , senators , and high - ranking military officers . She used her connections to pass along key military information to the Confederacy at the start of the war . In early 1861 , she was given control of a pro - Southern spy network in Washington , DC by her handler , Thomas Jordan , then a captain in the Confederate Army . She was credited by Jefferson Davis , the Confederate president , with ensuring the South ' s victory at the First Battle of Bull Run in late July 1861 . Captured in August , Greenhow was subject to house arrest ; found to have continued her activities , in 1862 after an espionage hearing , she was imprisoned for nearly five months in Washington , DC . Deported to the Confederate States , she traveled to Richmond , Virginia and new tasks . Running the blockade , she sailed to Europe to represent the Confederacy in a diplomatic mission to France and Britain from 1863 to 1864 . In 1863 she also wrote and published her memoir in London , which was popular in Britain . After her returning ship ran aground in 1864 off Wilmington , North Carolina , she drowned when her rowboat overturned as she tried to escape a Union gunboat . She was honored with a Confederate military funeral . 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 honor , following publicity about her exploits in a TV movie the previous year . A new biography of her was published in 2005 . Early life . She was born in 1813 or 1814 as Maria Rosetta O ' Neale on a small plantation in Montgomery County , Maryland , northwest of Washington , DC . ( Note : The biographical note on Greenhow at the National Archives and Record Administration , which holds a collection of her papers , says that O ' Neal was born in 1817 in Port Tobacco , Maryland , but it is unclear what the documentation is for this . ) She was the third of five daughters of John O ' Neale , a planter and slaveholder , and his wife Eliza Henrietta Hamilton , who were Roman Catholic . Called Rose as a child , O ' Neal was the third born and close to her next older sister Ellen ( Mary Eleanor ) and the final " e " was dropped off the family name in Rose ' s early childhood . Their father died in 1817 , murdered by unknown assailant ( s ) . His widow , Eliza O ' Neal , had four daughters to support and a cash - poor farm . After being orphaned as children , Rose and her sister Ellen were invited to live with their aunt in Washington , D . C . about 1830 . 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 . As a young woman , O ' Neal was considered beautiful , educated , loyal , compassionate , and refined . Her olive skin " delicately flushed with color " earned her the nickname " Wild Rose . " In the 1830s , she met Robert Greenhow , a prominent doctor , lawyer , and linguist from Virginia . Their courtship was well received by Washington society , including famed society matron Dolley Madison . In 1833 , Rose ' s sister Ellen O ' Neal married Dolley ' s nephew James Madison Cutts . In 1856 their daughter Adele Cutts married the widower Stephen A . Douglas , the senator from Illinois . Marriage and family . In 1835 , Rose married Dr . Robert Greenhow with Dolley ' s blessing , and by the 1850s had long been an established socialite in the capital . Robert Greenhow worked at the U . S . Department of State . The Greenhows had eight children ; four daughters : Florence , Gertrude , Leila and Rose , lived past infancy . Their youngest child was named Rose O ' Neal Greenhow ( her middle name being her mother ' s maiden ) , and was nicknamed " Little Rose " . 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 of months , giving birth to her last daughter in 1853 . Her husband died in a fatal accident in San Francisco in 1854 . Being a widow did not disrupt Greenhow ' s popularity in the capital . A short time later , their oldest child Florence married Seymour Treadwell Moore , a West Point graduate , career army officer and Mexican War veteran . They moved west to Ohio . 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 recruited as a spy . Her recruiter was U . S . Army captain Thomas Jordan , who had set up a pro - Southern spy network in Washington . He supplied her with a 26 - symbol cipher for encoding messages . 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 . In the spring of 1861 , Greenhow ' s daughter Gertrude died . Leila and Little Rose remained with her . 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 . Confederate President Jefferson Davis credited Greenhow ' s information with the Confederates securing victory at Manassas over the Union Army on July 21 . After the battle she received the following telegram from Jordan : " 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 became known as " Rebel Rose " for her work for the South . Capture and prison . 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 Greenhow Moore , whose husband Seymour Treadwell Moore had become a captain in the Union Army . ( He was breveted a brigadier general in May 1865 for his services and achieved a rank of lieutenant colonel after the war in his army career . ) 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 . Due to the activities of visitors , he arrested her and placed her under house arrest at her 16th Street residence . His agents traced other leaked information 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 . The materials included numerous love letters from the abolitionist Republican US Senator Henry Wilson from Massachusetts . She considered him her prize source , and said he gave her data on the " number of heavy guns and other artillery in the Washington defenses , " but he likely knew far more from his work on the Military Affairs Committee . The seized Greenhow papers are now held by the National Archives and Records Administration , with some available on line . 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 . When a letter from Greenhow to Seward was publicized that complained of her treatment , there was Northern criticism for what was perceived as too lenient treatment of a spy . Pinkerton transferred Greenhow on January 18 , 1862 to Old Capitol Prison , shutting down Fort Greenhow . 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 . Her youngest daughter , " Little Rose " , then eight years old , was permitted to stay with her . Greenhow continued to pass along messages while imprisoned . 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 . International acclaim . On May 31 , 1862 , Greenhow was released without trial ( with her daughter ) , on condition she stay within Confederate boundaries . After they were escorted to Fortress Monroe at Hampton Bay , 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 , traveled 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 . Death . On August 19 , 1864 , Greenhow left Europe to return to the Confederacy , carrying dispatches . She traveled on the " Condor , " a British blockade runner . 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 " . Fearing capture and reimprisonment , Greenhow fled the grounded ship by rowboat . A wave capsized the rowboat , and Greenhow drowned . She was weighed down by $ 2 , 000 worth of gold sewn into her underclothes and hung around her neck , returns from her memoir royalties , which she intended to donate to the Confederate treasury . When Greenhow ' s body was recovered from the water near Wilmington , searchers found a small notebook and a copy of her book " Imprisonment " hidden on her . Inside the book was a note meant for her daughter , Little Rose , which read :