Greenhow, Rose O'Neal (c. 1817–1864)

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Greenhow, Rose O'Neal (c. 1817–1864)

Washington socialite, confidante of Senator John C. Calhoun and President James Buchanan, who was a daring Confederate spy during the Civil War. Name variations: Wild Rose, Rebel Rose. Born around 1817 in Port Tobacco, Maryland; drowned on October 1, 1864, in the Cape Fear River near Wilmington, North Carolina; daughter of John O'Neal (a Maryland planter); had little formal education, but was tutored by South Carolina Senator John C. Calhoun; married Robert Greenhow (a Virginia doctor, lawyer and linguist), in 1835; children: four daughters, Florence Greenhow; Gertrude Greenhow; Leila Greenhow; Rose Greenhow.

Moved as an infant to Montgomery County, Maryland, after the murder of her father; moved to Washington, D.C., and lived in the boarding house of her aunt, Mrs. H.V. Hill (c. 1830); married Robert Greenhow (1835); widowed while living in California (1854); established herself as the most influential woman in Washington during James Buchanan's presidency (1857–61); organized an effective spy ring and supplied military information to the Confederate government (June 1861); arrested for espionage and imprisoned (August 1861); released from prison and deported to the South (June 1862); sent by President Jefferson Davis on a diplomatic and intelligence mission to England and France (August 1863); published her memoirs, My Imprisonment and the First Year of Abolition Rule in Washington (November 1863); became engaged to the 2nd Earl of Granville in London (1864); boarded the blockade runner Condor, carrying secret dispatches and gold for the Confederacy(August 1964); drowned in a storm off Wilmington, North Carolina (October 1864).

On the eve of the Civil War, in the District of Columbia, Rose Greenhow had a reputation for witty repartee and political intrigue. Her intelligence and vivacity, in addition to her carefully nurtured connections to men of power, made her easily the most influential and persuasive woman in the capital. Wild Rose, as she was called by friends and detractors alike, had a gregarious charm and a striking appearance which made it easy for the men of Washington to overlook her Southern secessionist sympathies. For almost 30 years, Greenhow had cultivated the friendship of political greats and military rising stars. She moved with ease in the highest social circles and counted among her intimates many of the city's elite, including diplomats, senators, congressional representatives, cabinet secretaries, generals, and U.S. presidents.

I employed every capacity with which God has endowed me, and the result was far more successful than my hopes could have flattered me to expect.

—Rose O'Neal Greenhow

After the secession of the Southern states, Greenhow remained in Washington to begin a career as one of the most successful spies of the Civil War. An outspoken Southern sympathizer, she was happy to capitalize on her access to information carelessly spoken by friends in high places. Furthermore, she was quite willing to exploit the affections and indiscretions of her numerous male admirers. At the outbreak of hostilities, Greenhow organized an efficient spy ring, complete with couriers and a secret coded cipher. Her very first attempts at espionage provided the Confederate Army with information which assured an overwhelming Southern victory at the Battle of Bull Run (also known as Manassas).

Rose O'Neal was born into a family with ancestral ties to the Calverts and other original holders of the Maryland colony. Her father, John O'Neale (who dropped the final "e" in his name before Rose's birth) was not a wealthy man, but as a planter he was able to provide a comfortable living for his family. Rose's life took a drastic turn during her infancy when her father was killed by one of his slaves. The family moved to Rockville, Maryland, about 15 miles from Washington, where Rose and her sisters spent the remainder of their childhood. By the time Rose had reached her early teens, she and her older sister Ellen Elizabeth O'Neal were sent to live with their aunt, Mrs. H.V. Hill , who ran the Congressional Boarding House in the old U.S. Capitol building. A popular residence for members of Congress, the boarding house afforded Rose her first exposure to the people and issues which would preoccupy her for the rest of her life.

Life at the boarding house, in the company of men like Henry Clay and Daniel Webster, was truly educational for young Rose. Preeminent among her tutors, however, was John C. Calhoun, the fiery senator from South Carolina, who became her mentor. She listened with rapt attention as Calhoun fulminated about Southern rights and grievances, and his convictions became her own. "I am a Southern woman, born with revolutionary blood in my veins," she wrote, "and my first crude ideas on State and Federal matters received consistency and shape from the best and wisest man of this century." Though many years separated them, Calhoun and Greenhow grew quite close. After a friendship of 20 years, it was Rose who nursed the aged Calhoun as he died in the boarding house in 1850.

Rose's first serious romantic interest was Cave Johnson, a somewhat dour congressional representative from Tennessee, who would ultimately serve as postmaster general under President James Knox Polk. Johnson noticed Rose while he was residing at the Congressional Boarding House and began to court her even though she was only 16 years old at the time. Though she eventually came to feel that Johnson was somber and uninteresting, Rose was for a time his constant companion, and it was he who initiated her into the Washington society which so fascinated her. A short time later, she met Virginian Robert Greenhow, geographer, linguist and historian, who also had background in medicine and the law. Rose's senior by 17 years, Robert was working as a translator for the State Department and was considered an authority on Mexico and the West. They married in 1835 and spent the next 15 years in Washington where three of their four daughters were born.

Greenhow enjoyed the life of a State Department official's spouse and took advantage of every opportunity to learn more of political affairs and to make friends of those in power. There is no indication of unhappiness in the Greenhows' marriage, although the quiet scholar and his wife were of entirely different temperaments. Her counsel was sought by many men in Washington, but it was James Buchanan upon whom she exercised the greatest influence. She became one of the most ardent supporters of his political

aspirations, and he would not forget their friendship when he was elected president in 1856.

In 1850, the same year that Greenhow's mentor John C. Calhoun died, she and her family left Washington. Robert resigned his position with the State Department and became an officer with the U.S. Land Commission in San Francisco. During this time, California became a state, and Greenhow continued to be politically active on behalf of Southern interests and those of James Buchanan, with whom she kept up a lively correspondence. Greenhow returned to Washington in the winter of 1853 pregnant with her fourth child. In February or March of 1854, while still in San Francisco, Robert suffered a serious accident, falling six feet from a plankway down an embankment to the street. Robert had no idea of the critical nature of his injuries, so he did not send for his wife. He died after six weeks of acute pain and partial paralysis. By the time Rose was notified of his death, she found it impossible to make the long journey to California with a newborn infant in tow.

When Greenhow brought suit against the city of San Francisco, she won a judgment large enough to enable her to purchase a fashionable house on Washington's 16th Street. Having no intentions of playing the withdrawn widow, she soon reestablished herself as the leading host of the Democratic regime, and her house became a mecca for political powerbrokers of both parties, from the North as well as the South.

Numerous aspiring politicos became indebted to Greenhow for their appointments, thanks to her skill at parlor diplomacy. When her friend James Buchanan was elected president in 1856, Greenhow's relationship to the old bachelor became the subject of endless gossip. Her neighbors on 16th Street, and indeed speculators all over Washington, were scandalized by the fact that Buchanan's easily identifiable carriage stopped at Greenhow's home frequently and stayed so late. As Major William E. Doster, provost marshall of Washington, wrote, "There was much gossip at this time arising from the intimacy between Mrs. Greenhow and the President."

By the late 1850s, political storm clouds were gathering in Washington. By 1861, the secession crisis was forcing Southern politicians and military leaders to leave Washington in a steady stream, in preparation for the coming conflagration. Colonel Thomas Jordan, who resigned his commission in the U.S. Army to serve with Confederate General Pierre Beauregard as adjutant, suggested that Greenhow remain in Washington in order to supply information to the Confederate military. Rose was eager to use her numerous friendships in Washington to help the Confederate cause.

Jordan gave her a secret cipher with which to encode her messages and set up for her use a string of couriers charged with moving information out of Washington and into Confederate territory. Almost immediately, Greenhow found herself in a perfect position to spy for the Confederates. In July, she learned from her Union contacts that General Irving McDowell was moving south from Washington with a large force toward Manassas Junction, Virginia, with the intention of crushing the rebellion with one mighty blow. Greenhow quickly penned a message to Beauregard, "In a day or two twelve hundred cavalry plus four batteries of artillery will cross Bull Run… for God's sake heed this, it is positive."

When Beauregard received this message from a courier, he lacked specific information regarding the time and place of the planned assault. Another dispatch from Greenhow on July 10 was smuggled through Union lines by her close friend, Betty Duvall , who hid the message inside the curls of her hair. It was more specific: "McDowell has certainly been ordered to advance on the sixteenth." Thanks to Greenhow's timely intelligence, Beauregard was able to mass together several scattered divisions at Manassas in time to confront McDowell's green recruits with sufficient strength to accomplish a complete rout of the Northern army. Greenhow soon received the following grateful dispatch, which she proudly carried with her for the rest of her life, "Our President and our general direct me to thank you. We rely upon you for further information. The Confederacy owes you a debt."

Greenhow was almost certainly receiving this sensitive military information from her most ardent admirer, Senator Henry Wilson of Massachusetts. There exists a group of passionate love letters among Rose Greenhow's papers in the National Archives. These letters, written on Senate stationery and signed simply "H," were undoubtedly written by Wilson and are anything but platonic. "H" vows: "You well know that I love you and will sacrifice anything. Tonight, whatever the cost, I will see you, and then I will tell you again and again that I love you." How fortunate for a Confederate spy that these sentiments were written by the chair of the Senate Military Affairs Committee; through Wilson, Greenhow was privy to classified information from the war department, the White House, and the staffs of generals McDowell and McClellan. She bragged openly in Washington that she knew what McDowell was going to do before he knew it. McClellan complained, "She knew my plans, and has four times compelled me to change them."

During her brief but successful spying career in the summer of 1861, Greenhow gathered information on Lincoln's personal guards, the strength of Washington's defenses, and other data which would have been useful had the Confederates successfully invaded the Union capital. After Greenhow plied Secretary of State William Henry Seward with generous amounts of wine until he was "properly attuned with the gifts the gods provide," he let slip several compromising tidbits regarding the state of the Union navy. Soon, Greenhow was sending daily reports from Washington to Richmond.

Within weeks, suspicious Union leaders began regarding Greenhow as a potential leak in their security; the defeat at Bull Run was widely blamed on the existence of an espionage ring. All of Washington knew of her open advocacy of the Confederate cause and of her close relationships with several Union officials. Thomas A. Scott, assistant secretary of war, hired the famous detective Allan Pinkerton to stake out Greenhow's house, convinced she was actively engaged in spying for the South. On the night of August 22, 1861, Pinkerton and two other detectives arrived at her house on 16th Street in a pouring rainstorm. Frustrated in his attempts to see into her parlor windows, which were situated half a story above ground level, Pinkerton took off his shoes and stood on the shoulders of his subordinates to give himself a clear view.

Inside Greenhow's parlor Pinkerton saw a Union officer, who appeared to be showing her a map of Washington fortifications. After several minutes, Greenhow and her companion left the room for a longer period, after which the couple emerged holding hands. Soon thereafter, the man left the house to the sound of a vigorous goodnight kiss.

The next day, Pinkerton and his entourage were waiting at her door as Greenhow approached with a diplomatic acquaintance. Greenhow was arrested, and the men set about ransacking her house for evidence. While Pinkerton's men tore apart pictures, bed frames, closets, and drawers looking for evidence, Greenhow remained inside. Bits of paper with messages written in cipher were found in the fireplace, shredded but unburnt. When the searchers reached her liquor cabinet, she opened a bottle of brandy and passed it around. Then, while the search turned into revelry, Greenhow quietly stole upstairs, removed her secret papers from a top shelf, and slipped them into her maid's stocking. As the officers continued their search, the maid spotted a blotter, on which was a perfect mirror image of Greenhow's last message. She quickly destroyed it. Later, her maid was allowed to leave, taking the most incriminating evidence with her. Greenhow's daughter, Little Rose, ran to an upstairs window, where she yelled repeatedly to passersby: "Mother's been arrested! Mother's been arrested!"

All Washington was buzzing the next day with news of the arrests, which eventually included many prominent figures. For the next several months, Greenhow was kept under house arrest. Her spying continued, however, as she was able to send messages through her maid and her daughter Rose. She once used a carrier pigeon to dispatch crucial information to Confederate President Jefferson Davis. She boasted at her ability to carry on her espionage activities under the noses of her captors. Frustrated law enforcement officers eventually confined Greenhow to the Old Capitol Prison, formerly the boarding house where she had grown up. She was assigned to the very room where she had nursed the dying John C. Calhoun in 1850.

Although possessed of sufficient evidence to try her for treason, Union officials feared a trial would implicate high-ranking officers and prominent politicians in her activities should they be made public. Wanting nothing more than to be rid of the pesky widow, Union officials offered her a safe conduct to Confederate territory. On the day of her release, Greenhow emerged, wearing a heavy shawl, to a curious throng of spectators. Just before boarding the carriage that was to take her to Baltimore, Maryland, she lifted the edge of her shawl to reveal a full-sized Confederate flag.

Rose Greenhow became the toast of the town upon her arrival in Richmond on June 4, 1862. President Jefferson Davis assured her, "But for you there would have been no Battle of Bull Run," and paid her a bounty of $2,500 for her "valuable and patriotic service." In August 1863, Davis sent Greenhow to Europe to act as a propagandist and courier. She was charged with gathering intelligence and spreading good will regarding the Confederate cause. She was received warmly in Britain, where she found strong sympathy for the Southern effort. She was less warmly received, however, in France at the court of Napoleon III. In 1863 London, Greenhow published her memoirs, entitled My Imprisonment and the First Year of Abolition Rule in Washington. Her book sold well in Britain and brought her generous royalties. While in England, she met and dazzled the second earl of Granville, recently widowed, who asked for her hand in marriage. Though she agreed to marry the earl, she felt that the information she had gathered was too sensitive to be entrusted to a courier; so she insisted on delivering the news to Davis personally back in the States.

In August 1864, Greenhow boarded the blockade runner Condor and proceeded across the Atlantic without incident. But when the ship reached the Cape Fear River, above Wilmington, North Carolina, a fierce storm blew up. In his haste to reach the protection of the guns of Fort Fisher, the captain stranded the vessel atop a sandbar. Fearing capture by a pursuing Federal gunboat, Greenhow insisted that the captain provide her with a rowboat to take her to shore. The captain hesitated, fearing the raging storm, but he was no match for the insistent Greenhow. As she entered the shaky boat, around her neck she wore a heavy bag filled with $2,000 worth of gold coins she had received as royalties from her book, which she intended to donate to the Confederate cause. Within yards of the ship, the rowboat capsized. Greenhow was immediately swept under the waves with the weight of the gold and her own voluminous skirts. Her body was discovered the next morning by a Confederate soldier, who stole the money and pushed her corpse back into the surf. Later, search parties found her body, and when news of her death was published in the local newspaper, the guilt-stricken soldier turned himself in, along with the money he had taken. Rose Greenhow was buried with full military honors in Oakdale Cemetery in Wilmington, North Carolina.

A daring and courageous woman, Rose Greenhow was one of the most successful spies of the Civil War, prompting Senator Charles Sumner of Massachusetts to claim: "Mrs. Greenhow is worth any six of Jeff Davis' best regiments." There is no doubt that her efforts contributed strongly to the early victories of the Confederate Army.


Bakeless, John. Spies of the Confederacy. Philadelphia, PA: J.B. Lippincott, 1907.

Kane, Harnett T. Spies for the Blue and Gray. NY: Doubleday, 1954.

Kinchen, Oscar A. Women who Spied for the Blue and the Gray. Philadelphia, PA: Dorrance, 1972.

Ross, Ishbel. Rebel Rose: Life of Rose O'Neal Greenhow, Confederate Spy. NY: Harper & Brothers, 1954.

suggested reading:

Garrison, Webb. A Treasury of Civil War Tales. Nashville, TN: Rutledge Hill Press, 1988.

Stern, Philip Van Doren. Secret Missions of the Civil War. NY: Bonanza Books, 1959.

Peter Harrison Branum , Ph.D., Philosophy, Auburn University, Auburn, Alabama