Rose O’Neal Greenhow was the perfect example of a Southern martyr. She was born in Montgomery County, Maryland in 1817, and acquired her nickname at an early age. Rose’s father was murdered by his slaves the same year she was born, so her mother was forced to raise four daughters and take care of the family farm. When Mrs. O’Neal died, Rose and her younger sister were sent to Washington D.C. to live with an aunt, who ran a fashionable boardinghouse at what would later become the Old Capitol Prison. Now a teenager, Rose learned the art of social etiquette. Considered to be educated, refined, loyal, and beautiful, with olive skin and a rosy complexion, she was the epitome of high society, and cultivated relationships with politicians and military officers, including Daniel Webster and James Buchanan. Her closest confidant, however, was John C. Calhoun, the powerful statesman from South Carolina who served as senator, secretary of state, and vice president.
“I am a Southern woman,” Rose wrote, “born with revolutionary blood in my veins, and my first crude ideas on State and Federal matters received consistency and shape from the best and wisest man of this century.” When Calhoun succumbed to his final illness at the Old Capitol, Rose was in constant attendance.
In 1835, she wed wealthy Virginian Dr. Robert Greenhow with the blessing of famed society matron Dolly Madison. Rose was 26, and Greenhow was 43. The couple had eight children. In 1850, the family moved to Mexico City with the promise of greater financial gains, and then to San Francisco. Dr. Greenhow died from an injury in 1854, so Rose and her children moved back to Washington D.C., where she resumed the role of popular socialite.
When the War Between the States broke out in April, 1861, she was 44 years old. Staunchly pro-slavery, Rose immediately set to work contacting Confederate friends with information she obtained from pro-Union contacts. She and a close associate, Lieutenant Colonel Thomas Jordan, formed an extensive spy ring that included both men and women.
In July, Rose obtained one important piece of information that she sent to General P.G.T. Beauregard prior to the Battle of First Manassas (Bull Run). Written in secret script, she sent the ten-word message via her assistant, Betty Duvall, who carried the note wrapped in silk and tied up in the bun of her hair. The note stated that the enemy, 55,000 strong, would commence from Arlington and Alexandria to Manassas. Because of this vital information, Beauregard and General Johnston were able to deflect the Union army’s advance and win the battle. Afterward, Jefferson Davis commended her achievement.
Rose’s activities raised the suspicions of Allan Pinkerton, head of the newly organized federal government’s Secret Service. After he spied into the windows of her home on 16th Street NW, and thought he had enough sufficient evidence, Pinkerton placed Rose on house arrest in August. Union soldiers showed her no dignity as they ransacked through her belongings, discovering maps, letters, notes, ciphered messages, and papers that she had attempted to burn. Rose didn’t hesitate to let everyone know about her plight by writing to Mary Chesnut and Secretary of State William Seward, whose letter was leaked to a Richmond newspaper. Defiantly, she still continued her spying activities, so Pinkerton sent her and her youngest daughter, 8-year-old “Little Rose,” to Old Capitol Prison in January. Rose reportedly wrapped the Confederate flag around her torso as she was being led to prison. Ironically, she and her daughter were contained in the same room where she spent hours with John C. Calhoun while he was dying. Needless to say, Confederate propaganda mills were given ammunition about the “brutal Yankees who would imprison a mother and child.”
While she was in prison, “The Rebel Rose” waved the Confederate flag from her window nearly every day, and continued her espionage. After a judge decided in March 1862 that it was too volatile to put her on trial, Rose was exiled to Richmond in June, once again draping herself with the Confederate flag upon her exit from Washington. She was greeted by cheering crowds as a heroine. In August 1863, President Davis appointed her to a diplomatic mission in France and England, and while there, she penned her memoirs, My Imprisonment and the First Year of Abolition Rule at Washington in an effort to gain European support for the Southern cause. The book immediately became a best seller. She was received by Queen Victoria and Napoleon III, was granted an audience with the Emperor at the Tuileries, and became engaged to the Second Earl of Granville.
Rose missed her home, however, so in September, 1864, she decided to return to America with classified information for the Confederacy. Sailing aboard the blockade runner Condor, she and her traveling companions attracted the attention of a Union ship on October 1. In an attempt to outrun it, the Condor ran aground on a sandbar at the mouth of the Cape Fear River. Afraid that she would be captured, Rose convinced the captain to let her take a lifeboat. Regardless of the stormy weather, he relented, and she set off with two others and $2,000 in gold sovereigns that she had earned from book royalties. Tragically, the tiny rowboat capsized, and the three people aboard were drowned.
The following day, Rose’s body washed up on shore. A Confederate soldier discovered it and took the gold, then pushed the body back into the sea. It washed up again, however, and was recovered and identified this time. (The soldier was so wrought with guilt that he returned the gold.) Rose’s body was taken to Wilmington, North Carolina, where it was laid out in state in a hospital chapel with a Confederate flag for a shroud. She was given a full military funeral, and her coffin was also draped with the Confederate flag. The marble cross marking her grave bears the epitaph, “Mrs. Rose O’N. Greenhow, a Bearer of Dispatchs to the Confederate Government.”
Rose’s diary, dated August 5, 1863 to August 10, 1864, and describing her mission in detail, is held in the North Carolina State Archives in Raleigh. The National Archives has digitalized and made available in the Archival Research Catalog 175 documents that the U.S. Intelligence Service seized from Rose’s home in August 1861. (The photograph of Rose and “Little Rose” was taken during their incarceration at Old Capitol Prison by Matthew Brady Studio.)