Just before 11 a.m., Rose O’Neal Greenhow, a dark-haired, dark-eyed Washington widow in her 40s, walked toward her house on 16th Street. Greenhow circulated among the capital’s elite social circles, and her home stood within sight of the White House. Despite the sweltering heat, she stopped to talk with a neighbor. A Union guard, she learned, had been placed in front of Greenhow’s house earlier that morning.
Library of CongressRose Greenhow
Greenhow looked around and saw two men, one in uniform, watching her on the other side of the street. Just then an associate passed her by. “Those men will probably arrest me,” she said. “Walk to Corcoran’s corner and see. If I raise a handkerchief to my face, give out the information.” She then removed a handwritten note from her pocket, put it in her mouth, and swallowed it before going to the home she shared with her eight-year-old daughter, Little Rose.
As Greenhow reached her front door, Allan Pinkerton, the famed Chicago detective, raced toward her with one of his men. Now in charge of counterintelligence in Washington for Gen. George B. McClellan and disguised as his nom de guerre, Maj. E.J. Allen, Pinkerton announced her arrest. While Greenhow demanded to see a warrant, she wiped her cheek with her handkerchief. Satisfied that her signal had been seen, she turned back to Pinkerton. “I have no power to resist you, but had I been inside of my house, I would have killed one of you before I submitted to this illegal process,” she said.
Greenhow was already well-known as a fervent supporter of the Confederacy. But Pinkerton was arresting her for more than her inconvenient political leanings. She was also one of the South’s most valuable spies.
Though the Civil War began on April 12, 1861, by then the South had spent months preparing a network of spies across the North, concentrated in Washington. Much of the groundwork in the capital was done by Capt. Thomas Jordan, at the time still an officer in the United States army. Knowing of Greenhow’s sympathies and social position, he recruited her to lead the spy ring. As one of the premier hostesses in the city and a longtime friend of former President James Buchanan, Greenhow frequently entertained members of Congress and diplomats with elaborate dinner parties. She was also known for her beauty and charm, which she willingly used to get tight-lipped men to talk.
Greenhow was also familiar with tragedy, which likely added to her resolve to risk everything for the Confederacy. Born in southern Maryland to a wealthy family and nicknamed “Wild Rose,” her father had been murdered by one of his slaves when Greenhow was still a girl. She and her siblings were separated and sent to live with relatives. In 1854, her husband was killed in an accident, and by August of 1861, five of the eight children she’d given birth to were dead. Her daughter Gertrude, who suffered for months from typhoid fever, had died that spring.
In the few months since the war began, Greenhow had already proved herself as an effective spymaster. In addition to passing along critical information collected by her agents, she used her sources to find out when the Union Army would march south to attack Manassas. On July 9, Greenhow sent a coded message to Gen. Gustave Toutant Beauregard, commander of Confederate forces in Northern Virginia, through her 16-year-old courier, Bettie Duvall. Duvall carried Greenhow’s coded message in a black silk purse tucked in a chignon at the nape of her neck; she drove a wooden milk cart 20 miles through Union territory until she reached Beauregard’s headquarters. The Confederates won the battle largely because Greenhow’s message gave Beauregard time to request more troops. After the battle, Greenhow received a note from Richmond: “Our President and our General direct me to thank you. The Confederacy owes you a debt.”
But now the game was up. On this hot August day, detectives escorted Greenhow into her house and ransacked her home. While they collected letters and notes that implicated her as a spy, Greenhow went to her bedroom under the guise of changing her clothes. As soon as she was alone, she destroyed papers she’d been carrying, including the cipher she used to communicate with Manassas.
The detectives arrested other women that day for “corresponding with the enemy” and within a week sent them to Greenhow’s home, which would become known as “The House of Detention for Female Rebels.” Newspapers called it “Fort Greenhow.” Guards camped out for another week while they searched every corner of the house, tossing everything in their path, including the personal effects of Greenhow’s recently deceased daughter.
For nearly five months, Greenhow was kept under house arrest with Little Rose. She was interrogated daily. Despite her confinement, some of her intelligence, gleaned from the guards or visitors, continued to reach Confederate headquarters. Pinkerton wrote, “She has not ceased to lay plans, to attempt the bribery of officers having her in charge, to make use of signs from the windows of her house to her friends on the street, to communicate with such friends and through them… to the rebels.” She even wrote a biting letter to Secretary of State William Seward, complaining about her poor treatment, and sent a copy of the letter to a Richmond newspaper. Seward and other Union officials were embarrassed and furious.
On Jan. 18, 1862, Pinkerton, having grown tired of Greenhow’s behavior, insisted that all paper be removed from her home and the windows boarded up. In the late afternoon, Greenhow, Little Rose and another female prisoner were transferred to the military prison on Capitol Hill under the gaze of newspaper reporters. As the notorious spy left her home, she said to one of the guards, “I trust that in the future you may have a nobler employment than that of guarding defenseless women.”
The women were the first females to arrive at the prison, which was packed with Confederate soldiers and crawling with vermin and disease. Greenhow’s elitist and racist attitude, as well as her open disdain for the guards, only made her situation worse. She wasn’t allowed out of her room for the first three months.
After five months of house arrest and more than four months in prison, Greenhow was finally brought before a commission to decide her fate. They finally agreed to release her, along with her young daughter, on the condition that Greenhow stayed in the South until the war was over.
Rose Greenhow with her daughter.
The South greeted her as a heroine, and President Jefferson Davis asked her to travel to Europe on a diplomatic mission. While she championed the Confederacy overseas, she published her memoir, “My Imprisonment and the First Year of Abolition Rule at Washington.” Her earnings were intended to be donated to the Confederacy.
On her way back to the South in October 1864, Greenhow’s blockade runner, the Condor, encountered Northern forces and ran aground on Federal shoals. Despite the captain’s warning, Greenhow insisted on trying to escape in a rowboat with several others. Wearing a heavy black silk dress, Greenhow carried dispatches and about $2,000 in gold from her book. Waves quickly battered the small boat and tossed its crew into the water. Greenhow drowned, carried under by the weight of the gold. Her body washed ashore the next morning; she was given a hero’s funeral and buried in Oakdale Cemetery in Wilmington, N.C.
Cate Lineberry, New York Times
)