Greenhow, a widow in her 40s at the time of her arrest, had been born in Maryland but spent her teenage years in the capital living with her aunt. She married a well-to-do older man named Dr. Robert Greenhow and the couple and their children lived in Washington DC, Mexico City, and San Francisco before his death in 1854.
Greenhow returned to the capital and expanded her role as an influential hostess, with important friends in political and military circles. When the Civil War started, Greenhow fervently supported the South but chose to remain in Washington. She was recruited to use her position of power in society to spy for the Confederacy and developed an espionage ring of both men and women.
Her most famous piece of spy work was the information she smuggled to PGT Beauregard before the First Battle of Bull Run (Manassas) in July 1861 alerting him to Union troop numbers and movements. President Jefferson Davis later credited her with helping to win the battle.
Washington authorities became suspicious of Greenhow’s activities and arrested her on August 23, 1861. She was kept under house arrest until January 1862, when—because she had managed to continue passing on information to the Confederacy—she was moved to Old Capitol Prison. She remained incarcerated until late May, when she was deported to the South and received a warm welcome in Richmond.
Wanting to continue aiding the Confederate cause, Greenhow traveled to Europe, where she appealed to leaders in London and Paris to help the Confederacy. During this time she also published her memoir, which was successful in England.
Upon her return to the United States, her ship, the Condor, was spotted trying to run the blockade outside Wilmington, North Carolina, on October 1, 1864. In its attempts to escape the Union gunboat, the Condor ran aground on a sandbar. Anxious to escape, Greenhow and a couple other passengers set out in a lifeboat, but it overturned in the rough water. Greenhow drowned, and when her body was discovered the following day, she was laid out in state in Wilmington and buried there.
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