The life of a spy is always filled with risk, but sometimes the risk has nothing to do with spying. At the start of the Civil War, Rose O’Neal Greenhow, a Maryland native, resided in Washington, DC, with her four children. Her late husband had been wealthy and well-connected in the capital, and Greenhow used her influence to support the Southern cause. Collaborating with Lieutenant Colonel Thomas Jordan, she created an intricate spy network in Washington.
Greenhow’s prowess became evident with the operation’s first success. Greenhow obtained information about General Irvin McDowell’s army movements just before the First Battle of Bull Run in July 1861. She instructed a female courier to deliver messages from Greenhow to Confederate General Pierre G T Beauregard at his headquarters in Fairfax, Virginia. Beauregard later stated that this intelligence prompted him to request reinforcements from General Joseph Johnston’s nearby command. The actions contributed to the Confederates’ significant victory over the Union in the war’s first major battle. The day after the battle, Confederate President Jefferson Davis sent Greenhow a letter of gratitude.
As careful as she was, federal authorities quickly uncovered the security leaks anyway. They soon traced them back to Greenhow’s residence, and she was put under house arrest. Before long, other suspected female spies were also detained and joined her there. The house soon became known as “Fort Greenhow” and continued to supply intelligence to the Rebels, despite the house arrest. During a visit from her close friend, Massachusetts Senator Henry Wilson, he inadvertently shared crucial information, which Greenhow passed along to her operatives. He had no idea he was being deceived and plied for information. After five months, Greenhow and her youngest daughter, “Little Rose” were moved to the Old Capitol Prison in Washington, probably in an effort to quell the information leaks. She remained there until June 1862, after which she was exiled to the South. Her husband had been killed in an accident. Greenlow’s other daughters, were no longer in the home. Florence had married. Gertrude had passed away. She sent Leila to live with Florence, leaving just her and Little Rose.
Choosing safer accommodations for her daughter, Greenhow and Little Rose chose to spend the next two years in England, where she penned a memoir titled “My Imprisonment” while they traveled to England and France, drumming up support for the Southern cause. She then decided to return to the Confederacy to contribute more directly to the war effort. Greenhow and her daughter boarded the British blockade-runner, Condor. Coming into Cape Hatteras, the Condor was intercepted by the USS Niphon off Cape Hatteras, North Carolina. 
The Yankee ship forced the Condor aground near Fort Fischer. Greenhow, who was carrying Confederate dispatches and $2,000 in gold, demanded to be taken ashore. She boarded a small lifeboat, but it overturned in the rough surf. The weight of the gold dragged her under the surface, where she drowned. Her body washed ashore the following morning. She was given a hero’s funeral and buried in Oakdale Cemetery in Wilmington, North Carolina, wrapped in the Confederate flag.


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