As the Civil War began, Greenhow made no secret of her pro-Southern feelings. One day, Captain Thomas Jordan approached her about serving as a spy for the Confederacy. Jordan was a member of the Union Army and the U.S. War Department, but he secretly recruited spies for the South. Greenhow agreed to act as a spy and also to serve as the center of a Confederate spy ring in Washington. Her spy network included other prominent Washington residents, clerks in several government departments, and a number of female couriers. Greenhow collected information about the Union's war plans from the network, as well as from her friends and admirers in Washington. She then passed the information along to Confederate leaders in Richmond, Virginia.
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