The Confederacy’s Most Famous Spies: The Lives and Careers of the South’s Secret Agents during the Civil War

Given the necessity of spies to hide in plain sight, on some level it is perfectly sensible that women played a larger and more decisive role in espionage operations, because during the Civil War, women were not taken seriously as threats. They openly moved through areas that men in uniform could not easily penetrate, and they were able to publicly receive callers, visit prisoners, manage households, carry on the ordinary commerce of social life, and cross lines that military authorities maintained without bringing any attention upon themselves. A woman bringing food and medicine to prisoners seemed to be a humanitarian, not a security concern, and a woman maintaining the social routines of an established household was a hostess, not an intelligence coordinator. Ironically, both sides used several women as spies precisely because they drew less suspicion.

At the start of the war, the most formidable spy on either side of the conflict was a Washington widow named Rose O'Neal Greenhow. She was perfectly situated for espionage as a politically connected woman of extraordinary intelligence who had social reach and the desire to use every connection she had. In the first year of the war alone, she helped win a battle, ran a spy ring from inside her own house while under house arrest, and charmed her jailers in ways that allowed her to continue to pass intelligence from prison. 

Of course, the most notorious Confederate spy is arguably the most controversial individual of the entire war. John Wilkes Booth was a member of the prominent 19th century Booth theatrical family from Maryland, and he was a well-known actor throughout much of the country by the 1860s. But Booth was also a Confederate sympathizer who dabbled in espionage, and he was increasingly outraged at the Lincoln administration. His early plans to kidnap and ransom President Lincoln, which may have had official Confederate sanction, ultimately gave way to a wide-ranging conspiracy to kill Lincoln.