Rose O’Neal Greenhow: The Life and Legacy of the Washington Socialite Who Became a Confederate Spy 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, yet neither the Union nor Confederates took potential women spies seriously enough.

At the start of the war, the most formidable of these women 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 on behalf of a cause she believed in absolutely. 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. She was exiled to the Confederacy rather than tried, because the government that arrested her recognized, rightly, that trying her in open court would be an embarrassment. She lobbied Jefferson Davis directly, and then she crossed the Atlantic and met Napoleon III and Queen Victoria as an unofficial Confederate envoy. She published a memoir in London that sold thousands of copies and made her case to the European audience her government desperately needed.