13 Cunning Civil War Spies Who Played Huge Roles in the War

The American Civil War was not fought only on battlefields - Civil War spies also waged a secret war of intelligence and covert activities in North America and abroad. Espionage in the Civil War was neither formal nor centralized, and both the Union and the Confederacy relied on networks of amateur scouts, couriers, and secret agents to gather information about enemy plans and movement. 

In the North, General George McClellan hired Allan Pinkerton, founder of a successful Chicago detective agency, to head the Union's secret service in 1861. But as the war progressed, different generals hired their own spymasters who developed separate networks of agents. In the South, the Secret Service Bureau focused much of its energies on obtaining intelligence in Washington, D.C.

Men, women, soldiers, freedmen, and slaves fought this secret war and risked their lives on a daily basis. Civil War spy stories are filled with colorful characters who enlisted their wit, grit, and intelligence in the war effort. Though the identities of many agents were so well guarded that they have since been lost to history, these badass Civil War spies nonetheless made their mark on the war.

  • Belle Boyd Was the Tough-As-Nails "Cleopatra of Secession"

    Belle Boyd Was the Tough-As-Nails "Cleopatra of Secession"
    Photo: Metaweb (FB) / Public domain

    This Southern "Belle" was one of the most colorful, dramatic Civil War spies. Her career for the Confederacy began with a bang: she shot a Union soldier in her home as a teenager. Dubbed the "Siren of the Shenandoah," Boyd often charmed information out of Union officers and delivered it to the likes of Stonewall Jackson and P.G.T. Beauregard. Before 1864, she would be arrested, banished, exiled in England, and, ironically, married to a Union officer. Like so many Civil War spies, in 1865 Boyd published a memoir chronicling her wartime experiences.

  • John Scobell Used the Confederacy's Racism Against Itself

    John Scobell Used the Confederacy's Racism Against Itself
    Photo: The Supervisory Committee For Recruiting Colored Regiments / via Wikimedia

    Born as a slave in Mississippi, John Scobell was a literate, educated freedman by the time war broke out. In late 1861, Scobell got the opportunity to put his keen mind to good use, joining Allan Pinkerton's secret service. Pinkerton was recruiting former slaves as "black dispatches" for his spy ring - he believed their knowledge of and role within Southern society would make them essential players in the secret war. Impressed with Scobell's intelligence and acting skills, Pinkerton invited him to become an agent.

    Working alongside fellow Pinkerton agents Hattie Lawton and Timothy Webster in Richmond, VA, capital of the Confederacy, Scobell proved to be a valuable asset. Confederate officers often viewed him as unintelligent, and Scobell was able to take advantage of their racism and low expectations by going unnoticed and gathering information. He also worked with the "Legal League," a slave resistance group in the South.

  • Mary Bowser Brought Down the Confederacy from Inside the South's White House

    Mary Bowser Brought Down the Confederacy from Inside the South's White House
    Photo: Metaweb (FB) / Public domain

    Mary Bowser, a former slave, was perhaps Elizabeth Van Lew's best agent. Her position was risky, but vital: she was placed as a spy in the so-called White House of the Confederacy, Jefferson Davis's household in Richmond, VA. This meant that she had intimate access to all of the officials, documents, and secrets that passed through the door. Van Lew prized Bowser's intelligence - indeed, though Bowser was known to be witty and bright, she had to play the role of an unintelligent slave to avoid detection. Her position within the Davis household and contributions to the Van Lew spy ring were significant.

  • Harriet Tubman is best known for helping thousands of slaves escape to freedom through the Underground Railroad. Lesser known - but no less important - are her subversive, badass contributions to the Union war effort. Tubman served as a spy for the Union by crossing enemy lines to gather information about Confederate movements. More often than not, her information came from slaves. Tubman thus not only helped slaves physically escape slavery; by relying on their intelligence, she also empowered them and gave then a chance to play a role in the very war that would bring about their freedom. Tubman also served as a scout and even led Union soldiers on raids in South Carolina in 1863.

  • Elizabeth Van Lew Gave Union Prisoners a Role in the War
    Photo: Metaweb (FB) / Public domain

    An ardent abolitionist deep in Confederate country, Elizabeth Van Lew secretly supported the Union in her native Richmond, VA. Her first brush with social alienation due to her political sympathies came in 1861 when she volunteered to nurse Union soldiers at Richmond's Libby Prison. Though she continued to profess her loyalty to the South, her friends and neighbors disapproved of her conduct and treasonously soft heart.

    Rather than giving in to their tuts and sighs, Van Lew used her outsider status as a way to help the Union. She took advantage of her contact with Union prisoners by passing them secret notes and helping to coordinate prison breaks. By early 1864, she was managing a significant spy ring for Union General Benjamin Butler.

    Despite her service to the country in one of its darkest hours, she did not get the happy ending she so deserved: after the war, her close ties to Ulysses S. Grant and the Reconstruction government further alienated her from her Southern neighbors, who labeled her a traitor and excluded her from Richmond society.

  • Theodore Roosevelt's Uncle Was a Confederate Agent in England

    Theodore Roosevelt's Uncle Was a Confederate Agent in England
    Photo: Metaweb (FB) / Public domain

    James Dunwoody Bulloch was the Confederacy's principle European agent. Based in England, Bulloch was in charge of financing and constructing ships for the Confederate navy in Liverpool shipyards - indeed, he was responsible for building the infamous raider the CSS Alabama. The problem? Great Britain was technically neutral in the American Civil War: Great Britain was opposed to slavery and could not find a way to acknowledge the Confederacy without abandoning those sentiments. As such, Bulloch was essentially a covert agent acting in the Confederacy's interests. As an operative on a secret mission in the heart of the British Empire, he came across as a dashing character, and his exploits even left a deep impression on his young nephew, and future US president, Theodore Roosevelt.