Spies in the American Civil War

Spying and espionage has been a part of war for centuries and the American Civil War (1861-65) was no exception. Here, James Adams shares an overview of spies and spying on both the Union and Confederate sides in the early part of the war.

Allan Pinkerton, President Abraham Lincoln, and Major General John A. McClernand, 1862. Pinkerton was the head of the Union Intelligence Service during the early years of the war.

Although neither the Union nor the Confederation had an official military intelligence network during the US Civil War, each side obtained crucial information through espionage. From the start of the war, the Confederates set up a spy network in the federal capital of Washington, D.C., which was home to many supporters of the South. 

The Confederate Signal Corps also included a secret intelligence agency known as the Secret Service Bureau, which managed espionage operations along the so-called secret line from Washington, D.C., to Richmond, Virginia.

As the Union did not have a centralized military intelligence agency, the generals took charge of collecting intelligence for their own operations. General George B. McClellan hired prominent Chicago detective Allan Pinkerton to create the Union's spy organization in mid-1861.

Confederate spies in Washington

Located 60 miles south of the Mason-Dixon line, Washington, D.C. was full of southern sympathizers when the Civil War broke out in 1861. Virginia Governor John Letcher, a former member of Congress, used his knowledge of the city ​​to set up an emerging spy network in the capital in April 1861, after the secession of its state, but before its official entry into the Confederacy.

Thomas Jordan, a West Point graduate from Washington before the war, and Rose O'Neal Greenhow, an openly pro-South widow who was friends with a number of northern politicians, including Secretary of State William Seward and Massachusetts Senator Henry Wilson, were key in this network

In July 1861 Greenhow sent coded reports across the Potomac to Jordan (now a volunteer with the Virginia militia) regarding the planned federal invasion. One of his couriers, a young woman named Bettie Duvall, dressed as a farmer to pass Union Sentries from Washington, then drove at high speed to the Fairfax Courthouse in Virginia to transmit messages to the Confederate officers stationed there.

Confederate General P.G.T. Beauregard later credited information received from Greenhow in helping his rebel army achieve a surprise victory in the First Battle of Bull Run (or Manassas) on July 21, 1861.

Confederate Signal Corps and Secret Service Bureau

The Confederate Signal Corps, which operated the semaphore system used to communicate vital information between armies on the ground, also set up a secret intelligence operation known as the Secret Service Bureau.

Led by William Norris, the former Baltimore lawyer who also served as chief communications officer for the Confederation, the office managed the so-called secret line, an ever-changing mail system used to get information from Washington through the Potomac and Rappahannock rivers to Confederate officials in Richmond, Virginia. The Secret Service Bureau also managed the transmission of coded messages from Richmond to confederate agents in the North, Canada, and Europe.

A number of Confederate soldiers, particularly cavalrymen, also acted as spies or "scouts" for the rebel cause. Among the most famous were John Singleton Mosby, known as the “Gray Ghost,” who led guerrilla warfare in western Virginia during the final years of the war, and in particular J.E.B. Stuart, the famous cavalry officer whom General Robert E. Lee called "the eyes of the army".

Union Spies: Allan Pinkerton’s Secret Service

Allan Pinkerton, the founder of his own detective agency in Chicago, had gathered intelligence for Union General George B. McClellan during the early months of the civil war, while McClellan headed the Ohio department. The operation soon grew and Pinkerton soon set-up a Union spy operation in the summer of 1861, working under McClellan. 

Calling himself EJ Allen, Pinkerton built a counterintelligence network in Washington and sent undercover agents to the Confederate capital of Richmond. Unfortunately, Pinkerton's intelligence reports on the ground during the 1862 peninsula campaign systematically miscalculated the Confederate numbers at two or three times their actual strength, fueling McClellan's repeated calls for reinforcements and reluctance to act.

Although he called his operation the United States Secret Service, Pinkerton actually only worked for McClellan. Union military intelligence was still decentralized at the time, as generals (and even President Lincoln) employed their own agents to seek and report information. Lafayette C. Baker, who worked for former Union General-in-Chief Winfield Scott and later for War Secretary Edwin Stanton, was another important Union intelligence officer. 

The courageous but ruthless Baker was known to have gathered Washingtonians suspected of having sympathies with the South; he later led the manhunt for John Wilkes Booth, the Confederate sympathizer who shot and killed Lincoln at Ford’s Theater in April 1865.

Prominent civil war spies

One of the first Confederate spies targeted by Allan Pinkerton was Rose O’Neal Greenhow. Shortly after the southern victory in the First Battle of Bull Run, Pinkerton placed Greenhow under surveillance and then arrested her. Imprisoned in Old Capitol Prison, she was released in June 1862 and sent to Richmond. Belle Boyd, another famous southern spy who became a Confederate, helped pass information to General Stonewall Jackson during his campaign in the Shenandoah Valley in 1862. Like the Confederacy, the Union also had female spies: Elizabeth Van Lew of Richmond, risked her life running a spy operation from her family's farm, while Sarah Emma Edmonds disguised herself as a black slave to enter into Confederate camps in Virginia.

Born in Britain, Timothy Webster, a former New York police officer, became an early double agent in the Civil War. Sent by Pinkerton to Richmond, Webster pretended to be a courier and managed to gain the trust of Judah P. Benjamin, the Confederate Secretary of War (later Secretary of State). Benjamin sent Webster to deliver documents to the Baltimore secessionists, which Webster quickly passed on to Pinkerton and his staff. Webster was eventually arrested, tried as a spy, and sentenced to death. Although Lincoln sent a message to President Jefferson Davis threatening to hang the Confederate spies captured if Webster was executed, the death penalty was carried out in late April 1862.

What do you think about spying in the US Civil War? Let us know below.

Harriet Tubman: A Black US Civil War Heroine who Led a Spy RIng

The American Civil War created all manner of heroines. One such person was Harriet Tubman, a courageous African-American lady who led a spy ring and fought slavery during the US Civil War. Melissa Havran explains her courageous life.

Harriet Tubman in the 1860s.

Courage is not the absence of fear. Courage is feeling that fear, insecurity, and doubt, but deciding that something else is more important. It's a quality that separates the ordinary from the extraordinary. Harriet Tubman, I believe, epitomized what it meant to be courageous. She believed in what she was doing, and continued to do it, regardless of the dangers involved.  As I began to research her role as a spy, I couldn't help but to question my own courage. If faced with the same dilemma, would I have been able to make the same choices Harriet made, even if those choices were a threat to my own wellbeing? Her story continues to amaze me. 

They called her “Moses” for leading enslaved people in the South to freedom up North. But Harriet Tubman fought slavery well beyond her role as a conductor for the Underground Railroad. As a soldier and spy for the Union Army during the Civil War, Tubman became the first woman to lead an armed military operation in the United States in what is known as the Combahee Ferry Raid.

By January 1, 1863, when the Emancipation Proclamation went into effect, Tubman had been in South Carolina as a volunteer for the Union Army. With her family behind in Auburn, New York, and having established herself as a prominent abolitionist in Boston circles, Tubman, at the request of Massachusetts Governor John Andrew, had gone to Hilton Head, South Carolina, which had fallen to the Union Army early in the war.

Spy ring

For months, Harriet Tubman worked as a laundress, opening a washhouse, and serving as a nurse, until she was given orders to form a spy ring. Her orders came as a result of her role gathering clandestine information, forming allies and avoiding capture, as she led the Underground Railroad. In her new role, Tubman assumed leadership of a secret military mission in South Carolina’s low country.

Tubman partnered with Colonel James Montgomery, an abolitionist who commanded the Second South Carolina Volunteers, a black regiment. Together, the two planned a raid along the Combahee River, to rescue slaves, recruit freed men into the Union Army, and obliterate some of the wealthiest rice plantations in the region. 

Montgomery already had 300 men and, combined with the 8 scouts Tubman had recruited, the two were able to map the area and send word to slaves when a raid would take place.

One characteristic that made Tubman a successful spy ringleader, was that she could get black people to trust her when the Union officers knew that they were not trusted by the local people.  Perhaps the most interesting piece of this story is that Tubman was indeed, illiterate, yet she had great success as a spy leader. Since she couldn't read or write, she also couldn't write down any intelligence she gathered. Instead, she committed everything to memory, guiding the ships towards strategic points near the shore where fleeing slaves were waiting and Confederate property could be destroyed.

While it seemed Tubman, for the most part, was able to compartmentalize her role as spy, some of her missions seemed to have more of an effect on her than others.

On one particular raid, where Tubman and Montgomery were working together to bring gunboats up river, Tubman vividly recalled the horrific scene that day with running slaves, women, babies and crying children being chased down by rebels and killed.

Legacy

After researching Tubman’s life as a Union spy, what stands out most is that she was recognized a hero, but never paid - largely because she was a black woman. Often, Tubman’s brave work was documented by local newspapers. She was never referred to by name, but instead as "She Moses", because just like Moses, she led an enslaved people to freedom. Perhaps writing that a black woman was leading Montgomery’s band of 300 men was unfortunately a little too much for the 1860s.

But Tubman’s anonymity came to an end in July 1863 when Franklin Sanborn, the editor of Boston’s Commonwealthnewspaper, picked up the story and named Harriet Tubman, a friend of his, as the heroine.

In the end, Tubman petitioned the government several times to be paid for her duties as a soldier and was denied because she was a woman.

Tubman would eventually get a pension, but only as the widow of a black Union soldier she married after the war, not for her courageous service as a soldier.  To think of the lives saved because of the courage of another is truly what makes Tubman’s story stand out as one of the greatest in American history. If we all possessed this incredible characteristic of courage, I often wonder how our world would be different.

What do you think of Harriet Tubman? Let us know below.

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