1. Harriet Tubman- Abolitionist and Civil War Spy
Tubman was recruited by the Union to spy on the Confederacy. She had already established a network of Union sympathizers to help slaves escape to freedom, so she was perfectly positioned to leverage that network for information.
Aside from being a Civil War spy, Tubman also became the first woman to lead a military raid in the US. She helped Col. James Montgomery free slaves from plantations along the Combahee River.
Tubman and James lead hundreds of black soldiers in gunboats up the river to attack a Confederate supply depot. The journey was perilous, with the river full of mines, or “torpedoes“, as they were called.
They were able to avoid the mines and strike a blow to the South. The Confederate supply depot was destroyed and many slaves were freed. This was just another victory for Tubman in what I’m sure was a fascinating life.
2. Belle Boyd- Confederate Spy
Belle Boyd was Southern to the core. She was arrested at the age of 17 for shooting a Union soldier who had insulted her mother. Though there is no historical evidence to support this, I like to imagine Belle could spit with the best of ’em.
Union troops investigated the altercation and eventually dropped all charges. The soldier she shot had broken into their home, so the shooting was justified. She was no longer under arrest but would continue to be under suspicion.
The Union was right to suspect Boyd. Afterall, she had become a spy for the Confederacy. Boyd’s attractiveness and charm would serve her well in gaining information for the Cause.
Eventually, the Union troops would send Belle away to live with family in Front Royal, Virginia. Once there, Belle made herself even more useful. She would carry messages between Generals “Stonewall” Jackson and P.G.T. Beauregard.
Belle was arrested multiple times for her actions, but never stopped spying. She would serve her time and then return to duty. Intriguingly, she would eventually marry a Union officer who was one of her captors. I guess opposites really do attract.
3. Pauline Cushman- Union Spy
Civil War spies were fairly common, particularly women. They were perfect for the task because they were often underestimated. One such spy, Pauline Cushman was able to help expose many other Civil War spies during her time serving Union troops.
Cushman was an actress. During one of her performances, she was dared to give a toast to the Confederacy. She would use the toast to ingratiate herself with the troops.
The ploy worked, and soon she was getting valuable information to share with Union soldiers. The federal marshal in Kentucky was happy to have her services.
Once Cushman was recruited to spy for the Union, she was immediately sent to Nashville, TN. In Nashville, she would do most of her work gathering information and exposing Confederate spies.
Eventually, Cushman was exposed herself. Falling under suspicion, the Confederates arrested her. She was sentenced to hang, but in a stroke of luck, Union troops arrived earlier than expected in Shelbyville freeing Cushman.
Elizabeth Van Lew- Abolitionist and Spy
Van Lew was a Union sympathizer. She would bring food to Union troops imprisoned by the Confederates. The troops in grey were suspicious, but they didn’t want to mess with an affluent lady such as Elizabeth.
Van Lew eventually helped a Union officer escape. He would make a recommendation to General Benjamin Butler that she would make a perfect spy.
Butler invited Elizabeth to join them as a spy and she consented. Van Lew was able to develop a network for the Union. One of the spies she recruited was Mary Elizabeth Bowser, who we will talk about in our next section.
Mary Elizabeth Bowser- Slave and Civil War Spy
Being a spy was risky, but some Civil War Spies risked more than others.
That was the risk Mary Bowser took on a regular basis. She was originally a slave to the Van Lew family. When the patriarch of the Van Lew family died, his daughters eventually granted Bowser her freedom.
Though much of Bowser’s story is difficult to validate, it is speculated that she was a vital part of Elizabeth Van Lew’s spy network. Some stories have her infiltrating the Southern White House itself as a house slave.
Mary Elizabeth funneled information from the Confederate White House to the Union, putting her life in grave peril. She would eventually fall under suspicion from Jefferson Davis late in the war. Bowser fled the White House, and even attempted to burn it down in the process, though she was unsuccessful.