Liar, Temptress, Soldier, Spy: Four Women Undercover in the Civil War

In 1861, when Emma Edmonson enlisted in the Union Army, she had already been living as Frank Thompson for four years. Emma’s background in farm work made it easy for her to keep up; she even had experience with loading and firing rifles. Prior to enlisting, Emma sold Bibles in Canada and Michigan. Many men slept fully clothed and rarely washed, making it easy for Emma to go undetected.

Emma had adopted her male persona to avoid being married off by her abusive father, Isaac. In 1859, homesick, Emma visited her family, hunted pheasants for them, and then left. On enlisting, Emma was eager for battle. Though Brigadier General McDowell believed the troops to be too green, President Lincoln pressured him into sending the army to Virginia.

Rose O’Neal Greenhow was a wealthy widow and socialite living in Washington, DC. Rose believed in the Confederate cause. She formed a network of couriers and spies who reported to her and passed messages to Confederate generals about the Union Army’s movements. Rose felt she was integral to the Confederacy, believing it would crumble without her.

One of Rose’s couriers was a 16-year-old girl named Bettie Duvall. Rose dressed Bettie as a farm girl to sneak by Union guards on the border of the Confederacy. Part of Bettie’s disguise included an intricate hairstyle that Rose designed to hide a small silk pouch containing a coded message. Rose also created a complex cipher with Captain Thomas Jordan to protect any intercepted messages. With the message secured in her locks, Bettie crossed the Potomac, avoiding suspicion. She delivered the missive to General Beauregard. The intelligence was gleaned from Rose’s sources: in this case, a high-ranking official with a copy of McDowell’s plans and another with access to the Senate military affairs committee.

At the start of the First Battle of Bull Run, many civilians looked on nearby. The gore and violence were not anticipated; even the Union’s cavalry shied away from looking at the injuries while posted near the surgical tent.

Emma’s division was on the Northern side of the battlefield. Undeterred by the violence, Emma ran to help wounded soldiers. The Union thought they were winning, but the Confederates rallied, swarming the Union. Dehydration and chaos led to a Union retreat. Emma was stunned at her fellow troops’ cowardice.

Rose’s two eldest daughters were in San Francisco to wait out the war. Her youngest, Little Rose, remained with her. Rose received a note sharing the thanks of the Confederate president and general for her battle-winning intelligence.

Elizabeth Van Lew was the spinster daughter of the deceased John Van Lew, a prominent businessman. Elizabeth was born in Richmond and educated in Philadelphia by an abolitionist because Elizabeth’s mother wanted her abolitionist heritage to pass on to her children. Elizabeth’s father taught his children the subtle ways to uphold their abolitionist values while fitting into wealthy Richmond society.

The Van Lews were the wealthiest family in Richmond, but despite their status, their Northern background made them outsiders. Elizabeth’s sister-in-law, Mary, the wife of her brother, John, strongly supported the Confederacy, yet Elizabeth and John often “hired out” enslaved people. Through this practice, enslaved people were allowed to find employers and could keep part of the wages to buy their freedom. “Hiring out” was only way the Van Lews could free enslaved people without the former enslaved people’s freedom papers being brought into question.

After the Battle of Bull Run, Elizabeth went to Ligon’s prison. The prison held captured Union soldiers and other prisoners of war. She met the commander of Ligon’s Prison and asked to be a hospital nurse for the prisoners he oversaw.

Though Elizabeth was the only woman in Richmond to volunteer to care for enemy soldiers, the commander denied her request. He suggested she speak instead to the secretary of the treasury of the Confederacy, who referred her to General John Winder, the commanding officer of the prison system. The general granted Elizabeth access to the prisoners, albeit as a way to keep an eye on her.

Elizabeth gathered provisions for the prisoners, drawing attention from the Richmond public. Newspapers anonymously accused her of traitorous acts. After bringing gifts, Elizabeth requested to care for a dying prisoner, Calvin Huson, in her home. General Winder agreed and sent Huson to the Van Lew mansion.

The soldier Belle shot died later that day. The general investigating the matter, wanting to avoid Belle becoming a Confederate martyr, chose not to punish her beyond posting sentries around the Boyd home. Belle flirted with Union officers, charming military intelligence out of them. She had her enslaved maid take the information to the nearby Confederate camp. Belle believed that no one would bother an enslaved woman doing a task for her mistress.

In July, Belle’s missives were intercepted by a Union soldier, and Belle was brought into the local Union headquarters. She was warned of the consequences of spying and sent home. Belle was not deterred. Eventually, only one regiment remained to maintain order in Martinsburg. Hearing about Rose Greenhow’s espionage work, Belle visited her uncle, a lieutenant in Stonewall Jackson’s army. He introduced her to Turner Ashby, head of the Confederate military scouts. Ashby used Belle as a courier between Confederate generals.

Belle learned the signals and passcodes to cross Confederate lines freely. Over time, she convinced Union soldiers to share theirs so she could easily cross borders, lying to Union soldiers if stopped.

Haunted by the Battle of Bull Run, Emma struggled with her daily tasks. The army was disorganized and pathetic, prompting Lincoln to recruit Major General George McClellan. McClellan was a young, accomplished national hero. Guided by Christian values and a strong military background, McClellan imposed a high moral code of conduct and started drilling the army daily for hours on end.

McClellan was hesitant to mobilize the army. While he hesitated, a major general declared martial law in Missouri, freeing every enslaved person in the state. Lincoln was furious and worried that border states would decide to secede. Southern newspapers used the event as proof that Lincoln wasn’t interested in unity, but rather abolition. Lincoln was torn between trusting McClellan’s hesitancy and yielding to his advisors’ pressure to force McClellan to act.

While Emma and her fellow pious regiment members went to church on Sunday, the rest visited brothels and saloons. Yet if Emma’s gender was discovered, she’d be arrested for prostitution, the default charge for women discovered in the army. The hypocrisy frustrated her.

Emma joined the regiment’s chaplain, his wife, and the doctor to watch the pickets, only for the group to walk into the path of Confederate pickets. Emma led the group in evading capture, guiding them to the Union soldiers. A skirmish ensued in which Emma narrowly avoided being shot; a fellow soldier was wounded in his shoulder. The fighting ended as quickly as it started, and Emma helped the man back to camp.

Though Rose and her various lovers were under surveillance, Rose continued her intelligence gathering. She met with the women of her spy ring to celebrate the Confederate victory at Manassas and the pivotal role that Rose had played in securing it. One woman present declared Rose’s methods to be as practiced as they were effective: “She has all her life been for sale” (68).

To catch Confederate civilian spies and gather intelligence on potential traitors, McClellan hired Allan Pinkerton, a famed detective with his own network of male and female spies. Investigating Rose’s connections led the detective to Julia Taft, daughter of a government official. Julia told the detective that Rose and her daughter visited often. Little Rose played with Julia’s two young brothers. Importantly, the brothers were also playmates of Lincoln’s sons, Willie and Tad.

Rose wrote to Beauregard, warning him to be careful. One day, one of her informants dropped off a letter, asking Rose to send it to a colonel in Richmond, Virginia. Worried that the letter was part of a setup, Rose demurred. She informed Thomas Jordan that she was being investigated. Then she used one of her large ballgowns to conceal contraband for the Confederate Army, including maps and intelligence.

Elizabeth attempted to use Christian values to explain why she was caring for a prisoner of war, but her neighbors were not convinced. Elizabeth nonetheless cared for Calvin Huson until he died. As rumors about her Union sympathies grew, a man followed Elizabeth on one of her walks, threatening her.

To allay suspicions, Elizabeth invited a Confederate captain to board with her until his lodging was ready. She couldn’t be accused of disloyalty if she had the new head of the Tobacco Warehouse Prison Complex in her home. Housing the captain also let her gather information about the prisons, inmates, and escapes.

However, the longer the captain and his family stayed, the more emboldened Elizabeth’s sister-in-law became. Mary started openly abusing the servants, calling them the n-word. Mary focused much of her vitriol on Mary-Jane Bowser, a young woman who Elizabeth saw as a member of their family.

Elizabeth decided to use the secret room in her mansion to hide the prisoners until they could safely run to the North. As Elizabeth planned, she read an ad in the Richmond Dispatch asking for someone to provide “suitable servants” for the Confederacy’s first lady, Varina Davis. It was the perfect opportunity to get Mary-Jane involved and into the Confederate White House.

In August, accompanied by three fellow detectives, Pinkerton waited outside Rose’s home. Captain John Elwood, a provost marshal, eventually walked up to Rose’s front door. Once the captain was let in, Pinkerton peered into the window, standing on the shoulders of his men to reach. Rose seduced information out of the captain, drawing him further into her home and out of Pinkerton’s view.

At midnight, Elwood left, and Pinkerton trailed him until being stopped by Union sentries suspicious of Pinkerton’s movements. The sentries took the detective to the captain, who detained him after a brief interrogation. Pinkerton sent a message to the assistant secretary of war, Thomas A. Scott, who had Pinkerton released into his custody without drawing Elwood’s attention. After hearing the detective’s concerns about Rose, Scott told him to keep watching her.

Pinkerton incorrectly assessed the Confederate forces as 150,000 soldiers strong; in reality, there was less than a third of that figure. Even some of the cannons aimed at the Capitol were just logs painted black. The erroneous report cemented McClellan’s hesitancy to attack.

Emma continued to work shifts at her regiment’s hospital. In the persona of Frank, Emma noticed the soldiers were at ease in her presence. To her, it was a sign that God approved of her work. While working at the hospital, she met Jerome Robbins, a pious scholar who had enlisted for the same reason as Emma.

As a child, Emma read a book about a pirate named Fanny Campbell; the story inspired her to escape her home and live as a man. However, as Jerome and Emma grew close, with Emma starting to fall in love with him, she considered telling him her secret. Jerome, in turn, often journaled about his meetings with Emma, writing about their close bond. When he told Emma about a letter he received from his sweetheart, though, Emma began avoiding him.

As a courier and spy, Belle stayed in safe houses along her route, exchanging information with fellow operatives. Belle boasted about her part in the Confederate’s blossoming intelligence network. In Union territory, she’d visit military camps and openly ask about tactics and troop numbers. Her brash behavior worked as a disguise, making people underestimate her.

At night, Belle would sneak into Union camps to steal unattended weapons, which she then hid in outhouses, barns, or underground to be transferred to Confederate soldiers. Other women joined her, and they eventually smuggled away hundreds of weapons. The South was dealing with shortages in almost everything due to the Union’s blockade. Quinine, the medicine used to treat malaria, had also become scarce and expensive as outbreaks became more common.

Belle, while carrying a bottle of whiskey with her, was approached by a soldier asking for some. She offered him a pint for $2. He tried to haggle, but she refused. The man ripped the bottle from her. Belle brandished her knife, and chaos ensued. Some soldiers rallied behind Belle, and others rallied behind their comrade. A brawl broke out as Belle charged the man. Belle evaded the fight, but some 30 of the rebels supporting her were injured.

Rose’s lover, Captain John Elwood, died by suicide after Pinkerton accused him of disloyalty. Undeterred, Rose continued using her connections for intel, including Henry Wilson. On seeing Henry leave Rose’s home after one of their meetings, the detective decided it was time to arrest Rose.

Soon after, Rose left her home to pass intelligence on to one of her scouts. However, on realizing she was being followed, she didn’t make the drop. Instead, Rose stuffed the letter in her mouth and swallowed it to avoid it falling into Union hands. She was arrested and placed under house arrest.

The detectives searched through Rose’s things, finding love letters from many powerful suitors. By flirting with the detective guarding her, Rose convinced the man to let her go to her room and change her dress. Once in her room, she destroyed any dispatches and evidence that would incriminate her. The detective barged in, and Rose pulled a pistol, threatening to shoot him. However, as she had not cocked the gun, he informed her it wouldn’t fire.

Rose was strip searched, and Pinkerton arrested many of her associates. Rose once again took advantage of distracted guards to grab documents hidden in her library. She slipped the documents to one of her scouts to take along when the girl was released. By the next day, though, the scout had been arrested again.

Rose taught Little Rose to accept and send along encoded messages. Rose held off accepting any offer to deliver messages made by her guard until, out of desperation, she asked him to take a letter to Thomas Jordan.

Pinkerton identified many women in Rose’s spy ring, detaining them in Rose’s home. Rose’s arrest made national headlines, provoking heated debate about women’s involvement in war. Yet as months passed, Pinkerton failed to break Rose’s resolve.

Though many offered to negotiate her release, Rose refused. She assumed that Pinkerton and the Union would tire of her and exile her to the Confederacy, and even if they didn’t, she had another option. A scout would bring her a fruitcake with instructions for an escape baked in.

Emma finally told Jerome the truth about her identity and past. Jerome was initially taken aback, and Emma feared her friend might betray her secret. Jerome did decide to keep it, even knowing that meant he could face a court martial; for a time, though, the two kept their distance from each other.

The Army of the Potomac began to set up winter quarters. McClellan’s lack of action was starting to make some radical Republicans doubt his loyalty to the Union. At Christmas, the Union troops were in a festive mood, singing carols as they received holiday donations of lavish meals, new clothes, and dried fruits. Emma requested transfer to a hospital in Alexandria, hoping to stay there as a nurse for the rest of the war.

Elizabeth followed news about Rose Greenhow closely. Rose became the talk of Richmond, lauded as a hero, which annoyed Elizabeth, who had long been cast as a villain. While the Confederate Capitol relished Rose’s infiltration of Washington, DC, the events intensified concerns about spies doing the same to Richmond. Nonetheless, Mary-Jane Bowser agreed with Elizabeth’s plan. Mary-Jane, pretending to be an uneducated enslaved woman, would apply to work as a servant in the Confederate White House. She’d hide in plain sight, reading any missives she happened to come across while cleaning.

When Elizabeth met with Varina Davis, the Confederacy’s first lady, she was struck by their similarities. Both were viewed as outsiders by the Richmond elite. Both had been educated in Philadelphia, leading to a complex view of Southern culture. Eventually, Elizabeth seized an opportunity to offer Varina “the qualified help” she was seeking, noting that Mary-Jane, while not intelligent, was dedicated and hardworking. Varina quickly accepted.