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

Rose waited to receive a fruitcake concealing her escape plan. When a guard finally brought her one, she was disappointed to find he had replaced the original, as there were so many unusual ingredients. Rose and Little Rose were sent to Old Capitol Prison. The prison consisted of buildings intended to be a temporary place to house Congress after the Capitol burned in the War of 1812. Rose lived there as a child when it was her aunt’s boarding house.

Rose was born on a farm in Maryland. When her father died, his death was blamed on an enslaved person. Shortly after, Rose’s mother sold the farm and sent her daughters to stay at her sister’s boarding house in Washington, DC. Rose’s primary education came from getting to know the many congressmen boarding there; she quickly picked up on body language cues and cronyism.

Rose and Little Rose were placed in a typical filthy cell. The air was fetid, and the window in their cell was boarded up to prevent Rose from communicating with anyone outside. Little Rose became deathly ill, but Rose refused to allow the prison doctor to treat her, demanding her personal doctor instead. Rose spent her time gathering any information about the Union she could. When direct questioning didn’t work, Rose pried up a plank of wood and dropped her daughter down to the Confederates below. They’d then return her daughter to her with reports of the Union Army’s activities.

Emma became her regiment’s mail carrier. By March, her army, the Army of the Potomac, was finally mobilized and traveled to the Virginia Peninsula to fight their way west. As the army set up camp, Confederate soldiers attacked. During the fighting, a group of fugitive enslaved people, known as “contraband,” found the Union Army and took refuge with them. Emma sat with the formerly enslaved people and got to know them.

Emma was often sent to find supplies in the hostile 60-mile expanse between Fort Monroe and Richmond. The Confederate military and civilians were ready to shoot any Union soldier they met. While looking for supplies, Emma found an isolated farmhouse. As the woman living in it gathered supplies, Emma sensed that something was off and left—the woman chased her, shooting at Emma. Emma returned fire, shooting the woman through the palm, and took her prisoner. However, as the woman screamed for help, Emma released her, fearing they were drawing too much attention.

To advance on Richmond, McClellan had to take Yorktown. The general overseeing Yorktown, who was known for his flamboyance and love of stagecraft, choreographed his troops to make his army appear much bigger than it was. McClellan fell for the trick, and his resulting lack of initiative gave an opening for real reinforcements to arrive.

Three of Pinkerton’s “top detectives” were captured. One, Timothy Webster, was hanged. Emma was asked by her regiment’s chaplain to replace him. Emma agreed and was sent back to Washington, DC, for “examination.”

Richmond was placed under martial law. Despite the heightened risk, Elizabeth continued her work, focusing on another newly converted tobacco warehouse: Libby Prison. The conditions within the prison were atrocious, and inmates were often “lost,” a euphemism for being killed by Confederate guards. The clerk, 21-year-old Erasmus Ross, was believed to “terrorize” his charges; in fact, Ross was part of Elizabeth’s growing network. As a clerk, he oversaw roll call, ensuring all prisoners were accounted for. By taking prisoners to his office, presumably to kill them, Ross was able to help them escape to the Van Lew mansion. Elizabeth would provide food and detailed instructions to escape to the North while hiding them in a secret room.

Rose was brought to the repurposed home of a congressman who had fled to the South. The commission overseeing her case was tasked with “resolving the cases of thousands of civilian prisoners being held on suspicion of disloyalty” (168). Rose met with General John Adams Dix and Judge Edwards Pierrepont. As they questioned her, Rose made complex rhetorical arguments that confounded the proceedings. The two men told her they would have to consider their verdict carefully. Potential outcomes were either pledging loyalty to the Union or being sentenced with sedition, treason, or espionage and accordingly returning to prison or being executed.

On arriving in Washington, DC, Emma was interviewed by the Union generals. Her answers during the intense questioning impressed the generals. She was briefly examined by a doctor, who focused on her phrenology, and then sent to Yorktown, disguised as an enslaved woman. Once in Yorktown, she blended in, carrying water to soldiers in the camp. She counted the artillery and sketched fortifications. When her disguise weakened, Emma returned to Union territory and passed the information to McClellan. The Confederacy fled from Yorktown, and the Union advanced; McClellan ordered his army to chase the Confederate troops, resulting in a bloody battle.

Belle’s mother sent her further south to stay with her aunt in Fort Royal. Belle quickly discovered that she was not well liked by the local women, who thought that she was boy crazy, shallow, and boring. Belle’s aunt owned a hotel that hosted Union officers when the town came under federal control. Belle stayed in the cottage behind the hotel with her aunt. General James Shields used the hotel as his headquarters, and Belle took advantage of his proximity, charming him into sharing Union secrets. One night, Belle snuck into the hotel and eavesdropped on one of Shields strategy meetings. Belle wrote down what she heard and immediately left, riding her horse 15 miles to deliver the details to Ashby, her contact and head of the Confederate military scouts. Then, she returned to Fort Royal, riding through a massive storm.

Emma was sent behind enemy lines again, this time disguised as an older Irish peddler woman. She had to swim across the Chickahominy Rive and hike through the area swamps. On her journey, she caught malaria and was stranded with a fever in the swamp for two days. Eventually, Emma crawled out and crossed enemy lines. She came to an abandoned house, where an ill Confederate soldier lay, abandoned. Emma cared for him, and the two talked. When he was on the brink of death, the soldier asked Emma to take his gold watch to Major McKee. She agreed. After he died, Emma covered him with a blanket, cut a lock of his hair, and left. On finding Major McKee, Emma passed on the watch and lock of hair. He asked her to show his men where the solider had died and offered to pay her. She turned the money down, immediately drawing McKee’s suspicion. Emma insisted that her conscience would not let her take money for delivering a man’s dying wish. McKee let her go, giving her a horse for her trouble. Emma led his men to soldier’s body and parted ways with them. She kept the horse and made her way back to the Union.

When a job as a courier opened in Winchester, another town in Virginia intersecting the Union and Confederacy, Belle took it. Flirting with a Union lieutenant got her across enemy lines. Once in Winchester, she met a colonel who gave her two packages to deliver to Stonewall Jackson and a note. However, a servant had noticed her taking the packages and letters from the Confederate colonel; as a result, on the return journey, Belle was questioned by two Union detectives. Though the moment was tense, she was eventually allowed to leave. Once in Fort Royal, Belle realized the note warned of an impending Union invasion. Though she asked a group of Confederate sympathizers to take her information to Stonewall Jackson, they urged her to go herself. Belle ran past Union pickets, avoiding gun fire, and managed to cross the Confederate line. She found a rebel private who finally passed on her information. Jackson secured a Confederate victory soon after, and Belle gloated about her achievement to the Union prisoners who once stayed in her aunt’s hotel.

In Washington, DC, as Rose and her daughter walked the yard of Old Capitol Prison, Rose received word of Jackson’s win. Rose tried to help two Confederate inmates escape afterward, but her plan failed. Word of a Confederate defeat in Tennessee came next, which greatly distressed Rose. One of her lovers, Senator Henry Wilson, visited her and boasted about the recent Union wins. Some relief came as she received the final decision: She would be exiled to the South.

After the Battle of Fort Royal, McClellan ordered Emma’s regiment to join troops on the outskirts of Richmond. A storm raised the levels of the Chickahominy River, splitting the Union Army and giving the nearby Confederate general an opportunity to attack. As fighting broke out, Emma rode the horse she’d gotten from Major McKee into battle, delivering messages and orders from Union officers. When a Union general was shot in the arm, Emma quickly ran to treat him. As she did, her horse bit her hard enough to rip flesh from her bone. She wrapped her arm and tended to the general anyway before going to a field hospital; on finding the hospital overwhelmed with injured men, she took on the role of nurse. Supplies ran out quickly, and Emma ran to the nearest house to find more. On her journey back to the hospital, Emma was forced to rest, unable to continue. A Union chaplain rode past her, ignoring her. Emma assumed that he was rushing to the hospital. However, when she made it to the hospital, she found him sleeping on hay. She found him pathetic.

Rose arrived in Richmond at the start of June. She and Little Rose stayed at the Exchange and Ballard Hotel. Letters arrived indicating that Pinkerton’s detectives would be executed shortly, begging her to intervene; she ignored them. Rose navigated the Richmond aristocracy, aware the women of Richmond disliked her. As she started to write her memoir, she met Jefferson Davis; he was struck by how tortured Rose looked as he thanked her for her service to the Confederacy.

General Robert E. Lee ordered Stonewall Jackson and his troops to leave the Shenandoah Valley and go to the peninsula. With the Confederacy army gone, the Union moved into Fort Royal. Union officers took 160 prisoners, Belle among them. She was placed under house arrest. Southern papers dubbed her “Secesh Cleopatra.” When Belle’s request to go to Louisiana was denied, she returned to her strategy of spying under the guise of flirtation. Pinkerton put together a file on Belle, reporting her activities to the US Secretary of War.

Belle met a man who claimed he was on his way to join Stonewall Jackson’s campaign; the two had dinner together, and he offered to take a letter with him to give to Jackson. Belle gave him a letter about Union forces heading to the Shenandoah Valley. The man, in fact, was a federal spy.

The Battle of Beaver Dam Creek at Mechanicsville resulted in over 1,000 Confederate deaths to the Union’s 361. Despite an opening to attack and take Richmond, McClellan focused on moving his headquarters, leading to a Union retreat. Emma warned the medics, including Jerome, of the impending retreat.

Elizabeth, upset by the Union retreat, decided to work even harder, increasing the numbers of prisoners she helped escape. McClellan’s new headquarters happened to be close to Elizabeth’s vegetable farm, so she developed a new form of communication, pricking holes in books such that the stabbed letters formed words. Elizabeth brought a book and new shirts filled with straight pins to the prison hospital. She passed the book on to a prisoner and whispered to him to read the pinpricks. Days later, Elizabeth got answers, and she transcribed the prisoner’s responses. She placed her transcribed letter under the driver seat of a wagon, where it would be picked up and delivered to McClellan.

Elizabeth decided it was time to connect with Mary-Jane to verify the intelligence she had gathered. She arranged a meeting. Scrutiny was intensifying, however. One day, a man followed Elizabeth, trying to pressure her to tip her hand as a spy. Elizabeth pretended she didn’t understand and walked away.

Belle was taken to Washington on July 29. At Old Capitol Prison, Belle was questioned by a detective who pressured her to confess and take an oath of allegiance to the United States. Belle refused. Belle flirted most with a rebel soldier named Clifford McVay. They passed notes back and forth. Belle was allowed to cross the hallway and reach her hand through the bars to hold his. When a sentry ordered her to step back and she refused, the sentry sliced into her upper arm with his bayonet. Belle was shocked by the pain, but when the wound healed, she was proud of the scar.

Though demoralized by the retreat, Emma learned that Jerome was luckily put on parole instead of being taken prisoner. On her next scouting mission, Emma again disguised herself as an enslaved woman. She gathered the required intelligence and quickly returned to the Union camp. During the second Battle of Bull Run, Emma rode a mule while delivering messages to the front. The mule threw her into a ditch, breaking her leg, foot, and finger. At the hospital, Emma requested morphine and chloroform, refusing a proper exam. The Union lost the battle.

Belle taunted Union soldiers as they returned from their loss. McClellan let his troops rest, but Lee pressed on, invading Maryland. Lee’s progress was stopped after two Union soldiers stumbled on a copy of his orders and passed it to McClellan. The resulting fight turned into the Battle of Antietam.

Belle didn’t expect that, a month after she was imprisoned, she’d be released as part of a prisoner exchange. She was brought to Richmond, where she stayed at the same hotel as Rose Greenhow. When Belle met her, she was star struck.

Elizabeth met with Mary-Jane, and the two decided to recruit another worker at the house, the seamstress, to their cause. Elizabeth also connected with a fellow Union sympathizer, Thomas McNiven, who had his own network of spies, including immigrants and sex workers, thereby expanding the Richmond Underground. Mary-Jane played her role well, cleaning Jefferson Davis’s office and memorizing everything she saw. When General Lee was summoned to Richmond, Mary-Jane eavesdropped on his conversations at the Confederate White House. Mary-Jane wrote down all she learned at the end of the day and passed it on to Elizabeth, who then took it to her brother, John.

John would go on trips to the North to check on their hardware business. Elizabeth knew how much risk he took and, as his older sister, felt guilty. She knew her sister-in-law still posed a threat, even more so now that John had taken custody of their daughters, Eliza and Annie.

Belle enjoyed following Rose and Little Rose around while in Richmond, but while Martinsburg was under Confederate control, Belle paid her family a visit. She rode to Stonewall Jackson’s headquarters, only for an aide to tell her that the general didn’t want to see her. Stunned, Belle left. She dreamed of a better reunion with her favorite general.

Pinkerton erroneously reported that Lee’s army was twice the size it really was. For once, however, McClellan didn’t hesitate to mobilize his own troops. Though still struggling with her injuries, Emma continued her work as a mail carrier. On her way back from a mail run, she lost track of where her regiment was and searched for shelter. She spotted Confederate guerillas patrolling and quickly rode away before they saw her. The next day, she met with Union cavalry who were looking for guerillas. She guided the group to where she had seen the guerillas, only to lead them into an ambush. Emma played dead as her pockets were searched, and after, she led the surviving calvary officers in tracking her regiment.

The Army of the Potomac made slow progress through Virginia, finally forcing Lincoln to replace McClellan with General Burnside. Emma and Jerome wrote to one another, and Jerome came to relish being the only one who knew her secret. Burnside ordered his troops to Falmouth, a town near Fredericksburg. Emma was sent to Washington to collect and deliver mail. There, she met Lieutenant James Reid. Emma returned to Falmouth with mail and supplies. Burnside made plans to mobilize the army, knowing the Confederacy wouldn’t expect an attack.

Belle visited Fredericksburg and spied on the nearby Union troops. She also wrote to Stonewall Jackson, hoping to get a response telling her she could return to Martinsburg. He warned her not to.

On December 11, the Battle of Fredericksburg began. Emma became an aide-de-camp. Her bravery on the field was commended by many fellow soldiers. She watched in horror as 3,000 Union soldiers died that day. Emma left her saddle once to save a wounded officer, who, she realized, was James Reid.