Cyrena Bailey Stone

Union Civilian in the Civil War South A Unionist circle of women in Atlanta was led by Vermonter Cyrena Stone, who had moved there in 1854. Although the city was under military government, she and her pro-Union cohorts risked their lives to assist the escape of Union prisoners, to protect slaves, and to provide intelligence to General William Tecumseh Sherman‘s advancing army. Image: War Is Hell, by Mort Kunstler General William Tecumseh Sherman destroyed key military, rail and industrial sites with a blaze that gutted much of Atlanta. Early Years Cyrena Ann Bailey was born in 1830 in East Berkshire, Vermont, the fifth child of a Congregationalist minister Phinehas Bailey. Less than ten miles from the Canadian border and situated…

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Charlotte Sprowles Webster

Wife of Union Spy Timothy Webster Charlotte’s husband Timothy Webster was an agent of the famous Pinkerton Detective Agency and a spy for the Union during the Civil War. Timothy Webster was Allan Pinkerton’s most trusted agent during the Civil War, and he was partially responsible for stopping an assassination attempt on president-elect Abraham Lincoln. Webster was later captured by Confederate forces and sentenced to death. Marriage and Family Timothy Webster was born in England in 1822, and his family immigrated to Princeton, New Jersey in the 1830s. Charlotte Sprowles married Webster on October 23, 1841 in Princeton, New Jersey. They had four children. As a young man, Webster learned the machinist trade. Sometime in the 1840s the Websters moved…

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Union Women Spies

Civil War Women Spies for the Union The Union Army employed several other methods of gathering information about the South during the Civil War, but agents in the field – men and women – were the major source of espionage and intelligence gathering activities. Many agents operated under several different names. Due to the clandestine nature of their work, records were poorly kept or intentionally destroyed and the identity of most of these operatives will never be known. Image: Elizabeth Van Lew Union Spy in Richmond, Virginia Pinkerton’s Women Agents A former sheriff and native of Scotland, Allan Pinkerton had established a detective agency in Chicago in 1850. Pinkerton gained fame early on by foiling a plot to assassinate President…

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Women and Civil War Prisons

Civil War Women Prisoners of War Many of the arguments against women fighting in combat is the fear that they will become prisoners of war. Documentation proves that some soldiers who were discovered to be women during the Civil War were briefly imprisoned. Madame Collier was a Union soldier from East Tennessee who was captured and imprisoned at Belle Isle, Virginia. She continued concealing her gender, but another prisoner learned her secret and reported it to Confederate authorities, who sent her North under a flag of truce. Castle Thunder At Castle Thunder in Richmond, Virginia approximately one hundred female inmates were held throughout the war. Although Confederate authorities created a department at the prison specifically for the detention of “depraved…

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Confederate Women Spies

Women Spies for the South Although the exact number is unknown, it is speculated that several hundred women served as spies and smugglers for the Confederate Army during the Civil War. Whatever their duties, these new jobs redefined their traditional roles as housewives and mothers and made them an important part of the war effort. Confederate military leaders actively recruited women for undercover operations, mainly because of their familiarity with local customs and geography. Many women spies in the South remained at home, supplying critical information about the daily activities of nearby soldiers and military leaders. Southern belles invited enemy officers to their parties, hoping to pick up some new tidbit of information. As the Civil War unfolded, there was…

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African American Women Spies

Black Women Intelligence Agents in the Civil War Other than a very few famous African American women spies, little is known about the black women who gathered intelligence for the Union during the Civil War. We do know that some were former slaves and others were free women who volunteered to spy on the Confederacy, often at great risk to their own personal safety. Image: Unidentified African American Woman Escaped slaves served as a primary source of intelligence for the Union Army. Throughout the official records of the war, however, there are frequent references to bits of intelligence coming from contrabands, a term that dates back to early 1861 at Fort Monroe, Virginia. General Benjamin Butler refused to return three…

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Civil War Women Spies for the North

Women Spies for the Union Image: Illustration of Sarah Emma Edmonds on horseback dodging a bullet fired by a southern woman. American society was still quite Victorian in many ways during the 1860s. Therefore, women spies were not as likely to be roughly interrogated or hanged when their true identity was discovered. These heroines exhibited great courage and were willing to suffer imprisonment or death in the service of their country. Elizabeth Van Lew From a wealthy family well-known in Richmond society, Elizabeth Van Lew was educated in Philadelphia and returned home an ardent abolitionist. Elizabeth was in her forties when the War began, and steadfastly loyal to the Union. She started writing to Federal officials to tell them about…

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Civil War Women Spies for the South

Female Confederate Spies Washington, DC was an ideal place for Confederate operatives to gather information against the North. Not only was it adjacent to slave-holding states, it was full of Southern sympathizers, many of whom were members of Congress or held other government positions, which gave them easy access to valuable intelligence. Confederate recruiters only had to find the men and women who were brave enough to act as agents. Image: Rose O’Neal Greenhow with her daughter Old Capitol Prison, Washington, DC, 1862 The earliest known spy recruiter was Virginia Governor John Letcher, who immediately set up a spy network in the federal capital. He had been a Congressman in the 1850s and knew the inner workings and social life…

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Kate Warne

Union Spy and First Female Private Investigator Not much is known about Kate Warne prior to the day she walked into the Pinkerton National Detective Agency in 1856. Answering an ad in a local newspaper, Warne went to Pinkerton’s Chicago office and asked to see Allan Pinkerton about a job. There is still debate whether or not she intended to become a detective or a secretary. There were no women detectives until well after the Civil War. Pinkerton himself claimed that she demanded to become a detective. According to Pinkerton’s records, he was surprised to learn Kate was not looking for clerical work, but was actually answering an advertisement for detectives he had placed in a Chicago newspaper. Pinkerton said,…

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Olivia Floyd

Confederate Spy and Messenger Image: Olivia Floyd Marker One of the more fascinating figures during the Civil War was Miss Olivia Floyd. She lived at a plantation house known as Rose Hill in Charles County, Maryland. Rose Hill was built in 1730, and was the former home of Dr. Gustavus Richard Brown, a physician to George Washington. In later years, Rose Hill was purchased by Ignatius Semmes, who willed it to Olivia Floyd, her sister Mary and their brother Robert in 1843. Annie Olivia Floyd was born on July 2, 1826 to David and Sarah Semmes Floyd. In early childhood, Olivia broke her back, and remained crippled her entire life because the break had never been set properly, but that…

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