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Confederate Spy

Guerrilla Warfare in Civil War Missouri, 1862 This book examines all known guerrilla operations in Missouri during the year of 1862, identifying the leaders, the regions in which they operated and their unique style of fighting. Also includes a chronological presentation of individual events and military experiences to highlight the relationships between seemingly isolated activities.

Turner Ashby

Virginia-born Turner Ashby descended from A long line of soldiers dating back to the American Revolution. He lived in relative comfort, his family owning a large estate, Rose Bank. Ashby was privately tutored and later spent his time farming the estate. When John Brown raided Harper's Ferry in 1859, Ashby gathered relatives and friends and rode to the site, but by the time he arrived Brown was in custody. Ashby patrolled the Potomac for some time, in the event another insurgent group made a similar attack, and he was on hand to witness the hanging of Brown.

Ashby was not a secessionist but when Virginia left the Union in 1861, Ashby vowed to remain loyal to his native state. He joined General Thomas Jonathan "Stonewall" Jackson and soon proved to be one of the South's most brilliant cavalry commanders. When Jackson called for aid in establishing an extensive and effective espionage system, Ashby volunteered, proving himself to be a resourceful and daring spy.

In early 1861 Ashby assumed the role of a horse doctor, a subject about which he had considerable knowledge. In this disguise he worked his way behind Union lines at Chambersburg, Pennsylvania, where he easily determined troop dispositions and movements. This information allowed Jackson to properly deploy his own troops and successfully repulse several minor Union sorties.

Ashby then served as a cavalry commander for Confederate cavalry commander J. E. B. Stuart. Through skillful maneuvering of his vastly smaller cavalry forces, Ashby managed to delay Union forces so that Confederate troops under General Joseph E. Johnston could abandon Harper's Ferry and join a Confederate army commanded by General P. G. T. Beauregard at Bull Run. Johnston's troops arrived just as Union forces were about to break through Beauregard's lines and turned the battle into an overwhelming victory for the South.

Organizing a spy ring behind Union lines, Ashby was able to provide Jackson and Stuart with important information. On one occasion, however, Ashby's spies failed to detect a large Union force at Kernstown, Virginia, which led to a Confederate defeat in 1862. Ashby more than made up for this failure a short time later when he personally spied on Union forces at Front Royal, Virginia. The information he brought back to Jackson was so detailed that it enabled Jackson to correctly second-guess all Union movements and led to a smashing defeat of Northern forces.

Ashby's priceless espionage work led to his promotion to brigadier general. Union leaders, however, came to loathe the sound of Ashby's name and put a price on his head and an order that if he were found in disguise behind their lines he was to be shot on sight. This order was never carried out. While deploying a cavalry screen for Jackson's troops movements in the Shenandoah Valley, Ashy led a charge against a strong force of Union cavalry and was killed in the saddle.

Isabelle Boyd

Born in Martinsburg, Virginia, Isabelle Boyd was the true role model of the southern belle as portrayed later in countless books and films. Beautiful and charming, she was, however, a very determined young lady. Her prosperous store- owner father sent her to the exclusive Mount Washington Female College in Baltimore where she was taught Latin, French, music and horsemanship. She graduated in 1860 and by then she had shortened her name to simply Belle.

Returning to her home in Martinsburg, Boyd was living with her mother in the family home when the Civil War began. Her father quickly joined the army led by Thomas Jonathan "Stonewall" Jackson. Martinsburg, which was just inside the Virginia border, was occupied by Union troops in July 1861. Some federal troopers came to the Boyd's front door, demanding entrance so they could place the Union flag from a top window.

Mrs. Boyd stood in the doorway, holding the door slightly open and refusing to allow the soldiers inside. One hulking trooper shouted at the woman and smashed the door open with his shoulder. As he was about to enter the house Belle appeared in the hallway with a pistol. Without a word she fired a shot which ploughed into the trooper's head, killing him (This scene Boyd was to later describe in her memoirs which was not lost on Margaret Mitchell who, when later writing Gone With the Wind, used the same scenario for Scarlett O'Hara who shoots a bruttish Union soldier who invades her home.)

Arrested, Boyd was taken before a tribunal of Union officers. When she explained that the soldier she shot was abusing her mother and violating the sanctuary of her home, the chivalrous federal officers declared that she had committed justifiable homicide and released her.

Boyd quickly collected information on the Union troops in Martinsburg and then, excellent horsewoman that she was, rode through the Union lines to visit her father and Stonewall Jackson. Boyd delivered her information to Jackson's spymaster, Turner Ashby. She would continue to supply Ashby with vital information on Union forces in months to come. At one point, while she was caring for wounded Confederates, Union forces overran the area. Boyd brought Ashby a detailed report as to the numbers and direction of the federal troops.

Upon returning home, she was arrested and held as a spy. Allan Pinkerton, the famous detective and head of Union espionage at the time, personally interrogated Boyd and concluded that such a charming young woman could never be a spy. "There is no reason to hold her," he informed the Union commander. Boyd was released and immediately wrote out a report to Ashby which outlined Pinkerton's interrogation methods.

In 1862, Boyd was once again arrested as she rode through Union lines but she explained that she was merely out for her morning ride and was released. She then moved from Martinsburg to Front Royal to live in a small hotel owned by a relative. Union officers arrived to commandeer rooms in the hotel and Boyd was able to overhear their battle plans through air vents, a spying technique portrayed in John Ford's epic Civil War film, The Horse Soldiers.

Boyd then saddled her horse and rode wildly to the Confederate army, reporting to Ashby and urging General Jackson to attack Front Royal immediately, telling him that the weak Union forces could be overrun if he moved quickly before the federals blew up the bridges. Jackson accepted her story and ordered his army to march. The Confederates thundered into Front Royal, capturing the town and its garrison before the federals knew the enemy was present in force. For this victory, Jackson personally thanked his favorite spy, telling Boyd that he was grateful "for the immense service you have rendered your country today."

In 1863, Boyd made the mistake of giving a report to a man she believed was a southern sympathizer. The report was to be delivered to a Confederate commander but it was, instead, delivered to then Union spy chief Lafayette Baker, who ordered Boyd brought to Washington, D.C., where he could personally interrogate her. Boyd proved to be an unyielding prisoner. She gave the fulminating, boisterous Baker nothing.

Boyd was detained in special quarters and allowed to have a maid servant. The trunks she had brought with her were never searched, perhaps out of chivalry. They contained information that would have convicted her as a spy, as well as more than $25,000 that Boyd had been given by Confederate spymasters to use in paying for information. Baker finally gave up trying to break Boyd and ordered her to return to Confederate lines and remain there until the war was over. He told her that if he saw her again he would have her shot.

The spy went to Richmond where her exploits had long been known. She was given a hero's welcome with bands playing and crowds cheering her carriage as it was paraded through the streets of the Confederate capital. Boyd then returned to Martinsburg but undertook no more espionage assignments until 1864 when President Jefferson Davis asked her to personally deliver important dispatches to British contacts in London. She traveled to Canada and from there sailed to England but her mission, which was to urge the British to come to the aid of the Confederacy proved futile. The war ended a short time later.

Boyd published her memoirs of the war in 1865, embellishing her espionage activities with fanciful tales that were less than trustworthy. The glamorous spy was one of the most celebrated persons of the war and she capitalized upon her fame by appearing on stage in London in 1866. A gifted actress, she was a great success and she later appeared on the New York stage, a career that lasted for more than a decade.

Boyd married three times and at the time of her death left several children. In her final years, she gave stirring lectures on her Civil War experiences and though the audiences knew that much of this was fiction they nevertheless rewarded her with thunderous applause. Belle Boyd was by then, like the Civil War itself, the stuff of legend.

Jay Robert Nash. Spies: A Narrative Encyclopedia of Dirty Tricks and Double Dealing from Biblical Times to Today. M. Evans and Company, Inc., New York. 1997.

Quantrill of Missouri The Making of a Guerrilla Warrior. Peterson. Though the war in Missouri was vastly different from the encounters in Virginia and Tennessee, Quantrill's accomplishments rivaled those of Mosby's rangers and Forrest's Cavalry. But his victories are labeled as massacres and his men are judged to be murderers. In this book you will read of a vastly different Quantrill - a leader who, assessing the border situation and devising an effective military solution to the problems he faced, employed what we know now as modern guerrilla warfare.

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