William J Engle. Encyclopedia of Espionage, Intelligence, and Security. Editor: K Lee Lerner & Brenda Wilmoth Lerner. Volume 1. Detroit: Gale, 2004.
During the great American conflict of the middle nineteenth century, the Civil War, efforts by both the North and South to engage in espionage and intelligence-gathering activities were unparalleled in the history of the relatively young nation. Although daring, these efforts were often quite amateurish by modern standards.
The physical environment of America greatly facilitated covert activities. With America as the “melting pot” of the world, people throughout the nation represented every race and nationality in the world. Unionist and secessionist alike came from every corner of the country and both sides consisted of people of every race, creed, and color. Visually, covert combatants could not be easily identified one from another. Americanized English was the common language, but even with many regional dialects, there were few specific speech patterns unique to either side. State or region of origin was no guaranty of which side one might take in the conflict.
People were free to travel practically at will. Boundaries between Union and the Confederate held areas existed primarily as lines on a map and posed no controlled barrier to travel. Many major rivers traversed the land north to south. Major mountain ranges trended north/south. Railroads and roadways had been developed in all directions. Getting to and from one area to another was relatively easy and borders were difficult to control. Spies and agents were free to roam practically at will restricted more by their own skill and courage than any other factor. With travel being relatively unimpeded it was fairly easy to pass written or memorized verbal messages through the lines. Both sides developed methods to encrypt messages using various forms of alphanumeric sequence codes and cipher wheels. The telegraph was the leading communication technology of the period. Anyone with a portable key set could tap into any line and monitor, receive, and send massages often confusing and countermanding orders being sent over the wire. Confederate cavalry leader John Hunt Morgan habitually included a telegraph operator on his staff just for this purpose. Hunt was so daring as to send a message to the U.S. Commissary Department over telegraph lines operated by the U.S. Army complaining about the quality of mules being supplied to units opposing him and being captured by his men. Requisitions for supplies were often submitted in similar fashion in anticipation of capture from the adversary.
Hot air balloons were introduced by both sides for observing troop movement and disposition, spotting artillery fire and relaying signals.
The Confederacy led in the development of “infernal weapons” such as mines and torpedoes that were, at the time, considered violations of the rules of war as they acted upon unsuspecting prey. The concept of these devices was relatively simple in including a black powder charge within a watertight container and a detonation device. The Brooke buoyant torpedo consisted of a metal dome with contact detonators on top mounted on a metal conical shaped container attached to a wooden spar anchored on the bottom of a waterway. At times a Turtle torpedo containing as much as 100 pounds of explosives would be attached by wire to the base of the spar. Attempts to remove the adjacent buoyant torpedo would pull the wire and detonate the Turtle. Other torpedo designs included floating containers detonated by contact or electrical charge from a shore based agent and free floating drifting mine detonated by an attached propeller mechanism after coming to rest against the hull of a ship. River and sea torpedoes could be placed by agents or troops in advance of the arrival of the opposing force.
However, the Coal torpedo required placement in a fuel storage depot or bunker by an agent and quite often in the presence of the enemy. The Coal torpedo was made of a hollow chunk of iron cast to look like a piece of coal. The fake coal contained a charge of powder and was coated with tar and coal dust and exploded with tremendous effect when fed into the boiler fire of a steam engine either on board a ship, on a train or in a factory.
Agents on the ground were the backbone of the espionage and intelligence gathering efforts of the period. Unfortunately the identity of most of the agents of the conflict was lost as many operated under multiple names; records were often poorly kept, and lost or intentionally suppressed or destroyed. Contraband and escaped slaves served as a primary source of intelligence for the U.S. Army. However, a former barrel maker, sheriff and native of Scotland organized a detective agency in 1850 that served the Union effort extensively and is still in business today. Alan Pinkerton formed the National Detective Agency and gained fame by foiling a plot to assassinate President Lincoln in 1861 and went on to create the secret service of the U.S. Army. Neither Pinkerton nor his agents had any training in intelligence gathering and were notorious for their tactics and the over-estimation of Confederate troop strength. During the Peninsula Campaign over the spring and summer of 1862, General G. B. McClellan (U.S.) had advanced the Army of the Potomac and its 108,000 effectives to within sight of the church spires of the Confederate capital city—Richmond, VA. However, based on intelligence gathered by Pinkerton that suggested a potential opposing Confederate force nearing 200,000 who were well fortified with reinforcements en route, the general paused to plead his case with Lincoln for more troops. In fact, General R. E. Lee never had more than 85,000 effectives under his command during this time, as his smaller force drove the Federal horde before him in full retreat. Pinkerton’s unintended misinformation may well have served the defense of the Confederate capital city better than the mythical reinforcements that were not coming. It would be some two and a half years before the U.S. Army would get that close to Richmond again. Yet, Pinkerton and his organization remained in Federal service well beyond the war. Much of Pinkerton’s information came from criminals and escaped slaves who lacked the skills of espionage and were thus, prone to exaggeration, along with agents who may have spent more time enjoying Richmond’s pleasures than actually counting troops in the field. In time, the Confederates learned to appreciate the value of misinformation and intentionally sent men forward to become captives of the Federal forces and spread inaccurate information.
American culture was still quite Victorian in many ways during the 1860’s. Women agents had a decided advantage over their male counterparts, as they were not likely to be as roughly interrogated or possibly executed upon discovery. Both sides took full advantage of the opportunity.
Belle Boyd shot and killed one of two drunken Union soldiers who had entered her Martinsburg, VA home on July 4, 1861. She was acquitted and set free. Thereafter, Boyd voluntarily forwarded her written observations of Union activity in her area to local Confederate authorities. During General “Stonewall” Jackson’s Shenandoah Valley Campaign, Union troops occupied the town of Front Royal, VA where Miss Boyd happened to be at the time. Observing the panic that developed among the invading Federals upon their learning of Jackson’s approach and overhearing their plans to burn a large supply depot in town and the bridges across the South Fork of the Shenandoah River as they retreated northward, seventeen year old Belle decided to inform the Confederate forces personally. Under fire from Union pickets, Boyd dashed several miles to carry her knowledge to the approaching Confederate column. The leading elements of the column then dashed forward to save the bridges that later enabled Jackson to drive up the valley driving the forces of Union General Nathaniel Banks before him and freeing the vital area’s food supply to Confederate purpose.
Belle Boyd continued her activities until arrested on July 29, 1862, and was transferred to the Old Capital Prison in Washington, D.C. No charges were pressed and she was released one month later, where upon she returned to Richmond and continued her work as a spy. Later she was arrested aboard the blockade runner Greyhound outbound for England but managed to persuade Federal Lieutenant Harding, who had been placed as prize master of the captured ship, to permit Confederate Captain Lewis to escape en route to Boston. Before the end of the war, Miss Boyd and Lt. Harding married.
Elizabeth Van Lew, a native of Richmond, VA who had attended a Philadelphia Quaker school, was an ardent opponent of slavery and pro-Union. After the war broke out, Van Lew was granted permission to care for Union prisoners. Many of the prisoners had observations of Confederate positions and troop dispositions that they hoped to get back to Union authorities. Miss Van Lew established a network of couriers, developed a secret code, and began passing messages through the lines to Union forces. Many in Richmond referred to her as “Crazy Bet” as she hummed and mumbled to herself as she traveled the town, while believing her sympathy for the Union was part of her mental illness. “Crazy Bet” is credited with procuring for Mary Elizabeth Bowser, a former slave whom she had freed before the war, a job as a house servant in the home of Confederate President Jefferson Davis. Together, the two women collected valuable information that was passed on to Union officers. “Crazy Bet” managed to maintain her cover throughout the war and was one of the first people to be visited by General U.S. Grant upon the taking of Richmond. Later, President Grant appointed her postmaster of Richmond though the people of the city shunned her once they realized the harm she had rendered to the Confederate cause.
Emma Edmonds, who was able to join a Michigan volunteer company by posing as a man, gathered information for her company by “posing” as a woman.
Legends and folklore are rich with stories of individual daring and accomplishment as agents and double agents during the Civil War, but verifiable documentation is only available in a few cases. Some of the best intelligence gathering opportunities came about as random luck. Perhaps one of the most significant instances of pure luck delivering critical information into the hands of the enemy was the discovery of a copy of General R. E. Lee’s order of march as he moved northward in September of 1862. A note was found on the ground wrapped around three cigars by Federal soldiers that contained details of the order of march of General R. E. Lee’s divided forces marching through the Shenandoah Valley on their way to carry the war to the North on their home ground. Some historians assume that a member of General D. H. Hill’s subordinate command dropped this bit of critical information. Union General G. B. McClellan had been cautiously seeking the Confederate force, and the discovery of General Lee’s order of march enabled McClellan to unexpectedly close on them and force an unplanned battle near Sharpsburg, MD along Antietam Creek. The battle unfolded to become the most deadly single day of combat in American history, and ended in a tactical victory for the South in that its army escaped annihilation and withdrew southward in good order after Union forces refused to attack the following day. However, the North claimed a major strategic victory that changed the nature of the war, and ended consideration of European intervention on the side of the South.
Both the Union and the Confederacy had agents working throughout the territory of the other. The Northern media proved to be of great aid to the Southern intelligence gathering effort. Northern papers continually ran articles describing current events, Union troop dispositions, and future movement in such detail that undercover Confederate agents kept a constant supply of daily newspapers heading south from major cities such as New York, Philadelphia, and Boston to commanders in the field.
Spying was not limited only to opponents. There was considerable spying by various political factions on their own battlefield commanders and faction against faction. This was particularly true on the Union side where trust between President Lincoln, the cabinet, prominent congressmen, and the military staff was particularly low during the early years of the war, as the search for a commander who could defeat the secessionists created considerable turmoil. Many Federal commanders also dreaded the political opponents in their rear as much as the combat opponents to their front, as many officers were removed to satisfy public whim.