The Dark Game

by Paul B. Janeczko

  The final scene of Major John André’s undoing began the following morning, September 23, as he approached Tarrytown, New York. Three men, who were set to rob him, accosted him at gunpoint. The major thought these men were Tories and said, “Gentlemen, I hope you belong to our party.” “What party?” one of the highwaymen asked. When André told them that he meant the British, the men assured him that they were, indeed, loyal to the king. Relieved, André quickly told the men that he was a British officer and he could not be detained. His relief turned to shock when the men replied that they were Americans and he was their prisoner.

  Because of the evidence against him — traveling in civilian clothes, bearing a false name, and carrying military intelligence — Major André was condemned by Washington to be hanged as a spy. Sir Henry Clinton, quite fond of his adjutant, did almost everything he could to secure André’s release. What he would not do, however, was swap André for Benedict Arnold, who had fled to New York after he had gotten word of André’s capture. Washington stood firm in his decision. In fact, when Clinton requested that André be given a soldier’s execution by firing squad, Washington refused. On October 2, 1780, Major John André was hanged.

  As for the scoundrel in all this, Benedict Arnold found a lukewarm welcome among the British soldiers. He was given the rank of brigadier general and commanded a regiment that raided supply depots in New London, Connecticut, and Richmond, Virginia. In fact, it was Arnold’s men who burned Richmond during one of their raids. Arnold was particularly brutal to the civilians in his path, burning ships and grain supplies.

  General Washington was so incensed by Arnold’s betrayal — personally and militarily — that he approved a plan to kidnap the traitor and bring him to trial. However, circumstances never permitted the American agents to get close enough to Arnold to nab him. In late 1781, Benedict Arnold sailed to England; he spent the remaining years of his life in poor health, shunned by the people he thought would consider him a hero.

  By the time the American Revolution officially ended in 1783 with the Treaty of Paris, the young American government had made strides in espionage operations. However, the new nation had more pressing business to deal with than the development of an intelligence agency. It took a major national crisis — the Civil War — to force the government and the military to think again about espionage.

  WE’VE SEEN HOW THE CULPER SPY RING made effective use of coded messages. They also used another trick: invisible ink. The ink they used — most commonly referred to as stain and also known as white ink or sympathetic ink — was developed in England, of all places, by Sir James Jay, brother of the Patriot John Jay. This special ink disappeared when used on white paper. An agent would later brush a developer — frequently sodium carbonate (baking soda) — over the writing, and the message would reappear. What was in the stain? The formula remains unknown.

  Having a good invisible ink can make it easier to send intelligence. However, using it in a clever way is also important. At first, agents simply wrote their messages with stain on a blank sheet of white paper, then sent it off by courier. General Washington soon realized that a blank sheet of paper would arouse suspicions if it fell into the wrong hands, so he offered some recommendations to his agents who sent messages in invisible ink. They included:

  Write messages on the pages of a pamphlet or on the first few pages of a common pocket notebook, on the blank pages at the end of an almanac, or in “any publication of small value.”

  Write a friendly letter in regular ink, but add intelligence in stain between the lines of these letters.

  Fold the letters in a particular way to alert the recipients of the stain contents.

  Write a brief letter and use the remainder of the sheet of paper for secret intelligence.

  Culper Jr. devised his own method of hiding a secret message in packages of writing paper that he shipped to his customers on Long Island, including Culper Sr. Culper Jr. wrote his messages in stain on one of the sheets of paper, then slipped it into the package of sheets in a predetermined spot, say the thirtieth sheet from the bottom. When his partner received the shipment of paper, he simply counted to the thirtieth sheet from the bottom and found the sheet with the secret message on it.

  The rebels were not the only ones using invisible ink to keep their intelligence messages hidden from the enemy. Major John André told British secret agents to mark correspondence written in invisible ink with an F (for fire) if it was to be developed by heat and an A (for acid) if the reader should use some sort of chemical solution. No matter which method the agents used, all needed to exercise care in handling invisible ink letters because water or other liquids would easily smear the secret writing and make it unreadable.

  To further conceal intelligence, couriers needed to hide their secret messages in the event they were stopped. Messages were sewn inside of buttons and hidden in small silver balls that were made of two hollow halves.

  When Daniel Taylor, a British spy carrying a message in a silver capsule, was stopped by rebels, he quickly popped it into his mouth and swallowed it. The rebels gave Taylor a hearty dose of a vomit-inducing potion, which did its work. But Taylor grabbed the ball and swallowed it again. When the American general informed the spy that the rebels would hang him and cut the silver ball out of his stomach, Taylor agreed to a second dose of the potion. The rebels found the military intelligence in the capsule and hanged him anyway on October 16, 1777, after a court-martial.

  When the first shot of the Civil War was fired at four thirty in the morning on April 12, 1861, many believed that it would be a short conflict. Even though Fort Sumter had to endure thirty-four hours of Confederate bombardment before the Union surrendered it, the Union enjoyed a number of significant advantages over the Confederacy. Yet, by the time Robert E. Lee surrendered to Ulysses Grant at Appomattox, Virginia, some four years later, about 620,000 soldiers had died on the battlefields, more than American battle deaths in all other wars from the Revolution through the Vietnam War.

  Most of the war was fought in states south of Washington, D.C., so Southerners saw the Union army as an invading force. For the Union soldiers, this meant they had to fight in unfamiliar and hostile territory. This matter of geography affected the spies who worked behind enemy lines. Northern spies could not often count on much hospitality from Southerners. On the other hand, since so much of the war was fought in the South, Confederate spies could usually find a safe house, or at least a sympathetic soul who was willing to allow a “good southern boy” to hide in their barn until the danger had passed.

  Just as in the Revolutionary War, most of the spies of the Civil War were amateurs. The United States government had not developed any systematic framework for gathering military intelligence in the nine decades since the Revolution. By some accounts, there were thousands of amateur spies at work during the early years of the Civil War. The spy game at that point was very much a vocation that relied upon on-the-job training. And, since neither side had any significant experience in the areas of intelligence gathering and counterintelligence, spying was, in a sense, easy for both sides. With no counterintelligence system, the chances of getting caught were low. Things tightened up as the war progressed, when some spies were caught and executed. But, as in other wars, the fear of capture and death did little to deter the intrepid spy.

  Another thing that changed very little in the years between the wars was the means of obtaining military intelligence. Although the use of photography and the telegraph brought some technological advances, the craft of spying on the enemy’s army still relied on fieldwork. For the most part, intelligence was gathered in simple ways. Prisoners of war and deserters were interrogated. The Union army was always interested in hearing what runaway slaves had to report. And, of course, both armies relied on cavalry scouts, signal intercepts, visual observation, and captured correspondence.

  One of the main functions of the cavalry was reconnaissance. When it was impractical to send a cavalry unit to gather i
ntelligence, a division commander might send an individual scout or a small scouting party. Scouts made visual observation of troop placement and movements and also intercepted messages sent from elevated signal stations. Later in the war, observation balloons also began to be used for intelligence gathering.

  Another valuable source of intelligence, which may seem hard to fathom for us in our world of e-mails, instant messages, and cell phones, was enemy newspapers. Field commanders always felt fortunate when they could get their hands on a recent newspaper from enemy territory. News reports might contain information about troop movements, recruitment, and transportation disruptions. However, as valuable as some of this intelligence might be, it was worthless if it arrived too late to be helpful.

  Spies in the Civil War, particularly Confederate spies, relied on courier systems to help speed their information to battlefield generals. Often these courier systems included female operatives. In fact, the Civil War saw an increase in the number of women involved in espionage, a few gaining legendary status in the process.

  Elizabeth Van Lew was a quiet aristocratic woman who was not afraid to take a firm stand against slavery and secession. More important for the Union war effort, she was destined to become one of the most successful and productive spies in the war.

  Elizabeth Van Lew was born in 1818 to upper-class parents who were raised in the North. They settled in Richmond, Virginia — destined to become the capital of the Confederate States of America — where Elizabeth spent nearly her entire life. But in the early 1830s, Elizabeth was sent to live with her relatives in Philadelphia, where she attended the same private academy that her mother, Eliza, had attended. More than likely it was while she attended school in Philadelphia that she heard much of the talk about the abolitionist movement. One historian believes that the young girl had a governess who spoke to her of the need to emancipate the slaves. By the time she returned to her family’s Richmond mansion, Van Lew had a strong and growing belief that slavery was immoral. As she wrote in her journal, “Slave power is arrogant — is jealous, and intrusive — is cruel — is despotic.” Because of her abolitionist views, Van Lew was shunned by many in her social circle, writing in her journal that she felt as if she and her family were “plague-stricken.”

  When the war began, Elizabeth Van Lew was considered a southern “spinster.” She was in her early forties and unmarried. What could she do, she wondered, to serve her country? The answer came to her when she recalled her father’s aunt Letitia telling her how she had ministered to the captured troops of the Continental army during the American Revolution, especially those who had been wounded in action.

  But Elizabeth wanted to do more than simply minister and comfort the wounded. A Unionist, believing in “one nation . . . indivisible,” she needed to do more. When she learned of Virginia’s secession from the Union in 1861, she felt, in the words of one historian, “profoundly betrayed.” She believed that the secessionists did not represent the majority of the citizens of Virginia. She was compelled to act in any way she could to help repair a nation torn apart.

  Elizabeth Van Lew decided she would carry on the tradition of her great-aunt by caring for federal troops imprisoned in Richmond. In 1862, nearly 50,000 prisoners were kept in Libby Prison, a converted warehouse six blocks or so from the Van Lew home on Church Hill.

  At first, Van Lew’s scheme was rejected, when Brigadier General John H. Winder, inspector general of military camps for Richmond, denied her permission to enter the prison. She was, however, allowed to visit injured Yankee soldiers in the prison hospital. One soldier noted in his journal that “she alone went from cot to cot where lay a sufferer in blue.” She did what she could for the wounded soldiers, bringing them messages and money, and no small amount of food.

  In hushed tones, she talked to the men about where they had been and what they had seen and heard. The more she listened to the prisoners, the more she realized that they possessed information that could be of value to the Union army. Alert federal soldiers took notice of rebel troop strength and movement. They recognized who commanded which rebel armies. Overhearing conversations of the Confederates who captured and transported them to prison often offered insight into the morale of the rebel troops. As any good spy will do, Van Lew listened attentively to the information the soldiers provided, and then, with the help of the Richmond underground, she passed it on to Union army commanders.

  No one in Libby Prison hospital paid much attention to this tiny, birdlike woman with a thin nose and alert blue eyes as she went about her business of visiting the hospitalized soldiers. She read to them and brought them baskets of goodies. The Confederate guards had no idea that this kindhearted woman was gathering military intelligence from the prisoners and laying the groundwork for espionage activities.

  Realizing that they could do more if they banded together, groups of the Richmond Unionists began to organize. As Van Lew built stronger relationships with wounded soldiers, the Unionists made plans to hide Union soldiers who escaped from Libby Prison. In fact, the Van Lew mansion became a primary safe house, a place where escaped prisoners would be hidden and cared for. Elizabeth, her mother, and their servants did all they could to prepare the escaped soldiers for the treacherous journey behind enemy lines as they attempted to rejoin their fellow soldiers. The Unionists well understood that every escapee was a potential source of valuable military intelligence, and they made certain that each soldier was debriefed before starting back to the Union lines.

  The use of the Church Hill mansion emboldened Van Lew. She was ready to take a more active role in the service of her country. Her official recruitment as a spy came late in 1863. In November, General Benjamin Butler was placed in charge of the Department of Virginia and North Carolina, putting him in command of much of the area of eastern Virginia, which included directing the Army of the James against Richmond. He was savvy enough to realize that any chance he had of capturing Richmond would be significantly improved if he received inside help from Richmond Unionists. If they could provide him with accurate intelligence, he and his troops would take care of the rest. Butler needed a “correspondent in Richmond,” as he put it to a friend.

  On December 8, 1863, two Union soldiers, Harry Catlin and John R. McCullough, escaped from the Libby Prison hospital. The Richmond newspaper carried details of the audacious escape. This was a propaganda triumph for the Richmond Unionists that infuriated Southerners who couldn’t believe that villainous Yankee sympathizers lived among them.

  Ten days after the escape, McCullough reached the Union camp. In the intervening days, he helped the underground in its espionage activities, passing along information about General Lee’s recruiting efforts in Richmond and about Confederate shortages of staples such as sugar and coffee, as well as iron, which was needed for the manufacture of ammunition. When McCullough finally met with General Butler, he told him about the operations of the Richmond Unionists, especially the work of Elizabeth Van Lew. From that discussion, Van Lew met with General Butler at William Rowley’s farmhouse a few miles south of Richmond, one of five safe houses that were especially comforting to the Union couriers and escapees. At Rowley’s house, Butler explained that he required, as he had put it in an earlier letter, a person who could “write me of course without name or description of the writer, and . . . only incur the risk of dropping an ordinary letter by flag of truce in the Post Office, directed to a name at the North.” (Both the Union and the Confederacy had agreed to permit the uninterrupted flow of mail between civilians, be they Northerner or Southerner.) Van Lew would need to write her secret messages in invisible ink. She was to write her message in the space between the lines of an innocuous letter that a “dear aunt” might write.

  Armed with invisible ink, a cipher system, and a passion to end the war and preserve the Union, Elizabeth Van Lew became Butler’s eyes and ears in the Confederate capital city. Truth be told, however, she became much more than that. She became a spymaster, the person responsible for runn
ing a network of agents, couriers, and safe houses that was very active during the war. In addition to the spying, Elizabeth Van Lew continued to maintain her Church Hill home as a safe house and something of a local Union spy headquarters.

  It may seem surprising that no Confederate sympathizers took action against Van Lew, given her strong and public views on secession and slavery. Surely there were suspicions, especially among her upper-crust neighbors, but the matter never went beyond those suspicions. Historians have suggested that the secessionists were victims of their own cultural bias, believing that no aristocratic person, and certainly not a lady, would ever consider taking part in anything as impolite as spying. A true lady managed her servants, prepared parties and gatherings, and blindly supported her husband. Such attitudes worked in Van Lew’s favor, diverting suspicion from her.

  Van Lew continued to be alert to any helpful information she was able to overhear when she visited the prisoners. The guards were often careless in their speech when Van Lew was within earshot. She instructed her operatives to be on the lookout for loose-lipped soldiers who might unwisely let slip a tidbit of military intelligence. By the summer of 1864, she was sending her handler about three messages per week, filled with news of troop movement, supply shortages, and the psychological state of the soldiers as well as of Richmond’s citizens.

  To assure that the intelligence reached the commanders as quickly as possible — the postal services having become slow and unreliable — Van Lew created a system of couriers that moved the intelligence on its way without burdening one operative with the responsibility (and danger) of making the entire trip. She also created a credible cover story for each of her couriers, should they be stopped and questioned along the way.