The Dark Game

by Paul B. Janeczko

  In addition, Van Lew did not hesitate to use her servants as couriers, once again taking advantage of a Southern attitude (shared, unfortunately, by many Northerners as well) — in this case, that blacks were too slow-witted to be part of an espionage ring. For their part, the servants, well aware of what was at stake in the war, were eager to assist Van Lew in any way they could. One servant, for example, carrying a basket of eggs along a country road was not apt to arouse any curiosity. However, hidden among the fresh eggs was one hollowed-out egg that held a secret message. A black seamstress would hide the intelligence among the paper dress patterns she carried with her sewing supplies. The guards at Libby Prison were used to seeing black servants bring food and other items to the prisoners, unaware that the servants were also swapping information with them. One of the Van Lew servants was often sent with a plate of homemade food on a lovely family platter; the platter had a false bottom that was meant to hold hot water to keep the food warm. Van Lew, however, used that space to hide her secret messages.

  When the campaign around Richmond intensified, the prison commandant clamped down on visitors, forbidding any conversation during visits. Undeterred by the strict prison rules, Van Lew found ways to continue her intelligence swap with the prisoners. She realized, for example, that the books she frequently brought for the prisoners could offer a variety of ways to exchange information. She could tuck enciphered messages down a book’s spine. She also developed another way of using books to conceal secret messages. She opened a book to a prearranged page and made a pinhole above each letter on that page that spelled out her secret message. Prisoners could easily respond in the same way.

  In addition to getting valuable military intelligence from Union soldiers, Elizabeth Van Lew and the Richmond underground helped them plan escapes. Van Lew knew that, in addition to freeing soldiers and officers to continue to fight for the Union, escapes were also valuable propaganda for the Richmond newspapers. She and her agents helped a number of soldiers escape, but no escape was more spectacular than the 1864 escape of more than 109 soldiers from Libby Prison.

  The escape was the brainchild of Colonel Thomas E. Rose and Major Andrew G. Hamilton, who were captured in the Tennessee campaign of September 1863. These officers organized a small team of prisoners to dig an escape tunnel. Over the next seven months, the diggers made three attempts to complete the tunnel without success. The first tunnel flooded with water from a nearby canal. The second collapsed. They then attempted to connect the third tunnel to a sewer line, but found that the sewer was too narrow to use for passage.

  Early in February 1864, the diggers thought they had dug far enough, but they discovered that the tunnel exit hole was still in the line of vision of the guard tower. After making a few calculations, Rose decided that they needed to shift the digging more to the left. On the night of February 9, they broke through the ground again and discovered that they were exactly where they’d wanted to be: in a tobacco shack that was hidden from the guards by a plank fence. Under cover of night, they made their way to prearranged Unionist safe houses, including the home of Elizabeth Van Lew.

  Prison officials were furious when morning roll call revealed the escape. But they reacted quickly and sent messengers in every direction to notify rebel pickets of the escape. More guards were placed on bridges and on the roads in the area around Richmond. About half of the escapees were captured, returned to Libby Prison, and immediately placed in chains in “narrow and loathsome” cells, with nothing but bread and water. Robert Ford, who took care of the prison’s horses and was a Unionist, was treated viciously for his role in aiding the prisoners who escaped. He received five hundred lashes and was whipped “nearly to death.”

  About fifty-five Union soldiers remained free and were able to return to their fighting units. Elizabeth Van Lew and the underground worked together to pass on intelligence about the escape. Union sympathizers were very pleased with the propaganda victory that was achieved by the escape. People in Richmond would not soon forget the “Great Yankee Wonder.”

  The last few years of Van Lew’s life were not happy years. Her brother and sister died in 1895. But by far the worst loss was the unexpected death in May 1900 of her beloved niece, Eliza, whom Elizabeth had treated like her daughter. Elizabeth Van Lew died four months later at the age of eighty-two and was buried vertically rather than horizontally because of the limited space remaining in the family cemetery plot.

  In death, as in the last years of her life, her benefactors saw to it that Elizabeth Van Lew received the honor she deserved. A boulder was shipped from the grounds of the State House in Boston to the Shockoe Cemetery in Richmond. The stone bore a bronze panel that said, in part, that:

  SHE RISKED EVERYTHING THAT IS DEAR TO MAN — FRIENDS — FORTUNE — COMFORT — HEALTH — LIFE ITSELF — ALL FOR THE ONE ABSORBING DESIRE OF HER HEART — THAT SLAVERY MIGHT BE ABOLISHED AND THE UNION PRESERVED

  THE CIVIL WAR did bring a few technological advances that began to change the way intelligence could be gathered and reported. Although largely untested, observation balloons and the telegraph were first used for gathering intelligence during the Civil War. The overall effect of this new technology on the war was not significant. Nonetheless, each of these innovations was only at the start of its place in espionage and intelligence gathering. Each developed further in subsequent wars.

  The first balloon flight in time of war lifted off the ground on June 18, 1861, in a test flight over Washington, D.C. The balloon, carrying Thaddeus S. C. Lowe, rose five hundred feet — about as high as a fifty-story building — and hovered over the capital. A transmission cable ran from the balloon’s gondola to the office of the War Department, and Lowe earned a place in history for initiating the first wartime air-to-ground communication ever recorded in America. His demonstration introduced the generals to a breakthrough tool of aerial reconnaissance for gathering intelligence in real time. Lincoln was sold on the idea of spying from the sky. He ordered his commander in chief, General Winfield Scott, to organize a Balloon Corps with Lowe as its chief aeronaut.

  Lowe wound up making espionage flights over Yorktown, Virginia, as well as over other battles in the state during the Peninsular campaign of 1862. After flying a balloon named Intrepid over the battle of Fair Oaks, he returned with timely intelligence that allowed General Samuel Heintzelman to escape an approaching Confederate army. Other flights provided generals and mapmakers with intelligence that helped them draw maps of enemy fortifications. On another flight over Richmond, Lowe brought a map with him and marked Confederate positions in red.

  The rebels, of course, tried to shoot down the balloons, without success. Musket fire did not have the range to hit a balloon. And they learned that cannon fire had a trajectory that was far better suited for ground-to-ground firing than ground-to-air firing. The rebels soon realized that by firing on the balloons, they were merely calling attention to their own positions.

  The rebels did soon figure out some ways to reduce the success of the balloonist spies. They camouflaged their camps with tree branches, and they also blacked out the camps at night, forbidding campfires, so the spies hovering above could not make an accurate estimate of troop strength. In addition, they painted logs black and set them up to look like cannons from a thousand feet above. These fakes were dubbed Quaker guns.

  The rebels did launch their own balloon program, but it struggled with technological problems. For one thing, their aeronauts had trouble controlling their balloons once they were aloft, a problem that Lowe had solved for the Union army balloons by tethering the balloon to a steam locomotive, which pulled it to an advantageous site. The Confederates attempted to have a tugboat pull a balloon down the James River, but this plan flopped when the tug ran aground on a sandbar and Union soldiers soon captured both the boat and the balloon. While the balloon flights by both sides in the war were of historical importance, their impact on the war was minimal.

  The biggest technological advance in the intellige
nce arena was the use of the telegraph, which enabled field commanders to quickly communicate with other commanders and with the War Department. It was not out of the ordinary that 4,500 messages, usually encrypted and some as long as a thousand words, passed between the War Department and the Union commanders each day. More than anything else, speed of communication over many miles was the most important strategic advantage of the telegraph. And, since intelligence becomes useless if it is not received in a timely manner, the speed of telegraph messages was a significant military advance.

  But like most technological advances, the telegraph brought its own problems — the most obvious stemming from the fact that a telegraph system needed wooden poles with transmission wires strung between them. Poles were cut down and burned. Wires were cut. It proved impossible to guard the many miles of telegraph lines from the work of saboteurs. And, of course, telegraph wires could be (and were) tapped, allowing each side to read the other’s messages. Before long, both sides realized that a more successful tactic was to capture an enemy telegraph station. Such a takeover not only allowed soldiers to intercept every message, but it also gave them the chance to send out disinformation using the enemy’s own telegraph wires.

  The Union Army did try to make their telegraphic messages more secure by enciphering them using what is called a route transposition. In such a system, the message to be sent was written in a grid of, say five rows and five columns for a message of twenty-five words. So the grid below would be used to send the message: Be advised that the troops of the enemy forces will pass by the valley in two days. Prepare to meet them no later than sunrise.

  The enciphered message was then sent by telegraph using columns rather than rows and look like this: be of pass two them advised by the days no that enemy the prepare later the forces valley to than troops will in meet sunrise. When the message arrived at its destination, the receiver knew to write it out in a five-by-five grid to read the secret message.

  Despite its shortcomings, the telegraph was a huge improvement over the flags and torches used earlier by army signalizers. A signalizer sent messages using a wigwag system, which was a two-part enciphering system created by a Union medical officer. A signalizer would move a flag or a light to the left for 1, to the right for 2. Each letter was represented by a combination of left and right movements. For example, the letter T might be sent as 2122. Or right-left-right-right. Such messages were obviously insecure, easily seen by other signalizers scanning the horizon for the sender. While cipher systems were used in messages, they were generally elementary and easily deciphered by signalizers on either side.

  The “clothesline” code used by the Culper spy ring during the Revolutionary War was also used in the Civil War. Union sympathizers might, for example, hang three shirts on a clothesline to indicate to Union agents that the local rebel army had been reinforced. An empty line, on the other hand might mean that the rebels had withdrawn from the area. Related to this simple system was the “window-shade” code in which a raised and lowered window shade at a particular window would really be a message sent to a watching signalizer.

  Like Elizabeth Van Lew, Rose O’Neale Greenhow drew praise from one side of the Mason-Dixon Line and revulsion from the other side for her espionage activities. Her supporters in the Confederacy called her Wild Rose, in admiration of her espionage exploits. Northerners, appalled by the treachery of this Washington socialite, called her Rebel Rose. Regardless of the feelings for Greenhow, it is difficult to ignore the espionage work she did for the cause she supported.

  Rose O’Neale Greenhow loved the social life of prewar Washington, D.C. Like Elizabeth Van Lew, she moved in upper-class social circles. She was disappointed when she had to leave the excitement of Washington to follow her husband, Robert Greenhow Jr. He had served for twenty years as a translator and librarian at the State Department but took a job in San Francisco, working for the California Land Commission.

  Although San Francisco offered some of the amenities of the nation’s capital, Rose O’Neale Greenhow’s life took a tragic turn on February 17, 1854, when her husband fell from a wooden sidewalk to the ground six feet below. Robert Greenhow suffered a broken leg and internal injuries; he then probably developed an infection as well. He lingered in and out of consciousness until he died on March 27, six weeks after his fall.

  Rose O’Neale Greenhow, a widow at forty, returned to Washington to resume the social life that she had left. She quickly learned, however, that things had changed as the divided nation had gone to war. While many men in positions of responsibility in the government and in the military left the capital to fight for the Confederacy, some remained. One Confederate sympathizer who remained in Washington was Captain Thomas Jordan. On the staff of Union general Winfield Scott, Jordan was the officer responsible for drawing up the initial war plans used against the Confederacy. Jordan had one reason for wanting to remain with Scott as long as he could: to learn more about the battle strategy of the Union army. In addition to reading Scott’s battle plans, Jordan established a spy network of some fifty agents. Some had espionage experience, but most were amateurs.

  Rose O’Neale Greenhow was one such amateur recruited by Jordan. Greenhow, in fact, became the spymaster for a band of Confederate agents. She had the qualities that Jordan was looking for: an intense dislike of Northerners and their attempt to impose their will on the established Southern culture, as well as complete disdain for anyone — particularly Northerners — who wanted to abolish slavery. In addition, like Elizabeth Van Lew, she held fast to her convictions and was not afraid to speak her mind about them.

  Jordan taught Greenhow a very basic substitution cipher, in which a letter, symbol, or number stood for a different letter or, in some cases, an entire word. For example, Z might stand for C — or for troops or railroad station. The new Confederate spymaster spent hours practicing her enciphering skills. She soon turned her Sixteenth Street house in Washington into the unofficial headquarters of her espionage ring. The spies who worked with her supplied intelligence about troop movements in and around Washington. Some were adept at getting intelligence from people in the U.S. government.

  By some accounts, Rose O’Neale Greenhow was considered “irresistible.” She was quick to use her appearance to attract men, although she wasn’t interested in just any man. She was only interested in men who could furnish information that might aid the Confederacy.

  One such man was Senator Henry Wilson of Massachusetts, chairman of the Senate Military Affairs Committee. As the prospect of war grew, Greenhow did her best to cultivate her relationship with Wilson without tipping her hand about her secessionist allegiance. In her autobiography, Greenhow claimed that Wilson wanted to marry her. Although she also claimed that he furnished her with military intelligence, there is no solid proof that supports her assertion.

  There is evidence, however, that one piece of intelligence Greenhow passed on — one based on her own observations in Washington — had a significant effect on the war. On July 10, 1861, she sent an enciphered message to Confederate general Pierre Beauregard, informing him that General Irvin McDowell, commander of the Army of Northeastern Virginia, had been ordered to march on Richmond and that he would be leaving Washington in sixteen days. Beauregard sent a courier to confirm the message. The courier returned with Greenhow’s confirming enciphered message hidden in the hollowed-out heel of his boot: Order issued for McDowell to march upon Manassas tonight.

  Beauregard moved his troops into position and surprised McDowell at Bull Run Creek, near Manassas, soundly thrashing the Union army. The defeat was devastating to the Northern war effort. Many in the North had thought that the war would be over in a short time, but the crushing defeat at Bull Run showed them otherwise. On the other hand, the Confederate victory against a superior foe made the secessionists in Washington jubilant, believing that the rebel army would soon be marching down Pennsylvania Avenue.

  Some historians are not sure of Greenhow’s influence on the Battle
of Bull Run. They point to the fact that Beauregard did not call for reinforcements until after his troops were pushed back by federal troops. It is possible that Beauregard disregarded Greenhow’s message, found himself and his troops in serious trouble, and then sent a frantic call to General Joseph E. Johnston for help. By giving Greenhow credit for her intelligence — and the stunning victory — Beauregard may have been playing the Southern gentleman while covering up his blunder.

  In any case, after Manassas, Greenhow received congratulations from Jordan, who wrote: “We rely upon you for further information. The Confederacy owes you a debt.” Buoyed by the success at Manassas, Greenhow continued to send reports through couriers to Confederate field commanders, providing them with valuable information on troop strength, movement, and position that she would receive from her operatives who met regularly at her home. She even found some helpful information in the Washington newspapers. However, her Sixteenth Street neighbors began to grow suspicious. And unfortunately for Greenhow, they weren’t the only ones who had taken note of her activities.

  Allan Pinkerton, head of the Union’s intelligence service and the man who would come to be “the agent of Rose’s undoing,” was on the case. He had his own undercover agents trying to ferret out the rebel spies working in Washington. Fortunately, Pinkerton, guilty on many occasions of seriously overestimating enemy troop strength for the government, was a better detective than military analyst. He assigned Thomas A. Scott, the new assistant secretary of war, to the case.

  It didn’t take Greenhow long to figure out that Pinkerton’s counterintelligence net was closing around her. She developed a detailed escape plan. She spent many of her hours at home at the sewing machine, hiding secrets about Union troop movements in the lining and cuffs of her gowns. Despite feeling that her time as spymaster might end at any moment, Greenhow continued to receive military intelligence from her agents and made sure she passed it on to the field commanders, often through couriers. Because of her connection with rebel intelligence agents near Washington, she believed that the Confederacy would spirit her away to safety if the situation worsened.