The Dark Game

by Paul B. Janeczko

  However, Rose O’Neale Greenhow’s luck ran out a few months after the fall of Fort Sumter. She was arrested on August 23, 1861, but was not sent to prison. Rather she was placed under house arrest, at what came to be known as Fort Greenhow. Women thought to be spies were treated differently from men by both sides. On the other hand, the fate suffered by men like John André in the Revolutionary War typified what happened to men accused of spying in the Civil War. In fact, Timothy Webster, one of Pinkerton’s bright young agents, was caught spying behind enemy lines and hanged, the first such execution of the war.

  Although confined to her home, Greenhow soon realized that she could learn a great deal by simply listening to the talk of her guards. Her mail was censored, but she still managed to hide secret information in innocuous-sounding letters. She also used colored yarn — what she called her “vocabulary of colour”— for sending information to rebel commanders. She wove tapestries in which military intelligence was enciphered, in a sense, in the colors of the yarn that she used. Granted, this method of transmitting intelligence was limited to very simple information, but there were times when that was all that was needed.

  Before the guards made it more difficult to communicate with the rebels — Greenhow never went anywhere without a detective following close by — she wrote one of her more elaborate enciphered messages. In this message she included detailed drawings of the fortifications around Washington, as well as notes about the system’s weak points. According to Greenhow, the rebels were very pleased with her drawings, which they complimented “as being equal to those of their best engineers.” Rose later added, “as well they might.”

  In October 1861, Greenhow befriended a guard and bribed him to deliver a secret message. The guard betrayed her, however, and Pinkerton increased the guards at “Fort Greenhow.” Despite Greenhow’s loud and frequent complaints, Pinkerton never stopped trying to keep her from sending intelligence. At one point he put another woman prisoner in with her, hoping that Rebel Rose would incriminate herself by divulging the details of her espionage. But it didn’t take Greenhow very long to figure out that the new “prisoner” was really one of Pinkerton’s undercover agents.

  Pinkerton next ordered that all the windows in Greenhow’s home be covered with boards. Then he had all paper removed from the house. Finally, Allan Pinkerton had seen enough of what Rebel Rose could do and felt she needed to be locked up in a real prison.

  She was taken to the Old Capitol Prison. Her time there was most unpleasant. She was approaching fifty, her sharp face now lined with deep wrinkles. Her cell was a mere ten by twelve feet and contained none of the finery that she was used to. Her only pieces of furniture were a straw bed and a wooden table. She was fed the same food the soldiers received. As a further indignity, her cell was infested with bedbugs and all manner of small, four-legged vermin. If prison officials expected Greenhow to give in to the rigors of her new life, they were mistaken. She behaved as she had in her life to this point. Her haughtiness did not sit well with the guards. She treated them like servants who were put there to satisfy her wants.

  Greenhow found her treatment from the federal guards demeaning. Because of her fame, she was something of a tourist attraction, like a tiger in a cage. Visitors may have been surprised to find that Rebel Rose was ready to chat amicably with any of them who were so inclined. But Greenhow had only one thing on her mind during these conversations: learning any morsel of news that might help the Confederate army.

  Despite all the efforts by prison officials to keep Greenhow from interacting with other prisoners, they could not completely stop her. In her autobiography, Greenhow tells of one incident that occurred when she was walking in the prison yard. Out of nowhere, a small bundle of folded paper landed at her feet. She carefully opened the paper and read that Stonewall Jackson had soundly defeated federal forces at Front Royal in the Shenandoah Valley. As Greenhow later wrote, the news “made my heart leap with joy.”

  After nearly ten grueling months in the Old Capitol Prison, Greenhow was set free on the last day of May in 1862. As she left the prison, she was given a warning never to return to Washington, D.C. In Richmond she took up residence in the upper-class Ballard House and soon contacted her handlers, suggesting that the rebel army take advantage of new technology by using hot-air balloons to deliver spies behind enemy lines. Soon Confederacy president Jefferson Davis made plans for her, more practical plans that he hoped would change the course of the war for the South. He wanted Rose O’Neale Greenhow to sail to Europe, to meet with heads of state in an attempt to get them to support the Confederacy, either with direct financial or material assistance or at least with a pledge that they would stay neutral in the war.

  Given her love for socializing with the rich and famous, Greenhow must have been pleased with the assignment and left for London at the end of the summer of 1863. She spent a few months meeting with various British statesmen, but her requests for aid were politely rejected. Disappointed but not discouraged, she sailed across the English Channel to Paris for more negotiations. After months of spying and being confined to prison, Greenhow was ready to immerse herself in the gala parties in the City of Light. Despite her enjoyment of the city’s social life, however, she made little progress toward getting a promise of aid from France.

  Greenhow set sail for home on August 10, 1864. She brought with her gold coins that she had received as a contribution to the Confederacy war effort. The journey was long, but she was glad to be returning to the South. As her ship approached the eastern coast of America, however, nature conspired against her. A storm hit as the ship was preparing to run the federal blockade. Greenhow begged the captain to let her try to make it ashore in a skiff. The captain refused, but Greenhow, recalling the horrors of the Old Capitol Prison, refused to risk capture by the Union navy. She pressed her case relentlessly until the captain finally agreed to let her join a few of his sailors who would handle the skiff.

  Greenhow boarded the small boat, bringing the gold coins, probably in a leather bag she had slung across her shoulders. The boat had not gone very far when it swamped and capsized. Greenhow was dragged into the sea by the weight of the gold. In the light of the next day, her body was found washed up onshore. A Confederate shore guard found the body and recovered the gold coins, for which he was given a small reward. When her body was brought to port for burial, women lined the pier in honor of Rebel Rose. Eyewitnesses reported that Rose O’Neale Greenhow looked as elegant in death as she had been in life. She was put to rest with full military honors in a local cemetery.

  When Robert E. Lee surrendered his command to Ulysses S. Grant at the Appomattox courthouse in 1865, the country faced years of healing. The question of slavery would take even longer to resolve. And, although the Civil War had introduced advances in the science of war, the field of espionage made but modest gains. Perhaps the most significant was the effort by President Lincoln and his military commanders to create an organized espionage network. This legacy set the stage for better organization during America’s involvement in World War I, less than fifty years after the end of the Civil War.

  THROUGHOUT THE CIVIL WAR, many African Americans were among those delivering intelligence to federal troops. The Union army was wise enough to make use of information provided by runaway slaves. General Lee believed that the Union army’s “chief source of information” came from African Americans, who provided details about terrain, as well as information about hidden stores of rebel guns, supplies, and treasure. Union colonel Rush Hawkins referred to such intelligence as “Black Dispatches,” and was quoted as saying, “If I want to find out anything hereabouts, I hunt up a Negro; and if he knows or can find out, I’m sure to get all I want.”

  Hawkins was talking about the likes of Mary Louvestre, a housekeeper for a ship’s chandler near the Gosport Naval Yard in Norfolk, Virginia. She overheard her master and some navymen talking about the rebuilding of the CSS Virginia into an ironclad ship. If the officers at the U.S. Nav
y Department were surprised to hear such news, they were even more surprised — and overjoyed — when Louvestre presented them with a copy of the plans that she had stolen. With such information, the Union navy was able to speed up development of an ironclad of its own.

  Without a doubt, Harriet Tubman was the most important African-American spy. Most people know Tubman as one of the foremost conductors on the Underground Railroad. In addition to helping runaway slaves escape to the North, the Underground Railroad also helped escaped Union soldiers return to their units. In fact, it was Tubman’s work on the Underground Railroad that led Union generals to learn of her. When the federal General Staff recruited Harriet Tubman as a spy in 1862, she in turn recruited nine African-American men for her intelligence unit. Some of them were riverboat pilots who knew every trickle and tide of the coastal waterways.

  The following year she formed a regiment of African-American soldiers under the command of Colonel James Montgomery of South Carolina. Union gunships manned by three hundred black soldiers from Tubman’s regiment successfully navigated treacherous waters laced with explosive mines because intelligence from other African Americans had pinpointed the mines’ locations. In enemy territory, Tubman’s regiment led about eight hundred slaves to freedom and destroyed an enormous cache of food, war supplies, and cotton.

  At the end of the nineteenth century, spying was the business of gentlemen. It was, in a sense, conducted in the open. And because the governments of Europe had only small agencies to gather political and military information about their enemies and would-be enemies, much of the intelligence was gathered in an informal way by individuals who were not working for any intelligence agency. For example, visitors to a port city would amble about, all the while noticing what was being shipped, how much was being shipped, and where it was going. Military attachés in cities like Berlin, Vienna, and Stockholm gathered military intelligence in the country in which they were posted. They would, for instance, watch for troop redeployment or changes in training schedules. As one British attaché put it, “Certainly [an agent] must keep his eyes and ears open and miss nothing, but secret service is not his business.” It soon became his business.

  With European nations spying and counterspying as their countries edged closer to war, President Woodrow Wilson kept the United States on a course of neutrality. He didn’t want the nation involved in any activities, including espionage, that might imply that the U.S. was taking sides in the growing tension. In one of the ironies of World War I, the entry of the United States into a war in Europe started in Mexico. President Wilson had long been uneasy about the unstable political situation in Mexico. In 1911 things took a turn for the worse when Porfirio Díaz, Wilson’s choice as leader of Mexico, was overthrown by Francisco Madero. Madero was then overthrown by General Victoriano Huerta in 1913. To make matters horribly worse, Huerta ordered the murder of Madero and his vice president.

  Outraged by such treachery, Wilson refused to recognize the Huerta government. Things turned against the Huerta regime when two insurgents threatened his leadership: General Venustiano Carranza and Francisco “Pancho” Villa. Despite the fact that Wilson supplied Villa with arms — a questionable move by a president with a noninterventionist policy — Villa and his men were unable to overthrow Huerta.

  Because the United States was receiving almost no intelligence from field agents about the situation in Mexico, President Wilson could only wait for events to unfold and then react to them. Faced with a situation that had the potential to sweep across the unprotected two-thousand-mile border between the two countries, Wilson did nothing to authorize an intelligence agency to gather information that could benefit the United States.

  To make matters worse, Villa used the arms that the United States had given to him against American citizens. On January 10, 1916, Villa and his small band of rebels stopped a train near Santa Ysabel in Mexico and kidnapped then murdered eighteen young American mining engineers. Two months later, Villa and an army of about five hundred men rode into Columbus, New Mexico, and shot up the town, killing fifteen Americans and wounding many others. Wilson was finally driven to action, ordering Brigadier General John “Black Jack” Pershing and a contingent of U.S. troops over the border into Mexico. But Pershing could not count on having any consistent and reliable intelligence, particularly from local citizens.

  Many historians consider 1915 to be the low point of American military intelligence. That was the year that intelligence work came to a halt in the General Staff’s War College Division. The timing could not have been worse for the U.S. Not only was the country facing problems with Villa, but Germany was also about to begin making overtures to Mexico about playing a part in Germany’s plans for victory in the war. Still, the U.S. did nothing to improve intelligence gathering.

  “Black Jack” Pershing was not about to wait for the government to debate the issue of intelligence. He moved quickly and resolutely to fill the intelligence void in which he was expected to operate by creating his own spy operation. Cavalry Major James A. Ryan was in charge of the operation for a short time before turning over command to Captain W. O. Reed, who increased the number of operatives to provide intelligence on Pancho Villa. Reed added twenty Apache scouts to his operations.

  Japanese-American relations had, meanwhile, been strained for some time over U.S. immigration policies. A 1905 peace treaty brokered by President Theodore Roosevelt had failed to completely satisfy the Japanese, and although the so-called Gentlemen’s Agreement of 1907–1908 eased the situation, Roosevelt remained wary.

  Roosevelt’s misgivings seemed to be validated in 1911 when it was rumored that Japan had sent representatives to discuss the possibility of establishing a base on Magdalena Bay, on Mexico’s west coast. There were even signs that a large number of Japanese soldiers had conducted training operations in the Sonoran Desert, to the north of the Gulf of California. It was believed that some of those soldiers had crossed the border into California. But, once again, the United States did not have the intelligence capacity to discover such operations before they were carried out.

  Faced with the pressing needs for information on these two fronts, then — the hunt for Pancho Villa and threats from the Japanese — as well as a significant German presence in Mexico, Wilson finally (and grudgingly) agreed to allow a spy operation in Mexico. The Office of Naval Intelligence (ONI) hired operatives in Mexico to report on activities involving both Japanese and German representatives. To bolster this meager operation, the ONI also solicited volunteer spies from some of the large U.S. corporations operating in Latin America, including Standard Oil and United Fruit. With so much at stake, these companies were eager to help. Although this effort improved the situation, Pershing and his team never were able to run Villa down.

  Germany’s covert operations in Mexico had so far been limited to the political arena, mostly connected with propaganda. Berlin secretly subsidized a handful of Mexican newspapers to serve as outlets for propaganda operations. At the same time, Carranza’s government was actively courting Germany in the hope of building a closer economic and military relationship with Berlin. The German foreign minister, Arthur Zimmermann, did everything he could to nurture such a relationship with a country bordering the United States, hoping that with the inducement of trade and arms, Carranza would engage the U.S. in conflicts that would require troops and supplies, forcing America to focus its attention and military funding south of the border rather than in Europe.

  Getting Mexico into position to engage the United States remained high on the list of German covert operations in the Western Hemisphere. Living in exile, President Huerta was more than willing to draw the U.S. into war. In return Huerta wanted money from the Germans to buy arms and munitions, which he wanted delivered by German submarines. He also wanted reassurance that Berlin would stand behind him if needed.

  When Huerta was arrested by U.S. agents on June 25, 1915, the Germans decided to change tactics and bring their espionage operations across th
e border into the U.S. By this time, it was clear to Berlin that the war was not going to be short and swift, as they had expected. Further, if they wanted to win the war, they needed to make certain that the U.S. stayed out of it. They also wanted to put a choke hold on the flood of arms and other war supplies from U.S. ports to England. To reach that goal, Walther Nicolai, cunning German spymaster, created an espionage plan for his operatives in the United States that would make use of political, psychological, economic, and paramilitary strategies.

  To begin their campaign of psychological and political dirty tricks, Berlin hired an American public relations man, William Bayard Hale, to serve as their propagandist. In addition to inserting pro-German articles in American city newspapers, Berlin funded The Fatherland, a weekly newspaper in the U.S. Berlin also purchased the Mail and Express, an established New York City newspaper, as another outlet for their propaganda.

  In addition to out-and-out blatant propaganda, the newspapers published features that were aimed at Americans who were not necessarily pro-German but who could be counted on for help. For example, they tried to appeal to the Irish, with their strong anti-British attitude. Germany also tried to attract isolationists and pacifists, who felt the United States should not meddle in the affairs of sovereign European nations. The Germans were hoping to ignite a grassroots movement that would forcefully protest any American involvement in the war, including sending arms or troops.