Rose O'Neal Greenhow was born in Montgomery County, Maryland in 1817. "Wild Rose", as she was called from a young age, was a leader in Washington society, a passionate secessionist, and one of the most renowned spies in the Civil War. Among her accomplishments was the secret message she sent to General Pierre G.T. Beauregard which ultimately caused him to win the battle of Bull Run. She spied so successfully for the Confederacy that Jefferson Davis credited her with winning the battle of Manassas.

She was imprisoned for her efforts first in her own home and then in the Old Capital Prison. Despite her confinement, Greenhow continued getting messages to the Confederacy by means of cryptic notes which traveled in unlikely places such as the inside of a woman's bun of hair. After her second prison term, she was exiled to the Confederate states where she was received warmly by President Jefferson Davis.

Her next mission was to tour Britain and France as a propagandist for the Confederate cause. Two months after her arrival in London, her memoirs were published and enjoyed a wide sale throughout the British Isles. In Europe, Greenhow found a strong sympathy for the South, especially among the ruling classes. During the course of her travels she hobnobbed with many members of the nobility. In Paris, she was received into the court of Napoleon III and was granted an audience with the Emperor at the Tuileries. Rose's diary (August 5, 1863 - August 10, 1864), held in the North Carolina State Archives in Raleigh, NC, describes her mission in great detail.

In 1864, after a year abroad, she boarded the Condor, a British blockade-runner which was to take her home. Just before reaching her destination, the vessel ran aground at the mouth of the Cape Fear River near Wilmington, North Carolina. In order to avoid the Union gunboat that pursued her ship, Rose fled in rowboat, but never made it to shore. Her little boat capsized and she was dragged down by the weight of the gold she received in royalties for her book.

In October 1864, Rose was buried with full military honors in the Oakdale Cemetery in Wilmington. Her coffin was wrapped in the Confederate flag and carried by Confederate troops. The marker for her grave, a marble cross, bears the epitaph, "Mrs. Rose O'N. Greenhow, a bearer of dispatchs [sic] to the Confederate Government."

Molly Pitt union spy in richmond

"Major" Pauline Cushman

Espionage in the Civil War

        By the outbreak of the war, neither the Union nor the Confederacy had established a full-scale espionage system or a military intelligence network. The South, however, was already operating an embryonic spy ring out of Washington, D.C., set up late in 1860 or early in 1861 by Thomas Jordan. A former U.S. Army officer, now a Confederate colonel, Jordan foresaw the benefits of placing intelligence agents in the North's military and political nerve center.

        By summer 1861, Jordan had turned the ring over to his most trusted operative, Rose O'Neal Greenhow, a local widow of Southern birth. Mrs. Greenhows high station in Washington society enabled her to secure intelligence of great value to the Confederacy. Much of it reportedly came from an infatuated Suitor, Henry Wilson of Massachusetts, chairman of the Senate Military Affairs Committee. Through a ring of couriers that included a woman named Bettie Duval, Greenhow smuggled information about the southward-marching army under Brig. Gen. Irvin McDowell to Confederate troops in the vicinity of Virginias Manassas Junction. There it was received by Colonel Jordan, now chief of staff to the local commander, Gen. P.G.T. Beauregard. The intelligence helped turn First Bull Run into a Confederate victory.        Two other intelligence networks in the Federal capital, both of later vintage, were supervised by cavalrymen turned spies, Capt. Thomas N. Conrad and Pvt. J. Franklin Stringfellow. These amazingly resourceful operatives were connected with the Confederacy's first organized secret-service bureau, formed in 1862 as a part of the CSA Signal Corps. The head of the bureau, Maj. William Norris, eventually coordinated the activities of dozens of espionage and counterespionage agents who operated along the "Secret Line," an underground link between Richmond and the Washington-Baltimore region. In time, Norris and his assistant, Capt. Charles Cawood, sought to extend this network of intelligence outlets well above the Mason-Dixon line--as far north as that great base of Confederate espionage operations, Canada. Arguably the most effective military intelligence establishment of the war, Norris's bureau directed all espionage activity along the Potomac River, supervised the passage of agents to and from enemy lines, and forwarded dispatches from the Confederate War and State departments to contacts abroad.        A second Confederate secret-service unit was organized early in 1864. A prototype commando outfit, it was attached to the Torpedo Bureau of Brig. Gen. Gabriel J. Rains, but was neither as large nor as well administered as Norris agency.        The Confederacy was also served by countless private operatives. Probably the most celebrated civilian spy was Belle Boyd, who risked her life to bring intelligence to Maj. Gen. Thomas J. "Stonewall" Jackson during his Shendoah Valley Campaign of 1862. Less heralded was James Harrison, an itinerant Richmond actor who late in lone 1863 rode to Gen. Robert E. Lees Pennsylvania headquarters with word that the Army of the Potomac was about to enter the Keystone State in hot pursuit. The unexpected news permitted Lee to mass his scattered army prior to Gettysburg.         Confederate spies in uniform (known as "scouts" when wearing their own armys attire, and liable to summary execution if captured in enemy garb included the cavalry raiders of the "Gray Ghost, "John S. Mosby. Others served the equally daring Turner Ashby and the Marylander Harry Gilmor. Among other soldier-spies were the young Kentuckian Jerome Clarke and Sam Davis, the Tennessee farm boy who died a hero's death after refusing to reveal to his Union captors the identity of his raiding leader.        Despite the triumphs of individual spies, most large-scale Confederate espionage efforts failed. Carefully planned but ultimately unsuccessful projects included the Oct. 1864 raid on St. Albans, Vt.; the attempt the following month to burn large sections of New York City; and the Northwest Conspiracy.        The Union waited till the shooting started to take steps toward creating an espionage establishment. Its first secret-service bureau was set up in mid-1861 by Allan Pinkerton,

founder of the famous Chicago detective agency. While serving Maj. Gen. George B. McClellan in the Department of the Ohio during the wars first summer, Pinkerton, acting alone, penetrated the Confederacy as far as Jackson, Miss., before returning north with information on Southern war preparations. Following McClellan to Washington, Pinkerton almost single handedly broke up Greenhow's spy ring. As military intelligence experts, however, Pinkerton and his band of agents were out of their depth. In 1862, as secret-service chief for McClellan's Army of the Potomac, Pinkerton sent his employer outlandish estimates of enemy strength and dispositions, hindering rather than facilitating McClellan's operations.        The wars first double agent, Timothy Webster, regularly penetrated Southern lines, gathering intelligence in such diverse locales as Baltimore, Louisville, and Memphis, and infiltrating the militant Baltimore society of Confederate sympathizers known as the Knights of Liberty. Webster's services ended in Apr. 1862, however, when a combination of events led to his arrest and execution in Richmond.        One Union spy who made notable contributions throughout the war was Elizabeth Van Lew, a longtime resident of the Confederate capital. "Crazy Bett," as the eccentric Unionist was known to her neighbors, ran the largest and most successful spy ring concentrated in any city. Her team of operatives included a freed slave whom she placed as a servant in the Confederate White House to eavesdrop on Pres. Jefferson Davis and his visitors.        An equally infamous Union espionage leader was Brig. Gen. Lafayette C. Baker, chief of War Department detectives. As the bullyboy of Sec. of War Edwin M. Stanton, he shadowed, apprehended, interrogated, and imprisoned a multitude of Washingtonians, many on the merest suspicion of disloyalty. Though personally brave, Baker was a ruthless, unsavory character whose high-handed methods and unassailable power made him feared even by associates.        Union espionage work was advanced by dozens of lesser-known Northerners, in and out of uniform. Civilian spies and counterspies included, as in the South, numerous women--~ whose sex usually spared them the harsher consequences of their actions, if apprehended. One of the most resourceful was Sarah Emma Edmonds, who gained entrance to Confederate camps near Yorktown, Va., disguised as a black slave. Much less enterprising and successful was the actress Pauline Cushman, whose double-agent activities won her undeserved fame as the "Spy of the Cumberland." Male civilians who spied for the North included William A. Lloyd and his business associate, Thomas Boyd, who, as Southern transportation agents of long standing, were able to roam, more or less freely, to Richmond, Savannah, Chattanooga, and New Orleans--Lloyd all the while carrying his espionage contract, signed by Abraham Lincoln.        Union spies in uniform were more numerous. Probably the most noted was Maj. Henry Young of Rhode Island, whose 58-man band of scouts served Maj. Gen. Philip H. Sheridan during the wars final year. In the Appomattox Campaign, the scouts tapped enemy telegraph wires and misdirected supply trains critically needed by Lees army. Another effective operative in uniform was Col. George H. Sharpe, who in 1864--65 ran the highly efficient military information bureau attached to Ulysses S. Grant's headquarters. One of the most publicized espionage operations was conducted by civilian agent James J. Andrews in an ambitious but failed attempt to sabotage Confederate rail lines.

Spying in the Civil War

       Agents for the Blue and the Gray . . . In an era of hydrogen bombs, guided missiles, and germ warfare, the subject may have an Arcadian sound, the ring of a simpler, more romantic time. But in that respect, as in others, the conflict of North and South was a paradox, a combination of paradoxes.        That war of over one hundred and thirty years ago produced the nation's first mass armies, and a brutality and mechanized slaughter that shocked the sensibilities of the day. It had aircraft-balloons that floated over the lines-submarines, ironclad warships, automatic guns, trenches, a military draft-and the first organized espionage that the country ever knew. On both sides the spying involved treachery, filching of official secrets, the skillful seduction of loyalty. This war between Americans probably saw more espionage, involving more people, than any in our history.        It has been called the first of the modem conflicts; it was also the last of the romantic ones. In its spying, the generation that thrilled in admiration of Sir Walter Scott usually observed "rules" of knightly, or at least gentlemanly, conduct. Had that not been true, had Northern and Southern leaders not played Ivanhoe on endless occasions, scores of undercover agents would never have survived to tell their stories.        It was a spy-conscious war, and sometimes it seemed that everybody was spying on everybody else and talking volubly on the subject, in newspapers, parlors, bars, and at street corners. Nevertheless, few officials did anything to stop the enemy's espionage. The present-day reader may be astonished at the ease with which agents made their way across the lines and through opposition territory. Repeatedly they presented themselves to civilian and military officials, pumped them of information, and rode off with a bright good-by.        The nature of the war made espionage easy to carry on and difficult to stop. A Tennessean looked and acted much like a Pennsylvanian, a Texan like an Ohioan; if he simply paid attention to regional accents, an agent had little trouble. Repeatedly Southern and Northern commands turned apoplectic on discovering that the man whom they had escorted proudly over their fortifications was a spy for the other side. By that time he was usually well on his way to his home base.        Yet by and large these agents for the Blue and Gray played an amateur's game. Espionage had not yet become a high art or achieved the status to which Continental masters soon elevated it. The American spies improvised, experimented, and what they lacked in finesse they made up in energy and determination. They broke rules usually because they had never heard of them. They were a mixed crew, gentle and flamboyant, earnest and brazen, ingenious or crafty. They ranged from shoe clerks to young plantation owners, lawyers to grandes dames, actresses to plump housewives.        The ladies were terrific. In this war they made their American debut in espionage, and never since have the nation's women taken such an active part as spies. No matter how raging a partisan a man might be, his wife or sister was probably still more impassioned. They became the best recruiting sergeants; they were "not at home" to those who lagged in enlisting, and they sent such friends white feathers or boxes containing dresses. They connived endlessly, they took great risks, and they pushed through to success in ways impossible to simple males. They showed again that the female is not only the deadlier of the sexes, but also the livelier.

        In the eighteen-sixties the double standard prevailed in spying as in other matters, and to the ladies' benefit. Neither side did a great deal about it, even when the identities of women agents were well established. As the war grew slowly more bitter, men operatives were hanged, one by one. The women received threats, or perhaps a prison term, and then freedom to try again. That war saw no Ethel Rosenbergs, and no Edith Cavells. After all, a lady was a lady. . . . A gentleman could not bring himself to order her shot or swung from a gallows.        In part this is a tale of two cities, Washington and Richmond, with scenes in Louisville and New Orleans, Nashville and St. Louis and Baltimore. By an accident of geography the capitals of North and South lay only a hundred miles apart. Their proximity made them obvious targets for rival armies and no less for rival spies.        At the war's beginning neither Union nor Confederacy had a security organization nor a secret service; the nation had never known one. The general war effort started as an exercise of amateurs. Struggling to create a colossal military machine of a kind that the country had not previously visualized, each side floundered. In no field was the process of trial and error more pronounced than in espionage.        In Richmond and Washington roughly organized intelligence units gradually emerged. Inconspicuously located in the Richmond War Department was an office halfway between that of Jefferson Davis and the War Secretary's. Most Richmonders considered the Signal Bureau only the headquarters of that newfangled branch of operations which used "flagfloppers." Confederates teased the dapper young men who carried blue and scarlet cloths: "Mister, is the flies a-botherin' of you?"        The Signal Bureau, however, had special functions. Its offices carried on an unending correspondence in cipher with Confederate agents in Washington, Baltimore, and other key points in Union territory. Early in the war the North tried to establish "land blockades" to cut off communication as well as thousands of items not available in the nonmanufacturing South. But representatives of the Confederate Signal Bureau managed to run courier lines in all directions over land and water.        Several offices beside the Signal Bureau involved themselves in Southern espionage-that of Jefferson Davis, the successive War Secretaries, the provost marshal. So many had a part, in fact, that the effort suffered; responsibilities were scattered, confused, and Union spies appeared to slip in and out of the Confederacy like fish through a wide-meshed net.        The North stumbled on in its own way. Arriving for his inauguration, in the face of threats against his life, Abraham Lincoln lacked even an official bodyguard. In the early months of the war Southern agents had a field day, working almost without hindrance. The first Federal defeat brought an awakening, a shake-up, and the North's first secret service bureau.        Authority over the new service was transient. The State Department supervised intelligence matters in the beginning; then they went over to the War office, and as in Richmond the provost marshal and other officials had a finger in the pie. Sometimes Washington spies seemed to be spying on other spies. But then, if only because of the war's course, which brightened steadily for the North, the Union system became more expert than the Confederacy's, boasting some rare feats of espionage.        Early and late, spies for both sides had a superb asset-the almost unbelievable carelessness of officialdom and citizenry alike. Little or no effort was made to check

clacking tongues, and casual gossip told all an enemy needed to know about an impending advance or a strategic installation. A man had an "open face," so he must be on our side, you understand.        Another aid to spying lay in the newspaper situation. In Dixie as in the North the press blandly printed vital information. Preparing for the Battle of Chickamauga in Tennessee, Confederate General Braxton Bragg received a New York Times clipping which explained precisely how the Unionists would fool him into a shift of position. Bragg stayed put. Near Vicksburg a Northern spy brought his superior a newspaper story in which a correspondent described in full the Federal plans for a "secret canal" behind the Mississippi. The project had to be dropped.        More than perhaps any other Southern general, Robert E. Lee used secret agents to supply him with every available Northern newspaper. The Virginian studied them by the hour, noting, comparing, questioning. A Southern spy with a copy of the Philadelphia Inquirer provided information of a withdrawal by McClellan; as a result, Lee shifted thousands of troops. The Southerner's military shrewdness kept him from accepting false stories planted for his benefit, and Lee himself once inserted a fake in Confederate papers.        The complete story of American espionage of 1861-65 will, of course, never be known. Much of it was never committed to paper; countless incidents were understood by only three or four people, who never gave out the facts. Innumerable agents died obscure deaths, shot down on a dark road or succumbing to exposure.        When Richmond fell, one of the last acts of Judah Benjamin was reportedly the burning of most of the South's secret service papers. Years later Jefferson Davis discouraged attempts to give out details of Confederate spying. On the Union side General Grenville Dodge similarly opposed efforts to reveal names and activities. Too many people might be hurt.        Nevertheless, a great deal of data is available from a variety of sources. In the Official Records of both armies were recorded thousands of pages of correspondence, orders of inquiry and arrest, some of them carrying evidence of all too human rage and puzzlement over the episodes.        These episodes chiefly concern civilian spies, though related work of military scouts is involved at some points. The story is at times bizarre, almost unbelievable. A plotmaker concerned with credibility would hesitate to let his characters do some of the things these spies did in real life.Source: "Spies for the Blue and Gray" by Harnett T. Kane

Confederate Operations in Canada

        From the earliest days of the Civil War the Confederacy had a secret operation in Canada with two main purposes. First, Canada provided a safe haven for Confederate prisoners of war who escaped from the prison camps in the North, and second, it served as a relay point for communications between England and the Confederacy. During the early days of the war Rose O'Neal Greenhow, of Washington, served as an intermediary between Washington and Toronto.        On 7 April 1864, the mission of the Toronto operation was drastically changed. On that day President Jefferson Davis sent the following telegram to the Honorable Jacob

Thompson, in Mississippi:  "If your engagements permit you to accept service abroad for the next six months, please come here immediately." Mr. Thompson, a lawyer, statesman, ex-member of Congress, and Secretary of the Interior under President Buchanan, was above all a loyal Confederate. He quickly responded to President Davis call.        The reason for his summoning by President Davis was that the Confederacy, in a last desperate action, wanted Thompson to go to Canada and from there direct a secret operation to create hostile activities in the Northwest, specifically another secession movement against the Union government--thereby, hopefully, the Union would sue for peace to prevent a further breakup.        Thompson accepted the challenge and was joined in Canada by Clement Clay, an ex-senator from Alabama, who was given the title of Commissioner of the North. The action officers assigned to the effort were James P. Holcombe, a University of Virginia law professor, and Captain Thomas Henry Hines, a veteran Confederate spy (even though he was only in his early twenties).        Why go to Toronto? By 1864, Toronto was much like Lisbon during the Second World War. Everyone had spies there and it was not infrequent that the spies traded information. In addition, C.L. Vallandingham, who was the Grand Commander of the Sons of Liberty and an outspoken sympathizer for the Confederacy, had fled from the U.S. to Canada in 1863. He purposed to detach the states of Illinois, Indiana and Ohio from the Union, if the Confederacy would move sufficient troops into Kentucky and Missouri to ensure their entry into the new Confederacy. Vallandingham wanted to form the five states into a new Northwestern Confederacy and thereby break the Union into three distinct pieces. He felt this action would force the Union to sue for peace. It is for all of these reasons that President Davis sent his powerful delegation north to Canada in the spring of 1864.        Hines and his fellow agents did work closely with all of the Copperhead organizations in the Northwest, mainly the Knights of the Golden Circle, the Order of the American Knights, and the Sons of Liberty, in attempts to create uprisings. All that resulted from this liaison was a great deal of inflammatory talk and no action. It appears that Captain Hines, in his youthful optimism, often misread the rhetoric as a guarantee of action--action that never came to fruition.        The following chronology summarizes the action undertaken by the Toronto operation:

    • During May, June and July of 1864 Maine coastal residents noticed artists sketching along the shore. These artists, about 50 in number, were in reality Confederate topographers sent to Maine to map the coastline. They were looking for coves and inlets that could be used by armed steamers in a joint land and sea attack on Maine. The full attack never took place, again stymied by Union actions, and their scaled down attempt met with disaster. On July 14, 1864, the governor of Maine, Samuel Cony, received a telegram from the U.S. Consul in St. John, New Brunswick, Canada. The telegram warned Governor Cony that a Confederate party of 14 men was planning to land on the Maine coast. A later telegram stated the team was headed for Calais, in Maine, to rob a bank. It further stated the team was led by a man named William Collins.    • On July 18, 1864, the man named William Collins and two other men, Phillips and the famous Confederate courier Francis Jones, were captured on the Main Street of Calais

walking towards the bank. When arrested and searched, a Confederate flag was found on Collins and he openly stated he was a Confederate, claiming to be a captain in the 15th Mississippi Infantry Regiment. No trace could be found of the other reported 11 men.    • No real connection could be found between the intended robbers and the Confederacy in Richmond or the operation in Toronto, and therefore the men were tried merely for "conspiracy to rob." Each was sentenced to three years in the Maine State Prison.    • Francis Jones, a disenchanted Confederate, confessed not only to his part in the Maine plot but also supplied information regarding Confederate weapons caches in the North as well as the names of 20 key Confederate agents operating in the Union. The operatives were in Maine, Massachusetts, New York, Pennsylvania, Maryland, Illinois, Mississippi, Kentucky, Tennessee and Ohio. Based on the disclosure mass arrests were made and weapons confiscated.    • In early June of 1864, Captain Hines planned an uprising in the Northwest timed with a raid by General John Morgans raiders in the Ohio/Kentucky area. General Morgan commenced a raiding mission in Kentucky on the 11th of June and was successful until he met the forces of General Burbridge who drove him out of the area and into Virginia. The raid did not create the desired unrest in the Northwest states.• An uprising was planned for August 29, 1864, timed with the Democratic Convention in Chicago. While the planning was extensive and assurances were given--no actual uprising occurred in Chicago as planned. President Davis comment after the failure of the mission was that the Copperheads did not do well as they had no military leaders.    • Political methods were also attempted. The Toronto operation funded the campaign of Democrat James C. Robinson for governor of Illinois. They were led to believe that if elected Robinson would turn over the states militia and arsenal to the Sons of Liberty. He lost the election.    • In the fall of 1864, operatives from Toronto did go to St. Louis, Missouri, to destroy the Union transports used to ferry Union troops and supplies on the Mississippi. They intended to use an inflammatory known as "Greek fire" (a Molotov cocktail), which was only successful about 50 percent of the time. The group did in fact manage to destroy or damage 5 to 10 of the 75 Union transports in port.    • In need of money, the Toronto operation staged a robbery in St. Albans, Vermont, in mid-October of 1864. The robbery was successful and the agents returned with over $200,000 in gold and U.S. currency. (When pressed by the U.S. for the return of the bank robbers, Canada refused since they were able to prove they were on a military mission--they produced their orders from Richmond).    • Uprisings were next planned in Chicago, New York, Boston, Cincinnati and other locations for Election Day, November 8, 1864. The operation in Canada supplied the money and weapons to make the uprisings happen--but to no avail.    • On November 25, 1864, Confederate operatives from Toronto came to New York City with the intention of "flaming" the city. They selected 19 hotels as targets and hoped to create a riot similar to the New York City draft riots. While some of the hotels did in fact sustain fires, in several cases the Greek fire did not ignite and the total effect was not what was desired. All of the operatives did manage to escape from the city which was a neat trick since a double agent, Godfrey Hyams, had informed the Union of the threat to New York.    • The next target was the USS Michigan, the only gun ship on the Great Lakes. The

attempt, made on December 19, 1864, was abortive due to a Union counter spy, J. Winslow Ayer, placed in the Confederate prison camp on Lake Michigan as a patent medicine salesman. He heard the Confederate prisoners talking about the fact that when the ship was taken over they were to rise up, take over the camp and then depart on the steamer.    • In December of 1864 Confederate operatives working for Hines decided to kidnap Vice President-elect Andrew Johnson on his way to Washington for the inaugural. They had a specific plan to capture him in his hotel room in Louisville, Kentucky, and take him away in a covered coach. The first night they attempted to execute the plan events made it impossible. On the second attempt, the agents rushed into the vice presidential suite all too easily, then found that the official party had left about an hour earlier. Vice President Johnson had decided to continue on his journey by boat instead of train.    • After the war, at the Lincoln assassination trial, a witness testified that the Toronto operation actually attempted "pestilence warfare" late in the war. The effort was reported to involve the delivery of "Yellow fever infected" blankets and clothing to Washington, D.C., in hopes of infecting the President and his cabinet with the disease.

        The Union was well aware of the threat represented by the actions of both C.L. Vallandingham and the Toronto operation and a major effort was made to infiltrate one of the Copperhead organizations to avert surprise. They were very successful in this endeavor in the person of Felix Stidger. Stidger was a Midwesterner by birth and was very familiar with Indiana, Kentucky and Ohio. He was a Union soldier under the command of Brigadier General Henry Carrington, who headed the intelligence operations in Indiana. On orders from Carrington, Stidger successfully infiltrated the Knights of the Golden Circle in Indiana in early 1864 and over time rose to the rank of Secretary General of the Grand Council of Indiana. Until October of 1864 Stidger submitted continual reports on the activities of the Knights of the Golden Circle and their involvement with the Toronto Confederate group to General Carrington. In October of 1864, Stidger along with over 100 of the Knights of the Golden Circle hierarchy were arrested. The Knights did not realize that Stidger was a Union agent until he appeared to testify against them.        All in all, it is estimated that the Confederacy spent over a million dollars funding their efforts to get the Copperheads to rise up, all to no avail due largely to Captain Hines. He was a young idealistic officer who believed that everyone with whom he had contact had the same genuine enthusiasm for the cause that he did. Therefore his reports back to Thompson in Toronto were glowing and full of guarantees that all was well and indeed moving the way the Confederacy wanted it to go. The operation finances could well have been used by the Confederacy for many other purposes, however, in his desperation President Davis felt an uprising had a chance and he refused to let his hopes die.        The overall failure of the Toronto operation was not only the fault of Captain Hines; it was also due to the excellent counter-espionage efforts of the Union. By this late stage of the War the Union had a very sophisticated counter-espionage organization that had great successes--due in no small part to the lack of appreciation of their work by the Confederacy. While the Union began the war well behind the Confederacy in the world

of espionage and counter-espionage, by the final stages the situation was completely reversed.

Source: "Spies and Spymasters of the Civil War" by Donald E. Markle

    Timothy Webster was recognized as Allan Pinkerton's most famous active agent in the Civil War and was partially responsible for thwarting an assassination attempt on president-elect Abraham Lincoln. It is impossible to know exactly how events would have transpired at that time without Lincoln at the helm, but it is certainly true that the history of the United States would have been dramatically different if Pinkerton and Webster had failed in their mission and Lincoln had been killed before entering the Presidency.        Born on March 12, 1822 in Newhaven, Sussex County, England, Webster immigrated to America in August 1830 with his parents and settled in Princeton, New Jersey. After finishing school, in 1853 he became a policeman in New York City and performed skillfully. Around 1854 was he was noticed by a friend of Allan Pinkerton's who recommended him for detective work. After accepting work with Pinkerton, Webster quickly became their best agent.        Timothy married Charlotte Sprowles on October 23, 1841 in Princeton, New Jersey and the couple had four children, two of whom died young. Their son, Timothy Jr., born in 1843, joined the Union Army from Onarga, Illinois on July 30, 1862 and was wounded in the Battle of Brices Crossroads near Ripley, Mississippi on June 11, 1864, and taken to a confederate prison in Mobile, Alabama where his leg was amputated. He subsequently died there on July 4, 1864. His body was transported north to Onarga, Illinois and buried in the Onarga Cemetery next to his grandfather, Timothy Webster Sr., who died in Onarga in 1860.        At the beginning of the Civil War General George McClellan asked Pinkerton to enter Federal service, which he readily agreed to. Timothy Webster joined him in this effort thereby changing from detective to Union Spy.         Because of the nature of his work, Pinkerton suggested that Webster move his family to a safer place and work out of the Chicago office. Pinkerton suggested Onarga, Illinois, located south of Chicago on the Illinois Central Railroad. Pinkerton was familiar with the area and had said that he would like to have a farm and house there somedayCan ambition that was carried out later. Charlotte and the children moved from New York to Onarga around 1858; Webster commuted easily and his family was safe.         Sent to pose as a Southern gentleman in the Baltimore area, Webster managed to become a member of the rebel group "Sons of Liberty" in order to report on their plans and activities. In February of 1861 president-elect Lincoln was to travel from Harrisburg through Baltimore and on to Washington for his inauguration. While Webster was investigating rumors that secessionists were planning to blow up the steamers that ferried trains across the Susquehanna River, he uncovered a plan to assassinate Lincoln as he changed trains in Baltimore. Because Timothy Webster was able to send a warning, Pinkerton was able to foil the attempt on Lincoln's life.        In 1862, Webster was continuing to gather information on the Confederacy in Richmond when he was stricken with inflammatory rheumatism, the result of several previous crossings of the Potomac River in frigid weather and was too ill to send reports

back to Pinkerton. As a result, two menCLewis and ScullyCwere sent to locate him. The two men were recognized as being Union spies, captured by the Confederacy and eventually revealed secret information incriminating Webster.        Confederate officers had trusted Webster many times with valuable documents and information and the Confederacy was extremely embarrassed by Webster's betrayal. While Lewis and Scully were eventually released, Webster was arrested, tried, and sentenced to death by hanging.        When Pinkerton heard the news of the sentence, he and President Lincoln sent a message to the Confederacy threatening that if Webster was put to death, the Union would reciprocate by hanging a Confederate spy. Previously, Union policy had been to keep spies in jail and eventually exchange them for Union prisoners.         The Confederacy ignored the threat and on April 29, 1862, Timothy Webster climbed the gallows in Richmond, Virginia. The noose was put around his neck and a black hood was fitted over his face. The trap was sprung but the knot slipped and Webster fell to the ground. After being helped back up the steps and re-fitted with the noose he said, "I suffer a double death!" The noose held the second time, and Webster died within minutes and was hastily buried in Richmond.        In 1871, at the pleadings of his widow, Charlotte, and to fulfill a promise he made to himself upon hearing of Timothy's death, Pinkerton sent George Bangs and Thomas G. Robinson (Timothy=s son-in-law) to Richmond to locate his body and bring it North for proper burial in "Northern soil." With the help of Elizabeth (Crazy Bet) Van Lew, a Southern-born Union sympathizer that operated out of Richmond during the war, they located Timothy=s body, and transported him to his final resting place in Onarga, Illinois. He was buried next to his father, Timothy Webster Sr., and his son, Timothy Webster Jr.        Timothy's widow, Charlotte, went to live with her daughter and son-in-law, Sarah and Thomas Robinson in Onarga. In September of 1874, this family moved to California where Charlotte received a pension and lived with her daughter until she died on December 1, 1907. She is buried in the Old City Cemetery in Sacramento. Sarah Webster Robinson is buried in the Masonic Cemetery on Riverside Boulevard in Sacramento. Sarah's children never married, therefore there are no direct descendants of Timothy Webster.

Intelligence Collection - The North

While the Confederacy focused on getting intelligence to Richmond via the couriers of the Secret Line, the Union did not have any similar system. Union generals handled intelligence gathering as a task for their own commands. Early in the war, for example, when Major General George B. McClellan became commander of the Union’s Army of the Potomac, Allan Pinkerton moved to Washington to gather intelligence for McClellan. Pinkerton worked for McClellan, not the entire Union Army. Even so, Pinkerton later called himself “Chief of the United States Secret Service.” A similar claim came after the war from Lafayette C. Baker, who performed counterintelligence and oversaw security for Lieutenant General Winfield Scott, commander-in-chief of the U.S. Army.

Lafayette Baker

There was no centrally directed intelligence agency in Washington. Pinkerton and Baker worked only for their superiors. They ran their organizations so independently and so competitively that, in at least two cases, the operatives of one “secret service” arrested or kept under surveillance the operatives of the other.

The Union never developed a need for a national intelligence agency. The gathering of intelligence was, in fact, so decentralized that President Lincoln himself even hired an agent on his own, paid him, and personally received the agent’s reports. William A. Lloyd, a publisher of railroad and steamer guides for railroads and steamers in the South, approached Lincoln early in the war, looking for a pass through Confederate lines so that he could continue his business. Lincoln had a better idea: “Use the pass to go to the South and spy for me”—at $200 a month plus expenses. (This would have the equivalent purchasing power of about $4,000 today.)

Lloyd signed a contract in which he agreed to provide Lincoln personally with such intelligence as the number and location of Confederate troops and the layouts of their forts and fortifications. Lloyd headed into the Confederacy with his wife and maid, along with a publishing company employee, Thomas H. S. Boyd.

Because Lloyd had contracted to send his information directly to Lincoln, he did not use Union Army communications. Instead, he mailed the intelligence in letters to Boyd’s family. Then a member of the family would take the letters to the White House with instructions to have them delivered directly to Lincoln, who presumably used the information to weigh against what he was getting from his generals.

Lloyd’s arrangement with Lincoln resembled Pinkerton’s with McClellan and Baker’s with Scott: each agent was serving a man, not an agency. Pinkerton added to his services by doing some political spying for McClellan while contributing little useful intelligence.

In July 1861, with some 35,000 Union troops in Washington and Northern patriots clamoring for an “On to Richmond” campaign, Scott desperately needed whatever information he could get about Confederate strength around Manassas Junction, Virginia. In that hamlet, 25 miles from Washington, near a creek called Bull Run, Scott would launch the war’s first major battle. Scott sent Baker to Manassas Junction.

According to Baker’s memoir, he set forth to Manassas under the cover of a traveling photographer named Samuel Munson of Knoxville, Tennessee. Arrested in Manassas by the Confederates, he was questioned and sent on to Richmond, where, he claimed, Jefferson Davis, president of the Confederacy, questioned him, but could not break Baker’s cover. Although he spent time in a Richmond jail and was under guard before being released, he said he had somehow managed to get enough information about Confederate forces to please Scott.

The information did not prevent a Union rout at Bull Run. The debacle ended Scott’s career and began Baker’s, for he became chief of what he sometimes called the National Detective Police. With about 30 employees and an appointment as “special provost marshal for the War Department,” Baker worked not only on spy cases but also tracked down deserters and subversives, an all-inclusive label for Southerners suspected of treasonable acts, and for “Copperheads,” Northerners with Southern sympathies. His most famous case involved the capture of Belle Boyd.

 

Belle Boyd

Belle Boyd

Belle, in her colorful biography, said that she had killed a Union soldier who demanded that she fly a U.S. flag over her home. By her account, she became a Confederate spy, and one day—as “the rifle-balls flew thick and fast about me”—she dashed through federal lines and gave vital information to Major General Thomas (Stonewall) Jackson. She was later arrested and brought before Baker, whom she portrayed as an arrogant rube she easily outwitted. Baker supposedly threatened her with life imprisonment (neither side ever executed a woman as a spy), but she was released without having been charged and sent to Richmond, where she was hailed as a heroine.

Pinkerton, meanwhile, was developing a different view of espionage, pursuing what today would be called actionable intelligence. He realized that when the war began, the Confederacy had agents-in-place in Washington, while Northerners had few assets in Richmond. Pinkerton knew he had to establish a counterintelligence presence in Washington—and that he had to get agents into Richmond.

Pinkerton started a Richmond connection by sending one of his best agents, Timothy Webster, to the Confederate capital. British-born Timothy Webster was a former New York City police officer skilled at making acquaintances with people who became willing, unwitting sources. As Pinkerton later wrote, everyone who met Webster “yielded to the magic of his blandishments and was disposed to serve him whenever possible.” Webster got himself into Richmond under the cover of a secessionist acting as a courier from Baltimore using the Secret Line, the Confederate communications system. He ingratiated himself with Brigadier General John Henry Winder, who, as Richmond provost marshal, ran counterintelligence there. Winder was also in charge of prisoners of war east of the Mississippi and in that role picked up kernels of intelligence. Webster put Winder in his debt by carrying letters to and from Winder’s son, William, who was a Union Army officer in Washington. Winder showed his gratitude by giving Webster a pass that allowed him to travel throughout the Confederacy.

Timothy Webster

On one of his trips across the Potomac River, Webster learned that Vincent Camalier, a Maryland secessionist, had been jailed as he attempted to cross into Virginia. Webster intervened, convincing the Union officer holding Camalier to release him. The act won Webster more friends among Southern sympathizers on both sides of the river. Webster probably did not know that Camalier was himself an agent for the Confederacy’s Secret Service Bureau.

Webster also impressed Secretary of War Judah P. Benjamin, who accepted him as a courier and gave him documents to deliver to secessionists in Baltimore. Webster, transformed into a double agent by Benjamin, could thus deliver to Pinkerton not only reports based on Webster’s own observations, but also Confederate documents. Pinkerton said that Webster’s reports were so long and richly detailed that Pinkerton and two operatives had to stay up all night to read and assess them. He gave precise descriptions of the fortifications protecting Richmond, reported on soldier morale, and noted food prices.

Suddenly, in February 1862, Webster’s reports stopped. Pinkerton sent operatives Pryce Lewis and John Scully to Richmond to see what had happened. They learned that Webster lay ill with inflammatory rheumatism in a Richmond hotel. He was being cared for by Hattie Lawton, posing as Webster’s wife, and her black servant, John Scobell. Both were Pinkerton operatives. A Richmond civilian who had lived in Washington recognized Scully and Lewis as Pinkerton men. Captured and jailed, they were threatened with hanging if they did not tell what they knew about Webster.

Both were released, presumably because they talked. Pinkerton, however, believed that only Lewis had betrayed Webster. (Lewis later went to New York and started a detective agency.

Webster was arrested, tried, and sentenced to death. Lawton was also arrested as a spy, but officials, believing that no slave could be a spy, let Scobell go. After learning about Webster’s death sentence, Pinkerton went to Lincoln, who sent Confederacy President Jefferson Davis a message threatening to hang Confederates then held as spies if Webster were executed. Despite Lincoln’s message, he was hanged on April 29, 1862. There is no record of an immediate Union reprisal, but records of executions by the Union and the

Confederacy are sketchy and, as the war went on, retaliatory executions of spies did occur.

Lawton maintained her cover as Webster’s widow until she was sent to the North in a prison exchange about a year after the hanging. While she was in prison, Elizabeth Van Lew, a Richmond woman who provided food and clothing to Union prisoners, asked in vain for Lawton’s release. Neither woman seems to have known that the other was a spy for the Union.

Van Lew sometimes showed touches of eccentricity—causing her to be known as “Crazy Bet.” But, in her role as selfmade spy, she was cunning, outwitting Confederate detectives, enciphering messages, and managing a clandestine operation that was both an underground, which helped Union prisoners to escape, and a spy network, which provided Union generals with valuable intelligence.

Through couriers she recruited, she sent intelligence dispatches containing specific information, such as, “eight guns have been sent to Chaffin’s farm to be put in position.” Once she used a Confederate deserter to carry out of Richmond a message warning that “the enemy are planting torpedoes [mines] on all roads leading to the city.”

In the spring of 1862, when Elizabeth Van Lew heard that McClellan was launching a campaign to take Richmond, she prepared a room for him—“a charming chamber” with “pretty curtains”—in her imposing Church Hill mansion. McClellan never made it to her home, or to Richmond. Pinkerton, who accompanied McClellan on the campaign, provided the general with extraordinarily overestimated reports on the number of Confederate troops between McClellan and Richmond.

McClellan, who himself was naturally inclined to embellish troop strength estimates, believed Pinkerton’s numbers. At one point, when 80,000 Confederates faced McClellan’s 100,000 troops, Pinkerton estimated that McClellan was outnumbered nearly two-to-one. This gave McClellan the right to claim, in a dispatch to Washington, that he was opposed by “greatly superior numbers.”

Not Pinkerton, but a corporal named Barton W. Mitchell gave McClellan one of the most important pieces of intelligence ever presented to a general in battle. On September 13, 1862, Corporal Mitchell had been resting with a sergeant in a campground near Frederick, Maryland, when he noticed an envelope in the grass. Inside were three cigars wrapped in a copy of General Robert E. Lee’s Special Orders No. 191, perhaps dropped by a galloping Confederate courier.

The two soldiers took the envelope to their company captain who started it on a swift upward path to McClellan. The envelope contained the most important intelligence discovery of the war. As McClellan wrote Lincoln, “I have all the plans of the rebels.” Incredibly, the discovery of the document was leaked and appeared in the New York Herald, but apparently the story was not seen by Confederate officers monitoring Northern newspapers. The order revealed to McClellan that Lee planned to divide his

army into four parts, three to head for Harpers Ferry and the fourth to Hagerstown, Maryland. The order was four days old when it fell into McClellan’s hands. But, instead of reacting speedily, he characteristically reacted slowly. The incredible intelligence coup had done him no good. Lee’s forces were not attacked when the cigar-wrapping document revealed his plan. The result was the bloody battle of Antietam, fought at terrible cost for both sides. And when Lee headed back to Virginia, McClellan did not pursue.

On November 7, 1862, Lincoln relieved McClellan of command. Pinkerton resigned in sympathy, taking with him the information he and his operatives had gathered on the Confederacy.

 

The Union's "Lady in Richmond"

Elizabeth Van Lew

Elizabeth Van Lew, whose wealthy family was wellknown in Richmond society, was educated in Philadelphia and returned home an ardent abolitionist who convinced her mother to free the family slaves. When the Civil War started, she became an outspoken supporter of the Union. At first, braving the contempt of her social peers, she cared for hospitalized Union prisoners. Then she began helping them to escape, sometimes hiding them in the attic of her mansion.

Late in 1863, escapees told Major General Benjamin Butler about Elizabeth Van Lew. Butler, then in charge of Union-occupied eastern Virginia, sent one of the escapees back to Richmond with orders to contact her and ask her to spy for the Union. She agreed. Butler gave her a simple cipher system for her reports. She kept the cipher key in the case of her watch and often wrote her reports in invisible ink.

Butler soon passed on to Secretary of War Edwin M. Stanton a sample of the quality of the information he had been getting “from a lady in Richmond.” She told where new artillery batteries were being set up, reported that three cavalry regiments had been “disbanded by General Lee for want of horses,” and revealed that the Confederacy “intended to remove to Georgia very soon all the Federal prisoners.” (They were sent to the notorious Andersonville prison.)

Once, at Butler’s request, Van Lew carried out a risky mission. She walked into the office of Brigadier General John H. Winder, who, as provost marshal, sought out subversives in Richmond. There, she handed to Winder’s chief detective a note that recruited him as a Union agent. Although she certainly was in peril as she stood in Winder’s headquarters, it was, according to her diary, the detective who “turned deadly pale.”

By June 1864, the Richmond underground had five “depots,” where couriers could deliver their reports for pickup by Union operatives slipping through Confederate lines.

One depot was the Van Lew family farm just outside Richmond. She was running more than a dozen agents and couriers, including her own African-American servants. Sometimes they carried messages in scraped-out eggs hidden among real eggs or among the paper patterns carried by a seamstress. Another agent was a baker who used his delivery wagon as a cover for picking up and passing on reports.

Elizabeth Van Lew

Van Lew left a journal that contained cautious references to her work for the Union. But after the war, she asked the War Department for all her dispatches, which she destroyed to protect her network from postwar retribution. In her journal, which survived destruction, she noted that she was called a traitor in the South and a spy in the North; she said she preferred “the honored name of ‘Faithful’ because of my loyalty to my country.”

She was appointed postmistress of Richmond by President Ulysses S. Grant, bestowing upon her one of the highest federal posts then available to a woman. The Richmond Enquirer and Examiner condemned the appointment “of a Federal spy” as a “deliberate insult to our people.” President Rutherford B. Hayes did not reappoint her.

In 1883, she passed a civil service examination “with the highest rating” and moved to Washington, D.C., where she became a U.S. Post Office clerk. She resigned in 1887, after being demoted by a vindictive supervisor. She returned to Richmond, where she became a recluse, “shunned like the plague.”

She died in 1900. A plaque attached to her gravestone reads in part: “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.”