Intelligence in the Civil War
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.
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, 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.
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.
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.”