Crime Library: Criminal Minds and Methods

Allan Pinkerton and His Detective Agency: We Never Sleep

Wartime Spies

"Those who would give up essential Liberty, to purchase a little Safety, deserve neither Liberty nor Safety."

Benjamin Franklin

With the first sound of the guns, a civil war split the nation in two. The United States, less than a hundred years old, faced destruction. Lincoln refused to believe, however, that the house would divide against itself, a fate that he feared could happen even when he was a Springfield legislature several years back. Now, as its Chief Executive, he felt it was his responsibility to keep the threads of the Union sewn even if it meant marching into the South with muskets, cannons and bayonets to kill the dissention. The Southern brethren, he said, needed to see the futility of the insurrection. "The Union must be preserved!" he exclaimed.

General McClellan (National Archives)
General McClellan (National
Archives)

One of his first deeds as President was to call to Washington two men whom he believed could help preserve it. One was George Brinton McClellan, West Point graduate, Mexican War hero and peacetime executive of the Illinois Central Railroad. Of McClellan, Lincoln asked him to lead the Army of the Potomac, the guard dogs of the capital city. The other fellow he summoned was a Scottish detective from Chicago who proved his loyalty, bravery and genius by saving him from an assassin's bullet before he even took office. That man was Allan Pinkerton.

It was the President's wish for Pinkerton to organize a secret service in Washington City. Everyone knew, top down, that the town crawled with spies working for the Confederacy's central espionage unit, the Signal Bureau. "Washington, D.C., more a southern than a northern city, was virtually brimming over with Confederate sympathizers willing to supply intelligence to the South," reports Alan Axelrod in The War Between the Spies. "At the outbreak of the war, (Signal Bureau Chief) Thomas Jordan took it upon himself to harvest the bumper crop of spies Washington yielded."

When Lincoln brought the detective before his Cabinet for approval, however, the two men encountered dawdling; General Winfield Scott, who currently served as Commander in Chief of the Army was already considering another man to head up the secret police, an ex-lawyer from Ohio named Lafayette C. Baker. Still, Lincoln insisted that Pinkerton, to whom he felt he owed a favor as well whom he considered very capable, should be considered. While Pinkerton and Lincoln awaited a decision, McClellan, forming his strategy to combat the rebels in and around Washington, decided that, in the meantime, Pinkerton would prove valuable as his personal spy.

Accepting the General's offer, Pinkerton brought with him a number of operatives such as Timothy Webster and Kate Warne, whom he placed in and around the South to pick up information that the Northern armies could use. Kate, for instance, shared her time between Virginia and Tennessee posing as a Southern belle, familiarizing herself with other ladies of the South who spoke freely about their husbands' and boyfriends' regiments. Webster, in Southern Maryland, continued his association with the Knights of the Golden Circle who, because they took part in many undercover assignments for the South, provided a conduit of information about espionage activities in Northern cities. Through charade, these and other Pinkerton agents found that data was not hard to come by. Loitering in camp towns and ingratiating themselves with the local soldiery in the hotbed of the South, they were able to pick up such vital information as what army corps was stationed where; who commanded; who were the Confederate operatives and mail runners; where fortifications existed; and what was the strength of artillery emplacements.

Pinkerton himself partook in special assignments. To ascertain the strength of Memphis' defenses, he disguised himself as a rich Southern gentleman about town who wined and dined local commander, General Pillow. Over bottles of burgundy, Pillow divulged the size of his regiment, the location of breastworks, even the names of his underground contacts from Richmond, Virginia, the capital of the Confederate States.

Like any successful agent, Pinkerton's safety teetered at any given time; an operative never knew who might recognize him, who might be a counterspy and know him at a glance. He had a couple of very close shaves literally.

One came in Memphis. Whether or not General Pillow caught on, no one knows, but one warm morning while Pinkerton was in the act of shaving, his face full of lather, a Negro porter burst into his room crying, "If you want to keep your head, mister, you'd better flee, now. They're coming up the stairs with a rope!" Pinkerton tossed him a silver dollar, didn't bother to wipe off the shaving soap, and high-tailed it down the gutter spout to his horse.

Another time, while receiving a shave in a barber's chair in Jackson, Mississippi, the German barber, who had been eyeing him curiously from the start, asked, "Aren't you Mishter Pingerdon, ze detective vrom Zicago?"

Others in the shop, waiting for a trim, suddenly looked up from their seats with ice-cold stares. Pinkerton chuckled. "Of course not! Don't know the man."

"Vell, zat ish ze shtranchest ting! I shaved Pingerdon once in ze Hotel Sherman in Zicago, und you not only looks like him, but you talks chust likes him, too!" the barber replied, shaking an incredulous head.

Needless to say, Pinkerton darted for the nearest train station the moment he left the barbershop and grabbed the next train to Cincinnati.

Pinkerton (seated right) with some of his operatives in the field (James Horan)
Pinkerton (seated right) with some of his
operatives in the field (James Horan)

General McClellan, after a succession of rather small but victorious engagements in Virginia, was appointed Commander in Chief of the Union Army in 1861 with the retirement of the aged Winfield Scott. McClellan ceremoniously credited his battlefield wins half to Pinkerton agents who supplied necessary information beforehand on enemy movements and strength. Taking the military reins, he hoped that Pinkerton would continue to support him undercover, but Lincoln had other plans for The Eye: to root out traitors and spies from their nests in Washington City itself. Simply, too much important information had been leaking to the Southern Legislature, as well as to General Robert E. Lee's Army of Northern Virginia.

Pinkerton promised McClellan the use of his operatives, but he remained in the city, quartering in offices on I Street. Doing so, he organized the first government-approved spy ring in American history.

During the Civil War years, Pinkerton took on a new but very special recruit. Even though he was quite young, only 16-years old, he found in him a willingness to learn and a high intelligence to grasp the complex nature of the job. As well, he proved a trusting confidante. His name was William Pinkerton.

With his boyish face and still-gangly manner, he could wander through Washington and hang out for hours on a street corner surveying anyone or anything his father told him to survey without suspicion. And at the end of the day, he would report to his father his findings, written out in well-detailed terms, indicating a highly observant pair of eyes as good as many of the agency's best spies.

As William's experience grew, so did his responsibilities with his father's agency. "William Pinkerton not only ran agents across the border into Confederate territory, but he was also present at the first flight of an observation hot-air balloon," historical writer Ben Macintyre tells us. While accompanying the Army south on a scouting mission, William "was wounded in the knee by an exploding shell at the Battle of Antietam," Macintyre adds.

The author also touches upon the intimate side of the relationship between father and son. While Macintyre admits Allan was a "superb detective," he attests he could also be "a fantastic prig who hammered the virtues of honesty, integrity and raw courage into his children."

True, Pinkerton demanded the best people and their best work. His obsession with achieving it speaks well for the agents he trusted with difficult obligations, especially when faced with the heavy responsibility given him in the defense of America.

One agent who never failed him was Kate Warne. Gliding through capital city society with ease under assumed name and created background, that of a transplanted Southerner come northward she used her acquired knowledge of Southern tradition and etiquette to grace the calling rooms of many Southern-minded families in Washington and suburban Georgetown. It didn't take long before the lovely new belle with whimsical giggle, flashing eyes and a flip-flap of a wrist fan found herself doted on by some of the district's most eligible gentlemen with secessionist secrets. At balls, she sometimes spotted famous faces that, she learned surprisingly, were suspected members of Southern-sympathy groups. One was the handsome Shakespearean play actor John Wilkes Booth. The information she acquired, the whispers she heard, she fed everything to her boss on I Street.

Another agent who made a particularly important impact on the war years was a recent addition to the Pinkerton corps of spies, a young flower named Elizabeth Baker. Albeit from Richmond, Virginia, her principles were steadfastly Unionist. She believed in the Federal cause and pleaded with Pinkerton to assist it wherever she could. Recommended by Kate, Pinkerton assigned her to a special project.

Rumors insisted that the Tredegar Iron Works in Richmond was building a new kind of ship that could float underwater; they called it a submarine. Its purpose was to blow up the Union gunboats blocking the mouth of the James River, preventing commercial trade from leaving or entering the city, thus starving the town of supplies and food. Since this "submarine" could prove lethal to the Federal blockade, the North needed: 1) confirmation of such a vessel, and 2) a sketch of it. As the Confederacy was certainly to be keeping the existence of such a device under wrap that is, if it existed acquiring what Washington wanted would be a precarious task.

Elizabeth Baker firmly believed she was the only agent who could pull off that task. Pretending to be "coming home" to Richmond to see old friends, she resided at the home of an upscale couple, the Captain and Mrs. Atwater. Steeped in Southern elegance and charm, she finagled information from many a love-struck Confederate beau in Atwater's command, affirming what Pinkerton suspected: the submarine was no myth. While she secretly plotted her next move getting inside the walls of the factory to make a quick sketch of the miracle machine Captain Atwater surprised her one morning at breakfast by announcing he was taking his wife and boarder on an interesting visit.

"Today I am going to show you something, ladies, that might very well change the course of the war!" They piled into the family carriage and, much to Elizabeth's delight, they soon passed under the immense tunnel-like entrance of the vast Tredegar plant.

Following the captain and his wife into a warehouse on the grounds, her attention was drawn to the din of mallet upon iron and the screech of iron sheeting being laid in place. She watched in awe as dozens of men swarmed across the outer shell of what looked like a huge dark bumblebee set on a framework of heavy timber.

"Will something like that really float?" Elizabeth played the wide-eyed innocent.

Atwater grinned. "Not only float, ma'am, but creep below the sterns of Yankee ships so that our divers can attach special timed explosives to them. By lighting self-contained fuses, Elizabeth, that thing you see there can make a round of a dozen ships in no time while above them we blow the enemy to Hades, you pardon the expression, my dear."

She nodded, faked a blush, then, when they arrived home, she illustrated in pencil what she had seen that morning. One aspect of the submarine, she noted, made it highly vulnerable in order to breath, the submerged operating crew would have to depend on a series of air hoses, devices that protruded above water. Someone on the surface, knowing what to look for, could spot them quite easily.

Once back in Washington, she presented her findings to a gleeful Naval Secretary, Gideon Welles.

The South never did break the Union blockade.

As quickly as agents arrested informers, however, the leak of important information continued to flow southward. Somewhere, Pinkerton knew, was a dripping faucet untapped, well concealed and, he believed, coming from on high. No low rank in the armed forces would be privy to the kind of data that, counterspies warned, was being divulged. Not discouraged, he plunged his agents into the recesses of the city to unearth the leaking drainpipe.

They found it or, rather, her. Attractive Rose O'Neal Greenhow, widow of a popular editor whose paper upheld the doctrine of slavery, had, despite her political beliefs, become an intimate with many of Washington's corps d'elite. Through her sister's marriage to the nephew of Dolly Madison (widow of the late President James Madison), she met and partied with high-level political figures and Union officers, some of the latter who wooed her. According to the concise Civil War Dictionary by Mark M. Boatner III, Greenhow "knew everybody who counted." Invitees to her constant dinners, which she held at her fashionable home on 16th Street near the White House, were Lincoln's predecessor James Buchanan, Secretary of State William H. Seward, Senator Henry Wilson and many more.

Employing the cipher code of the Confederate Signal Corps, she passed vital Federal military plans, of which she had access to through her friendships, to Thomas Jordan, head of Southern underground in Richmond.

Greenhow & daughter (Library of Congress)
Greenhow & daughter (Library
of Congress)

"No spy ever worked with more enthusiasm than Mrs. Greenhow...having set up a tightly knit espionage unit that worked remarkably well," writes author Sigmund A. Lavine in Allan Pinkerton America's First Private Eye. "After (the battle of) Bull Run she had sent the Confederacy all the details of the North's battle plans by a young woman courier who carried the message in her hair (Southern General) Beauregard wrote a letter to Mrs. Greenhow, expressing his appreciation for 'the most accurate information.'"

Greenhow was arrested on August 23, 1861, by Pinkertons while strolling with her daughter near her home. She was placed under house arrest. In her home detectives uncovered much evidence, letters in code, diagrams, names and addresses of Southern legislatures, as well as a journal of her dealings with other Confederate agents.

Greenhow's arrest led to the apprehension of other Washington-area spies, mostly women, whose comings-and-goings were traced to her. As they were taken, the females were incarcerated along with Greenhow at the latter's residence, which was kept under heavy guard 'round the clock. Washingtonians, noting the surplus of sentries parading in and out of, and around, the house on 16th Street, jokingly referred to the spy's home-now-jail as "Fort Greenhow". Because of her sex and her child, Greenhow was not hanged. She and her sister agents were held in custody until a time deemed appropriate to escort them back to Richmond where they could no longer do damage to the Union.

This act of charity boomeranged, and spelled doom to Pinkerton Special Agent Timothy Webster.

Timothy Webster (Pinkerton's, Inc.)
Timothy Webster
(Pinkerton's, Inc.)

Since the outbreak of the war, Webster had racked up one notch after another on The Eye's spy-catching list. In Baltimore, he had served as double agent, supplying the Knights of the Golden Circle with useless information while relaying important research to the federal government through Pinkerton. Going south, he joined another couple of crack detectives, John Scully and Pryce Lewis, to infiltrate the inner workings of the rebel's secret service. Because of the high esteem he had gained with the Knights in Baltimore, Webster was welcomed to Richmond personally by Judah P. Benjamin, the Confederacy's Secretary of War, who hired him as advisor to the underground.

However, the U.S. War Department accidentally released Rose O'Neal Greenhow earlier than had been agreed upon and while Webster and company were still focally active in the Confederate seat. The usually cool Pinkerton panicked. He hastened a scout to Richmond, but by the time the scout arrived, the trio had already been arrested. The deported spies had spotted them in their hotel, and knew them by sight.

Despite protestations from the North's Secretary of War, Edwin McMasters Stanton, the Confederate legislature voted to hang the spies as enemies to the South.

This terrible mishap foreshadowed the end of Allan Pinkerton's contributions as the government's wartime spy catcher. Colonel Lafayette C. Baker, a spy apart from the Pinkertons, and a near paranoid who saw Confederate spies hidden in every bush, wormed his way into Pinkerton's position. He won the trust of the Secretary of War by convincing him that Pinkerton's methods were too vague and that Pinkerton himself too lenient. Stanton, who shared Baker's loathing for anything Southern, to the point of obsession, finagled to have Baker's snarling group of operatives appointed the official espionage unit in Washington.

At the same time, a dissatisfied Lincoln replaced George McClellan as Commander in Chief of the Union Army. McClellan, more of a strategist than a fighter, didn't push the South fast enough nor win enough battles to convince the President that he had the right man leading his forces.

His potential gone and his best ally fired, Pinkerton withdrew from the capital in 1862 and spent the remaining two-and-a-half war years serving the government in a number of other ways. Among these was tracking down crooked suppliers who were taking advantage of its client in turmoil by overcharging for equipment and deliveries.

To his death, Allan Pinkerton rued the fact that he wasn't in charge of Washington City's security measures on the evening of April 14, 1865, when actor John Wilkes Booth fired a bullet into Lincoln's head. He believed that had Pinkerton detectives been in charge Booth would have never gotten near the President.

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