Allan Pinkerton:
Skilled Detective,
Dubious Spymaster

General George McClellan, commanding the (Union) Army of the Potomac, the largest Federal force in the East, established the Union Army’s first intelligence organization. To lead it, he selected Allan Pinkerton, who had been actively involved in the underground railroad and whose National Detective Agency was then the largest in the country.

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From left: Kate Warne; President-elect Abraham Lincoln traveling to Washington, D.C., 1861; A crowd waiting on President-elect Abraham Lincoln; General George B. McClellan

General George McClellan, commanding the (Union) Army of the Potomac, the largest Federal force in the East, established the Union Army’s first intelligence organization. To lead it, he selected Allan Pinkerton, who had been actively involved in the underground railroad and whose National Detective Agency was then the largest in the country.

The two men were already acquainted, as Pinkerton once provided protection for the Illinois Central Railroad when McClellan was its vice president. Pinkerton had also earned McClellan’s respect several months prior to the attack on Fort Sumter, South Carolina, when he and a number of his detectives foiled a plot to assassinate President-elect Lincoln.

The Spy Who Saved a President

Infiltrating a group of Southern secessionists in Baltimore, Maryland, Pinkerton’s operatives learned the group was planning to kill Lincoln as he traveled from his Illinois home to Washington, D.C., for his inauguration, a journey that would take 13 days and cover nearly 2,000 miles across eight states. Pinkerton advised Lincoln to alter his arrival time in Baltimore, and the President-elect, whom he had codenamed “Nuts,” complied. Pinkerton, who had taken the codename “Plum,” posted agents along the route for security, and the telegraph lines had also been cut to stifle news of Lincoln’s departure. The plan was a success, which Pinkerton relayed in a telegraph to Philadelphia that simply read: “Plum arrived here with Nuts this morning—all right.”

This ruse was executed with the help of a female Pinkerton detective, Kate Warne, who first approached Pinkerton in 1856, assuring him she could gain access to secrets that male detectives could not. Indeed, the New York-born Warne, feigning a southern accent and pretending to be recently arrived from Alabama, was among the detectives who penetrated the group of secessionists and discovered the plot to assassinate Lincoln—a plot that may well have included the local police force’s complicity in failing to provide security for the delegation. Warne also accompanied a disguised Lincoln, whom she claimed to be her sick brother, to a private train car, in which he safely completed his journey to the capital.

Though Pinkerton often referred to himself as “Chief of the United States Secret Service”—an agency that did not yet exist—he managed to develop a network of more than two dozen undercover agents operating throughout Washington, D.C., the Confederate capital of Richmond, Virginia, and other Southern territories.

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From left: Final moments before Timothy Webster's execution, 1862; Pinkerton letter to President Lincoln, 1863; Union spy Timothy Webster

A Leading Operative Betrayed

One of Pinkerton’s most accomplished agents was Timothy Webster. Early in the war, the former New York policeman ventured through several Southern states, cultivating friendships with Confederate soldiers and collecting intelligence on Confederate military strength and morale. He also traveled frequently to Richmond, Virginia, establishing connections with high-level Confederate government and military leaders, including the Confederate Secretary of War, who unwittingly provided sensitive information to the Union agent.

On one occasion, Webster convinced a Confederate confidante to give him a tour of Richmond’s defenses. On another, he observed the ironclad CSS Virginia, a powerful Confederate Navy vessel that had been rebuilt from salvaged parts of a scuttled Union ship.

Webster’s impersonation of a Southern sympathizer was so convincing, the Confederate government used him as a courier between Richmond and Southern sympathizers in Baltimore, Maryland. When traveling through Washington, D.C., Webster carried the Confederate dispatches to the Provost Marshal—the Union Army commander responsible for maintaining order and other police functions—where they were carefully unsealed, reviewed, and sealed again. Webster then delivered them on to their intended recipients in Baltimore, who were none the wiser.

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From left: Final moments before Timothy Webster's execution, 1862; Pinkerton letter to President Lincoln, 1863; Union spy Timothy Webster

Webster’s exploits ended in April 1862 when fellow Pinkerton operatives Pryce Lewis and John Scully were captured by the Confederates and divulged his name in exchange for more lenient sentences. Webster’s espionage was deeply embarrassing to the Confederacy, and he was subsequently arrested, tried, and sentenced to death by a Confederate court that found him guilty of “lurking about the armies and fortifications of the Confederate States [while] at the time an alien enemy and in the service and employment of the United States.” Despite President Lincoln’s threat to execute a Confederate spy in retaliation, Webster was hanged—the first American spy since Nathan Hale to be executed for espionage. At his hanging, the rope came loose and Webster fell to the ground. “I suffer a double death,” he quipped to the hangman. “Oh, are you going to choke me this time?” The rope did not come loose a second time.

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From left: The Union ironclad USS Monitor, 1862; Navy Secretary Gideon Welles; Letter from Mary Louveste to Secretary of the Navy Gideon Welles, 1868; Blueprint of the USS Merrimac; CSS Virginia, 1862

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Battle of Hampton Roads, 1862

Mary Louveste A Pioneer in Naval Espionage

Another individual to collect intelligence on the Confederate ironclad CSS Virginia was Mary Louveste, a free Black woman who ran a tavern with her husband in Norfolk, Virginia, across the river from the Confederate Navy Yard in Portsmouth. During the winter of 1861 – 1862, Louveste gained access to documents detailing the Confederate Navy’s progress in transforming the hull of the captured and burned USS Merrimac into its first ironclad warship, the CSS Virginia.

With the valuable intelligence in hand, Louveste traveled north where she delivered it personally to Union Navy Secretary Gideon Welles. At the time, the Union Navy was developing its own ironclad, the USS Monitor, but Louveste’s intelligence made clear that work on the Virginia was nearing completion. This may have inspired Welles to expedite deployment of the Monitor and to inform its crew of the Virginia’s armament and defenses. Regardless, by March 1862, both ships had been launched and were soon dueling in the Battle of Hampton Roads. It was the first naval clash between ironclads, and though it was largely a draw, the Union notched a strategic win, preventing the Virginia from breaking the Union Navy blockade of the southern coast. Louveste was later recognized for her contributions, with Welles praising her “zeal and fidelity” and Congress awarding her a pension for her wartime service.

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Battle of Hampton Roads, 1862

Pinkerton’s Successes and Shortcomings

Union spymaster Allan Pinkerton’s team made headway with its counterintelligence efforts, arresting several significant Confederate agents early in the war. In August 1861, Pinkerton himself captured notorious Confederate spy Rose O’Neal Greenhow, the politically-connected socialite in Washington, D.C., credited by some Southerners as having contributed intelligence that enabled the Southern victory at the First Battle of Bull Run. Alfred Cridge, another Pinkerton agent, apprehended Confederate spy Belle Boyd, who provided intelligence on Union forces to General Thomas “Stonewall” Jackson during his Valley Campaign in 1862.

Remarkably, Pinkerton’s counterintelligence operations weren’t limited to the Confederacy. A mistrustful Union General George McClellan ordered Pinkerton at one point to spy on President Lincoln and the War Department. The insult would later be returned when Secretary of War Edwin Stanton ordered his own spy, Lafayette Baker, to spy on McClellan and Pinkerton.

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From left: Operatives of Allan Pinkerton, 1862; Union reconnaissance balloon, 1862; Map of Richmond, Virginia

Pinkerton, who occasionally used the pseudonym Major E.J. Allen, excelled at sending agents behind enemy lines and ferreting out Confederate spies, but with few exceptions, such as Timothy Webster, his agents largely failed to collect any meaningful intelligence about Confederate forces. The scant information reported to McClellan was often grossly inaccurate and routinely inflated numbers of enemy troops, sometimes by more than double the actual number. Pinkerton’s information came chiefly from questioning of prisoners, defectors, and refugees, but he lacked access to additional sources of information that could have shaped his reporting.

McClellan, however, received an intelligence windfall prior to the Battle of Antietam, September 17, 1862, but it didn’t come from Pinkerton. Union troops found a copy General Lee’s orders, Special Order 191, at a former Confederate camp in Monocacy, Maryland. Wrapped around several cigars, the “Lost Order” revealed Lee’s army was dispersed in western Maryland and Virginia, allowing McClellan to boast, “Here is the paper with which, if I cannot whip Bobby Lee, I will be willing to go home.”

McClellan failed to act aggressively on the intelligence, and the two armies fought the Battle of Antietam, the bloodiest one-day battle of the war, to a draw. Less than two months later, President Lincoln sent McClellan home, believing that he was too cautious in engaging the enemy. Loyal to his former commander, Pinkerton resigned from the Army, finished out the war investigating government contracting fraud cases, and eventually returned to his detective agency. Following the war, he wrote a book on his Civil War exploits and more than a dozen detective books. He died in 1884.

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From left: Allan Pinkerton, with visitors from Washington, D.C; Allan Pinkerton, chief of intelligence for the Army of Potomac; Allan Pinkerton with President Lincoln, 1862