Union Spies: Allan Pinkerton

This entry is part 11 of 12 in the series Spies of North and South

Allan PinkertonNo series on Civil War spies would be complete without a profile of that most famous of American detectives, Allan Pinkerton. He was the nation’s original detective who created and used many of the methods that modern-day detectives still use. These methods include “shadowing”, disguise and surveillance.

Pinkerton was born in Glasgow, Scotland in 1819 and became a cooper by trade. In 1842, he immigrated with his family to Dundee, Illinois where he set up his barrel-making operation. He was regarded as a business owner of impeccable credentials. Pinkerton was also a staunch abolitionist whose home became a station on the Underground Railroad.

Seeing the need for additional policemen in the rough-and-ready city of Chicago, Pinkerton joined the force of 12 policeman. He had been a police officer and detective in his native country so police work was second nature for him. He soon became the top detective in the city.

With a growing family Pinkerton formed his own detective agency in 1850. He named it the Pinkerton National Detective Agency and he designed a logo featuring an eye, wide open, with the caption, We Never Sleep. The company still exists and the open eye is still used as a logo.

Many of  these potential clients were the numerous railroads that crisscrossed Chicago. One of the railroads was the Rock Island and Illinois Central, whose president was George B. McClellan and the attorney a Springfield man named Abraham Lincoln.

Early in 1861 the Pinkerton agency was hired by the Philadelphia, Wilmington and Baltimore Railroad to protect the line from train robbers. In the course of the investigation, they discovered a plot to assassinate the new President, Abraham Lincoln, as he traveled through Baltimore to his inauguration. Pinkerton accompanied Lincoln and his personal bodyguard, Ward Hill Lamon, safely to Washington.

Lincoln wished to employ Pinkerton as the head of a secret service to root out spies in the Union capital but others in his administration had other candidates. While he was waiting for some resolution, Pinkerton came to the notice of General George McClellan who employed his and his agency’s services in and around Washington infiltrating the circles of southern sympathizers. Pinkerton’s team included Timothy Webster and Kate Warne.

Timothy Webster was tall, self-assured, aggressive, loyal and possessed intelligence, guts and skill. Webster would go to any length to accomplish a mission and return with information that no one else could have obtained. He became a key informant during the civil conflict.

Kate Warne, a young widow, with dark hair and a slight frame, convinced Pinkerton to hire her as an undercover detective in 1856. She had no experience in the field, but possessed a talent of ingratiating herself into a suspect’s trust. She was also, a master of disguise. Pictures may depict Kate Warne as a young Union cavalry trooper. Warne’s successful career convinced Pinkerton to hire other women agents and to promote Kate to Supervisor of Women Detectives.

Pinkerton himself assumed the role of Major E.J. Allen and for a time was attached to General McClellan’s staff. The team’s focus was to use assumedPinkerton with Lincoln and General John McClernand names, disguises and false southern sympathies to elicit vital military and clandestine motives from Confederate loyalists operating within the Union lines. In addition, the Pinkerton Detectives were to gather intelligence in the southern states of Tennessee, Georgia and Mississippi.

Timothy Webster gained so much trust in southern sympathizer’s circles that he was able to travel to Richmond to verify his intelligence. It was here that he met the Confederate Secretary of War Judah P. Benjamin, who offered him a job as an informer. It was while he was in Richmond that his identity was unmasked by recently-released Confederate spy Rose O’Neal Greenhow. He and three associates were arrested, tried and hung as spies on April 29, 1862.

After the Battle of Antietam, General George McClellan was removed from the command of the Army of the Potomac. At the same time Pinkerton was also removed as the nation’s primary spy. Some members of the cabinet claimed that Pinkerton’s results, particularly on Confederate troop dispositions, were less than complete. The agency spent the rest of the war investigating war profiteers.

After the Civil War, the Pinkerton National Detective Agency continued to be the largest and most effective company of its kind in the United States. Pinkerton detectives were employed by a number of railroads to capture train robbers. Pinkerton chased Jesse James for years but was never able to capture him. The agency was also employed by corporations to protect them from labor unions.

Allan Pinkerton died in Chicago on July 1, 1884. At the time of his death, he was working on a system that would centralize all criminal identification records, a database now maintained by the Federal Bureau of Investigation.


Union Spies: Lafayette C. Baker

This entry is part 8 of 12 in the series Spies of North and South

Lafayette Curry BakerMuch of the Union intelligence gathering was decentralized with the principal commanders employing their own network of agents. It has been said that Ulysses S. Grant had at least 100 spies throughout the Western Theater. Other commanders had their own networks. The President even had a spy, William Alvin Lloyd, to report directly to him.

One of the Union’s most daring spies was Lafayette Curry Baker who was rough-and-ready character who was not afraid of some violent work. Born in upstate New York in 1826, he moved to Michigan in his teens. In 1849, Baker joined the thousands who trekked to California after the discovery of gold.

Baker didn’t find gold but he found adventure. In San Francisco, he became a member of the Vigilance Committee, patrolling the fog-bound streets of the Barbary Coast at night in search of desperate criminals, or so Baker later advertised that adventurous episode of his life. In reality, he was a bouncer at a saloon and a police informer.

At the start of the war, Baker returned to the East where he endeavored to get an appointment as an officer. Unsuccessful in New York, he journeyed to Washington and sought an appointment with the General-in-Chief Winfield Scott in 1862. Pestering Scott’s aides, he finally got an appointment and dazzled the general with his plans for spying on the Confederates in Richmond.

Scott explained to Baker that his going to Richmond would not serve the Union Army’s needs. He needed detailed reports from the fields, how many men were in the Confederate Army of General P.G.T. Beauregard, where were they positioned, and where were they headed? How many pieces of field artillery did Beauregard have and how much rolling stock? All of this important data could not be found in the tearooms of Richmond, but in the field.

Baker assumed the identity of Sam Munson, a photographer, to infiltrate the Confederate lines. He was detained by Union troops who thought that he was a Confederate spy. Scott had him released and he crossed into Virginia where he was arrested by the Confederates as a spy.

He managed to get a note to General Beauregard and when he met in person he convinced him that he was a photographer. To make his story more believable, Baker gave Beauregard detailed information of Union troop movements, positions of heavy gun emplacements, and locations where ammunition and goods were stored.

After further interviews with Jefferson Davis and Vice-President Alexander Stephens, Baker was released on Davis’ orders and given a pass that allowed to photograph any of the southern military commanders, their troops, and camp sites, as he saw fit. However, he had no glass plates for photographs and that fact almost sent him to the hangman.

He was in Fredericksburg when he met several Confederate officers who he had photographed earlier. They were angry because they had not gotten their pictures. Growing suspicious, they had him arrested as a spy and when a real photographer revealed his camera to be useless, Baker realized that he could be executed. Using a penknife, he managed to loosen the bars and escape the prison and return to Union lines.

General Scott was so impressed that he made Baker a captain on the spot and put him in charge of his Intelligence Service. However, the truth was more mundane. He was, indeed, captured, and taken before Jefferson Davis who did not give him a pass to photograph the whole of the Confederacy but listened for some minutes to Baker’s inept lies and then pronounced him a spy and ordered him held for trial.

Baker did escape from the Richmond jail, then wandered for weeks through Virginia, living in shacks and the woods, stealing food where he could find it, as he desperately tried to regain the Union lines. He was picked up in Fredericksburg as a vagrant and later held as a spy, but he again escaped, this time with the help of local prostitute whom he had been staying with, and finally managed to return to Scott’s headquarters.

The information regarding Confederate forces he later relayed to Scott he had learned from a Union officer he had met in the Richmond prison and all of this information was outdated by the time Baker passed it on to Scott.

It was through his service for General Scott that Baker met Secretary of War Edwin McMasters Stanton, who took Baker under his own wing. He became the Secretary’s personal secret agent, conducting close surveillance of those Stanton distrusted most, other members in Lincoln’s cabinet, and high-ranking officers who were Lincoln’s appointments.

Stanton also wanted Allan Pinkerton out of the way as head of the Union Intelligence Service. Pinkerton answered only to Lincoln, and Stanton resented that. He, Edwin Stanton, should be in complete charge of the war, not this well meaning but uninformed Lincoln.

Stanton, through Baker’s intrigues, discredited Pinkerton, and, equally, General George McClellan, who had taken over the army, brilliantly organized and trained it to a peak fighting machine but proved indecisive in battle. Baker spent much of this time discovering McClellan’s mistakes and having reports of his blunders brought before Lincoln, or leaked to the Union press.

Pinkerton was relieved of duty after the Battle of Antietam for a supposed inability to learn of the true strengths and positions of Confederate forces under General Robert E. Lee. Stanton proposed that Baker be promoted to command the Intelligence Service with rank of full colonel.

Apparently, Baker’s techniques were identical to those he had practiced in San Francisco as a vigilante. He terrorized, threatened, and blackmailed suspects, both Union and Confederate, to obtain information. For three years, he continued to operate a haphazard espionage system for the North but most of his information was learned second-hand from scouts working directly for Union cavalry commands. He continued to have some spies behind the Confederate lines but Pinkerton had picked the best of these first.

Baker bragged that there is no single Confederate spy or agent behind Union lines who is unknown to him. Yet, flourishing within Washington were dozens of conspirators all plotting the assassination of the President. One group met regularly only a few blocks from Baker’s offices throughout the early part of 1865. Its leaders were, John Surratt, Jr. and a vainglorious actor from an illustrious theatrical family, John Wilkes Booth.

Within two days of his arrival in Washington from New York, Baker’s agents in Maryland had made four arrests and had the names of two more conspirators, including the actual presidential assassin John Wilkes Booth. Before the month was out, Booth along with David Herold were found holed up in a barn and Booth was himself shot and killed. Baker was promoted to the rank of brigadier general and received a generous share of the $100,000 reward.

However, Baker was sacked from his position as government spymaster by President Johnson who accused him of spying on him, a charge Baker admitted in his book which he published in response. He also announced that he had had Booth’s diary in his possession which was being suppressed by the Department of War and Secretary Stanton. When the diary was eventually produced, Baker claimed that eighteen vital pages were missing. It was suggested that these would implicate Stanton in the assassination.

Lafayette C. Baker died in 1868, supposedly from meningitis. However, his death was as mysterious as some parts of his life. Using an atomic absorption spectrophotometer to analyze several hairs from Baker’s head, Ray A. Neff, a professor at Indiana State University, determined the man was killed by arsenic poisoning rather than meningitis. He had been unwittingly been consuming it for months, mixed into imported beer provided by his wife’s brother.


Confederate Spies: Rose O’Neal Greenhow

This entry is part 5 of 12 in the series Spies of North and South

Rose O'Neal Greenhow with her daughter RoseOne of the most renowned Confederate spies of the early Civil War years was Rose O’Neal Greenhow of Washington, D.C. Mrs. Greenhow who was 48 or 49 when the war began (her birth year is given as 1813 or 1814), was a Washington socialite who moved in the very highest circles of society.

Rose Greenhow’s early life was not the easiest. She was born at Port Tobacco, Maryland as as Maria Rosetta O’Neal. Both of her parents died by the time that she was a teenager. She was invited to live with her aunt, Maria Ann Hill, who ran a stylish boarding house at the Old Capitol building in Washington.

Through the assistance of her aunt, Rose met a number of personages and frequented capital society. In 1935 she married Dr. Robert Greenhow. He taught her history and gave her access to government documents through his work in the U.S. Department of State.

The Greenhow’s had eight children but only four of them lived beyond infancy. Soon after her namesake last child was born, her husband died. Meanwhile one daughter moved West and another died.

Rose Greenhow’s sympathies were always with the Confederacy due to her friendship with John C. Calhoun. Soon after the war began, she was recruited by then-Union officer Thomas Jordan. He supplied her with a 26-symbol cipher for creating encoded messages. Jordan resigned his U.S. Army commission in May 1861 and received a captain’s commission in the Confederate States Army. He would end the war as a brigadier general after which he joined the Cuban Liberation Army.

On July 9, 1861, and July 16, 1861, Greenhow passed secret messages to Confederate General P.G.T. Beauregard containing critical information regarding military movements for what would be the First Battle of Bull Run, including the plans of Union General Irvin McDowell. Assisting in her conspiracy were pro-Confederate members of Congress, Union officers, and her dentist, Aaron Van Camp. Confederate President Jefferson Davis credited Greenhow’s information with securing victory at Manassas.

Greenhow’s spying career was shortlived. On August 23, 1861 Allan Pinkerton, head of the recently-formed Secret Service, apprehended Greenhow and placed her under house arrest. Leaked information was traced back to Greenhow’s home, and upon searching for further evidence, Pinkerton and his men found maps of Washington fortifications and notes on military movements.

On January 18, 1862, Greenhow was transferred to Old Capitol Prison. Her daughter, “Little Rose”, then eight years old, was permitted to remain with her. Greenhow continued to pass along messages while imprisoned. She was said to have sent one message concealed within a woman visitor’s bun of hair. Passers-by could see Rose’s window from the street. The position of the blinds and number of candles burning in the window had special meaning to the “little birdies” passing by. Greenhow also on one occasion flew the Confederate Flag from her prison window.

Rather than continue her incarceration, the Union government deported her to Richmond, Virginia where she was hailed as a heroine by Southerners. Jefferson Davis welcomed her home and enlisted her as a courier to Europe. From 1863 to 1864, Greenhow traveled through France and Britain on a diplomatic mission for the Confederacy. While in Britain, Greenhow wrote her memoirs, titled My Imprisonment and the First Year of Abolition Rule at Washington, which sold well there.

In September 1864, Greenhow left Europe to return to the Confederate States, carrying dispatches. She traveled on the Condor, a British blockade runner. On October 1, 1864, the Condor ran aground at the mouth of the Cape Fear River near Wilmington, North Carolina, while begin pursued by a Union gunboatUSS Niphon.

Fearing capture and further imprisonment, Greenhow fled the grounded ship by rowboat. A wave capsized the rowboat, and Greenhow, weighed down with $2,000 worth of gold in a bag around her neck from her memoir, royalties intended for the Confederate treasury, drowned.