Civil War Spies and the Rise of the Pinkerton Agency

The Civil War was the most different war America ever fought, since there was no clear-cut way to tell friend from foe. No bright red uniforms, no British or French accents. Everyone was an American. They looked the same and sounded the same. The ability of a man from the north to infiltrate into southern society was relatively easy to accomplish. But easy or not, a spy needed a network to operate within, and have the ability to pass information along via a channel to the north.

Since there was no central military intelligence organization at the time, the Union generals formed their own operations. General George B. McClellan hired an already prominent detective, Allan Pinkerton, to create an espionage agency. At the time, Pinkerton was head of a well-known detective agency in Chicago, and had supplied McClellan with information during the early months of the war, so McClellan had reason to rely on Pinkerton to set up an agency in early 1861.


Allan Pinkerton



Pinkerton assembled a group of spies to infiltrate the southern forces in Richmond. One of these gentlemen was Timothy Webster.



Timothy Webster

Webster came to America from England in 1830 with his parents, and settled in Princeton, NJ. He was eight years old at the time. He joined the police force in New York City as an adult, where he had occasion to meet Allan Pinkerton. He then joined the Pinkerton establishment in 1856. In 1861, Pinkerton sent Webster south with another spy, a female named Hattie Lawton. They posed as a married couple and infiltrated a pro-Southern group where they were privy to details on the south’s activities and plans. Through this pair, a plot to assassinate President Lincoln at his inauguration was uncovered and thwarted.  Webster also managed to gain the attention of the Confederate Secretary of War, Judah P. Benjamin, who recruited him to act as a courier of Confederate missives between Baltimore and Richmond, so he became, in effect, the first double agent in America. He copied the letters and passed them to his Union affiliates at Pinkerton.

Webster continued to work for Pinkerton through 1862, remaining in Richmond, where he fell ill. Pinkerton sent two other men to find Webster, who had ceased sending reports north. The two men were recognized as Union spies, and captured. One of them gave up the goods on Webster, who by this time had worked his way deeply into the Confederacy. The Southern officers were very embarrassed when hWebster’s true leanings were uncovered and the court-martial was swift. The two men who exposed him were released, but Webster was arrested, tried, and court martialed. Hattie Lawson was also imprisoned but later released.

The Court having maturely considered the evidence adduced, and two-thirds concurring therein, they find the prisoner guilty of the charge.”

Whereupon, two-thirds the Court concurring, it was adjustment that the accused ‘Suffer death by hanging.’ ”

When Pinkerton heard of the capture and the death sentence, he asked President Lincoln to send a message to the Confederacy that if Webster was sent to his death, the north would reciprocate by hanging one of the Confederate spies they had in their jails. Undeterred, the Confederacy hanged Webster, but he did not go down without a fight. The first rope was faulty and only partially hung him. The stunned man was quickly walked up the gallows a second time. It took two tries of hanging by a rope before his life was finally extinguished.

Pinkerton would later say, “No braver nor truer man died during the War of the Rebellion than Timothy Webster.”

Lincoln removed General McClellan from his command in November, 1862, and Pinkerton resigned in solidarity, where he returned to his detective agency in Chicago.We_never_sleep

In the 1870s, Franklin Gowan, president of the Philadelphia and Reading Railroad, hired the agency to investigate the labor unions cropping up among the railroad employees. And famously, in 1874, agents were hired to track outlaws Jesse James, The Reno Gang and The Wild Bunch, Butch Cassidy and the Sundance Kid’s gang, which launched the agency into fame. Pinkerton agents were hired as muscle when transporting money and high quality merchandise throughout the west, which made them prime targets for outlaws. They were well paid and well-armed men.


The Pinkerton Agency in action against the labor unions.

As America evolved, so did the Pinkerton Agency. In the 1960s, the word “detective” disappeared from the company logo, as they performed more protective services. Today, the focus is on threat intelligence, risk management, and executive protection. In 1999, the firm was purchased by a Swedish security company, for $384 million.


Gambling On Forever is Becky Lower’s tribute to these Civil War Spies. Her hero, James Garnett, infiltrated the South as a favor to his commanding officer from West Point and once the war ended, he used his ability to read people’s body language to become a riverboat gambler. Visit Becky’s website, to catch up on her latest works.