By Walter Giersbach

Few people admire a spy who lives by duplicity, subterfuge and lies, even if he or she is your ally. However, Timothy Webster was a man of honor serving an honorable cause. And he was the first Union spy hanged by the Confederates for it.

Webster was born into a large family in Newhaven, Sussex County, England in 1822. Foreshadowing the mass emigrations to come, the Websters moved to Princeton, N.J. in 1830. About ten years later, he moved again, to New York City, and in 1841, at the age of 19, he married 23-year-old Charlotte Sprowls. A year later their first child, a son, was born. They would have four children in all. [1]

While Webster had been trained as a machinist, the need to support a family led him to become a policeman. The Municipal Police Act, signed into law in 1845, set up a larger police organization that was the foundation for the modern New York Police Department.

In 1853, Webster was assigned to work at the Crystal Palace exhibition, which became known as America’s first world’s fair. While on duty there, he was introduced to Allan J. Pinkerton, head of the North-Western Police Agency. If a job was offered, however, Webster turned it down.

Among Nativist Americas, fear of foreigners prompted an investigation by the city aldermen. The feeling among some was that there were too many foreign-born officers in the city’s police department. (A decade hence there would be race rioting in the city streets.) English-born Webster was called to testify, but refused to cooperate every time he took the stand. The aldermen’s investigation led nowhere, but Webster may have been discouraged enough to leave the force. He had been offered a job with Allan Pinkerton’s recently founded agency based in Chicago. In fact, he had been recommended by a captain of the police. It may also have cemented the relationship that Pinkerton had been born in Glasgow, Scotland, in 1819 and was just three years older than Webster.

Pinkerton apparently liked the young man and he was hired as a detective. [2]

Webster moved his wife Charlotte and their four children to Onarga, Illinois, 90 miles south of Chicago. The North-Western Police Agency would soon change its name to the Pinkerton’s National Detective Agency with offices all over the country, but when Webster joined it was still a growing regional agency.

As a marginal note, Pinkerton’s sense of ethics foreshadowed noir crime fiction involving noble operatives that would be fictionalized by Raymond Chandler 80 years hence. Pinkerton’s “Agent’s Code of Ethics” stated agents would accept no bribes, never compromise with criminals, partner with local law enforcement agencies, refuse divorce cases or cases that initiate

scandals, turn down reward money (agents were well paid), never raise fees without the client’s pre-knowledge, and keep clients apprised on an on-going basis. [3]

Webster would have taken on a variety of investigations of the sort today’s FBI agents might encounter. We’ll never know details because many of the records of Pinkerton’s National Detective Agency were destroyed in the Great Chicago Fire of 1871.

One of Webster’s more noteworthy cases involved working with another operative to track down renowned forger Jules Imbert, alias Alexander Gay. Imbert would approach bankers asking to sell them bills of exchange and then later redeem or buy such bills. Imbert ran when a banker alerted Pinkerton, Webster and another operative, taking off for Michigan and then Montreal. Imbert voluntarily returned, hoping to plea bargain, and received seven years for forgery. [4]

Webster also investigated graves in a Chicago cemetery that were being robbed for medical research, and spent two years in Davenport, Iowa, working to find the culprits behind an attempt to burn down the Rock Island Bridge. These cases would have taken Webster away from his family for long periods of time. Events were taking place, however, that changed the direction of his future. [5]

Abraham Lincoln’s election as President in 1860 divided the nation largely along North-South lines. Pinkerton was asked to investigate secessionist threats to destroy railroad bridges between Washington and New York City. Pinkerton took a small group of operatives with him, including Webster, to Maryland. Webster was joined by a female agent named Hattie Lewis (or “Hattie Lawton”) posing as his wife. The couple established themselves in Perrymansville, Maryland, in February 1861. With his cover in place, Webster worked to infiltrate a secessionist militia known as the Sons of Liberty. He soon learned of a plan to assassinate President-elect Lincoln. Abraham Lincoln, elected President but not yet inaugurated, was in Harrisburg, Pennsylvania, and was expected to soon return to Washington by way of Baltimore.

Just in time, Webster learned the plot would unfold while the President-elect was changing trains in Baltimore. He quickly alerted Pinkerton, who managed to sneak Lincoln through Baltimore on a different train and brought him safely to Washington. It may be said that Timothy Webster helped save Abraham Lincoln's life — the first time.

By the following month, war had been declared. Seven states had seceded and Union General George B. McClellan hired Pinkerton’s agency to gather intelligence for him. Webster’s career as a Union spy was gaining in importance. [6]

In his guise as a Maryland citizen, Webster was sent south with his “wife” Hattie to gather information in Mississippi, Tennessee, Arkansas, and Kentucky. A valuable asset became the friendships he developed with prominent leaders there. He was so successful in these relationships while in Memphis that he was offered a commission as colonel of the Second Arkansas Regiment. He declined, saying he had to go to Richmond. He departed with letters of recommendation, but first headed “home” Baltimore. In that northern city full of southern sympathizers, Webster collected more letters of introduction from his Sons of Liberty friends, the secessionist group he’d infiltrated earlier that year.

With these bona fides attesting to his loyalty to the cause, Webster could ingratiate himself into Richmond society. No less a person than Confederate Secretary of War Judah P. Benjamin recruited Webster to be a courier for the Confederate's “secret line” between Washington, Baltimore and Richmond. Webster had effectively become a double agent, carrying messages from Confederate spies in the north while informing Pinkerton.

He was stopped suddenly in February 1862 by a bout of inflammatory rheumatism. His bosses at Pinkerton’s dispatched two operatives, John Scully and Pryce Lewis, to see what had happened to Webster.

This turned out to be a near-fatal mistake. In July 1861, the socialite and infamous Confederate spy, Rose O'Neal Greenhow, had passed secret messages to Confederate General P.G.T. Beauregard. Certain notes contained critical information regarding Union movements leading to the First Battle of Bull Run. Pinkerton had the woman under surveillance, saw that she was put under house arrest and then convicted and incarcerated in Old Capitol Prison. Greenhow had been interrogated by Scully and Lewis before being imprisoned. She and two other ladies were released shortly afterwards and deported to Virginia. Happenstance and the worst of coincidences brought them to the same hotel where Scully and Lewis were staying, and Greenhow recognized the agents. [7]

Scully and Lewis were arrested and sentenced to death as spies. Scully may have turned over Webster in order to save his own life. A Catholic priest, Father Augustine McMullen urged Scully, now facing a death sentence, to confess to General John H. Winder to being a spy. He could still save himself, so Scully told Winder all.

Both Webster and Hattie were arrested. Lewis, concluding that their fate had already been sealed, opted to save himself and confessed as well, implicating Webster and Hattie (although he later claimed that he only confessed to being a spy). By turning on their fellow agents, Scully and Lewis avoided execution.

Years later, Pinkerton’s claimed Scully had been tricked. Their captors knew the agents had been visiting Webster, but he was so well respected that he remained above suspicion. Scully, they said, asked to see a priest to confess before his execution, but the Confederates sent in a pretender and thus learned the truth about Webster. Scully and Lewis were released. [8]

Hattie Lewis was sentenced to a year in Richmond's Castle Thunder Prison, but Webster was sentenced to death. No spy on either side had thus far been sentenced to death. The Union maintained a policy of imprisoning spies for a short time before releasing them. It may well have been that Webster became the first spy sentenced to death because he was so efficient at his duties and the humiliation the Confederates suffered by the damaging information he had obtained. He had infiltrated the highest ranks of the Confederate hierarchy and carried official and private documents for everyone up to and including the Secretary of War.

General Winder, who arrested Webster, had himself been personally duped by him. The embarrassed general wanted his revenge, and Confederate President Jefferson Davis saw to it that he got his wish.

The evidence of Webster’s spying was damning. The verdict: “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.”

Learning of the sentence, Pinkerton protested strongly. President Lincoln himself threatened that if Webster were hung the Union would in turn hang a Confederate spy. Until then, both sides had been civil in imprisoning culprits until they could be swapped for prisoners held by the enemy.

The Southerners were unmoved and on April 29, 1862, Webster was led to the gallows at Camp Lee in Richmond. Reportedly, “He asked the clergyman to read the Psalm of David, invoking vengeance on his enemies. He refused, and Webster grew indignant, causing the clergyman to take an early departure. When brought to the gallows, the prisoner was visibly affected by the sight of the preparations observable, and shuddered when he looked at his coffin. After the rope was adjusted around his neck, prayer was offered up by Rev. M.D. Hoge.”

The trapdoor was released, but there was a problem: “the [knot] slipped, and Webster fell on his back to the ground. The half-hung and partially stunned man was speedily raised and assisted up, and a new rope being ready, he was soon swinging, in accordance with his sentence.”

It was later reported that before the trapdoor released the second time, Webster cried, “I suffer a double death!”

Allan Pinkerton later eulogized Webster, saying, “No braver nor truer man died during the War of the Rebellion than Timothy Webster.” [9]

Timothy Webster, spy and secret agent extraordinary

Allan Pinkerton

Rose O’Neal Greenhow and her daughter, taken by Matthew Brady or his operatives at the Old Capitol Prison in 1862, National Portrait Gallery, Smithsonian Institution.

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Show Notes

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© 2024 Walt Giersbach

Written by Walter Giersbach.

About the Author:
Walter Giersbach’s fiction has appeared in a score of online and print publications. He also writes extensively on American history, with 10 pieces published in Military History Online. Two volumes of short stories, Cruising the Green of Second Avenue, published by Wild Child (www.wildchildpublishing.com) were available from online retailers until his publisher ceased operations. He served for three decades as director of communications for Fortune 500 companies, helped publicize the Connecticut Film Festival, managed publicity and programs for Western Connecticut State University’s Haas Library, and moderates a writing group in New Jersey.

* Views expressed by contributors are their own and do not necessarily represent those of MilitaryHistoryOnline.com.