Timothy Webster:

The Pinkerton Detective and the Civil War Spy

Essay by Corey Recko

In his career, Timothy Webster served as a New York City policeman in the earliest days of the department, worked as a private detective in the most famous private detective agency ever, acted as a Union spy during the American Civil War, and generally lived a life of adventure and daring. There is no telling what Webster would have accomplished had his life not been cut short.

Timothy Webster Jr. was born on March 22, 1822, in Newhaven, Sussex County, England, the fourth of eleven children born to Timothy and Frances Webster.  Two of the children died in infancy and one at the age of two.  The Websters immigrated to the United States in 1830 and settled in Princeton, New Jersey. Timothy was eight.

For a time Webster’s life was typical enough.  At nineteen he married twenty-three year old Charlotte Sprowls.  A year later their first child, a son, was born.  They would have four children in all. 

Sometime in the 1840s they moved to New York City and Timothy, now with a family to support, embarked on a career in law enforcement, joining the city’s then-fledgling police force.

Before 1845, the force was simply too small for the large metropolis.  The Municipal Police Act, signed into law in 1845, set up a larger department, based on London’s department.  It laid 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.  It was while he was policing the exhibition that Webster was introduced to Allan J. Pinkerton, who many have theorized offered him a job with his newly formed private detective agency.  If a job was offered, however, Webster turned it down.

At the time, xenophobia ran high in America. The fear of the foreigners prompted an investigation by the New York City aldermen, who were leery of the number of foreign-born officers in the city’s police department. The British-born Webster was called repeatedly to testify, but refused to cooperate every time he took the stand.  The investigation led nowhere. Soon after that, however, Webster decided to leave the NYPD. He took a job with Allan Pinkerton’s recently founded North-Western Police Agency, based in Chicago. Webster moved his family to Onarga, Illinois, ninety 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.

Like most operatives of the time, he would have taken on a variety of cases, ranging from the exciting to the mundane. Unfortunately, many of the records of Pinkerton’s National Detective Agency were destroyed in the Great Chicago Fire of 1871, but what has survived shows that Webster had already begun an impressive career as a private detective, demonstrating intelligence, cunning, and leadership skills over the next few years.

One of his more noteworthy cases invloved him tracking down renowned forger Jules Imbert, even jumping from a moving train to keep up with the man. He also investigated grave robberies in a Chicago cemetery, and spent two years in Davenport, Iowa, working to find the culprits behind an attempt to burn down the Rock Island Bridge.  Had he continued on this path he likely would have headed one of the many branches that Pinkerton’s agency would open in the coming years, but unfolding events changed his future.

Shortly after Abraham Lincoln’s divisive election as President of the United States in 1860, 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.

16 With female operative Hattie Lewis (aka "Hattie Lawton") posing as his wife, Webster established himself in Perrymansville, Maryland in early 1861, where he went undercover to infiltrate a secessionist militia. He soon learned of a planned attempt to assassinate President-elect Lincoln.

Meanwhile, Pinkerton and several of his other operatives had learned of similar threats from secessionists in Baltimore.  This led to a change in Lincoln’s public itinerary since it was no longer safe to openly travel through Maryland and stop in Baltimore on his way to Washington. Instead, Lincoln was sneaked through Maryland on a night train.

After the country fell into civil war, Pinkerton was placed in charge of espionage under General George B. McClellan. One of Pinkerton's first duties as head of this new "Secret Service" was to send Webster south to gather information regarding troop numbers and movement, supplies, possible strategies and the general morale of the south.  Several of these trips behind enemy lines took him to Memphis, and other Tennessee cities, as well.  Each time, he would return with detailed reports.

Webster's next residence was in Baltimore, a state that had remained in the Union, despite a large number of southern sympathizers.  It was in Baltimore that Webster reconnected with the secessionists he had met while investigating the threats against Lincoln. Soon he volunteered to act as a courier for the secessionists, bringing messages south and replies back north. 

16 Despite the danger of crossing back and forth over enemy lines so frequently, it was the perfect cover for a spy. It allowed him to travel freely in the south, including to Richmond, the Confederate capital, where he and Hattie, once more posing as his wife, established themselves in the early part of 1862.

There they were able to gain access to Confederate camps and the trust of Confederate officiers, including colonels and generals. He carried official documents for General John B. Magruder, messages of a personal nature for General John H. Winder, and received passes to cross enemy lines from Confederate Secretary of War Judah Benjamin himself. As far as these men were concerned, Webster was a trusted messenger and increasingly, a friend.

It was in the midst of one of these missions that Webster’s health became an issue.  The thirty-nine year old spy was suffering from rheumatism, the result of sleeping on the cold, wet ground on a previous journey South. Because Webster and Hattie, who was with him, had not been heard from, a concerned Allan Pinkerton sent two operatives, John Scully and Pryce Lewis, to find them. 

The operatives found them holed up in the Monumental Hotel in Richmond.  Unfortunately, Scully and Pryce were recognized by Chase Morton, a man who just happened to be visiting Webster. Morton had once lived in Washington, where his family’s home had been searched by the two detectives. Lewis and Scully were arrested, tried, and sentenced to death.

In a meeting with a Catholic priest, Father Augustine McMullen urged Scully, now facing a death sentence, to confess to General John H. Winder to being a spy, and save himself.  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, this seems doubtful). Thus, Scully and Lewis avoided execution. 

Hattie Lewis was sentenced to a year in in Richmond's Castle Thunder Prison, but Webster was sentenced to death, despite the fact that no spy on either side had thus far been sentenced to death, with the North at least adapting the policy of simply keeping spies in prison for a short time before releasing them (a mistake since many just picked right back up spying). Many have theorized that the reason Webster became the first spy to receive the ultimate penalty was the direct result of his efficiency and the humiliating amount of damaging information he had been able to obtain.  He had infiltrated and so completely duped the Confederacy hierarchy that he had been asked to carry both 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.

On April 29, 1862, still suffering from rheumatism, Timothy Webster was lead to the gallows in Richmond, Virginia. The first attempt to execute him failed, however, and as he once more had the noose placed around his neck, he was heard to proclaim "I suffer a double death!" The second attempt was more successful.

It was a tragic end for an American hero.

* * * * *


When Allan Pinkerton set about writing his memoirs in the years after the Civil War, he cared more about telling a good story than historical accuracy, and over the years many of these falsehoods have been repeated. While a few have set the record straight in regards to Pinkerton (David D. Horan did the best job), part of my goal with the Webster book was to eliminate some of the fiction from Webster's story, so here goes:

Hattie Lewis is often refered to as "Hattie Lawton," which is the name Pinkerton gave her in his book Spy of the Rebellion, (1883). However, historians have never been able to find a "Hattie Lawton" who matches her description, and Pinkerton's 1861 reports and pay-books only give her initials, so we've had to reluctantly accept "Lawton," knowing it may not be correct. †Pryce Lewis, in his memoirs, said her last name was also Lewis. A few years ago some letters came up in auction from Allan Pinkerton to the illustrator of Spy in which Pinkerton also calls her Lewis.

It's been written in several secondary sources that Timothy and Hattie were accompanied by John Scobell, an African-American operative, who posed as their servant when they were living undercover in Richmond. Unfortunately, Scobell didn't exist. He was created for Spy of the Rebellion and was likely a composite of/tip of the hat to the many refugees giving Pinkerton information. †Historians have known this for years but, because he's in Pinkerton's own book (and early books that used that as a source,) Scobell keeps coming back up.

* * * * *

Essay respectfully submitted by Corey Recko, April 2014. Photograph from the author's personal collection.

Corey's first book, Murder on the White Sands: The Disappearance of Albert and Henry Fountain (University of North Texas Press, 2007), won the Wild West History Association's award for the "Best Book on Wild West History" for 2007. Since its publication, Recko has written articles on a variety of historical topics for magazines and historical journals and has become a sought after speaker. While working on Murder on the White Sands he began to research Pinkerton's National Detective Agency. The result was the discovery of new information that Recko included in his book and in subsequent biographic articles that he wrote about Pinkerton operative John C. Fraser for the WWHA Journal and Wild West magazine. His research into Pinkerton's agency also led to his discovery of largely forgotten agent Timothy Webster, the subject of his most recent book, A Spy for the Union: The Life and Execution of Timothy Webster (McFarland & Co., 2013).

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