On April 29, 1862, Timothy Webster prepared to die. He would soon become one of the hundreds of thousands of Americans to perish because of the Civil War. But Webster was not a Union or Confederate soldier or an unfortunate civilian caught in the crossfire. Webster was a spy for the North—and the first spy to be executed during the four-year conflict.
Webster’s name doesn’t appear in many history books, except perhaps ones devoted to Civil War espionage. I came across his story while researching a You Choose book on spies of the Civil War (due out next year). His exploits provided the background for one of my three story threads, and after finishing that book, I began doing a little more research on Webster for a query I wanted to write for a children’s magazine profiling little-known heroes of the Civil War (you can read about my time at Yale University doing that research here).
Unfortunately, the deadline for submitting the query passed before I could get my act together and write it. But like any historian, I didn’t want my research to go for naught, hence the post you’re now reading.
Most of the information about Webster and his undercover work came from his boss, Allan Pinkerton, of the Pinkerton Detective Agency. Pinkerton and his operatives—including several women—formed the core of the Union’s first spy service during the war. Even before the fighting started, Pinkerton was involved in national security issues—more on that in a bit—and after the war he wrote about his and his staff’s deeds of derring-do in The Spy of the Rebellion.
Pinkerton, though, had a habit that has made life hard for historians: he liked to embellish the truth. For more than a century, popular writers took Pinkerton’s words about Webster as gospel and passed them along. It took Corey Recko, with his 2013 book A Spy for the Union, to poke holes in the tall tales with well-researched facts (I’m indebted to Recko’s work both for my You Choose book and this piece).
As it turns out, the truth is intriguing enough, painting a portrait of a calm, brave agent working behind enemy lines. Webster came to America from England when he was 12, and in his early 30s joined the New York Police Department. While on the force, he met Pinkerton, who convinced him to come to Chicago and join his detective agency.
Pinkerton assessed Webster this way: “There was such a decided mixture of sternness and amiability, of innate force and gentle feelings, of frankness and resolution stamped upon his features that he instinctively impressed the beholder at a glance.…Though not a man of great enlightenment, he was gifted with a large amount of natural shrewdness, which enabled him to successfully meet any emergency which might arise. From his association with people in the various walks of life, he had acquired that habit of easy adaptation which made him appear, and feel, perfectly at home in almost any society, whether in the drawing-room or the tavern, in the marts of trade, or laboring at the plow.”
That habit of easy adaptation helped Webster gain the trust of Confederate sympathizers in Maryland even before the start of the war. Along with Pinkerton agent Hattie Lewis, Webster went to Perryman, Maryland, shortly after Lincoln’s election. The two were supposed to gather information about rumored plots to blow up railroads in the state. Instead, Webster heard anti-Lincoln men talking about the possibility of the president’s assassination as he passed through Baltimore on his way to his inauguration. That and information gleaned by other agents convinced Pinkerton that the threat of an assassination was real, even if he didn’t have concrete evidence of a well-conceived plot.
When the time came for Lincoln to travel through Baltimore, he did it in disguise, secretly in the dead of night, with Pinkerton and several armed detectives traveling with him. Along the route, Webster stood watch, and as the train passed through Havre de Grace, he used a lantern to signal that all was clear. Lincoln reached the capital safely, though he regretted the clandestine trip. After being ridiculed in the press, he called the trip a “grave mistake,” from a political perspective. But as Lincoln scholar Harold Holzer notes in his book Lincoln President-Elect, given the real assassination plot of 1865, Pinkerton was not unwise to take the earlier rumors and threats seriously.
As for Webster, when the war broke out he found himself in Maryland, posing as a friend of the Confederacy. In that guise, he convinced real pro-South men that he wanted to arm Baltimore residents to battle Union troops. He also traveled into Rebel territory, visiting Tennessee and befriending Confederate officers, who openly talked about troop movements and strength. Everything he learned, Webster sent back to Pinkerton.
Later in 1861, Webster went to Richmond, maintaining his ruse as a Confederate supporter. He carried messages from Confederates in Maryland to the South’s capital, and once again he earned the trust of Confederate officers and government officials—so much so that they asked Webster to carry documents north for them. The South’s Secretary of War, Judah Benjamin, even wrote out passes for Webster so he could safely cross military lines. The Pinkerton operative coolly took on the role of double agent, with Union men copying down the contents of the messages he carried north before they reached their intended recipient.
In Richmond, Webster once again worked with Hattie Lewis; the couple posed as husband and wife. Early in 1862, Webster fell ill, and the pair stopped sending messages north for a while. A concerned Pinkerton sent two other agents to Richmond to check on Webster. Almost immediately, they were identified as Northern detectives by someone who had known them in Washington, D.C. They were arrested and sentenced to hang. To save himself, one of the men, John Scully, confessed his espionage activities and fingered Webster and Lewis as spies. Later the other nabbed agent, Pryce Lewis, followed Scully’s path. Both men avoided execution.
But not Webster. Neither side had executed a spy at this point in the war, but Corey Recko speculates that Confederate leaders were so angry at being duped that they wanted Webster dead. He was executed on April 29. In Pinkerton’s telling, Webster asked to be killed by a firing squad, rather than to be “hanged like a common felon,” but the Southern commander in charge refused. When the time came, Webster stood calmly with the noose around his neck. The trap door swung open, but something went wrong—the noose slipped and Webster did not die. As the Confederates prepared the gallows again, Webster said, “I suffer a double death.” This time the procedure went as planned and Webster was soon dead.
At this point in his narrative, Pinkerton waxed poetic for one of the unsung heroes of the Civil War: “Farewell, brave spirit! I knew thee well. Brave, tender and true; thou hast suffered in a glorious cause, and died a martyr’s death. Thy memory will long be green in the hearts of thy friends. When treason is execrated, and rebellion is scorned and despised, the tears of weeping friends will bedew the sod which rests above the martyred spy of the Rebellion—Timothy Webster.”