Confederates Execute First Civil War Spy

Photo By Erin Thompson | Union spy Hattie Lawton attempts to save Timothy Webster from execution.  

UNITED STATES

04.24.2023

Story by Erin Thompson 

U.S. Army Intelligence Center of Excellence

by Erin E. Thompson, USAICoE Staff Historian

29 APRIL 1862
On 29 April 1862, Pinkerton Agent Timothy Webster became the first spy executed in the Civil War. Confederate officials hanged Webster at Camp Lee in Richmond, Virginia, despite written warnings and threats against such action from both Union intelligence officer Allan Pinkerton and President Abraham Lincoln.

Prior to working for Pinkerton’s Detective Agency, British-born Timothy Webster served as a police officer in New York City in the 1850s. Sometime between then and 1861, Webster met Pinkerton and agreed to work for him, becoming one of Pinkerton’s “ablest agents.” Webster’s first known operation was undercover aboard a train to protect President Lincoln from assassination attempts on his inaugural procession towards the capital. [See This Week in MI History #14 6 November 1860] Shortly after, Maj. Gen. George B. McClellan approached Pinkerton to organize a military intelligence service for the Union Army’s Ohio Division, and later the Army of the Potomac. [See This Week in MI History #51 1 April 1861] Webster’s role thus transitioned from detective to spy.

Early in the war, Pinkerton sent Webster to Baltimore to ingratiate himself to secessionist circles there. He established himself as a courier between these sympathizers and the Confederate capital in Richmond, Virginia. This earned him a pass to travel between the two cities from Brig. Gen. John Henry Winder, Richmond’s provost marshal in charge of that city’s counterintelligence operations. General Winder also began using Webster as a personal messenger to send letters to his son in the Union Army.

Further actions taken in apparent support of Confederate efforts won Webster many friends in southern society. His activities soon caught the attention of Confederate Secretary of War Judah P. Benjamin, who also began using Webster as a courier between his office and the secessionists in Baltimore. The frequency of Webster’s travels through the Confederate capital and his access to documents from high-ranking officials quickly proved Webster’s merit as a spy. He made many trips throughout the fall and winter of 1861, reporting on the build-up of enemy strength in areas such as Manassas and Centreville.

Unfortunately, Webster’s luck soon ran out. He and four other Union spies—Hattie Lawton, Pryce Lewis, John Scully, and someone identified only as H.J.K.—were arrested in early April 1862. Pinkerton blamed Lewis and Scully for implicating Webster as a Union spy, as both had their own sentences commuted shortly after arrest and were released in 1863. Webster, however, was tried and sentenced to hang, despite attempts from other spies like Hattie Lawton to persuade Confederate officials of his innocence. Pinkerton likewise urged the president to help save Webster, and Lincoln did send a letter to Jefferson Davis through Secretary of War Edwin Stanton. On behalf of the president, Stanton asserted that, if Webster hanged, all Confederate spies held in Union prisoner camps would also be executed. Additionally, Pinkerton and Col. Thomas M. Key of McClellan’s staff went to Richmond under a flag of truce to negotiate Webster’s release.

Despite all these efforts, on 29 April 1862, the Confederates led Webster to the gallows at Camp Lee. The first attempt at hanging failed when the knot of the noose came loose during the drop. Webster was then returned to the gallows where he reportedly said: “I suffer a double death. Oh, you are going to choke me this time.” The second hanging was successful, marking the first execution of a Civil War spy. Although no Confederate spies are known to have been executed in the immediate aftermath of Webster’s hanging, executions of this kind became much more common as the war progressed.

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• Date Taken: 04.24.2023
• Date Posted: 04.24.2023 11:07
• Story ID: 443221
• Location: US