Timothy Webster Banner


Webster is allowed to escape from a police van

An employee of Allan Pinkerton's detective agency, Timothy Webster was one of the most daring and effective of the Union spies operating in the South at the beginning of the Civil War. His first mission, undertaken in May 1861, was to travel extensively through Tennessee and Kentucky and gather information about Confederate military units being formed in those states. He posed as an avid and vocal secessionist and was able to gather important information from Rebel officers he befriended. About to be arrested by a suspicious counterspy, Webster evaded the agent and slipped unseen onto a train departing for the North.

Next, he operated in the Washington, Baltimore, and Richmond area, where, again posing as a secessionist, he managed to infiltrate a Baltimore secret secessionist organization, the Knights of Liberty, and arranged a raid by federal troops on one of their midnight meetings. He was allowed to escape and continue his activities, but his disguise as a Yankee-hater caused him trouble when he was arrested and thrown in jail by another of Pinkerton's Baltimore agents. Again allowed to escape, Webster undertook four missions in the Confederate capital of Richmond.

Webster played his role as a spy well and gathered much useful information for the Union. He became a messenger for the Richmond Examiner and, with a pass signed by the Confederate secretary of war, he was able to visit Rebel fortifications and government offices. Webster became very sick in Richmond in the spring of 1862, and when Pinkerton did not hear from him, two other agents were sent to find him. The agents were captured by the Confederates and exposed Webster to save their lives. Webster was arrested, tried, and convicted in short order, and though he asked to be executed by firing squad, on April 24, 1862, he suffered a felon's death--he was hanged.