Timothy Webster, best known for his work as a spy for the Union during the Civil War, began his career as a New York City policeman. In the mid-1850s he left the police department and took a job for Allan Pinkerton with his newly formed detective agency. As an operative for Pinkerton’s agency, Webster excelled. His cases included tracking a world famous forger, investigating grave robberies in a Chicago cemetery, and seeking to uncover a plot to destroy the Rock Island Bridge. It was also as a Pinkerton detective that Webster made his greatest contribution to his country when he was part of a small group of operatives that uncovered a plot to assassinate then President-elect Abraham Lincoln in 1861. Webster went on to serve the United States as a spy in the Civil War. He traveled to the Confederate Capital multiple times and made many connections high up in the Confederate military and government. For a time he was the Union’s top spy, but his career came to an abrupt end when, in 1862, he was betrayed by fellow spies and became the first spy executed in the Civil War.