Timothy Webster Timothy Webster ( March 12 , 1822 – April 29 , 1862 ) , Pinkerton agent and Union spy , was the first spy in the American Civil War to be executed . Early life . Webster came to America with his parents in August 1830 and settled in Princeton , New Jersey . He became a policeman in New York City in 1853 and in 1854 was he was noticed by a friend of Allan Pinkerton ' s who recommended him for detective work . Webster married Charlotte Sprowles on October 23 , 1841 in Princeton , New Jersey and the couple had four children , two of whom died young . Their son , Timothy Jr . , born in 1843 , joined the Union Army from Onarga , Illinois on July 30 , 1862 and was wounded in the Battle of Brices Crossroads near Ripley , Mississippi on June 11 , 1864 , and taken to a Confederate prison in Mobile , Alabama where his leg was amputated . He subsequently died there on July 4 , 1864 . His body was transported north to Onarga , Illinois and buried in the Onarga Cemetery next to his grandfather , Timothy Webster Sr . , who died in Onarga in 1860 . Civil War . In early 1861 , Pinkerton sent Webster and Hattie Lawton to pose as a Southern gentleman and wife ( Mrs . Webster ) in the Baltimore area and became a member of a pro - Southern group in order to report on secessionists ' plans and activities . Some of the information provided by Webster gave support to Pinkerton ' s assertion that there was a Baltimore Plot to assassinate Lincoln as he moved through Baltimore on his way to his inauguration in 1861 . After the outbreak of war , Pinkerton began to provide agents to the Union armies under George B . McClellan . Webster continued to gather information on the Confederacy from 1861 through 1862 in southern Maryland and Richmond , Virginia . In Richmond in 1862 he was stricken with inflammatory rheumatism and was too ill to send reports back to Pinkerton . As a result Pinkerton sent Pryce Lewis and John Scully to locate Webster . The two men were recognized as being Union spies and captured by the Confederacy . Scully eventually revealed information that caused Webster and Lawton to be arrested . Confederate officers had trusted Webster many times with valuable documents and information and the Confederacy was extremely embarrassed by Webster ' s betrayal . While Lewis and Scully were eventually released , Webster was arrested , tried , and sentenced to death by hanging . Hattie Lawton was imprisoned and later released in an exchange of prisoners . Death . When Pinkerton heard the news of the sentence , he and President Lincoln sent a message to the Confederacy threatening that if Webster was put to death , the Union would reciprocate by hanging a Confederate spy . Union policy had been to keep Confederate spies in jail and exchange them for Union prisoners . The Confederacy ignored the threat and on April 29 , 1862 , Timothy Webster climbed the gallows in Richmond , Virginia at Camp Lee . After the initial attempt to hang Webster failed , he was helped to the gallows again and was heard to say , " I suffer a double death ! " before being killed on the second attempt . He was buried in Richmond , but in 1871 , Pinkerton sent George Bangs and Thomas G . Robinson ( Timothy ' s son - in - law ) to Richmond to locate his body and bring it to Onarga , Illinois for burial . He was buried next to his father , Timothy Webster Sr . , and his son , Timothy Webster Jr .