Spying in America: Espionage from the Revolutionary War to the Dawn of the Cold War

7. The Chameleon Spy: Timothy Webster

  77 7 The Chameleon Spy Timothy Webster I die a second death. Timothy Webster at his execution. Quoted by Markle, Spies and Spymasters, 147. Timothy Webster possessed uncanny abilities to adopt a persona, ingratiate himself in any company, and adapt instinctively to any circumstances— especially in a crisis. All these abilities made him an ideal candidate for the murky and hazardous world of Civil War espionage, and he was, before his untimely death, undoubtedly among the best spies of the war. Webster was born in England in 1821 and emigrated to the United States with his parents at the age of thirteen years. After serving as a New York City policeman, he worked for Pinkerton’s detective agency and followed his boss to serve in his new security service in Washington. On his first mission Webster posed as a fanatic rebel and infiltrated the Baltimore secessionists plotting Lincoln’s assassination. After the conspiracy was unmasked with Webster’s help, Pinkerton dispatched him to penetrate rebel subversives in Kentucky and Tennessee before summoning him back to Baltimore.1 78 The Civil War After returning to Baltimore, Webster posed as a wealthy socialite and plied locals with rounds of whiskey to convince them of his Confederate sympathies. He was accepted into the Knights of Liberty, a rebel organization dedicated to subverting the Union. One night, while Webster was regaling patrons in a Baltimore saloon, one of them fingered him for exactly what he was, a Union spy, and accused him in front of the other customers. Webster did not flinch. He seized the offensive with righteous indignation, called his accuser a liar, and goaded him into a fistfight . He was a physically imposing figure, and flattened his accuser with a punch. His accuser scrambled to his feet, knife in hand, ready to strike until Webster whipped out a cocked pistol and held it to the gentleman’s head. No one again challenged Webster’s Confederate credentials after the fight.2 His cover was so well established with rebel subversives that a new Pinkerton agent, tipped off by a source about Webster’s Confederate activities , arrested him in Baltimore. Pinkerton’s unit was so tightly compartmented that his new operative had no idea of Webster’s true identity, and Pinkerton himself had to arrange his “escape,” an exploit that once again enhanced the Union spy’s standing among the rebels. Webster’s career as a counterspy skyrocketed when he became a Confederate courier between Baltimore and Richmond. Because his reputation was impeccable among rebel sympathizers in Baltimore, he volunteered his services as a spy to Confederate secretary of war Judah Benjamin. Charmed as Webster’s other targets were, Benjamin entrusted him with batches of documents to carry to Richmond, including military plans and valuable counterespionage information about Confederate spies in the Union ranks. In return Webster provided marginal feed information about the Union that was supplied by Pinkerton. On one of his courier trips, Webster contracted rheumatism, which was later to play a key role in his demise. While en route to Richmond, he sought refuge from a rainstorm in an isolated cabin. His muscles ached from trying to sleep on the cold, damp floor of the cabin, and he spotted an oilskin packet on the floor and opened it. The packet contained maps of Union Army deployments, and he arranged to send the material to Pinkerton, which led to the arrest of a Confederate spy working as a clerk in the War Department. 79 The Chameleon Spy • Timothy Webster Webster’s fourth trip as a courier to Richmond proved to be his last. His rheumatism afflicted him so much that he was bedridden in Richmond for weeks and out of contact with Pinkerton. Worried about his best spy, Pinkerton dispatched two agents, Pryce Lewis and John Scully, to find him. In his concern for his prize agent, Pinkerton committed a major tradecraft error. Lewis and Scully had investigated and conducted searches in the homes of suspected Confederate sympathizers in Washington, and the possibility existed that some of these sympathizers could be visiting or living in Richmond and could identify them as Union agents. This tradecraft blunder proved fatal. The two agents were indeed identified by one of their earlier targets, a Richmond resident who owned a house in Washington that the pair had searched. Confederate counterespionage agents surveilled Pinkerton’s duo, who, disregarding basic security measures, found Webster’s room...