HISTORY OF THE CULPER SPY RING History of the Culper Spy Ring The origins of the Culper network lie with Benjamin Tallmadge, code named John Bolton. Benjamin Tallmadge started the network as an up-and-coming young cavalry officer, being groomed to take over intelligence duties for his commander, Charles Scott. Tallmadge proposed a new model of espionage, relying on a series of individuals instead of the lone ranger model used with Nathan Hale and many previous spies. Tallmadge returned to his hometown of Setauket, knowing both the local politics, and the reliability of extended family in town. To get to Setauket, Tallmadge enlisted a childhood acquaintance and friend of his brother, Caleb Brewster. Brewster served with the local militia, and developed a wartime reputation as one of the many “whaleboat” raiders prowling Long Island Sound, attacking British shipping and fleeing back to Connecticut. Brewster and the men he used to crew his whaleboat served as the ferry service for spy reports between Long Island and American-held Connecticut. Brewster relied on several people to collect the messages he carried. At some point, Tallmadge brought in Anna Smith Strong, his close relation. Strong was the wife of a local Patriot judge, and she is said to have arranged her clothesline to signal Brewster’s location. Strong’s role is documented beyond family lore in the counterintelligence reports provided to the British Commander General Clinton by an agent called “Hiram the Spy.” Abraham Woodhull, the first agent to travel to New York and report as “Samuel Culper,” was an acquaintance of Tallmadge’s as well. Woodhull’s father was another local judge, and Woodhull did serve briefly in the local militia. Using the guise of visiting his sister at her boardinghouse in Manhattan, Woodhull made several trips into the depths of enemy territory. Unfortunately, Woodhull was not particularly well connected to British powers, nor did he have a particularly good reason to be in Manhattan. Evidence suggests that British suspicions were not simply a creation of Woodhull’s fears, since at least on one occasion the British tried to arrest him. Given Woodhull’s risks of discovery, it makes sense that he recruited a friend and resident of his sister’s boardinghouse. Related to the rest of Tallmadge’s network, Woodhull’s recruit Robert Townsend, was the son of a Patriot judge. As a well- connected New York City merchant running both his father’s business and his own accounts, Townsend had a reason to be in Manhattan. While Townsend’s reports, written as "Samuel Culper, Jr." involved good quality Naval Intelligence, he could not get good Army Intelligence on his own. His involvement also required a greater role for a courier between Manhattan and Setauket, where Woodhull continued to write reports on British activities on Long Island. The network first worked with a Setauket resident named Jonas Hawkins, but later relied on the dependable local tavern keeper Austin Roe. Roe used the excuse of buying supplies for his tavern to travel to Manhattan. Culper letters reveal a system of Major John Andre's presence in New York, and there is a pattern visible in the timeline between Andre's activities and the Culpers' reports. The Culpers were one of Washington's best intelligence efforts, he kept working with them long after they ceased to provide good information, and he was willing to welcome Townsend back despite the fact that Townsend quite spying on more than one occasion. This suggests that the ring was one of his more reliable sources. Historians have frequently credited the Culpers with providing American leadership with warning of Arnold's treasonous correspondence. This is partly due to their success during the period, and their access to high level secrets. It is also reflected in the timing of their dispatches that survive, such as the "French Fleet warning". Most of all, these claims rest on the fact that the Culpers were Washington's most successful continuous intelligence source at British Headquarters during this period, and those secrets were extremely high-level. After Major Andre's capture and the discovery of Arnold's plans, the Townsend went into hiding at Woodhull's farm, and had one of his "friends who hath been ever serviceable" arrested by Arnold. Following these events, Townsend was reluctant to resume spying. Woodhull managed to keep the ring working until the end of the war, although Washington wrote that after 1780, the Culpers never provided any information of value. WORKINGS OF THE CUPLER SPY RING Woodhull, who began running the group’s day-to-day operations on Long Island, also personally traveled back and forth to New York collecting information and observing naval maneuvers there. He would evaluate reports and determine what information would be taken to Washington. Dispatches would then be given to Brewster, who would carry them across the Sound to Fairfield, Connecticut, and Tallmadge would then pass them on to Washington. Woodhull lived in constant anxiety of being discovered, and by the summer of 1779 he had recruited another man, the well-connected New York merchant Robert Townsend, to serve as the ring’s primary source in the city. Townsend wrote his reports as “Samuel Culper, Jr.” and Woodhull went by “Samuel Culper, Sr.” Austin Roe, a tavernkeeper in Setauket who acted as a courier for the Culper ring traveled to Manhattan with the excuse of buying supplies for his business. A local Setauket woman and Woodhull’s neighbor, Anna Smith Strong, was also said to have aided in the spy ring’s activities. Her husband, the local Patriot judge Selah Strong, had been confined on the British prison ship HMS Jersey in 1778, and Anna Strong lived alone for much of the war. She reportedly used the laundry on her clothesline to leave signals regarding Brewster’s location for meetings with Woodhull. .