The Culper Ring Analysis

The Culper Ring, the American spy network that provided George Washington with intelligence about the British in the New York area, was so shrouded in secrecy that there are still unanswered questions about how they operated. Initially, George Washington had appointed General Charles Scott in charge of intelligence. After several of the General’s men were captured and executed, (Jamestown-Yorktown Foundation, 2014) George Washington appointed Major Benjamin Tallmadge as Director of Military Intelligence in November of 1778. Tallmadge went on to form a spy ring in the New York for the next 5 years. While one member, Caleb Brewster, was identified by the British of being a spy, (History.com staff, 2010) no others were and in fact, even Washington
did not know who everyone was that was involved. (Mount Vernon Ladies Association, 2016) Initially, Tallmadge only recruited two others. Caleb Brewster, who he knew from his childhood on Long Island owned a whaleboat which made transporting the intelligence between Connecticut and New York easier. He was also a lieutenant in the Continental Army. Another childhood friend, Abraham Woodhull, was also recruited. Together these men started to collect intelligence. Woodhull would make trips into New York City, which was controlled by the British, to visit his sister Mary. While visiting with her, he would collect as much intelligence as possible, then he would return to Setauket, Long Island where he would pass the information on the Brewster. Brewster would take the intelligence he received from Woodhull across the sounds to Tallmadge in Connecticut. Tallmadge would then carry the information on to Washington. (Jamestown-Yorktown Foundation, 2014) This worked for a while but the British guards got suspicious about Woodhull’s frequent trips into the city. They began to stop and search him. While they did not find the letter he carried in his saddlebag, the close call made it clear they needed to be less conspicuous. Tallmadge, in an attempt to make it harder to find the identities of his spies, invented a sophisticated system in which numbers would substitute for words.
He provided code books to Washington, Woodhull, Robert Townsend, a new recruit, and himself. Each member of the ring was assigned numbers such as Washington was 711, and Tallmadge was 721. Places also received numbers. London was 746 and New York was 727. Then, to make things even more confusing, each letter in the alphabet was replaced by another letter. A “c” would have been written as a “q”, and a “w” as a “y”. While this is considered fairly easy to break by cryptography standards of today, the code system wasn’t discovered until 1939, by historian Morton Pennypacker, so it was sufficient for the time period. They also began to use invisible ink. Washington called the ink a “sympathetic stain” or a “white ink”. (Dewan, 1998). Invented by James Jay, it was used on a blank piece of paper. Then Washington would use a second solution on the paper once he received it to have the message appear. Later they started writing the invisible messages between the lines of regularly written letters because they were worried that carrying blank papers would be
suspicious. With all the new security procedures in place and a few new recruits, they were back in business. Austin Roe, a local tavern keeper, would travel to New York, to new recruited Townsend, who was only identified as a member of the ring in the 1930’s through the use of handwriting experts. (Meyer, n.d.) Townsend was a merchant as well as a journalist for the Rivington’s Gazette, a well-known Tory paper. These positions allowed him access to many British through social gatherings. Roe would them submit a written request for goods from a “John Bolton” who was, in fact, Tallmadge. Townsend would write a response, typically in invisible ink rather than in code, and slide the blank paper into a ream of paper as part of the order from Roe. He would then fill the order, and send Roe on his way with the goods. Roe would then return to Setauket, Long Island and place the letter in a box on a piece of property he rented to tend his cattle on.
Once he left the property, Abraham Woodhull would come and retrieve the letter from the box. After adding anything additional to the letter that he felt necessary he would use a spyglass to look across the bay to Anna Smith Strong’s home, otherwise known as Nancy Strong, whose husband had been imprisoned by the British. Nancy would place her black petticoat on the line when Brewster was ready to retrieve the message from Woodhull. The number of white handkerchiefs on her clothesline with the black petticoat would tell Woodhull the correct spot or cove in which to meet Brewster. Even today we do not know how Nancy knew when Brewster was ready for a pickup. (Dewan,
1998). After meeting with Woodhull, Brewster would row across the Devil’s Belt to Fairfield, CT where he would meet with Benjamin Tallmadge. At this point, the letter would go through several riders until it reached Washington in New Windsor, NY so that he could decode it. (University of Michigan, Clements Library, 1999) The Ring provided several types of information to Washington over the course of its life including information about key British troop movements, British fortifications and British plans in New York and the surrounding area. Perhaps the most important of those reports was in 1780 when the Culper Ring “uncovered British Plans to ambush the newly arrived French army in Rhode Island.” (History.com staff, 2010) After receiving the report, Washington moved his troops into an offensive position and the British were forced to cancel the attack. This may have saved the French-American alliance. The Culper Spy Ring disbanded with the official end of the war in 1783. Each of the member survived, living into the 1800’s. Benjamin Tallmadge went on to represent his district in Litchfield, Connecticut in the U.S. House of Representatives as a Federalist for 16 years. Abraham Woodhull went on to serve as a judge of the Court of Common Pleas and then was a Suffolk County Judge for 11 years. Robert Townsend continued as a merchant. Caleb Brewster was recognized by Congress for his actions. He went on to captain a revenue-cutter in the New York area. Austin Roe went back to his tavern and eventually opened a hotel. Anna (Nancy) Strong Smith reunited with her family after her husband was released from prison. (Dewan, 1999) Benjamin Tallmadge recruited only people that were well known by him and that he knew could be trusted. Townsend only joined with the stipulation that no one would know his true name, even Washington himself. It worked so well that he was not identified as part of the ring until the 1930s. Anna Strong Smith gave the signals on her clothes line so that Abraham Woodhull could meet with Caleb Brewster, but historians still do not know how Caleb informed her of his location and availability. They were certainly a ring of secrecy, one of great importance at the time.