Revolutionary Intelligence: Washington's Culper Ring
by Guest Contributor: Sarah Lamb
Wars are not fought with just the boom of guns. They’re fought with the quiet of written words and silent signals. Modern times give armies modern solutions to balance the two, but over two hundred years ago, the men (and women) fighting the American Revolutionary War under General George Washington had limited resources and long journeys through enemy territory to pass on information. The penalty for being caught was imprisonment, or worse, death. Washington understood the need for intelligence, and through trial and error, he built America’s first spy ring, often referred to as the Culper Ring, or sometimes Culper’s Gang. The ring was comprised of agents, sub-agents, couriers, and support personnel, and they shared two things in common: they were New Yorkers, and they had all suffered at the hands of the British crown. To protect their identities, the ring used codenames, and Washington himself knew only one agent’s name, that of Major Benjamin Tallmadge of the Continental Army, his intelligence chief and manager of the Culper Ring. This article explores the usefulness of Washington’s spies, as well the creation of the ring itself, its members, and how they conducted their assignments.
Having served as a Major in the British Militia prior to the Revolutionary War, Washington knew of their military advantage and that defeating them would be no small task. His army was undermanned, undertrained, undersupplied, and underfed. He could not rely upon battlefield tactics alone. Some questioned not just the tactics of spying, calling it dishonorable, but also the money and time that went into the effort, believing it would be better spent on preparing troops for the battles. Washington’s experience in the French and Indian War, specifically during the Battle of Wilderness on July 9, 1755, where the British suffered a defeat after a surprise attack by the French, showed him the importance of gathering intelligence. His plan though, was not without its failures. The first of two single trip missions by unexperienced agents resulted in the deaths of both agents, one of which was Tallmadge’s former classmate at Yale, Nathan Hale. Hale, eager to serve the cause he so fervently believed in, volunteered for the position after hearing that Washington was looking for recruits. Disguised as a Dutch school teacher, he traveled to Long Island, where he was to gather information on the enemy. However, Hale was not very good at spying and was quite careless as a result. Author Alexander Rose writes in his book, Washington’s Spies: The Story of America’s First Spy Ring, that Hale “spent too much time in the open and asked too many impertinent questions of the locals,”1 and was seen “scribbling notes whenever he saw a British detachment.”2 Hale was caught and sentenced to death by hanging. He was executed the very next day. His body left hanging from the noose for days as a warning to other spies. This event, caused by poor planning and bad decisions, caused Washington to rethink how they were going about gathering information if they were going to win this war.
Going by the code-name John Bolton, Benjamin Tallmadge was charged by Washington in 1778 with creating an intelligence network after the failure of previous efforts. He was to select and gather a group of confidants whose true identities would be kept secret even to Washington himself. The purpose of the network was to always remain unseen, even when passing on information. To accomplish this, the men and women in the network feigned loyalty to the British crown and operated from their homes and businesses using code names, a cipher system, secret signals, and eventually, invisible ink. The members of the ring collected information through their everyday lives rather than single missions, so as not to draw attention to oneself and remain undetected, an effort that was achieved as, according to author Kevin Gould in Britannica’s Culper Spy Ring, “none of Tallmadge’s intelligence agents were ever discovered by the British.”3 The name of the ring was Samuel Culper after two of its central members, Abraham Woodhull (code-named Samuel Culper, Sr) and Robert Townsend (code-named Samuel Culper, Jr.). Other members that formed the ring were Austin Roe, Anna Strong, and Caleb Brewster.
Robert Townsend/Culper Jr was the owner of a tavern and a dry goods store, as well as a society reporter for an American newspaper in New York City. He used his job as a reporter to attend social functions across the city, where he could talk to British soldiers without worry of being discovered. The Henry Clinton Papers, from the William L. Clements Library, states that Townsend’s tavern and store provided him “access to people in and outside the city who were in need of goods and, sometimes, a little extra information.”4 Culper Jr was charged with handing off his messages to Roe, who then took them to Setauket, New York where he rented a field. After Roe left the message, Woodhull/Culper Sr would retrieve it, add to it, and then look to Strong’s clothesline through which they had created a means of signals depending on what was hanging on it. If her black petticoat was hung it told Culper Sr that Brewster was there in his whale boat to receive the message, and the number of handkerchiefs hung provided the location of where Brewster could be found. Woodhull would then meet with Brewster to pass on the message. Brewster, through the use of his whale boat, then carried the message to Tallmadge/Bolton, where he waited in Connecticut. From there, a series of mounted riders known as dragoons would pass the message on until it reached General Washington in New Windsor, New York.
While this system worked well, it wasn’t always foolproof. A letter written by George Washington dated June 27, 1779 was intercepted when Tallmadge, unaware of raids being carried out as he traveled, lost his horse and Washington’s papers when he and roughly ninety men were attacked in Bedford, New York. While the letter did not reveal the true names of the Culper’s, who were mentioned, it did reveal a new potential member to the ring. In his letter Washington wrote, “There is a man on York / Island living on or near the North River, of the / name of George Higday who I am told hath / given signal proofs of his attachment to us, & / at the same time stands well with the enemy.”5 The intent was for Higday to be investigated to ensure his fitness for the role and his usefulness in creating a chain to gather and convey intelligence to and from Washington, from the North River. However, due to the letter’s capture, Higday was caught and ultimately not able to join them. The incident spurred Tallmadge to develop further secret ways to communicate, employing the use of invisible ink and a coded dictionary.
The invisible ink was created by Sir James Jay, brother of John Jay, a physician and fledgling chemist. When written on white paper, the ink became invisible until another chemical was applied that rendered it visible. While this means of communication was successful, the compound was not easy to come by as the ingredients and the space needed to make it were difficult to find. Because of this, messages were at times unreadable if the intended reader did not have the necessary chemical to make it visible. Due to this problem, Tallmadge increased security further by expanding the numbered codes already in use by their gang. In a letter to George Washington dated July 25th, 1779, Tallmadge writes, “Sir, enclosed is a Scheme for carrying on the Correspondence in future with C——. Some directions how to use sd Dictionary may be found annexed,”6 and he closes the letter with, “P.S. To make the plan of the enclosed dictionary more easy & familiar, I have wrote a Copy of this letter by the same, which is also enclosed.”7 This new dictionary, known as The Culper Cypher, was transcribed by George Washington’s Mount Vernon, and it reveals that new code consisted “of seven hundred and sixty-three numbers representing words, names, and places to communicate their information.”8 George Washington’s code number was 711, and the members of the Culper Ring were as follows: Benjamin Tallmadge/John Bolton, 721. Abraham Woodhull/ Samuel Culper Sr, 722. Robert Townsend/ Samuel Culper Jr, 723. Austin Roe, 724. Caleb Brewster, 725. New York became 727, Long Island, 728, and Setauket, 729. They even had a code for the British commander in chief, Henry Clinton: 712. Next, Tallmadge created a mixed-alphabet scheme, where the letters of the alphabet were reassigned in order. For example, the letter ‘a’ became ‘e,’ ‘b’ became ‘f,’ and ‘c’ became ‘g.’ The intent was to simply provide back up security, and it worked.
These new measures led the Culper Ring to one of its biggest successes. In 1780 their missives managed to save Gen. Jean-Baptiste-Donatien de Vimeur, comte de Rochambeau and his French troops when they arrived at Newport, Rhode Island, on July 11. Sir Henry Clinton made plans to attack them, knowing that they would not be ready for a fight after such a long journey. As a means to distract Clinton and his troops from attack, Washington led his men on a march towards New York City, and it worked. Clinton directed his men back to the city to defend it, and Rochambeau and his troops were able to recuperate from the journey overseas and later join the war.
While some claimed Washington spent too much time on subterfuge and not enough time on military tactics, the success of his spies is proof that his time was not wasted. The Culper Ring was instrumental in the Patriots winning the war against the might of the British Army. Tallmadge and his gang provided crucial information about British plans, unit strengths, and defenses which allowed Washington to make decisions to outwit the enemy that won battles and at times saved lives. This ultimately led to the establishment of the United States and laid the groundwork for the intelligence community going forward.
[Sarah Lamb is a writer of history and a history teacher in training.]
Rose, Alexander. Washington’s Spies: The Story of America’s First Spy Ring (New York: Bantam Books, 2006), 28.
Ibid.
Gould, K. "Culper Spy Ring." Encyclopedia Britannica, https://www.britannica.com/topic/Culper-Spy-Ring.
George Washington Letter to Benjamin Tallmadge, June 27, 1779. Henry Clinton Papers. “The Culper Gang.” William L. Clements Library, https://clements.umich.edu/exhibit/spy-letters-of-the-american-revolution/stories-of-spies/culper-gang/.
Ibid.
“To George Washington from Major Benjamin Tallmadge, 25 July 1779,” Founders Online, National Archives, https://founders.archives.gov/documents/Washington/03-21-02-0540.
Ibid.
George Washington’s Mount Vernon. “The Culper Code Book,” n.d. https://www.mountvernon.org/george-washington/the-revolutionary-war/spying-and-espionage/the-culper-code-book/#-.
Bibliography:
Primary Sources:
Benjamin Tallmadge Letter to Robert Townsend, November 8, 1779. “The Culper Spy Letter: A New Discovery at the Long Island Museum.” Long Island Museum, https://longislandmuseum.org/exhibition/the-culper-spy-letter-a-new-discovery-at-the-long-island-museum/.
George Washington Letter to Benjamin Tallmadge, June 27, 1779. Henry Clinton Papers. “The Culper Gang.” William L. Clements Library, https://clements.umich.edu/exhibit/spy-letters-of-the-american-revolution/stories-of-spies/culper-gang/.
“To George Washington from Major Benjamin Tallmadge, 25 July 1779,” Founders Online, National Archives, https://founders.archives.gov/documents/Washington/03-21-02-0540. [Original source: The Papers of George Washington, Revolutionary War Series, vol. 21, 1 June–31 July 1779, ed. William M. Ferraro. Charlottesville: University of Virginia Press, 2012, pp. 658–663.]
Secondary Sources:
George Washington’s Mount Vernon. “The Culper Code Book,” n.d. https://www.mountvernon.org/george-washington/the-revolutionary-war/spying-and-espionage/the-culper-code-book/#-.
Gould, Kevin. "Culper Spy Ring." Encyclopedia Britannica, January 18, 2024. https://www.britannica.com/topic/Culper-Spy-Ring.
Rose, Alexander. Washington’s Spies: The Story of America’s First Spy Ring. New York: Bantam Books, 2006.