Culper Spy Ring

Culper Spy Ring, American intelligence organization that was put together and managed by Maj. Benjamin Tallmadge for the Continental Army during the American Revolution. It operated in British-controlled New York City from 1778 to 1783. The ring was named for the operational names of two of its members: Abraham Woodhull (code-named Samuel Culper) and Robert Townsend (code-named Culper, Jr.). It comprised several other agents, including Caleb Brewster, Austin Roe, Anna Strong, Hercules Mulligan, and Townsend’s paramour, known today only by her code name “355.”

Because of his experience gathering intelligence in the 2nd Continental Light Dragoons and the high regard in which he was held by Gen. George Washington, the commander of the Continental Army, Tallmadge was asked in November 1778 to organize an intelligence service to operate in British-occupied New York City. He recruited Woodhull, a native of Tallmadge’s hometown of Setauket, Long Island, New York. Woodhull, in turn, promptly involved Townsend, who reinforced his cover by writing pro-Tory articles for the Royal Gazette. James Rivington, the editor of that publication, may also have served as an agent for the Continental Army, although that possibility was not discovered until 1860 and is still debated.

Instead of following the convention of dispatching scouts into British territory on single-trip missions, Tallmadge organized his network of agents to operate behind and just beyond enemy lines, from their homes in New York City, on Long Island, and in Connecticut, from which they reported on British activity. A single-trip mission had resulted in the capture and execution of Tallmadge’s Yale classmate Nathan Hale, whereas none of Tallmadge’s intelligence agents were ever discovered by the British.

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The American Revolution

Throughout the war, the Culper Ring made sketches of fortifications and reported on ship arrivals and departures; troop activities, strength, positions, and morale; and the status of British supplies. Most of the intelligence was gathered in New York City from Townsend’s tavern and dry-goods store or from Mulligan’s tailor shop, both of which were popular locations for British soldiers to gather. The Culper Ring was the most-professional of Washington’s espionage networks, and though Tallmadge was its manager, Washington himself regularly tasked the agents with very specific instructions, including techniques to be used to conceal their espionage activities to protect themselves. Washington had learned the importance of concealment and personal protection for his intelligence agents through the loss of Hale, an enthusiastic but completely untrained amateur spy.

The Culper Ring employed several methods of spycraft in its operations. In addition to providing his agents with code names, Tallmadge devised a cipher system for their intelligence reports. Key words and terms were encoded as a three-digit number based upon their position in John Entick’s The New Spelling Dictionary, a popular work of the day. Those reports were also written with invisible ink that required a special chemical compound to be brushed over it to reveal the writing. Moreover, the reports were frequently embedded in letters addressed to notorious Tory sympathizers on Long Island as an additional step to prevent their seizure by British troops inspecting material carried by Culper agents.

The Culper Ring reports were conveyed by a chain of agents as they conducted their normal daily activities rather than on special or unusual trips. Townsend gave his reports to Roe when Roe visited the dry-goods store to purchase supplies for his tavern on Long Island. Roe then carried the reports east across Long Island to Woodhull’s Setauket farm. Next, Brewster and his whale-boat crews rowed the messages across Long Island Sound to the Connecticut shore to a specific location, which, according to many accounts, was indicated by Strong by the number of handkerchiefs hung on her laundry line on the New York side. Tallmadge’s dragoons then would meet Brewster and, upon receiving the reports, ride west through Connecticut and New York to Washington’s headquarters in Morristown, New Jersey. While this process protected the agents, it slowed transmission of intelligence, as when reports of an impending British raid on the headquarters of Tallmadge’s unit, the 2nd Dragoons, arrived after the raid and the capture of intelligence reports and operational funds locked in Tallmadge’s personal trunk at the scene.

One of the ring’s most-important contributions to the war effort was intelligence that saved recently arrived French troops from potential disaster. Townsend learned that British Gen. Sir Henry Clinton was preparing some 8,000 troops to attack the French force of approximately 5,800 troops under Gen. Jean-Baptiste-Donatien de Vimeur, comte de Rochambeau, that had just arrived at Newport, Rhode Island, on July 11, 1780. After three months at sea, worn-out and sick from the voyage, the French troops likely would have been no match for Clinton’s battle-hardened force. Towshend hid his report on Clinton’s plans in a letter to a well-known Long Island loyalist, which Roe transported past the sentries around New York City. It was delivered to Washington’s headquarters in Morristown on July 21. Upon receiving the report, Washington led his troops across the Hudson River and marched toward Manhattan. Learning of Washington’s advance, Clinton returned with his troops to secure New York City, leaving Rochambeau free to rest and refit his troops.

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For most of the war the Culper ring kept Washington abreast of the British position in New York City and enabled him to make informed plans. As a result, the American Revolution owed many of its successes to intelligence reported by the ring.