Spies and Whispers: How Top-Secret Spy Rings Helped Win the American Revolution
June 30, 2026
The American defeat at the Battle of Brooklyn in 1776 left the newly formed United States in dire straits. But New York City was still a strategic hub; the city’s convenient harbor and waterways, which connected New England to the rest of North America’s eastern seaboard, were seen as vital to winning the American Revolution and establishing the fledgling country. Despite New York’s loss to the British and the odds against the Americans, General George Washington of the Continental Army believed the city could still give them an advantage.
With British military command established in New York, Washington sought the information now flowing through the city’s occupied streets — information that could shift the course of the war. So instead of relying on force alone, the general turned to espionage.
The Americans employed civilians and military officers alike to operate behind enemy lines in New York City. They gathered information in taverns, coffeehouses, tailor shops, social events and along the busy docks of Lower Manhattan. Among Washington’s spies, the most famous network was the Culper Spy Ring, led by Major Benjamin Tallmadge, who later wrote an account of Washington’s farewell at Fraunces Tavern in 1783.
In a letter dated March 21, 1779, to Tallmadge, Washington outlined his expectations for the new spy network. He wrote (sic): “As all great movements, and the foundation of all intelligence must originate at, & proceed from the head Quarters of the enemy’s Army, C— [Culper] had better reside at New York -mix with- and put on the airs of a Tory [those with allegiance to Britain] to cover his real character, & avoid suspicion.”
After the capture and death of American soldier and spy Nathan Hale in 1776, Washington recognized that this new intelligence ring must operate with caution and cunning so as not to repeat Hale’s tragic fate. A Long Island native and former classmate and friend of Hale, Tallmadge understood the risks at stake. And so, to build a trustworthy network, Tallmadge turned to his Long Island neighbors Abraham Woodhull, Caleb Brewster, Anna Strong and Austin Roe.
Pseudonyms were assigned to principal agents, especially those undercover in New York City. For example, Tallmadge’s alias was “John Bolton,” and Abraham Woodhull was known as “Samuel Culper Sr.” Although the name Culper serves as the ring’s namesake, the origin of the name is believed to have been chosen by Washington himself after Culpeper, Virginia, which he surveyed in his early career. As the British began casting suspicion onto Woodhull, another principal agent, Robert Townsend, was recruited. Townsend operated under the alias “Samuel Culper Jr.” and held strong ties to the mercantile community in New York. Washington was closely involved in the ring’s operations, frequently advising and directing Tallmadge and the other agents.
One of the most dangerous aspects of their work was transporting intelligence between Woodhull and Townsend in New York and Tallmadge in Connecticut. British checkpoints across Long Island made communication risky, placing both agents and couriers in constant danger. To prevent discovery, Tallmadge devised a numerical system that replaced names and places with three-digit numbers. For example:
Washington: 711
Tallmadge: 721
New York City: 727
Long Island: 728
To further encode traveling intelligence, the ring used invisible ink that would not reveal the text without a separate chemical. The hidden text would also be encrypted in ciphers and coded letters. Under Washington’s specific advice, messages were to be written in the margins of books, almanacs and pamphlets, as blank pages would raise suspicion if caught by a British officer.
Even with the intelligence encoded, the Culper Spy Ring took further steps to safeguard the agents and their reports. Once intel was collected, reports would typically be hidden in goods from Robert Townsend’s shipping firm in Lower Manhattan. Austin Roe would then retrieve the “goods” and transport them 60 miles to Setauket, Long Island, where the reports were hidden on land belonging to Abraham Woodhull. Anna Strong, Woodhull’s neighbor, used her laundry drying line to send signals to Caleb Brewster about the reports’ location. Brewster, who was stationed on the other side of the Long Island Sound in Connecticut, would then row across to pick up the reports and transport them to Tallmadge, who then reported the intel to Washington.
Although Washington understood the risks associated with espionage, he would often grow frustrated with the slow pace of receiving information. Despite Washington’s discontent, the Culper Spy Ring had a fairly successful run. Tallmadge played a role in capturing the British spy John André, in turn exposing Benedict Arnold’s betrayal in defecting to the British. The ring also uncovered a major plan to bombard America’s French allies off the coast of Rhode Island.
The ring’s network extended beyond Tallemadge’s inner circle and included notable individuals, such as the loyalist printer-turned-American spy James Rivington and the tailor, Hercules Mulligan. Although less closely connected to the ring, Mulligan used his tailor shop in New York City to extract information from British patrons during fittings. Mulligan would then have an enslaved man, Cato, transport intel to Washington’s headquarters under the guise of delivering packages. After the war, an appreciative Washington frequented Mulligan’s shop, to which the tailor proudly displayed a sign: “Clothier to Genl. Washington” for all to see. Cato’s fate remains uncertain due to the lack of historical records, but some historians theorize he was freed and went on to live in Massachusetts.
Over the five years the Culper Spy Ring operated, no agents or associates were uncovered, and it took years for their identities to be ultimately exposed — indeed, Robert Townsend’s involvement with the Culper Spy Ring was not revealed until the 1930s. In a revolution often remembered for its battles and ideals, another front was fought in New York, one where secrecy and deception proved just as decisive as victory on the battlefield.
Theresa DeCicco-Dizon is a public historian and museum educator based in New York City.
main image: “Hercules Mulligan and the Spy Network That Saved a Revolution,” by artists Kate Fauvell and Naderson Saint Pierre, as part of the Downtown Alliance’s Revolutionary Reflections project with the Gotham Center for New York City History and Art on the Ave.
