Agent "355" & the Culper Ring

Many intelligence historians consider her one of this country’s first female undercover operations officers. Still others refer to her as the “hidden daughter of the American Revolution.” While defending against British transgressions in and around New York, George Washington came to rely heavily on the information she supplied him. But even today, she is known only by the designation “355”, the code-number for "lady" in an encryption system used by the famous Culper Ring.

It was to the Culper Ring that “355” reported, having been selected for the silent service by Abraham Woodhull, chief of the clandestine group. A Long Island farmer, Woodhull’s nom de espionage was Samuel Culper, Sr. His principal agent was a Quaker dry goods merchant named Robert Townsend, who was known as Samual Culper, Jr. This fictitious father-son arrangement formed the basis of the highly effective Culper network.

Utilizing a variety of trade craft, including a type of invisible ink developed by the brother of future Chief Justice John Jay, the Culper Ring provided timely and accurate intelligence to American military leaders, most notably General Washington.

Routes Taken by the Culper Ring

It is believed that “355” was a member of a prominent Tory family, a position that would have allowed her virtually unrestricted access to British political and military leaders operating in the New York area.

For her part, “355” helped expose Benedict Arnold’s treasonous role in the surrender of West Point and neighboring military outposts, an act that earned him a £20,000 gratuity from the British government. She also facilitated the arrest of Major John André, the head of England’s intelligence operations in New York, who was eventually hanged as a spy on orders from General Washington.

While in New York, the debonair André kept company with any number of beguiling and available women. Taking advantage of this, “355” worked the parties he gave and attended, paying careful attention to what he offered during conversations that were often plied with considerable quantities of ale. Any substantive information “355” gleaned from these indiscretions, such as the deal to hand over West Point for payment, was surreptitiously passed by way of the Culper Ring to an appreciative George Washington.It is believed that “355” was actually Robert Townsend’s common-law wife, with whom he had a son. When Townsend learned that his prized operative and lover was to bear his child, he pleaded with her to forgo her dangerous espionage work. She refused, believing, and rightly so, that the information she was providing was of the highest value. Indeed, her days were numbered thanks, so the historical reflection goes, to the traitor Benedict Arnold, who gave her up once he had defected to Great Britain following the arrest of André.

Benedict Arnold

In October 1780, “355” was captured and ordered held in fetid conditions aboard the prison ship Jersey, which was moored in the East River. While incarcerated, she gave birth to a son, whom she named Robert Townsend, Jr., after the Culper Ring operative. She died shortly thereafter. (See note.)

To new intelligence service hires, “355” is often cited as an inspirational example of a trusted field agent, who has retained her anonymity even 222 years following her death. The young woman’s contributions to America’s War for Independence did not go unnoticed by the head of the fabled Culper Ring, Abraham Woodhull, who wrote that she “hath been ever serviceable to this correspondence” and could “outwit them all.”

This biography is excerpted and from the NWHM exhibition Clandestine Women: The Untold Stories of Women in Espionage, Curated by espionage historian Linda McCarthy (2002). She is the author of Spies, Pop Flies, and French Fries: Stories I Told My Favorite Visitors to the CIA Exhibit Center.

NOTE: Most academics debunk this story as mere legend however, Robert Townsend, Jr., a "son" of James Townsend (brother of Robert Sr.) became a lawyer and went into politics. One of his pet projects was the Prison Ship Martyrs Memorial Fund which eventually became the Prison Ship Martyrs Monument at fort Green Park in New York. This monument, which is nearly 150 feet tall, commemorates the men and women who lost their lives aboard these horrible prison ships. Which begs the question: Could Robert Townsend have asked his brother to raise a bastard son, to give him a chance at a respectable life?