The Truth About the Culper Ring, the First U.S. Spy Family — and the Real Agent 355

Agent 355, a vital character in the DC series Y: The Last Man, claims to be a member of the clandestine (and centuries old) spy organization, the Culper Ring. And it turns out there really was such an organization — and it began in the 18th century, under the orders of George Washington. There was even a real-life Agent 355.

The Truth About the Culper Ring, the First U.S. Spy Family — and the Real Agent 355

George Washington and Military Intelligence
George Washington knew the value of quality military intelligence, with first president serving as a British Colonial spy in 1753.

Washington surveyed the Ohio Territory during this time, gathering informational about French military presence and troop movements in the area.

Thanks to a first hand knowledge of the value of military intelligence, Washington allotted a considerable amount of money — over 10% of the total armed forces budget during the Revolutionary War — to establishing intelligence networks. General Washington tasked one of his most trusted officers, Major Benjamin Tallmadge, with forming this early intelligence community.

Operational from the summer of 1778 to 1783, the Culper Ring consisted of approximately twenty civilians from the village of Setauket, an area on the North Shore of modern Long Island. The group specialized in relaying information regarding movements of British troops through British-controlled New York City.

Washington did not know the true identities of most Culper Ring members, but this did not impact his trust in the group of patriotic spies. Two key code names appear repeatedly in tales of the Culper Ring — those of Samuel Culper, Senior and Samuel Culper, Junior. We now know that Culper, Sr. was really Abraham Woodhull, and Major Benjamin Tallmadge selected Woodhull due to their longstanding friendship. Woodhull led the Culper Ring, and recruited the pacifist Robert Townsend to aid in its operations as Culper Jr.

Washington directly addressed the duo using the Culper designation in written communication, but nobody knows whether General Washington ever knew the true identities of the duo.

The Culper Ring made used of dead drops, disinformation, and coded messages in its day-to-day activities. Members wrote in a variety of sympathetic stains — iron salt inks that appear invisible — to transfer intel, with these "invisible inks" often used to write in the gutter space and in between lines of traditional pen and ink messages. To hide particularly sensitive information, messages would be written on specific pages of enormous reams of paper en route to their destination.

The identity of Culper, Jr. remained a mystery into the mid-20th Century — until the discovery of a series of Culper Ring letters found in the home of Robert Townsend. The handwriting of Culper, Jr. matched that of Townsend.

The Truth About the Culper Ring, the First U.S. Spy Family — and the Real Agent 355

The Real Agent 355
While the fictional Agent 355 exists within the pages of Y: The Last Man (and claims to be a member of an extended Culper Ring), there was a real-life Agent 355 in the Culper Ring.

A number of members identified themselves via numerical cypher, with George Washington taking 711, while 355 belonged to a member by the name of "lady." Nobody knows the exact identity of Agent 355 — but historians believe Agent 355 to be a member of a wealthy British family. She made use of her lofty position and social standing to obtain information. Agent 355 probably died in the hands of the British, by hanging.

And Agent 355 wasn't the only female spy. "Nancy" Anna Strong also aided the Culper Ring, directing members to safe meeting locations. Nancy accomplished this task by arranging laundry on a clothesline to form a numerical code corresponding with local docks. British infantry captured Anna Strong's husband early in the Revolutionary War, but she secreted supplies and food to him aboard a prison ship, likely saving her husband's life.

The top image is a painting entitled The Washington Family by Edward Savage. The painting resides in the U.S. National Gallery of Art and is within PD. The second image of George Washington is a portrait by Rembrandt Peele, and is held at the M. H. de Young Memorial Museum/PD. Y: The Last Man Agent 355 image from Y: The Last Man #58. Sources are linked within the text. Read Y: The Last Man.