The Spy Who
The Spy Who

The Spy Who Betrayed the American Revolution | The Mystery of Agent 355 | 5

July 14, 2026 • 34m

Summary

⏱️ 7 min read

Overview

This episode explores the mystery of Agent 355, an unidentified female spy who worked with George Washington's Culper spy ring during the American Revolutionary War. Host Charlie Hickson speaks with historical fiction author Kit Sargent about the challenges of researching female spies from this era, the limited evidence surrounding Agent 355's identity, and how women's invisibility in society made them effective intelligence gatherers. The conversation examines various theories about who Agent 355 might have been and explores the crucial role of espionage in securing American independence.

The Mystery of Agent 355 and the Culper Ring

Kit Sargent introduces Agent 355, explaining that she was likely associated with the Culper spy ring during the Revolutionary War. The code name 355 meant 'lady' rather than 'woman,' suggesting she may have been from wealthy New York society. Despite nearly 200 surviving letters from the Culper Ring, Agent 355 is mentioned only once by Abraham Woodhull, making her identity one of history's enduring mysteries.

  • Agent 355 was likely associated with the Culper spy ring, though probably not an official member
  • The code 355 meant 'lady' rather than 'woman,' suggesting she was from high society
  • Only one reference to Agent 355 exists among nearly 200 surviving Culper Ring letters
  • The Culper Ring was a group of American spies based in British-controlled New York

Myths and Speculation About Agent 355's Identity

Kit Sargent discusses how historian Morton Pennypacker in the 1930s created many rumors about Agent 355 that have since been accepted as fact, including claims that she was Robert Townsend's lover, became pregnant, was held on the notorious Jersey prison ship, and died there after giving birth. Sargent explains there's no evidence women were ever held on these disease-ridden prison ships, yet these stories persist in popular accounts of Agent 355.

  • Morton Pennypacker uncovered Samuel Culper Jr.'s identity as Robert Townsend in the 1930s but also created unverified rumors about Agent 355
  • Popular myths claim Agent 355 was Robert Townsend's lover who died on the Jersey prison ship after giving birth
  • No historical records show women were held on prison ships, making the story unlikely
  • Three possible identities explored: Sally Townsend, Elizabeth Bergen, and Margaret Moncrief

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