This Mystery Woman Was One of America’s First Spies - OZY | A Modern Media Company

This Mystery Woman Was One of America’s First Spies

This Mystery Woman Was One of America’s First Spies

By Katherine George


History rarely covers the role of women in war, but one of America’s first spies was female.

By Katherine George

From her post in New York City, she wrote a letter in invisible ink filled with essential intelligence, folded it and prepared it for its journey to the Washington office. The American Revolution was in full swing, and this correspondence would relay vital information to Gen. George Washington through the Culper Ring. The sender? The faceless but pivotal female spy known as Agent 355.

The Culper Ring was a consortium of spies put together in 1778 by Benjamin Tallmadge under Washington’s orders during the British occupation of New York City. Agent 355 was allegedly selected for service by Abraham Woodhull, the ring’s leader, who went by the alias Samuel Culper, Sr. To this day, the mysterious spy is credited as one of America’s first female undercover operatives and was integral to America’s wartime efforts. Yet despite her bravery, her true identity remains unknown more than 200 years later.

Keeping the woman’s identity a secret might have been both calculated and necessary.

Despite her anonymity, Agent 355 was pivotal in exposing Benedict Arnold’s treason, and she was responsible for the arrest of Maj. John André, the leader of British intelligence in New York. Kenna Howat, a historian at the National Women’s History Museum, says her wartime “contributions are largely undisputed,” noting that Woodhull wrote that Agent 355 “hath been ever serviceable to this correspondence” and could “outwit them all.” In his book, Covert Operations Management, Robert Almonte says that 355 was one of the Culper Ring spies who had “the most success.” In fact, after her service ended, the ring ceased to exist a few short years later.


Benjamin tallmadge by ralph earl

Portrait of Col. Benjamin Tallmadge, organizer of the Culper Ring, with his son William Tallmadge. This is a 1790 portrait by American painter Ralph Earl.

Source Public Domain

So, who was this brave badass heroine? One theory is that she was part of a prominent Tory or Loyalist family, which would have granted her the ability to move through high society, mingling with political and military leaders stationed in New York. It would have made her invisible, the last possible suspect in espionage. Howat says keeping the woman’s identity a secret might have been both calculated and necessary to “protect her in the aftermath of the Revolutionary War.”

In George Washington’s Secret Six: The Spy Ring That Saved the American Revolution, Brian Kilmeade explores the possible identities of Agent 355. One of the most popular theories, he writes, is that she was Anna Smith Strong, a Long Island judge’s daughter with ties to the Culper Ring. Another theory says she was the common-law wife of Culper Ring operative Robert Townsend — or, if not, that he was in love with her. There are several other women, like Betty Floyd, Mary Underhill and Sally Townsend, who were connected to the ring that historians have speculated were Agent 355. 

Howat says it’s even been suggested that 355 was more than one person, as according to the Culper Ring’s sophisticated encryption system, 355 was the generic code number for “lady.” Some even go so far as to suggest 355 was a random woman who gave the ring intelligence, but wasn’t formally connected to them. Whoever she was, despite pressure on the ring to reveal her identity, and historical inquiries into the past, Kilmeade describes the protection of her name as “watertight.”

Culper ring code

A page from the Culper Ring’s code book, with noteworthy people and place names listed side by side with numerical representations.

Source Public Domain

It seems that Agent 355 met her untimely end in 1780, when she was finally captured by the British and died on a prison ship, the HMS Jersey, from severe maltreatment. Conspiracy theorists believe she might have given birth to a child on the ship before she died, but many historians debunk the theory, as the conditions on board were not favorable to a healthy pregnancy. Regardless of whether or not she bore an heir, Agent 355’s legacy lives on. Like all covert government agents, her anonymity “does not diminish” her contribution, says Howat.

“She represents all covert agents … whose true identities are never revealed and whose stories are never told, but who offer their service and their lives on behalf of their country,” writes Kilmeade. Agent 355 heroically shaped history, but will never completely be a part of that history, compared to the names we study and revere.

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