During the midst of the American Revolution, a mysterious figure known only by the code name “355” emerged. They became a crucial player in a shadowy, covert spy network known as the Culper Ring.
To this day, her identity remains shrouded in secrecy. But her bravery and cunning in the face of danger seem to have turned the tide of the war in favor of the fledgling United States.
There are many theories as to who she was. Possibly a woman of high social status, a commoner, or simply an informant with useful information. But 355’s actions helped to expose some of the biggest plots in American history.
From uncovering treachery to keeping her identity under wraps, her story is one of intrigue, danger, and sacrifice. It continues to captivate historians and amateur sleuths alike to this day.
The American Revolution and the Culper Ring
The American Revolution was a tense, violent period for the burgeoning nation. It needed all of the advantages it could muster.
The Culper Spy Ring became one such advantage. It was a group of covert American spies that fed George Washington critical information on British troop movements. The ring was led by Major Benjamin Tallmadge.
The Culper Ring operated mostly in and around New York City for five years. They used many protective measures like pseudonyms as well as a numerical identification system to safeguard their identities.
Tallmadge’s group played a crucial role in the war effort. They shuttled information across British territory and enabled Washington to take decisive actions.
This included alerting Washington to a planned British expedition in Rhode Island in 1780, which the Americans were then able to repel.
The group of undercover spies was never revealed. Their identities stayed a secret even to George Washington.
Altogether, the Culper Spy Ring’s successful intelligence-gathering efforts helped tip the scales in favor of the ultimately successful American Revolution.
During its active years, the Culper Ring likely had many agents working to procure and convey secrets to help win the war. Benjamin Tallmadge recruited numerous friends and made many connections in the effort.
Although none were unmasked at the time, modern historians have found many of their true names. These include Austin Roe, Caleb Brewster, and Robert Townsend, a reporter who posed as a Loyalist.
Tallmadge’s chief agent, Abraham Woodhull is believed to be the individual that recruited an agent whose identity has never been discovered for certain. This is Agent 355.
Agent 355 was an important member of the Culper Ring. But her real identity is still unknown, despite several theories about who she may have been.
Agent 355 likely lived in New York City. She maybe had some degree of high social status. Sources show that she had many connections with high-ranking Loyalists. She even may have been the lover of the aforementioned Townsend.
No historian can say for sure. Documents and other evidence for her identity are slim.
The only actual mention of Agent 355 comes from a coded letter sent in August of 1779 from Woodhull to Washington. In it, he mentioned he traveled to New York to seek the assistance of the lady “355.”
The term “agent” was not routinely applied to spies during that era. Some scholars question the existence of Agent 355 altogether.
Benedict Arnold’s Plot and Capturing a British Spy
Agent 355 was known for her involvement in exposing Benedict Arnold’s treachery. This was a key accomplishment of the Culper Ring.
Reportedly, 355 was one of the key players in uncovering Arnold’s plot to hand over West Point to the British. This was a plan that would have disastrous consequences for the Continental Army.
For some time, Agent 355 was gathering intelligence on Arnold’s activities. Her reports to her superiors ultimately led to his downfall.
During her investigations, Agent 355 also made contact with Major John André. This was a British intelligence officer who was working closely with Arnold.
André, head of the British Secret Service in America, was a crucially important figure in the British army. He had access to information that could have been extremely useful to the American cause.
Through her interactions with André, Agent 355 was likely able to obtain valuable intelligence on British plans and activities.
However, her relationship with André also put her in great danger. As the British became aware of André’s capture, they also may have learned of his connection to Agent 355. Her identity was compromised.
Agent 355’s Ultimate Fate
Agent 355’s fate is a subject of great debate. Shrouded in mystery and with little concrete information available about what happened to her, it’s possible we may never know.
According to some accounts, after the capture of André, she was arrested in 1780. She was then imprisoned in the HMS Jersey. This was a notorious prison ship used by the British during the American Revolution.
By these accounts, it was believed that she was possibly pregnant and gave birth to a son on the ship named Robert Townsend Jr. This speculation gave further credence to 355 being Townsend’s lover.
However, there is no definitive evidence to support this claim. Many historians wrote it off as completely false.
Therefore, there is no telling what ever happened to Agent 355.
Who Was Agent 355?
Despite many theories and speculations, the true identity of Agent 355 remains unknown. The code name appears only once in a letter, leaving historians to make educated guesses.
The most popular candidate for Agent 355 is Anna Strong. She was a neighbor of Woodhull. Woodhull played an important role in signaling between Culper Ring members.
Some historians believe that Strong was not an official spy. Rather, they believe that she was a supporter and occasional participant who lent her assistance when possible.
As discussed, many have also suggested that 355 was Robert Townsend’s common-law wife. Stories of their love tend to support this theory.
Otherwise, 355 could have simply been a nameless woman. Someone close to André, Tallmadge, and other important figures.
While some historians support the idea that 355 could have been a real person, others dismiss the concept entirely as a romanticized myth. Surely, many of the accounts of 355’s deeds and exploits are impossible to verify and the lack of hard evidence makes for even shakier ground.
In the end, the true identity of Agent 355 remains a mystery. Historians will continue to debate and make speculations, but it is more likely that we will never know.
Bleyer, Bill. “The Myth of Agent 355, the Woman Spy Who Supposedly Helped Win the Revolutionary War.” Smithsonian.com. Smithsonian Institution, March 21, 2022. https://www.smithsonianmag.com/history/the-myth-of-agent-355-the-woman-spy-who-supposedly-helped-win-the-revolutionary-war-180979748/.
“Culper Spy Ring.” George Washington’s Mount Vernon. The George Washington Presidential Library at Mount Vernon. Accessed April 18, 2023. https://www.mountvernon.org/library/digitalhistory/digital-encyclopedia/article/culper-spy-ring/.
Kilmeade, Brian. George Washington’s Secret Six: The Spy Ring That Saved the American Revolution. New York, NY: Penguin, 2013.