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In 1778, George Washington had a problem. He needed to get more accurate information about what the British were doing so that his Continental Army could better fight against them. His previous attempts to learn about their plans and resources hadn’t gone as well as he had hoped, so he turned to a young man in his army: Major Benjamin Tallmadge.
Benjamin Tallmadge was twenty-four years old and from the colony of New York. He had joined the Continental Army to fight against the British and win independence for the colonies. Tallmadge was intelligent, creative, and knew that a group could accomplish things that one person could not. With this in mind, he formed a secret organization called the Culper Spy Ring.
Tallmadge knew that he wouldn’t be able to get information from the British by himself because they would recognize him as a member of Washington’s army. He went back home to Setauket, New York, and asked his neighbor, Abraham Woodhull, for his help. Woodhull and Tallmadge had grown up together and Tallmadge knew that he could trust him. Woodhull agreed to be a spy and took on the alias “Samuel Culper.” Tallmadge and Woodhull recruited other friends
of theirs into the spy ring, including Anna Strong and the mysterious “Agent 355.” They were so secretive and did such a good job at keeping one another safe that to this day we still don’t know the identity of Agent 355. Even Washington didn’t know who all of the members really were!
The Culper Ring had several significant successes. It was able to feed information about the British to Washington. Tallmadge made up a code and wrote it down in a dictionary, so members of the ring could send each other secret messages. The code used numbers to represent letters or important words. Using this code,
for example, the numbers “711 282 736” would mean “Washington in New Jersey”. The ring printed these coded messages in friendly newspapers or wrote them
in invisible ink on otherwise boring pieces of mail. Tallmadge would gather all of the information together and report it to Washington.
There are many stories about how the spies carried out their activities under the guise of going about their regular lives. For example, Anna Strong lived near the coast and tradition has it that she would put her laundry outside to dry where another spy on a ship could see. Supposedly, she would hang up a black petticoat and a number of handkerchiefs.
This would indicate which of six coves the spy needed to meet Woodhull in. It is hard to say for certain, however, because the group did such a good job guarding their secrets and methods.
The Culper Ring was able to uncover the existence of a British spy in Washington’s ranks and it became their most memorable success thanks to the mysterious Agent 355. Agent 355 was likely a woman from a wealthy family that was friendly with the British in New York. Because of this, she learned that there was a spy high up in Washington’s forces. She didn’t know who the spy was, but she sent a message to Tallmadge to be on the lookout. Because of her warning, Tallmadge was on high alert when a British officer was captured and found to be carrying information on the American forces. This information was from Benedict Arnold, one of Washington’s trusted generals. Arnold had secretly switched to the British side and was feeding them information. Working together, the Culper Ring was able to put a stop to his scheme and help America break free from British rule.