Courtesy of: Smithsonian Magazine

One of many depictions of Agent 355.

During the American Revolutionary War, there was a spy agency called The Culper Spy Ring (also known as The Culper Ring) operating along New York City and Long Island.  Founded in 1778 by General George Washington and Major Benjamin Tallmadge, it was a way for a network of spies to bring information about British battle plans to Washington.  A few members of the Ring were arrested by the British, but their identities were never found out.  George Washington didn’t even know some of the spies’ real identities!  Many people didn’t know that this agency existed until 1929 when letters between Culper Ring spies surfaced.

Besides Washington and Tallmadge, other spies had a major impact on The Culper Ring.  Robert Townsend would pass along information he heard from British gatherings.  He also wrote for a loyalist newspaper where British officers “freely gave him information,” according to History of American Women.  Sarah “Sally” Townsend was Robert’s sister.  At 17 years old and working for The Culper Spy Ring, many found her very beautiful and bright.  She caught the attention of John Graves Simcoe, a British lieutenant colonel who openly told her British battle plans.  Anna Strong, another female spy, would hang certain clothes on her clothesline to alert other spies when someone would pick up and deliver new information that the Ring found or when someone was hosting a meeting.  For example, if a black petticoat was hung on her washline, members of The Culper Ring would know that Abraham Woodhull was at Strong’s house to deliver new findings.

Then there’s the spy, or so people say, whose role puzzles historians.  Woodhull wrote a letter to Benjamin Tallmadge regarding how the British would be reading every piece of mail that entered New York.  He also was concerned that the British knew their letter route.  But it wasn’t this that caught the attention of historians.  Towards the end of the letter, Woodhull wrote “I intend to visit 727 before long and think by the assistance of a 355 of my acquaintance, shall be able to outwit them all.”

A few things to note before we dive into this mysterious sentence.  The Culper Spy Ring used a series of numbers from one to 763, uppercase, and lowercase letters to conceal the meaning of their letters from anyone outside The Culper Ring.  This was called the Culper Code Book, written by Tallmadge.  Numbers one through 47 were used for words beginning with the letter A, 48 to 72 were used for words beginning with B, and so the pattern goes.  Numbers 711 to 726 were used for names of the members of the agency.  For example, George Washington was codenamed “711.”  Numbers 727 to 763 were reserved for places.  You can find the full Culper Code Book here (I suggest taking a look at it – it is very interesting).

Back to the sentence: 727 is the code for New York.  Woodhull intended to go to New York to meet up with “355.”  Many people assumed that 355 was a codename for a spy, so Agent 355 was created by a theory.  In the Culper Code Book, 355 is the code for “lady.”  Many then pointed out that Woodhull wrote “a 355,” meaning “a lady.”  701 is the code for “woman,” so Woodhull may have been talking about someone with a higher place in New York society.  But was this lady affiliated with the Ring?    But there are two names missing from the list of members: Anna Strong and Sarah Townsend.  A new theory emerged, stating that either woman was Agent 355, but many historians disagreed with the fact that code numbers for members of the agency were in the 700s.  Although not much is known about 355’s work in the Culper Spy Ring, we do know how she died, obscurely.   She was aboard a prison ship, while pregnant, and died after giving birth to her son.  Many sources have claimed that she was Robert Townsend’s mistress, birthing his illegitimate son.

Sadly, the letter between Woodhull and Tallmadge was the only time 355 was mentioned.  Maybe there were other letters containing Woodhull’s 355, but they are lost to history, making her all the more mysterious.  Even if she did exist, she has done her job as a secret spy very well.  Why, you ask?  Not a single person can determine her identity.  This would make Agent 355 one of the best spies to ever work for the United States.