The Tale Of Agent 355: An Elusive And Mysterious Female Spy Who Aided The Culper Spy Ring During The American Revolution
You may have caught a screening of “The 355” after it was released in January of this year. The spy thriller, directed by Simon Kinberg, was packed by a women-led cast and followed a CIA agent named Mason “Mace” Brown as she linked up with a rival German intelligence agent.
If so, you probably recall how at the end of the film, “Mace” finally explained the significance of the number “355”– it was in honor of the codename used by a legendary female spy who helped George Washington navigate the American Revolution.
And this mystifying yet true tale actually began back in November 1778. The Revolutionary War had already been underway for over three years, and it was at that point when George Washington instructed Major Benjamin Tallmadge to put together a secret intelligence service.
This service would be specifically used to spy on British operations occurring within New York City.
Tallmadge was originally from a small Long Island village known as Setauket, so it was there that he officially founded the Culper Sky Ring.
Much of the recruits he added to the service were friends from his hometown, including a sailor named Caleb Brewster, his childhood best friend Abraham Woodhull, and an Oyster Bay merchant named Robert Townsend.
Some of these spies went on to make regular pilgrimages to New York City, collecting information via inconspicuous means.
The others would send letters to Tallmadge, where he was stationed in Fairfield, Connecticut. Then, this intel would be relayed to George Washington.
And, of course, spies cannot be true spies without codenames– so each of the recruits had their own.
Elena – stock.adobe.com – illustrative purposes only, not the actual person
Tallmadge himself was known as John Bolton. Woodhull took on the name of Samuel Culper, and Townsend called himself Samuel Culper, Jr.
On top of the names, though, Tallmadge also took it upon himself to create an extensive code that substituted numbers for various words.
There were 763 words given distinct numerical codes. Plus, an alphanumeric key was also provided in the event spies needed to spell out a word that was not assigned a number.
Anyway, by August 15, 1977, Tallmadge had received a letter from Woodhull that detailed how the British were opening and reading all of the mail that passed through New York. Moreover, it was revealed that the British had found out about the Culper Ring’s courier route.
“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,” Woodhull also said in the letter.
“727” was the code term for “New York,” and “355” actually meant “lady.” So, in essence, Woodhull planned to travel to New York City again, where he would gain the help of a female confidante in hopes of evading enemy surveillance.
Interestingly, though, this mention of “355” was the only time this number sequence was ever found within surviving historical correspondence. Thus, the legend of “Agent 355” was born.
Now, many history buffs have jumped to the conclusion that this female confidante was an agent herself.
However, if we reference the codebook and look at Woodhull’s letter– which references “a 355” instead of just “355”– it appears that the mystery woman was not an official agent at all.
And despite “355” not appearing in the rest of surviving correspondence, some historians have correlated this mystery woman to the use of other terms throughout the communication. Most notably, the code “701,” which meant “lady” in a high societal sense.
This would make a lot of tactical sense, too, since a woman of high social standing would have been the perfect eavesdropping ear to pick up on British leader gossip and relay the intel.
For instance, a major named John André loved to party and was known for constantly being in the company of charming women.
Some of the Culper Ring’s most beneficial intelligence was even gathered when André and other men of his standing were in town. For instance, one tip gathered regarding Benedict Arnold’s betrayal was facilitated with the help of André.
This intriguing and mysterious legend of “Agent 355” as a deceiving and resourceful socialite is just one of many theories about the woman’s identity, though.
In fact, many scholars instead believe that this woman was Anna Smith Strong– one of Woodhull’s hometown friends and later cousin-in-law.
That theory claims that Strong issued signals to the other secret service spies by hanging specific laundry items out on her clothesline.
A black petticoat, for instance, meant that Woodhull had a message for Brewster to transport to Fairfield. The number of handkerchiefs that Strong put on her clothesline also correlated to different covert meeting sites.
The tale of Strong also led the way for another “Agent 355” legend– which paints “355” as Townsend’s wife who had become imprisoned on a British prison ship known as HMS Jersey. It was on that ship where Townsend’s wife died and also potentially birthed their son beforehand.
Again, though, there is a lack of evidence to support this theory. It is believed that Strong visited the Jersey once, though, in 1778– after Strong’s husband, Selah, was incarcerated.
According to historical records, Selah was imprisoned in the Jersey, and Strong was allowed to bring him food.
The final theory regarding “Agent 355” points toward Townsend’s and Woodhull’s younger sisters, Sally Townsend and Mary Underhill.
At the time, Sally was a teenager who also reportedly contributed her spy services to the Culper Spy Ring.
Similarly, Woodhull stayed at his sister Mary’s Manhattan boarding house anytime he visited New York City to collect intel.
So, while we will likely never know the true identity of the woman known as “355,” we can at least now be certain that women were turned to as valuable allies during the Culper Spy Ring’s efforts.
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