The Mysterious Agent 355 by Amber Leigh

She’s been fascinating people since 1948, when Long Island historian Morton Pennypacker first wrote about her.

The problem is, she might never have existed. Not as Pennypacker described her, that is. But I’ll explain.

We know Agent 355 was a real person…specifically, a woman who assisted George Washington’s Culper Spy Ring. Washington’s spymaster, Benjamin Tallmadge, devised a numerical code dictionary for the Culper spies to use when composing their intelligence letters.

And the code number for “lady” was 355.

These days, people often use the words woman and lady interchangeably. But in eighteenth-century parlance, a lady was distinct from a mere woman. Simply put, ladies were women from the upper classes…usually from the landed gentry or urban elites.

And ladies were very carefully brought up. They were educated in the feminine arts and social graces of the time. Not all ladies were wealthy, though; some lived in a state of what one might call “genteel poverty”.

In any case, we know 355 was real because Abraham Woodhull – that is, Samuel Culper, Senior – mentioned her in one of his intelligence letters. He didn’t say whether she was rich or poor or what exactly she did, only that she helped him in some way. Of her existence, this is the only real evidence we have.

But we don’t have any evidence at all when it comes to her actual identity. This is something historians have loved to speculate about.

Anna Smith Strong

If you haven’t yet read Washington’s Spies: The Story of America’s First Spy Ring by Alexander Rose, I highly recommend it. In my humble opinion, it’s the best (and probably the most accurate) book about the Culpers you’ll find out there.

Alexander Rose, by the way, was the co-writer and co-producer for the AMC series Turn: Washington’s Spies. The series was based on his book.

So…Rose puts forward Anna Smith Strong as 355. She was Woodhull’s neighbor in his hometown of Setauket, on eastern Long Island. On at least a few occasions, she traveled with him on his journeys to and from New York. Because the checkpoint guards were less likely to search men who traveled with their wives, she pretended to be Mrs. Woodhull, and the ruse succeeded.

Mary Underhill

Another candidate for 355 – though less likely, in my view – has been Woodhull’s sister, Mary Underhill. She lived in New York with her husband, where they ran a boardinghouse. Because Woodhull stayed there whenever he went to New York, Mary probably knew her brother was spying. Whether she ever helped him in his spying, though, is something we cannot know.

Sally Townsend

A more intriguing candidate for 355 is Robert Townsend’s sister, Sally. Morton Pennypacker strongly believed Sally shared important information with Robert – Culper, Junior – which he then passed on to George Washington.

Since then, the theory that Sally Townsend was a spy has been a popular one, though it appears Pennypacker never thought to identify her as the “lady” from Woodhull’s letter. Historian Paul R. Misencik, in Sally Townsend, George Washington’s Teenage Spy, explains why he believes Sally may have been 355.

The thing is, Sally would have had to be acquainted with Abraham Woodhull in order to be that lady. Perhaps they were acquainted, though there doesn’t seem to be any proof of that. And even if they did meet, it’s hard to say whether they knew each other well enough for the level of trust required to spy together.

So, as I do in the cases of Anna Strong and Mary Underhill, I have my doubts about Sally Townsend being 355.

Then who was she?

Woodhull’s word choice is key, as is the fact that he addressed all his intelligence letters to Benjamin Tallmadge, who later decoded them. In the letter I mentioned above, he told Tallmadge that “by the assistance of a 355 [lady] of my acquaintance, [I] shall be able to outwit them all.” Below is a caption of the sentence from that very same letter, written August 15, 1779:

From the George Washington Papers. Courtesy of the Library of Congress.

But Tallmadge, like Woodhull, was a Setauket native. He was close to Woodhull’s age, and they grew up together. And his connection to Anna Strong was as close as Woodhull’s, if not closer. His widowed father, the Reverend Benjamin Tallmadge, married Zipporah Strong on January 3, 1770. And Zipporah was the sister of Selah Strong, Anna’s husband.

Therefore, it seems strange that Woodhull, in addressing Tallmadge, would refer to Mrs. Strong as “a lady of my acquaintance [emphasis added].” That would infer that Woodhull knew her, and that Tallmadge did not.

But with Anna Strong, that couldn’t have been the case. Otherwise, he’d have written “a lady of our acquaintance” or “a lady we know.” Wouldn’t he?

Of course, Woodhull did know Mary Underhill much better, as she was his sister, and I’m sure Tallmadge knew her, too. But a close relative, with whom one grew up, is no mere “acquaintance.” So Mary Underhill was also probably not the mysterious unnamed lady.

Now it is very likely that Tallmadge never met Sally Townsend. And again, we don’t know for sure whether Woodhull ever met her or not. Even if he did, the odds are high that Robert Townsend would not have permitted Woodhull to stop off in Oyster Bay to glean secrets from his little sister.

That doesn’t mean Robert himself never gleaned a secret or two from Sally. But whether he did or not, the way Woodhull wrote the above sentence makes it sound as though he received direct assistance from this lady. That wouldn’t have been the case if Robert gathered the information from Sally and then shared it second-hand – and verbally – with Woodhull afterwards.

Like I said, the clue seems to lie in Woodhull’s word choice.

So…who, then, was 355?

This is a subject I will be returning to in the future!

Original post: https://amberleighauthor.com/2020/01/07/the-mysterious-agent-355/

Thank you to guest contributor, Amber Leigh!

D. K. Marley

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