The Spy Who - The Spy Who Betrayed the American Revolution | The Mystery of Agent 355 | 5
Episode Date: July 14, 2026Right on schedule for America's 250th birthday, we’ve wrapped our arc on Benedict Arnold - the American military officer who turned his back on his own country to spy for the British Army. ...Tucked away within this complex story, lives the unsolved identity (identities?) of Agent 355. The female spy who helped her country by gleaning military secrets from the British. In this episode, Charlie Higson explores just who this woman (or women) might have been, with ‘355: The Women of Washington's Spy Ring’ author, Kit Sergeant. Together, they break down this remarkable tale of betrayal and deception… all in the name of freedom.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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I'm Charlie Hickson and this is The Spy Who, an Audible original.
Thank you for joining us on our final episode of The Spy Who betrayed the American Revolution.
Right on schedule for the USA's 250th birthday,
we've wrapped our season on Benedict Arnold, the American military officer,
who turned his back on his own country to spy for the British army.
His actions jeopardised the future of 13 breakaway colonies
and their quest to free themselves of British rule.
And tucked away within all the layers of this complex story
lives the unsolved mystery of just who is Agent 355,
the female spy who helped her country
by gleaning military secrets from the British.
I'm joined now by someone who's going to help break up.
down this mystery. Kitt Sargent. A writer of historical fiction, Kitt's probably best known for her
women's spies series, stories that shed light on the often overlooked roles of women's spies throughout
history, particularly during World War II, the American Civil War and the Revolutionary War,
which she covered in her book, 355, the women of Washington spiring, which means that she's
absolutely the right person to help break down this remarkable tale of.
betrayal and deception, all in the name of freedom.
So Kit, thank you so much for joining us all the way from Chicago.
You're welcome. It's a pleasure to be here.
Now, I should probably let our listeners know that we're actually recording this in June,
and so I really should wish America a happy early 250th birthday.
Do you have any plans for the big day?
Not so much right now. I'm still trying to figure that out.
you're not actually no I'm not going to go there
I was going to ask if you're going to go for the big show
in Washington but let's not ask
yeah that's pretty me from that part
away from any of that
let's just celebrate all that is good
and wonderful about America
well I hope you find something exciting to do
on the day
maybe you could find an effigy
of a British person and set fire to it or something
but let's
let's dive right in and unspool the mystery
surrounding Agent 355.
We'll get into the question of our identity later,
but since Agent 355 only featured very briefly in our story,
could you just start off by summing up?
Just who was Agent 355?
Sure, so we believe that 355,
I'm going to call it 355 on accident,
it probably is 355.
We have a huge highway called 355
that runs right around Chicago that I use a lot,
So in my head, I'm always thinking 355 because of that highway.
Well, let's go with 355.
So she was believed to be associated with the Culper Ring.
And some people think she was the sixth member of the Culper Ring.
I don't think that she was an actual member, member.
And the real reason why is because we only have one reference to her.
And it comes from a letter written by Abraham Woodhull, who is also known as Samuel Coper, Sr.
and we have probably almost 200 surviving letters from the Culper Ring to and from each other,
Washington, Pelmage. And we only have that one reference. And so while she, I don't think she was
a sixth member of the Culper Ring, she definitely was associated with them. And Abraham Woodhull
knew her at least a little bit and had a high reference for her. Right. And I mean, correct me if I'm
wrong, but I believe that 355 was essentially code for a woman rather than that being her code number.
Yes, and actually it means lady.
And back then, lady.
So there is another code for woman.
So because it's lady, we think she might have been kind of rolling in high New York society, maybe of wealth,
because there was another code for woman, and they didn't use a woman, they used lady.
And just to clarify, the Culper ring was this group of American spies based in New York who were spying on the British.
How did you first come across Agent 355? And why did she become an inspiration for your book?
Well, I started publishing novels, contemporary women's fiction novels, and I decided I wanted to go historical fiction.
So I didn't know where to start. So I literally Googled Smart Women in History.
you never heard of. And the first thing that popped up was 355. And I was like, yeah, I've never,
I've never heard of 355. Who was she? Oh, she was a spy during the Revolutionary War.
And then I started digging and coming up with possibilities. And that became those, the three ones I thought
possible for her identity became the main characters in my book.
What's really interesting for me is that there's this huge mystery around her because
as you say, there's only that one very short reference.
to her. And, you know, the speculation ranges from it wasn't a person at all to a number of
different names. And can you talk us through how you ended up choosing the personality for Agent 355
that you did for your book? Yeah. And I'll say there's a lot of rumors that have popped up about her.
So when you Google her now, a lot of it has been accepted as fact, which we don't have primary
resources. And actually, a lot of it came from Morton Penny Packer, who was a Long Island
historian, and he had a huge collection of revolutionary war material. And he's famous because he
uncovered Samuel Coper Jr.'s true identity, who was Robert Townsend. And this was in the 1930s.
So Samuel Copeland Jr. was a huge part of the Culper Ring, but Washington did not want to know his
identity. And in fact, no one knew his identity until Morton Penny Packer confirmed it about
150 years later. So Morton Penny Packer knew his stuff, but he did make up a lot of rumors about
355 that have been accepted as fact nowadays. A lot of them stem from Robert Townsend themselves.
So part of it was that 355 was Robert Townsend's lover. She was impregnated by him. She was held on a
prison ship, the Jersey, which was one of the more infamous prison ships in New York Harbor,
and that she died aboard the prison ship, but she gave birth to Robert Townsend's son.
So all of this now, because it's basically been repeated so many times, are kind of accepted as fact that this woman really was Robert Townsend's lover and had this baby aboard this prison ship.
There's actually no record that women were held aboard the prison ships, and they were so disease-ridden that I can't imagine any woman would be able to viably carry a baby to just.
determine having aboard the prisonships.
So there are, since then,
other names have been put forward, haven't they?
Yeah, so I went with Sally Townsend,
who was Robert Townsend's sister,
and then also I went with Elizabeth Bergen,
who definitely, we have lots of actually records
that she did something with the prisoners.
It was rumored that they were the prison ships.
I think that she helped get people off Long Island, New York.
and free prisoners from there.
But she was definitely associated with Culper's for sure.
And then also Margaret Moncrief,
who was sort of a loyalist spy
that might have been living among patriots
and possibly could have switched allegiances at some point.
And, I mean, so did you create a sort of composite
out of those three characters,
or did you include them and Agent 355?
Yeah, so in my book, 355,
The Women of Washington Spiring,
I have them as three main characters.
and I sort of switch me viewpoints off chapter by chapter,
so I go through each one of them.
And as a writer,
was that one of the things that drew you to using 355 as a character,
the fact that so little is known about them,
it gave you space to create your own character
and tell the story that you wanted to tell?
For sure, yeah.
I've actually written nine historical fiction books,
and they're all almost about women's spies
that you are real-life people that most people haven't heard of.
And that was one of my goals is to bring these women to light
and make sure their stories get told.
And, well, presumably you must have done a huge amount of research into this.
I mean, can you talk about some of the stuff that you uncovered?
Sure. I actually have a science background.
So I have what I like to call a completely use of this degree in rain biology.
And I think my science background actually contributes a lot to my research.
And sometimes I spend my days researching and I forget to write actual words.
My sister lives outside of Detroit.
So she's near the University of Michigan and they have an amazing revolutionary library.
So I spent a lot of time there.
I got to see actual letters written between John Andre and Benedict Arnold.
So that was pretty amazing for sure.
And then most of it is online and or trying to get my hands on these books that are, you know, 150, 200 plus years old.
And in your research, did that kind of reinforce or change any ideas you had about America and about the war?
For sure. I should bring up coverture a little bit because it was a law that actually sort of just fizzled out, but not.
Part of it were still active in the 70s and 90s here in the United States where women were basically a married woman was not separated from her husband and she had no legal standing.
So everything she owned, even if it was a present given to her by her husband during her marriage, it belonged to him.
So she couldn't own property.
She couldn't own anything.
She couldn't be sued.
She obviously didn't have her own bank account.
So that really struck me as powerful that these women were really second-class citizens, but yet a lot of them came out onto their own right and were, you know, they were as patriotic as anyone else.
But then at the same time, they were underestimated because men really didn't think that they would be untrustworthy or that they would be, you know, listening to them when they talked about man wore things at dinner and that would be able to pass it on to British generals or American generals or British generals because there were spies that were working for the other side as well.
They were working on both sides.
but because the men never occurred to them that they could be double agents,
they would talk right in front of them and the women would go and report them
and get it to the right channels so that the right side knew what the other side was doing.
Now, Kit, bearing in mind what you said before about women having officially very little agency,
how much was written about the female characters that you researched and put into your books?
and how much were you having to kind of fill in the gaps yourself?
Yeah, I tried to go with primary sources, which are really just letters and tax records of that time,
because like I said, a lot of it came about later on that people were like,
where are the primary sources that you got that?
How much of that is you making stuff up and going through the sources?
So in the mid-1800s, and I wrote a book on The So, and I wrote a book on the source,
Civil War, so I know this was happening. There was a lot of embellishments. And I think even then,
they were going back to the Revolutionary War and embellishing stories that they heard. In the United
States, Molly Pitcher and Betsy Ross are like women that we associated with the Revolutionary War,
but there might not have actually been a Molly Pitcher or a Betsy Ross, or they were
combinations of different women. And I think part of that could be the coverture because
they didn't have the records of these women on their own outside of their husband.
So it was difficult sorting through fact versus fiction.
I mean, do you think that there might be out there somewhere buried under loads of other papers, somewhere obscure, some more information that would lead us to giving a definite identity to Agent 355?
Oh, for sure.
I spent last night I went down my rabbit hole again and I'm like, there's got to be something.
Like if you connect this piece to that piece to that piece, like, lo and behold, we will find it.
But as of right now, we haven't.
But, you know, maybe somewhere there's an attic with a trove of papers that were not, you know, no one ever went through.
And we're like, oh, wait a minute.
I heard a rumor that the CIA poisoned my granddad.
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So you're about to Agent 355.
We know this woman was an operative working for George Washington's Culper Spy Ring.
And she was introduced into the ring by Abraham Woodhull, another spy,
and that she mingled in elite circles in Manhattan,
including having some contact with the British spy chief John Andre.
So there's a certain amount of speculation about her life and identity.
So obviously there is speculation on how she might have died.
Yeah, and again, the prison ship came from Wharton Pennypacker,
and he also started the unofficial declaration that Sally was the one that helped get John Andre arrested.
I put forth Sally in my novel, but the more research I do,
I actually think it's Elizabeth now, Elizabeth Bergen.
Right.
I don't think that 355 was ever held on a prison ship.
I think that was something Morton Pennypecker kind of dug into Robert Townsend, Jr., who was the descendant of the Townsons.
I think he was probably Robert's brother's Williamson.
He once dedicated a plaque to the Jersey.
And so somehow that got connected to, oh, his mom was on a prison ship.
oh, his mom was 355, but there's no contemporary information that, and again, I don't think
women were ever held on those prison ships. They could barely go visit their husbands on them.
So are you going to have to write another book now to tell another story?
No, I'll just put it in my substack.
All these remarkable women in espionage that you write about, and leaving Agent 355 aside,
there are the other women involved in there
that we do know their identities
and a bit more about what they did.
What do you want your readers to take away from these stories?
Unforgotten women in history.
We have, in America we have our legends,
but we have actual real people
who were documented to have helped, you know,
bring about American independence
and that in America,
when we think about the founding fathers
and all, you know, the men involved,
we forget about the women,
but we do have women that we can celebrate.
And, you know, it was an extraordinary time what was going on there.
Can you just answer for me?
The Culper ring was based in New York.
So who was actually in control of New York at the time?
Was that the British or the revolutionaries?
At that time, it was the British.
Right.
And the Culper Ring is based there.
these are well-placed people in society to be able to deal with both sides without arousing too much suspicion.
Yeah, and another thing that surprised me was how much of a real civil war it was.
You had your loyalists who were loyal to the king and then you had your patriots who obviously were working towards American independence.
But it was pretty polarized as a society and within the same household you could have loyalists and patriots who were.
basically on either side of the war. And obviously in America we had the civil war, which
speaks to itself. But in a way, the revolutionary war was also sort of a civil war like that, too.
So you really didn't know who to trust because your neighbors and family and friends could all be
working for the other side. Yeah. And Benedict Arnold totally embodies that idea.
I mean, what's interesting, you know, he's described as being this, this, the great traitor
but from the point of view of the British
he's a great patriot in some ways, isn't he?
Because this is a British colony that is rebelling
and he's deciding, in the end, decide with the British.
And I mean, the other thing that I've always found fascinating
about the Revolutionary War is that
there were probably more English people on the American side
than on the British side
because, I mean, obviously they were Anglo-American,
Americans. But the British side, the British army at the time was mostly Scots and Irish. So there were
very few people English, very few English people fighting other than the officers, obviously. So
yeah, as you say, it's a really intriguing time. It's not a war that we in England actually
know very much about, probably because we lost.
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So Kit, let's zoom out from Agent 355 and talk about one of the kids.
figures in helping America to protect and reclaim its 13 colonies. Benjamin Talmadge,
as the Patriots spymaster, he created the Culper Spy Ring that Agent 355 was part of.
He was from Satakit. So he was a friend of Nathan Hale, who was the first American to be executed
as a spy. So Talmadge knew exactly what would happen if anyone were to catch him. And going back
to that loyalist patriot, you don't.
know who your friends are. He recruited most people, like the Culper Ring were all from
Sit-Talcott people that he had grown up with and knew that he could literally trust with his
life. So I know for sure that's the reasons why he recruited Abraham Woodhull, Caleb Brewster,
Austin Row. But there were women involved in the Culper Ring? There were associates, for sure.
There were definitely Sally's in there. Abraham Woodhull, his sister was named Mary Underhill,
and she ran a boarding house in New York City
and a lot of British officers stayed at this boarding house.
So while we don't have actual proof that Mary Underhill was a spy,
she definitely had access to these British officers.
And Abraham Woodhull and Robert Townsendville
stayed in her boarding house.
So she probably...
So these are wives and sisters
who may have done some spying
who wouldn't have been considered as spies
and maybe at the time they wouldn't have even discussed what they were doing and said that was spying.
It was just, can you just let me know anything you might overhear?
Exactly. That's probably one of the things as they did.
And spying was really not looked on very favorably for a really long time.
I would say even up until World War II, when Churchill created the SOE,
he didn't want to solely the Army's reputation with, you know, these sabotage clandesine missions.
Ian Fleming was sort of a liaison to MI6 and the SOE.
and then wrote James Bond after that.
And I think that's where we got this, like,
sort of romantic notion about spies.
Even in, obviously, with John Andre, if you were caught,
you're going to get hanged and you don't get prison of war status.
So it was sort of like a lot, I guess, dirtier in reputation.
So even if you were a spy, a lot of people didn't come out and say it,
because pre-James Bond, you might have been judged as treasonist,
sort of same with, you know, Benedict Arnold, he worked for both sides.
And here in America, we always say that England didn't like him either because of what, like,
he was just a traitor, but.
But these women were able to kind of be under the radar a little bit and be useful.
Because, I mean, in the letter Woodhull is quoted as saying he was confident Agent 355
would outwit the British when it came to gleaning military secrets.
For sure, I'm confident that women did all kinds of more things that we don't know about because of the way they were treated, coverture, the spies, you know, just historical record being lost.
But for sure, there's definitely women who had access to the information.
And, you know, Lydia Darrah was definitely one in Philadelphia, who's associated a little bit with John Andre.
She spied through the keyholes, under the doors, listened, and could pass on that information.
And I think that happened way more than we have historical documentation for.
And I guess they were just dismissed as like, well, what could a woman know?
What could a woman do?
We don't have to worry about them.
I mean, it's really interesting because our last guest was a guy called John Taylor.
And he's someone who knows the secret intelligence world very well.
And he was of the opinion that women make much better spies than men.
Yes, for sure.
Actually, going back to my World War II,
Captain Selwyn Jepson was a recruiter for a special operations executive, and he full on decided
that women were far by their spies, and especially if you're talking about occupied France,
where men could be conscripted into the war effort and sent to Germany. So you really couldn't be
an able-bodied man walking around the streets of Paris without a letter in your pocket,
saying why you weren't eligible to be conscripted. So women can get around a lot easier,
and they flew under that radar. A lot of people didn't suspect women.
of being, you know, sort of double-handed and doing these sort of dastardly deeds.
For sure, they could also do a little bit of flirting to get out of things as well.
Actually, Jepson has a quote where he says,
women have a cool and lonely courage that men don't have,
which I thought was really amazing.
And as you touched on before,
spying was not seen as being something that a gentleman should do.
It was seen as being pretty dishonorable at the time.
When Talmudgy's friend from Harvard, Nathan Hale,
volunteered to spy, many around him couldn't believe it.
The idea being that espionage was grubby
and beneath the conduct, as I say, of a true gentleman.
And presumably women faced similar attitudes, if not worse.
Yeah, I'm sure.
I don't know if we have documentation, but I can imagine that a lot of women were like, even the war itself, that's men's business. That's not our business. In America, women in the 1700s, they weren't well educated. They were basically trained to be a good wife. So I can see some women thinking, I'm not going to get involved in the war at all. But I think any woman that did get involved and maybe passed on information, it's not something she would probably tell her circle of friends.
Just to go back to Talmadge, Talmadge's desire to beat the British was also fueled by the hanging of his friend Hale, as well as his oldest brother dying on a British prison ship.
I mean, can you just very quickly just, you did touch on it before, but could you just talk us through the reality of these prison ships?
Yeah, so we didn't have formal buildings and jails outlined for prisoners of war.
So when the British captured and they captured hundreds of thousands during the Battle of New York, they didn't have anywhere to house them.
And so they decided to decommission these ships that were really old and dingy and pretty much just stuffed them full of prisoners.
And a lot of people were never released there because the 1700s weren't well known for their hygiene.
And you didn't have running water or toilets or anything like that.
So if, you know, I kind of liken it to a concentration camp, like any disease you can think of,
the worst of the worst smallpox, dysentery, tetanist, typhoid fever, like all of that ran rampant
through these prison ships. The conditions were so dire.
And it seems the death of Nathan Hale weighed heavily on Talmadge.
Do you think it's because of Talmud's personal losses during the war that that incentivized him
as much as it did to fight against the British?
I do, yes.
And I think one of the reasons,
and Talmad being definitely by documentation a gentleman,
I think one of the reasons he and even Washington got into spying
is because we as Americans,
rather untrained farmers, militiamen,
were going up against the might of the British Empire.
And we needed anything we could to give us an advantage.
So if we could provide disinformation,
which is the Culper ring did provide a lot of misinformation
to try to trick the British troops into thinking
the American Army was somewhere else
when really they were in New York City or Rhode Island.
So I think the reason they both got into this sort of spying
was to give themselves an advantage against the British Empire.
So it sounds like you think that the culp aspiring
was really important in the Patriots' ultimate victory in the war.
Yes, for sure.
It's documented that they did this misinformation, disinformation.
Clinton kind of got wind that Rochambeau was landing his troops in Rhode Island.
The French were coming, basically.
And so the culpers helped convince Clinton that Washington was going to raid New York City
so that Clinton need to keep his troops in New York City and not go to Rhode Island,
which allowed the French troops to land in Rhode Island.
It sounds just like all the deception around the D-Day landings in the South.
I think of old war.
Yep.
So, I mean, just as a bit of a thought experiment,
sorry to throw this at you,
to divert you into the realms of speculative fiction now,
do you have any sense of what the future of America would have looked like
had you not won the Revolutionary War?
Yeah, I don't think we really understand
how close we were to losing West Point.
You had that chance encounter with Andre
of the loyalists in the woods,
and then they let him go anyway.
They let him go back to Arnold.
before Talmadge came in and was like, wait, why did you do that? So I don't think that's really, like, we
we hear about Benedict Arnold and his near betrayal of West Point, but I don't think it's really
like driven home how close we were to losing West Point. And I think, obviously, if we lost West Point,
we would have lost the war. And we probably would be British subjects for at least another
50, 100 years somewhere in there, War of 1812, maybe would have, if we hadn't been already freed, that
might have been that point.
Yeah, probably with the whole war in Europe, with Napoleon,
it would have been, right, now's that chance they're looking the other way.
Yeah.
So just because I'm interested, why was West Point so crucial?
Just because that's like where everything was routed from.
So it was really, I think the central fortifications of everything.
And while it wasn't, it was more of a military stronghold right now.
Like today, West Point is where we train most of our military.
Obviously back then it was more of a stronghold.
But I believe we had control over the Hudson River through West Point.
And we literally had chains over the rivers blocking British ships from moving in.
And had we lost that, then the British ships could move wherever they needed to
and provide supplies upriver to, you know, further inland,
further inland of the United States.
So Andre being captured, Benedict Arnold being exposed,
it changed, massively changed the course of American history.
I mean, do you ever think about what America, as we know it now,
would look like if they hadn't been successful in your battle for independence?
Hmm.
That's a hard one because it's so well in green.
like we are taught from a very early age, the Revolutionary War and the War for Independence,
the Declaration of Independence.
We know all these names by heart, all of our founding fathers, who a lot of them became
our first few presidents.
And, you know, so I don't know if I could step away and imagine what it would be like
without all of those figures because it's, like I said, it is so ingrained us from the very,
you know, kindergarten who these men were.
I'm sure somebody somewhere must have written an old.
alternative history fiction story. I'm sure there's definitely one. If not, I'm going to do it.
I know. It sounds like such a great story. But as you say, I mean, the momentum was so strong that even
if the Americans had been knocked back at that point, it wouldn't have stopped there, would it?
Yeah, I think that fight was in us for sure. And we were so determined to get away from, you know,
being under the king's thumb and becoming our own country and our own right,
that it would have happened at some point.
Maybe if we had Lost West Point,
it's still what we would,
the war would have probably gone on longer,
but maybe we wouldn't have just given up and kept fighting.
Well, thank you so much for speaking with us, Kit.
Should we be on the lookout for a new upcoming book from you?
Sometime in 2026, Virginia Hall will be out.
And she's the Second World War Spie with a wooden leg.
Yeah, yep.
Excellent.
It was really interesting to talk to Kit about female spies,
although she actually hesitated to call them that.
And obviously because of the whole romance of spies,
although, as she said,
that idea of spying being romantic is a fairly new invention,
that we now go back and classify people as spies
who weren't necessarily that at the time.
The idea that these women were sort of,
embedded and invisible and therefore could learn secrets.
Men could tell them things that they wouldn't tell to another man,
and they were then able to pass this information on to people who might be able to use it.
And we've had a few series about female spies on The Spy Who,
and a big inspiration for Kit to write her books was to tell some of these stories
that should be better known.
And it does feel like we are hearing a lot more stories.
now about female spies, particularly from the Second World War,
when for the first time the British, at least,
were starting to actually recruit women for spying,
officially rather than just using them unofficially
as the women in this series were.
And it's great that these stories are being told,
and we're learning a lot more about these women.
But in the end, there is a central mystery about Agent 355.
Was she a real person?
And if so, which of these women from history might she have been?
And as Kit says, we all love a mystery.
Next time we open the file on Ursula Kaczynski, the spy who duped the Nazis and the West.
As Hitler seizes power in her homeland, newly married and pregnant Ursula turns Soviet agent.
She'll become one of history's greatest spies, aiding saboteurs, plotting assassins.
and stealing atomic secrets, all while playing housewife.
Follow The Spy Who now, wherever you listen to podcasts.
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The Spy Who is hosted by me, Charlie Higson.
It's a Yellow Ant production.
This episode was written and produced by Liam Garot
and researched by Louise Byrne.
The senior producer was Jay Priest.
The sound designer was Joshua Morales.
Music supervision by Scott Velasquez for Frisson Singh.
For Yellow Ant, the executive producer was Tristan Donovan.
For Audible, the executive producers were Estelle Doyle and Theodora Laudis.
