The Spy Who Betrayed the American Revolution | The Mystery of Agent 355 | 5

0:00Audible subscribers can listen to all episodes of The Spy Who ad-free right now. Join Audible today by downloading the Audible app. I'm Charlie Higson 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.

0:59I'm joined now by someone who's going to help break down this mystery, Kit Sargent. A writer of historical fiction, Kit's probably best known for her Women Spies series, stories that shed light on the often overlooked roles of women 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's Spy Ring, 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.

1:41So 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. We're 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 were going to go for the big show in Washington, but let's not ask. Yeah, that's me. Stay away from that part. Stay away from any of that. Let's just celebrate all that is good and wonderful about America.

2:20Well, 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 dive right in and unspool the mystery surrounding Agent 355. We'll get into the question of her 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, and I'm going to call it 355 on accident, it probably is 355. We have a huge highway called 355 that runs like right around Chicago that I use a lot. So in my head, I'm always thinking 355 because of that highway.

3:08Well, 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 Culper Sr. and we have probably almost 200 surviving letters from the Culper Ring to and from each other, Washington, Palmadge. And we only have that one reference. And so, while I don't think she was a sixth member of the Culper Ring, she definitely was associated with them.

3:51And Abraham Woodhull knew her at least a little bit and had 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... Oh, lady, right. 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 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.

4:33Mm-hmm. 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 of my book.

5:14What'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 Pennypacker, who was a Long Island historian, and he had a huge collection of Revolutionary War material.

6:03And he is famous because he uncovered Samuel Culper Jr.'s true identity, who was Robert Townsend. And this was in the 1930s. So Samuel Culper 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 Pennypacker confirmed it about 150 years later. So Morton Pennypacker 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.

6:58So 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. which 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 term and have it aboard the prison ships. 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 to get people off Long Island New York and free prisoners from there but she was definitely associated with culpers 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.

8:08And 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 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 spies that you are real life people that most people haven't heard of.

8:55And 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 useless degree in marine 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.

9:33So 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 parts 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.

10:18So 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 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 sorry, American generals or British generals because there were spies that were working for the other side as well.

11:09They were working on both sides. But because the men never, it 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.

11:48Because 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 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.

12:26Or 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.

13:07But 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.

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14:26So, going back 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.

15:14I 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 Townsend's, I think he was probably Robert's brother's William son. 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.

15:59They 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.

16:41And that when 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.

17:26Yeah. 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, you know, 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.

18:05Yeah, and Benedict Arnold totally embodies that idea. I mean, what's interesting, you know, is he's described as being 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, to side 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-Americans, but the British side, the British army at the time was mostly Scots and Irish.

18:51So 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. That's true. It's not celebrated.

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20:18Hey, Dan Taberski here. I'm a podcast host, a journalist, and now with my newest project, the author of my own manifesto. Well, it's a manifesto about manifestos. My search for inspiration in a world that feels more infuriating, more out of its freaking mind with each passing hour. Manifestos are a call to action, an artful scream. They capture our anger and they try to do something with it. This is my attempt to take the Manifesto back from mass shooters and nihilists and return it to its rightful place with the warriors, the visionaries, the regular folks with just the right amount of crazy.

20:53I compare notes with radicals, secessionists, internet trolls out for a laugh, and punk singers screaming their guts out, all trying to turn their anger into the world they want to see. Listen to Manifesto wherever you get your podcasts. Audible subscribers can binge all episodes of Manifesto early and ad-free right now. Join Audible in the Audible app or by subscribing on Apple Podcasts.

21:22So Kit, let's zoom out from Agent 355 and talk about one of the key 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 Setauket, and 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 Setauket, people that he had grown up with and knew that he could literally trust with his life.

22:07So I know for sure that's the reasons why he recruited Abraham Woodhull, Kayla Brewster, Austin Rowe. 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 Townsend both stayed in her boarding house. So she probably...

22:45So these are wives and sisters who may have done some spying, but 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 that 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 sully the army's reputation with, you know, these sabotage clandestine missions. Ian Fleming was sort of a liaison to MI6 and the SOE and then wrote James Bond after that.

23:25And 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 treasonous, 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 these women were able to kind of be under the radar a little bit and be useful.

24:10Because, 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 Dara was definitely one in Philadelphia who was associated a little bit with John Andre. she spied through the keyholes, under the doors, listened and could pass on that information.

24:52And 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 Jepsen was a recruiter for a special operations executive, and he full-on decided that women were far better spies, and especially if you're talking about occupied France, where men could be conscripted into the war effort and sent to Germany.

25:36So 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 still, they flew under that radar. They, 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, Jepsen 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.

26:24It was seen as being pretty dishonorable at the time. When Talmadge'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.

27:08But 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.

27:51And 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, tetanus, 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.