American History Hit - George Washington's Spies

Episode Date: April 30, 2026

During the Revolutionary War a vital web of intelligence was established, with General Washington at its head. Operating through coded letters, hidden signals, and a chain of ordinary civilians turned... spies, their secrecy and precision proved that even the quietest network could alter the course of a revolution.Our guest today is Dr. Alexander Rose, historian and author of Washington's Spies: The Story of America's First Spy Ring, was adapted into the AMC period drama series, Turn: Washington’s Spies.Don's new documentary on Fort Laramie is available to watch now for all History Hit subscribers. Sign up at https://www.historyhit.com/subscribe.Edited by Aidan Lonergan. Produced by Tomos Delargy. Senior Producer was Freddy Chick.All music from Epidemic Sounds.American History Hit is a History Hit podcast. Hosted on Acast. See acast.com/privacy for more information.

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Starting point is 00:00:00 Want to explore even more history? Sign up to History Hit, where you will discover history from around the world. From the American Revolution to prehistoric Scotland, there is plenty to discover. With your subscription, you'll unlock hundreds of hours of exclusive documentaries, with a brand new release every week, exploring everything from the ancient world to World War II. Just visit historyhit.com slash subscribe to bring the past alive. Hello American History Hit listeners. Before we dive into today's episode, I have some exciting news. A brand new History Hit documentary releases today, featuring Yours Truly. We filmed this on
Starting point is 00:00:42 location in Wyoming at a place called Fort Laramie, which you may know from our frontier series about the Western migration played a large role on the Oregon Trail. This film releases today on History Hits website for all subscribers. Go to historyhit.com to watch and subscribe. If you like the history of the American West, well, I think you'll like this. And you can see me walking and talking and moving my arms. So check it out. Home with the show. It's 1778, on a quiet stretch of rural Long Island here in New York State. A shirt lifts and falls in the summer breeze. To the passing eye, it's nothing. Laundry on a line. But it happens to be a signal, a sign, something noted and registered.
Starting point is 00:01:37 Later, out on the water in the fading daylight, a whale boat hides among the reeds, its occupants waiting for night to cover their treacherous crossing. And in British-occupied New York City, a local shopkeeper, listening more than he speaks, gathers fragments, rumors of troop movements, offhand remarks of British soldiers,
Starting point is 00:01:58 scribbling quietly onto a scrap of paper before he melts into the crowd. There are no guns here, no cannons or drums, yet this is war just the same. Secrecy and subterfuge, intelligence, gathered by spies, concealed in code, passed on to General George Washington, who will use it to steer the course of the American Revolution. Our guest today is Dr. Alexander Rose, historian author of Washington Spies, the story of America's first spyroes. which was rather famously adapted into the excellent AMC period drama series, Turn, Washington Spies.
Starting point is 00:02:42 I'm Don Wildman, and this is American History Hit. Alex, thanks for joining us in American History Hit. It's a delight to be here, and an honor. Thank you very much. I am a big fan of your book on my shelf, but also the series that came out of it, which I was rather addicted to. I was very pleased by it. We had a great time making it.
Starting point is 00:03:14 I was very lucky to just have the book adapted into a TV show that did pretty well. It is pretty enviable that. It's an amazing thing. So let's get started with this story, which I find one of the most intriguing ones of the entire revolutionary period. Let's first set the scene, the creation of this ring.
Starting point is 00:03:31 What is happening at this period in the American Revolution? Well, the ring was essentially came together in 1778. So, you know, a couple of years after the war had actually started. It's interesting. It's important to know that the context of it coming, together in that Washington had long, George Washington, that is, of course, had long been trying to put together an intelligence outfit of some kind. He had failed numerous times. It was a very difficult thing to do. He didn't have the experience to do it. Nobody really did. And then just by
Starting point is 00:04:06 happenstance in mid-1778, it all came together with a couple of voluntary walk-ins. And it turned out to be the culper ring. So that was, that really helped out Washington at a key moment in the war. You know, he was, he was, I wouldn't say it was on his, you know, back, I guess you could say he was on his back leg a little bit. He certainly wasn't winning. But again, the key thing about the culpas was that they provided him with a window, men on the ground in what was then occupied New York City and Long Island, which was, they were the bread basket of the British Empire in America. So it was a key moment for him. Yeah, these are the early days, of course, the United States. United States. It's interesting. For the British, this is the, we're still colonies, but for the
Starting point is 00:04:48 Americans, this has become the United States. So we're in the state of New York. The Brits at this point wildly regarded to crush this rebellion, of course, they have all the advantages of an established army and an excellent Navy. Do they have an intelligence network to speak of? Well, it's a great question. No, they didn't. It was one piece in the puzzle that was missing for them, mostly because they didn't think they really needed one. This was a rebellion. It would be put down with military force using the conventional military tactics and strategy that they had imported from Europe. It was regarded as, well, we'll just put down these insurrectionaries and especially these, you know, these awful rabble rouses in New England and we'll be done with it. And they never want to go back to paying their taxes and stuff. But so they didn't really, they never developed an intelligence network. And it's not because they were fools or idiots or anything like that. There were a couple of reasons. And just very simply, one is that the geography of America, the theater of war, was militated against developing the kind of intelligence networks that European countries could develop.
Starting point is 00:05:57 The territories were so colossal, like millions of square miles of undeveloped country, unlike in Central Europe, where there was a castle or a fortress or a stronghold every 20 yards or so. There were established roads. You knew exactly how long it would take you to get from old woodst to Kernigratt. You know, you could plan. out your military campaigns like clockwork, which is what they did in the 18th century. In America, that doesn't pertain. Here, you have all sorts of really annoying guerrillas.
Starting point is 00:06:22 For one thing, you have a population that shifts between patriotism and loyalism, depending on who's in charge of the particular area. Most people are just trying to get by, want this whole thing to end. So they're dealing with a lot of real problems like that. There's no embassies to spy on. There's nothing like that. It's all military. And Washington is this shadowy figure in the background.
Starting point is 00:06:44 The second thing is that they just didn't think they needed it, as I said, and that was because this was an uprising that would be put down by conventional military means. So they never thought about developing the kind of intelligence networks that we think of as being intelligence networks. These are 18th century people dealing with their own contexts. And in Europe, and for military campaigns, intelligence really wasn't really counted. Interesting. In the way of we think of like James Bond and Jason Bourne, it wasn't like that at all.
Starting point is 00:07:14 When people said military intelligence, they meant you would have some scouts or observers attached to your army and they would sally out and spend a day or two probing the enemy lines and coming back of the report. That's what they had. And they did that very well, but not the kind of behind the lines, man on the ground, in civilian clothing, passing on intelligence in a secure and timely way to the commander's chief. They just didn't have that at all. Yeah.
Starting point is 00:07:41 In so many ways, that's what distinguishes this story on the part of the. Americans. At this time, when we really focus in on the story, this is like August 1776, the British troops have occupied New York, which has resulted from the Battle of Brooklyn and the evacuation of the American troops, all of which has left the British in charge of this effective center of the colonies. New York was vital to the British because it would serve so much of the country that way. They owned that harbor and potentially the Hudson River above it. It had been patently clear to the rebellion, revolution, depending on you're looking at, would not work for the Americans without upping their intelligence game. This was about leveling a playing field in which one side had all the normal advantages.
Starting point is 00:08:25 There were other espionage efforts before what we're about to discuss by the Patriots. Can you explain those? Yeah, they were, again, remember you're dealing with the 18th century. There are no bureaucratic institutions. There are no organizations like CIA, for instance, where they have established modes of operation. They have training schools. They have financing. They have all of this, you know, a kind of a collective wisdom that's being garnered over the ages about how to do stuff.
Starting point is 00:08:56 In the 18th century, like Washington, you don't really know how to spy. It's not as easy as you think. It's very difficult. So when he starts, Washington, this is the 1775 or so, when he starts, Washington, goes the conventional way. And this is what leads to essentially the Nathan Hale debacle, which is what it was, where you send in an underprepared army officer like Hale, who doesn't have any training whatsoever. There's no plan to get him out. He's not given any money. He's not given any real, I mean, good cover stories. I think he went in as a Dutch schoolmaster
Starting point is 00:09:31 or something. He doesn't know his way around. He doesn't know what he's supposed to do or what kind of information he's supposed to get. He's just supposed to land in Long Island and try to get to New York and report back. This ends in, as we know, in disaster, he gets caught very quickly, and he's hanged. Washington learns a lot from this, but there's not much he can do about it. So over the next year or two, he's experimenting. Sometimes he tries to send in troops to a couple of soldiers to try and lurk undercover in enemy occupied areas for a couple of days and then come home. These were essentially in and out operations, and they were almost virtually useless. You can't pick up any information.
Starting point is 00:10:10 A stranger walking into town and just asking questions of the locals. You know, there's a lot of fantasists out there trying to sell information, a lot of adventurers, making up stories. So he's trying all these new things, and he can't do it. It's only by mid-1778 that he finally,
Starting point is 00:10:26 again, with the arrival of the culpring, that he works out how to do it. And that is to have civilians, living civilian lives in enemy-occupied areas for a long time. who have a secure method or a secure means of transmitting information back to his headquarters. Yes. And that is trustworthy and that can be evaluated and analyzed factually.
Starting point is 00:10:51 It's like an evolution of aspiring. And the agenda covering just didn't pop abracadabricably out from out of nowhere and worked perfectly. Right. It didn't. It just wasn't like that. So the key thing for Washington was that what was interesting about Washington was that he was a natural spy master. People would always say, oh, you know, he couldn't tell us.
Starting point is 00:11:08 a lie. Well, no, Washington told, Washington told a lot of lies and smiled as he did so, mainly when he was spying the daylight side of the British. He was very, very good at it. He had this natural caution and skepticism about reports. He wanted, you know, to triple confirm things, cross-reference, facts and figures, all the problems that come up with spies. Washington was just a natural. I want to circle back to Nathan Hale for a moment. I mean, he gets less attention than the poor boy deserves. you'll come out of Grand Central Terminal, you and I are both in this area, and walk across the street toward Vanderbilt, and there is a little plaque right on the edge of the Yale Club, the building that is the Yale Club. And it's a little plaque that says this was the spot where Nathan Hale was hanged. Most New Yorkers have no memory of this guy, let alone.
Starting point is 00:11:57 He was, an important point of Nathan Hale is that he actually knew the guy were about to talk about, who was Benjamin Talmadge, right? They went to school together. They were at Yale together. That's where they met. They were college buddies, and they were in lots of frothy fast together and did, you know, all the fun stuff that college boys do in the 18th century. Supposed to consist of getting very, very drunk, going to a lot of parties. That was what they did. But yes, they were so they were best of friends, and this is extremely important later, why Talmadge feels so strongly about Hale's death that he acts in certain ways later on.
Starting point is 00:12:34 And Hale, of course, was the famous quote, I regret having but one life to lose from my country, which he said just before he was hanged. The most famous quotes of the whole revolution, whether it was true or not. We've already mentioned the name. I just want to understand where this comes from. The Culper Spiring is the organization that is very resourcefully built by as much from the local perspective as it is from top down. Where does the name come from, first of all? Well, it's a bit of a mystery. it was named after one of the aliases or code names of one of the spies.
Starting point is 00:13:06 It was Samuel Culper, which is a very strange name to have chosen. So I was investigating. It was driving me nuts where this comes from. And I think my view is that I think when he was very, very young, George Washington was a surveyor, I think a land surveyor in maybe a mispernotty, in Culpeper County in Virginia. I, my, the coincidence of Culpepper and Culper is pretty, pretty close. So my view is that it was just a shortening or a little kind of an in-joke based on Washington's
Starting point is 00:13:42 past. That's where it comes from. I think nobody would, nobody ever wrote down why they chose that name, but that's what I think. So he establishes the necessity for this spiring. It's going to focus itself on New York. We've begun with the very basics, but when we come back after this break, we'll talk about the cast of characters involved.
Starting point is 00:14:12 Okay, we're back with Alexander Rose historian and author of Washington's Spies the Story of America's First Spy Ring. And we're discussing George Washington's Ring of Conspirators. Now, Alex, we'll fast forward a couple of years. This will all take time building a spy network. We're now in 1778, and we have the establishment of the Culper Spiring. There had been previous espionage efforts which had not worked out very well. So let's talk through the key figures who will comprise this intelligence network. Famous names, first of all, Benjamin Talmage, codename John Bolton.
Starting point is 00:14:47 Who was this guy? Benjamin Talmage was, as we mentioned, a close pal of Nathan Hales at Yale, and they keep in touch. You know, after the war, Talmud is this idealistic, I think he's the son of a minister from Long Island.
Starting point is 00:15:01 He's very well educated. You know, Greek, Latin, Hebrew, all the classical languages. You know, he's very idealistic. And yes, when the war breaks out, he joins a dragoons unit. You know, he was a well-bred young man. So it became, you know, as you would expect, a dragoons officer. Why not?
Starting point is 00:15:19 And so, you know, it's very dashing. He's very, he's quite handsome. You know, he wears a ridiculous hat with a big horse. Yes. The horse thing, you know, the whole ridiculous hat in an impractable charging or a horse. But anyway, so he does all that. And, you know, he's an up-and-coming young man. He falls in with Washington.
Starting point is 00:15:38 becomes a kind of an adjutant or a trusted contact. The real reason why he comes to Washington's attention is because he's friends with these guys on Long Island in Sotoket, Little Town, Oyster Bay. A couple of them were, you know, they became very important. The lead one was a man named Abraham Woodall. Woodhole, some people say, but I think it's Woodhull. He was a farmer out there,
Starting point is 00:16:04 and there was a couple of other guys later on, people like Austin Row, there was this kind of a whale boatman fisherman-fisherman-type figure called Caleb Brewster. All of these guys had grown up together in this little town. And as it was, you know, America's a very, I mean, it sounds odd, but a very small place at the time. People didn't travel very far. You know, their families are intertwined and intermarried for, you know, generations before. And so this was part of the reason for their latest success in that they were, they were like hounds in a fox pack or something. I mean, they had grown up together, they could trust each other implicitly, they knew that they would never
Starting point is 00:16:41 betray each other. And Talmadge is the leader of this, well, the cell leader on Long Island itself is Abraham Woodle. A little later on, they come to contact with a man called Robert Townsend, who's, you know, just down the road in Oyster Bay. And he's a, again, he's a half Quaker, half Anglican, I think, merchant. But they, you know, they had sort of known each other. But he was, Townsend was always a bit of the outsider here. They all come, as you're saying, from a place called Sotakot, or at least the two guys, Abraham and Benjamin, come from Stuttat, Long Island, which confused me even when I was watching Turn. That's a long ways away in those days. You know, Long Island's a massive place.
Starting point is 00:17:21 Today, we think of it as suburbs, but it was way out there. And when New York is the focus, New York City is the focus, it's surprising that that was where this ring would be based. Why there? That's where he had his friends. Okay. But they did expand. I mean, Satakotokin Oystabari is about 50, 55 miles from New York. So, you know, it's a few days ride.
Starting point is 00:17:44 It's not in the completely middle of nowhere. But they expanded what of the reasons they needed Robert Townsend, the Quaker, is that he would stay in New York. He had a business in New York. He was a well-established merchant there. So he's a very useful connection there. I see. And secondly, Sotoket, though it is out a little bit,
Starting point is 00:18:03 He's not downtown Manhattan. You know, it was that Long Island was the granary and the breadbasket, the storehouse of British logistics in North America, you know, through the port. It's where they kept their reserve regiments. That's where the ships came. You know, every ship that came into New York City, virtually all of them came through Long Island Sound. You could see them passing by as to talk it. So it's very useful for notes.
Starting point is 00:18:27 So, you know, they got the hay for their horses and cavalry. That's where they got it from, Long Island. It's a very important place to have, and especially when you're Washington, and all you want are facts and figures. It was very useful. It was also very seagoing, and this was the center of privateering, right? This was what Abraham Woodall had been up to. Well, Woodall was a, you know, horny-handed son-of-toil farmer figure. The guy who was the, you know, the crazy action man figure, who's very entertaining, is Caleb Brewster.
Starting point is 00:18:59 He's one of these people who live in a kind of a great... in that, you know, he was a whale boatman. There were a lot of whale boats around at the time. Technically, he was working for the Continental Army, but he would also, you know, on the side as a bit of a sideline, probably do a little bit of freebooting. Let's put it that way. A polite word for his private hearing. Smuggling. Well, yeah, that's an impolite word to use for what he was doing. But, you know, he would focus on loyalist-owned boats and just take their stuff and dedicate it to the great cause. Right. It's tax-free. Tax-free. Exactly. You're making a little money. No forms required.
Starting point is 00:19:36 Right. So Talmage knows Woodall. Woodall then is turning to his friends as well. And this is how this network is established. This very small circle of spies at this point. We've got Benjamin Talmadge, who's side by side with George Washington. He's in charge of the Simgitaph. But down at more local level, we have Abraham Woodall. He's codename Samuel Culper, Sr. We'll see how that figures in just a moment. Whereas Robert Townsend, who is engaged in the city, becomes Samuel Culper Jr.
Starting point is 00:20:05 These are codenames that will become very important in the way that they communicate. They're a bit unoriginal when it came to the code names with the junior and senior. They could have done a little better there, I think. It certainly emerges in the series that Abraham Woodall becomes quite the center of this thing. You know, he's quite a resourceful guy. He takes a lot of chances and he's presented as taking a lot of chances and things. I have a feeling, of course, that this is much more of a methodical, you know, very careful, less dramatic experience for these guys on the ground in real life as opposed to on television. But it's still real scary what they're doing, isn't it?
Starting point is 00:20:43 Absolutely. I mean, what comes through in all of their letters is that they all have very distinct characters. You know, you have Woodall, the farmer, who again is a bit of a, I mean, he seems to be on the verge of a nervous breakdown for most of the war. I mean, he's, he's a nervous Nelly. I mean, he's a bit panicked. He kind of freaks out at things. Robert Townsend is a much more of a cool customer, much more sort of dedicated to the objective, but also something of a prima donna. He could be a real diva and he would walk off the job, or off and a huff when he didn't get what he wanted. Caleb Brewster didn't even bother using a codename. He just went under his own name because he thought he was the bees, and he's, kind of challenged the British to catch him. So, you know, they all have their own very distinct characters.
Starting point is 00:21:32 And, you know, the point is that they had all sort of known each other. Again, Tomic knew all of them. And Tomic could probably best be classified or categorized nowadays as, as the case officer. He was based in Connecticut, and he very rarely went to Long Island. It was very dangerous. And that's what made Abraham Wood also nervous.
Starting point is 00:21:53 What they were doing was dangerous. They were spies. There's no sugar coaching this. And spies got hanged. That was, so, you know, it's not a little game where if they get caught, they just get a slap on the wrist. I mean, they're headed for the nearest,
Starting point is 00:22:09 for the nearest sort of local scaffold, probably. Sure. So, again, there's a reason why they're nervous and why they're cautious and why they're careful. And the reason they survived was because of that natural caution. At some point, there is a very close call from Woodall because he's going into the city under the cover of visiting his sister who lives in the city. Why would this kid from Long Island be showing up on a regular basis? Well, he's doing it because he says his sister lives there. But at some point, he's called out on that and taken aside.
Starting point is 00:22:36 That's where Caleb Brewster becomes much more active. but they're getting their information eventually from this man named Robert Townsend, who has his own connections in town, but often he's listening in on officers at an inn, right, at a drinking house. Yeah, they all played their part in acquiring intelligence. Townsend was, you know, he was a well-connected, fairly wealthy merchant. He, you know, he ran a few establishments. He could pick up the, you know, essentially the gossip.
Starting point is 00:23:09 you know, officers chatting to each other. I mean, he was a, you know, fairly, he was a very quiet, humble man in many ways. But he would just listen. He was a good listener. And he would pick up stuff. And he would transmit that to Abraham Woodhaw, who would supply his own information. I mean, he was, you know, he watched British logistics or, you know, supply trains going, you know, wagons, going past. And he would count how many haystacks there were or how many artillery pieces went by.
Starting point is 00:23:37 stuff that Townsend didn't do. Taylor Brewster would keep an eye on the water, see what ships are going in and out and keep track of those, and they would all send their stuff eventually to Woodhull, who would compile it in a report, and then get Caleb Brewster to sail it across the Sound north to Connecticut where it would be picked up by either Talmadge or one of his designated dragoons, and it would be speeded to Washington,
Starting point is 00:24:00 whose headquarters are most of the time in sort of around White Plains. Right. So the Culper Ring developed a number, of methods to relay their information, becoming more and more sophisticated as the war progressed, right? There were several ways that they actually inscribed it on paper, one being invisible ink. Yeah, but they don't know how to spy either, so they're learning as they go. And as the phrase goes, they got better as they went on. When they began, Abraham Woodall would fill his letters. And I read them all. He would fill his letters to Washington, almost as, you know, because he was
Starting point is 00:24:34 speaking to the commander and chief, the continental army. And, you know, it's a very 18th century way of thinking, he's a great man, I must respect him. And it was just full of these grand perurations about the importance of liberty and freedom and throwing off the oppressor's yoke and all this kind of stuff. And Washington just goes,
Starting point is 00:24:54 could you just tell him, just leave that stuff out, I just need the numbers. Just tell me how many artillery pieces they have. Right. Tell me how many horses they have, which regiments are there, how many haystacks there are. Have they brought in the food yet? So, Abraps for a while, Woodold learns, and he compresses his reports and keeps it strictly to the facts man kind of thing.
Starting point is 00:25:18 So, you know, and again, and over time, Washington supplies them with a kind of an invisible ink, developed by, I was good, isn't it, John Jay's brother, I think James Jay, who is a doctor. And he develops this invisible ink. And I go into some detail in the book trying to work out what the ingredients of this ink was. It was very difficult to find these chemicals. And it was a great invisible ink, especially compared to anything that anybody else had. The problem is, as they discover, that invisible ink is quite difficult to use, and it's in very, you know, short supply. So they have this brilliant plan once.
Starting point is 00:25:49 I think it was Woodall, and they were right between the lines a lot of the time or of a regular letter in Invisible Ink. And one time Woodall comes up with this brilliant idea. He gets a sheaf, a blank paper. and he writes the entire letter in Invisible Ink, and he inserts it somewhere in the sheaf of paper. Since it's Washington, Washington, says, okay, which one is it?
Starting point is 00:26:10 Because they forgot to mention where it was in the pile of paper. So they make mistakes, as does Washington. Tell me what the chemistry, you know, when I was a kid, I used this, from little spy books, but what was the mixture that they used for this ink? It's kind of a combination. At the time, most invisible inks were made out of, you know, that old, again, the kids one. The stuff is like kids play compared to, you know, we would think of it as kids. At the time, it was very advanced. You know, they would use lemon juice and you could expose it
Starting point is 00:26:39 over, over a flame. I see. You know, some, I mean, if you were really in a pinch, you could use urine. It worked pretty well, apparently, though a bit gross for the person receiving it or using it, I guess. I can't remember exactly what it was. It's in the book. There's sort of a recipe for it. It's kind of out of some sort of nut. It's called the sympathetic stain, kind of chemical mixture very basic, that is actually, you know, quilled in right between the lines of the letter. This was the way that they would read the message. How did that work exactly? Well, the reason it's called a sympathetic stain, the kind of catchy name for it,
Starting point is 00:27:14 and the reason it was so advanced is that it didn't use heat to expose the invisible ink. Again, that's what made it so quite mind-blowing. And the reason is that Jay develops what's known as the agent, the liquid, in a bottle that you would use and you would dip your quill into it and you write it and it would vanish wow amazing the trick was that there was something called a reagent it made it kind of sympathetic in the sense that you're the 18th century sense and that when you swabbed the chemical reagent over the letter with the invisible writing the letters would suddenly appear magical it was a very complex process yeah but that's what made it such a quite an astounding step forward I'd probably
Starting point is 00:27:59 used it in Europe before, but in the, in the U.S. or in North America, it had never been seen. And it took a lot, a long time to develop. I think of the sneaky Spanish and French is using all this stuff. Not the honest English. Well, that gets into a whole simple subject about why they didn't spy. It was regarded as a bit dishonorable. But that's a whole different subject. We can talk about that some other time. The code books also became more sophisticated, right? Well, yes and no. They started off in plain English, and they developed what's known as a code dictionary. This is essentially, and I'm going to use a little bit of jargon here, a mono-alphabetic, alpha-numeric substitution system. That is a long phrase for what you have is you switch out a name
Starting point is 00:28:40 or a word and you put a number in instead. It's something, again, an eight-year-old who likes to do nowadays. And it was alphabetical, which was a big security flaw in it, by the way. So Rhode Island would be 712 and Pennsylvania would be 456. kind of thing. Then you would switch out the various numbers, then you would try and mislead like that. You would use it for names. You would use it for numbers.
Starting point is 00:29:05 You would use it for places, that kind of thing. George Washington was 7-Eleven, right? 7-11 or 7-1-1. And they had a list of code names and so on, and 7-1-2, 7-13, and all this sort of stuff. Again, an experience code break at the time would have broken it in about 15 seconds. It was so easy to do.
Starting point is 00:29:24 But at the time, remember, you're dealing with untrained agents, They have, it has to be simple. They can't spend days trying to, to encrypt messages that take days to decryt. Right. They have to move fast. And it would, it would forestall just a casual cursory examination by someone. And they use dead drops and so forth, you know, familiar to all CIA people to pass on
Starting point is 00:29:47 this information, agreed upon locations, et cetera. And this is how they kind of kept things. So at the height, I'm just a review here, you've got Townsend Gathering Intelligence, intelligence in New York City. a guy named Roe, one of their other agents, transporting this. The courier. Yeah, the courier. Woodall compiling it to Satakit, Caleb Brewster delivering, Talmud's receiving it, Washington considers.
Starting point is 00:30:10 How fast did these messages travel through this network? Well, it sounds, it feels like an age today, but at the time, it was remarkably fast. I mean, to get a message from occupied, maybe you have to get it outside of that occupied, New York City, all the way to Long Island or across the sound, up into Connecticut. something that would take today a second with email. But then, you know, they did it in, at their height of their powers, it took about a week. Wow. Which to Washington was amazingly fast, and that was regarded as extremely timely intelligence,
Starting point is 00:30:40 which is why he valued them so highly. And over time, I imagine they're more often being sent. So he's maybe getting them every few days as a result, right? At key crisis moments, they would come in quite regularly. Other times when there was nothing much going on, especially later in the wall when a lot of the action moves to the south, the culp is really on anyone you're as useful as they used to be. So it becomes much more irregular at that point. Right.
Starting point is 00:31:05 All right, let's take another break. When we come back, we'll discuss the Culper Ring's biggest contributions to the war and how their efforts were uncovered years later. Alex, I want to talk about the impact and consequence of the Culper Ring. What a difference it really made in the war and how we now remember it. With any intelligence operation, you analyze the information, you separate the war, wheat from the chaff. What were the Culper Ring's biggest contributions to the war effort? Oh, well, they had a couple of big ones, you know, the things that we were regard as the
Starting point is 00:31:44 great intelligence coup. One was, I think, in 1779, summer of 79, they get early warning that the British are preparing a surprise, sort of naval attack on the recently arrived French fleet at Rhode Island. And Washington, in reaction, decides, oh, if Sir Henry Clinton, that's the British General, is about to launch that. He's going to denude New Yorker troops. Maybe I can launch a surprise attack and grab New York while he's not looking. Now, it doesn't come off. He decides not to do it.
Starting point is 00:32:13 It's too dangerous. And Clinton calls it off because he gets delayed anyway. But it was a, you know, the culpers had done sterling work there and getting this tip off to Washington. Second time is almost by accident. The culpers didn't have that much to do with it, but Talmadge did, in that Talmud is the guy who realizes that John Andre, the man who was handling the Benedict Arnold defection from West Point,
Starting point is 00:32:38 that he's in Westchester County contacting Benedict Donald who's about to betray West Point. So, Talmudges, the guy puts it all together, mostly because he'd heard the aliases before and so on. That's another important thing. But that stuff is actually not anywhere near as important as the continuity of the Culper ring. And that this was the only spiring, as far as I can, discern from reading quite a lot about these things, that served basically throughout the war, and it remained intact, and the network was never blown, it was never penetrated,
Starting point is 00:33:15 never infiltrated, despite the best efforts of the British. And it just provided a constant source of reliable, verifiable, trustworthy, timely information to Washington. And you've got to remember, there were times when New York, Washington was completely dark and silent. He was completely eyeless and earless in New York. There were times he didn't even know who the British commanders were. It was hard to get information out of New York. So he was reliant on things like newspapers that were six months old that were smuggled out and things like that. To have someone like Townsend and Woodall when he went into the city actually providing information from inside this fortified stronghold was of, I mean, colossal value in Washington.
Starting point is 00:34:03 That's why Washington spent so much time with the culpers dealing with them as a kind of almost their father figure. I mean, he was their confessor, their teacher, their father, and, you know, set the right when they erred kind of thing. So, you know, there's a very close connection between Washington and these men on Long Island. Did they ever meet? Not during the war. I mean, they, again, you're getting into 18th century
Starting point is 00:34:28 mentalities versus 21st or 20th century mentalities of, they were all regarded spying as, as dishonorable. They were embarrassed by it. Interesting. It was something that was underhanded. It was sneaky, you know, below the salt. Yeah. And so they never talked about it.
Starting point is 00:34:47 I looked at Talmadge's memoirs, which he wrote, I don't know, 50 years later. He was a very old man by then. He wrote his memoirs. And they're very, you know, very interesting memoirs. He devotes, I think, exactly one sentence to his spying career during the war. Wow. And it's something like, and during the war, I undertook certain services for George Washington. And it continued throughout the war.
Starting point is 00:35:11 And that's all he says. That's the whole thing. But it's all there in their letters for, you know, something like nearly 150 letters back and forth between the commander and chief of the army and these sort of obscure gentlemen on Long Island and New York. So it's an interesting, and so this stuff didn't really come out until many decades later.
Starting point is 00:35:29 Right. But I think one of them, maybe Brewster, I can't quite remember, met Washington briefly, I think it was 10 years after the war. Washington goes on this famous tour. Right.
Starting point is 00:35:41 Of Long Island. And Woodhull or Brewster or someone introduces himself. And, you know, Washington remembers them. Oh, yes, yeah, great. Interesting. Great work. Good work, boys. It's amazing.
Starting point is 00:35:52 I mean, what a difference. a few centuries make. I mean, today we would be doing a ticker tape parade for these guys. I mean, it's that completely different attitude about war. Well, they'd be on TikTok bragging about it. That's what they'd be doing. A TikTok parade. The fact is, though, as you say, they just disband. They go back to their regular lives. So we don't really hear anything about them until, I guess, more than a century, really. And it's not until the 1930s that there is any kind of historical research beginning about them. And that's when they find out of a Culper Jr. and Culper Senior and start beginning to patch it together.
Starting point is 00:36:27 But it was really your book that at least brought it to my intention, you know, in our age, which is pretty incredible. That's the weird thing. The original work was done by a man called with the immortal name of Morton Pennypacker. Just sort of a local amateur historian who did Sterling work piecing together who exactly Robert Townsend was and the relationship with the culprit in. And he wrote a book in the early 30s called George Washington Spice. and it's a fantastical read in the sense of, you know, he made up most of it.
Starting point is 00:36:59 Oh, really? Penny Packer was this kind of Victorian sentimentalist, and he swabbed all this sort of romantic varnish over the spies. He also didn't have any footnotes or anything like that, so you don't really know where any of the information came from. And then it was kind of romanticized over the, there were a couple of books that came out afterward that based on him. So I decided to go back into this and just, again, reopened this cold case. and try and just put the real story together. And there was actually a huge amount of information out there. It's just that hadn't really been put together in a history book
Starting point is 00:37:31 with proper noting and references and so forth. Right. Well, you knocked it out of the park. It's an amazing book. Alexander Rose's book we're discussing is called Washington Spies, The Story of America's First Spy Ring. You must get this book. It's been out for a long time, but it's really worth reading. It raised much awareness about the history. Of course, as we've mentioned, led to the big, multi-seasoned television drama, Turn, Washington Spies, which I'm sure you can still watch online. It will become an addiction.
Starting point is 00:38:00 But first, of course, buy and read the book. Thank you so much. Dr. Rose, Alexander Rose, it's been nice to meet you. I'll see you in the neighborhood. Well, thanks for having you on. Hey, thanks for listening to American History Hit. You know, every week we release new episodes, two new episodes dropping Mondays and Thursdays, all kinds of content from mysterious missing colonies to powerful political movements, to some of the biggest battles across the centuries. Don't miss an episode. By hitting like and follow, you help us out, which is great,
Starting point is 00:38:32 but you'll also be reminded when our shows are on. And while you're at it, share it with a friend. American History Hit with me, Don Wildman. So grateful for your support.

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