George Washington's Spies

Summary

AMERICAN HISTORY HIT
Host: Don Wildman
Guest: Dr. Alexander Rose
Episode: George Washington’s Spies (April 30, 2026)

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Episode Overview

In this compelling episode of American History Hit, host Don Wildman interviews historian and author Dr. Alexander Rose about the origins, operations, and legacy of George Washington’s famous Culper Spy Ring—the United States’ first organized intelligence network during the American Revolution. Dr. Rose, whose book "Washington’s Spies" inspired AMC’s acclaimed series Turn: Washington’s Spies, provides expert, often entertaining insight into the genesis of American espionage, key figures in the spy ring, their secretive methods, and the unsung role intelligence played in the Patriots’ quest for independence.

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Key Discussion Points & Insights

1. Setting the Scene: The Importance of Intelligence in the Revolution

• Context of Creation (05:43)
  • The Culper Ring formed in 1778, when Washington desperately needed reliable intelligence from British-occupied New York.
  • Dr. Rose: “Washington had long…been trying to put together an intelligence outfit…He didn’t have the experience to do it—not nobody really did…in mid-1778, it all came together…That really helped out Washington at a key moment in the war.” (05:43)
• The British held substantial advantages (army, navy) but overlooked the need for an intelligence network.
  • Dr. Rose: “No, they didn’t [have an intelligence network]…they never developed an intelligence network…One is…geography…millions of square miles of undeveloped country…Most people are just trying to get by, want this whole thing to end.” (07:12)
• The British assumed the rebellion could be quashed with conventional force.

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2. Early American Espionage Efforts & Revolutionary Learning Curve

• Washington’s early forays into espionage (e.g., Nathan Hale’s failed mission) were marked by naïveté and lack of structure:
  • Dr. Rose: “When [Washington] starts, Washington goes the conventional way…this is what leads to…the Nathan Hale debacle.” (11:11)
  • Hale was executed after being caught behind enemy lines, which had a profound impact on Benjamin Talmadge, his friend and a future Culper leader.
• Washington’s evolution: shifted from short-lived, untrained agents to embedding trusted civilian informants within occupied territories, with a reliable system for communication.

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3. The Key Cast: Who Made Up the Culper Spy Ring?

Benjamin Talmadge (Codename: John Bolton)

• Yale-educated, idealistic son of a minister, officer in the Dragoons, acted as Washington’s close intelligence contact and key network organizer.
  • Dr. Rose: “He’s quite handsome…very dashing…falls in with Washington, becomes a kind of adjutant…He falls in with Washington because he’s friends with these guys in Long Island.” (19:25)

Abraham Woodhull (Samuel Culper, Sr.)

• A farmer and emotional center of the ring, ran the operational cell on Long Island, often nervous but deeply committed.
• Used frequent visits to his sister in New York City as a cover for intelligence-gathering trips.

Robert Townsend (Samuel Culper, Jr.)

• Well-connected merchant in New York City, key infiltrator and collector of crucial military gossip and officer conversation—a “cool customer” and sometimes a “diva” about his role.

Caleb Brewster

• Daring whaleboatman, responsible for physically moving intelligence across Long Island Sound, sometimes acted outside the rules.
• Dr. Rose: “Caleb Brewster didn’t even bother using a code name…he thought he was the bee’s knees.” (25:20)

Austin Roe

• Courier who transported Townsend’s intelligence from NYC to Woodhull.

On Group Dynamics:

• Their mutual trust and shared backgrounds made the ring unusually resilient and less susceptible to British infiltration.

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4. Tradecraft: Methods and Innovation in Revolutionary Spycraft

Communication and Secrecy

• Early use of basic codes, but later adopted:
  • “Sympathetic stain”—an early form of invisible ink invented by Dr. James Jay, which required a special chemical to reveal.
    • Dr. Rose: “Jay developed what’s known as the agent, the liquid in a bottle…when you swabbed the chemical reagent over the letter…the letters would suddenly appear.” (31:47)
  • Codebooks and ciphers (often primitive but effective for that era), with numerical substitutions for names and places (e.g., Washington was “711”).
    • Dr. Rose: “It was alphabetical, which was a big security flaw…” (32:59)
• Dead drops and agreed-upon secret locations enabled clandestine information relay.
• Despite occasional mistakes (e.g., confusion over which sheet held a secret message), the methods grew increasingly sophisticated.
• Impressive speed—dispatches could reach Washington in about a week, which was considered "amazingly fast" (34:51).

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5. Contributions & Lasting Impact

• The ring provided a constant stream of vital tactical information from deep inside enemy lines—often the only way Washington knew British plans or troop strengths.
  • Notable Successes:
    • Warning about a planned British naval assault on the French at Rhode Island (38:01).
    • Talmadge’s role in foiling Benedict Arnold’s planned betrayal of West Point.
  • Dr. Rose: “The Culpas had done sterling work there in getting this tip off to Washington.” (38:01)
• Their greatest value was continuity, reliability, and immunity to infiltration; the network “remained intact” for the duration of the war (40:40).
• Washington formed a strong (if secret) attachment, acting as almost a father figure for the ring’s members.

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6. Post-War Silence & Rediscovery

• Cultural attitudes toward espionage in the 18th century fostered secrecy and even embarrassment—no boasting or victory parades for these heroes.
  • Dr. Rose: “They were all regarded [as] spying as dishonorable…so they never talked about it.” (41:00)
  • Talmadge devoted just a single sentence to the spy network in his memoirs.
• The truth about the Culper Ring did not really emerge until the 20th century, when local historian Morton Pennypacker pieced together their identities and operations in the 1930s.
  • Pennypacker, though romanticized the story, set the foundation for Dr. Rose’s more modern and rigorously researched history.
    • Dr. Rose: “[Pennypacker] swabbed all this sort of romantic varnish over the spies…he also didn’t have any footnotes…” (43:20)

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Memorable Quotes & Notable Moments

• On Washington as Spymaster:
  “People always say, ‘oh, you know, you couldn’t tell a lie.’ Well, no, Washington told a lot of lies—and smiled as he did so—mainly when he was spying the daylights out of the British. He was very, very good at it.” – Dr. Rose (13:11)
• On the Culper Ring’s Power:
  “They provided him [Washington] with a window—men on the ground in what was then occupied New York City and Long Island, which were the breadbasket of the British Empire in America.” – Dr. Rose (05:43)
• On Period Spycraft:
  “Remember, 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.” – Dr. Rose (28:55)
• On Historical Modesty:
  “Today we’d be doing a ticker tape parade for these guys…Well, they’d be on TikTok bragging about it—that’s what they’d be doing, a TikTok parade.” – Don Wildman & Dr. Rose (42:12)

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Timeline of Important Segments

• 05:43 – How and why the Culper Spy Ring was formed, Washington's intelligence struggles
• 07:12 – Why the British failed to develop a similar intelligence network
• 11:11 – Early Patriot espionage failures (Nathan Hale), and lessons learned
• 13:11 – Washington’s unlikely talent as a spymaster
• 19:25 – Introduction of the main participants (Talmadge, Woodhull, Townsend, Brewster)
• 25:20 – Colorful personalities and the inherent dangers the spies faced
• 28:55–32:29 – Development of spycraft: codes, invisible ink, and communications
• 34:51 – How fast information moved through the network
• 38:01 – Major intelligence coups and ongoing value of the ring
• 41:00 – Post-war silence and attitudes toward espionage
• 43:20 – Rediscovery of the Culper Ring story in the 20th century

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Conclusion

This episode pulls back the curtain on the shadowy but critical world of American Revolutionary spying, reminding listeners that battles are not just won by bullets and bayonets, but by information and the courage to deliver it. Dr. Alexander Rose’s lively expertise and anecdotes help humanize these unsung heroes—showing both their quirks and their historic importance—and cement their place in America’s founding story.

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Recommended Reading:
"Washington’s Spies: The Story of America’s First Spy Ring" by Alexander Rose
Turn: Washington’s Spies (AMC Period Drama Series)

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For those fascinated by hidden history, this episode is an essential listen—and keeps the spirit of the Culper Ring alive for modern America.

Transcript

[Don Wildman]

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[Dr. Alexander Rose]

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[Don Wildman]

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[Dr. Alexander Rose]

it just gonna be about machines talking to other machines? I mean, should you quit your job and start something on your own? What would that take?

[Don Wildman]

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[Dr. Alexander Rose]

These are the questions we answer each week on Lead Human with Jack Myers and Tim Spengler.

[Don Wildman]

Join us each week and subscribe at your favorite podcast platform and YouTube.

[Dr. Alexander Rose]

We'll tell stories, we'll hear from some of the best, and we'll try to figure this out together. We're lost.

[Don Wildman]

It feels like we're going round in circles. I'm gonna ask that man for directions. Hi there. We're trying to get to the state fairgrounds. Well, you're gonna take a left at the old oak tree at this here road.

[Dr. Alexander Rose]

Nah, I'm just kidding. Let me get my phone out. How is there signal out here?

[Don Wildman]

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[Dr. Alexander Rose]

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[Don Wildman]

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 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 Hit's 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 watching, 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. Later, out on the water in the fading daylight, a whaleboat 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 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 spy ring, which was rather famously adapted into the excellent AMC period drama series Turn Washington Spies. I'm Don Wildman and this is American History Hit. Alex, thanks for joining us on American History Hit.

[Dr. Alexander Rose]

It's a delight to be here and an honor.

[Don Wildman]

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

[Dr. Alexander Rose]

very pleased by it. We had a great time making it. I was very lucky to just have the book adapted into a TV show that did pretty well.

[Don Wildman]

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. What is happening at this period in the American Revolution?

[Dr. Alexander Rose]

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. You know, he, he didn't have the experience to do it. Not nobody really did. And then just by happenstance in mid-1778, it all came together with a couple of sort of voluntary walk inside and it turned out to be the Culpa 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 he 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 breadbasket of the British Empire in America. So it was a key moment for him.

[Don Wildman]

Yeah, these are the early days, of course, the United States. It's interesting for the British this is the, we're still colonies, but for the 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?

[Dr. Alexander Rose]

Well, it's a great question. No, they, 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 awful rabble rousers in New England and we'll be done with it. And they want to go back to paying their tax, 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, 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. 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 Olmutz to Koeniggratz. 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. 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. It's all military. And Washington is this shadowy figure in the background. 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 context. 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. 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 with a 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 troop. They didn't. They just didn't have that at all.

[Don Wildman]

Yeah, 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 how 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. There were other espionage efforts before what we're about to discuss by the Patriots. Can you explain those?

[Dr. Alexander Rose]

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 know. And, you know, a kind of a collective wisdom that's being garnered over the ages about how to do stuff.

[Don Wildman]

Yeah.

[Dr. Alexander Rose]

In the 18th century, like Washington, you don't really know how to spy. It's not as. It's not as easy as you think.

[Don Wildman]

Yeah.

[Dr. Alexander Rose]

You. It's very difficult. So when he starts Washington. This is in 1775 or so. When he starts, Washington goes the conventional way and that. 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 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, you know. No, you know, in disaster. He gets caught very quickly and he's. And he's hanged. Washington learns a lot from this, but he. There's not much he can do about it. But. 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. I mean, they. You can't pick up any information. 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, again, with the arrival of the Culpa Ring, 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 means of transmitting information back to his headquarters. Yes. And that is trustworthy and that can be evaluated and analyzed. Factually, it's like an evolution of aspiring in the agenda. Covering just didn't pop abracadabra out from out of nowhere and worked perfectly. 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 spymaster. People always say, oh, you know, you couldn't tell a lie. Well, no, Washington told. Washington told a lot of lies and smiled as he did so mainly when. When he was spying the daylights out of the British. He was very, very good at it.

[Don Wildman]

Interesting.

[Dr. Alexander Rose]

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. Yeah, Washington was just a natural.

[Don Wildman]

I want to circle back to Nathan Hale for a moment. I mean, he gets less attention than the port 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 he was he. An important point of Nathan Hale is that he actually knew the guy we're about to talk about, who is Benjamin Talmadge.

[Dr. Alexander Rose]

Right.

[Don Wildman]

They went to school together.

[Dr. Alexander Rose]

They were at Yale together. That's where they met. They were college buddies. And you know, they were in lots of frothy, fast together. And did you know all the fun stuff that college boys do in the 18th century supposedly consists 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 sudden ways later on.

[Don Wildman]

And Hale, of course, was the famous quote, I regret having but one life to lose for my country, which he said just before he was hanged. One of 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 spy ring 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?

[Dr. Alexander Rose]

Well, it's a bit of a mystery. It was named after one of the aliases or code names of one of the spies, and it was Samuel Culber, 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 I'm mispronouncing Culpepper county in Virginia. The coincidence of Culpepper and Culpa 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 past. That's where it comes from. I think nobody ever wrote down why they chose that name, but that's what I think.

[Don Wildman]

So he establishes the necessity for this spy ring. 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. This episode brought to you by Best Western Hotels and Resorts. Ah, spring. Trees blossoming, flowers blooming. Not having to defrost your fingers and toes when you get inside. Oh, yeah, and spring break freedom. Warmer climbs and memories just waiting to be made. And at Best Western, spring break isn't just what it used to be. It's better this spring. Stay three nights and get a $50 Best Western gift card. Life's a trip. Make the most of it at best Western. Visit bestwestern.com for complete terms and conditions.

[Podcast Advertisers/Hosts (Hayden and Stephen)]

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[Dr. Alexander Rose]

And I'm Stephen, your bookish Internet goofball, But you can call me the Smash Daddy.

[Podcast Advertisers/Hosts (Hayden and Stephen)]

And we are currently deep diving Brandon Sanderson's fantasy epic Mistborn. But here's the catch. Stephen here has not read Mistborn before.

[Dr. Alexander Rose]

That's right.

[Podcast Advertisers/Hosts (Hayden and Stephen)]

Hey.

[Dr. Alexander Rose]

Hey. So each week, you'll get my unfiltered raw reactions to every single chapter.

[Podcast Advertisers/Hosts (Hayden and Stephen)]

And along the way, we'll do character deep div dives, magic explainers, and Steven will even try to guess what's next. Spoiler alert. He'll be wrong.

[Dr. Alexander Rose]

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[Don Wildman]

Okay, we're back with Alexander Rose, historian and author of Washington's 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 culprit spy ring. There had been previous espionage efforts which had not worked out very well. So let's talk through the key figures who are, who will comprise this intelligence network. Famous names, first of all, Benjamin Talmadge, codename John Bolton. Who was this guy?

[Dr. Alexander Rose]

Benjamin Talmage was, as we mentioned, a close pal of Nathan Hale's at Yale. And you know, they keep in touch, you know, after the war. He's, you know, Talmadge is this idealistic, I think he's the son of a minister from Long Island. He's very well educated. You know, new Greek, Latin, Hebrew, all the, you know, all the classical languages. You know, he's very idealistic and yes, he, when the war breaks out, he joins a Dragoons unit. You know, he was a well bred young man, so became, you know, as you would expect, a Dragoons officer. Why not? 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, you know, the whole ridiculous hat in an impractical 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, becomes a kind of an adjutant or, you know, 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 Setauket, little town, Oyster Bay. A couple of them are, you know, they became very important. One of them, the lead one, was a man named Abraham Woodall, or Woodhull, as some people say, but I think it's Woodall, who was a farmer out there. And there was a couple of other guys later on, people like Austin Rowe. There was this kind of a whale boatman, 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 is 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. 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 betray each other. And Talmage is the leader of this, while the cell leader on Long island itself is Abraham Woodall.

[Don Wildman]

Right.

[Dr. Alexander Rose]

A little later on, they come into contact with a man called Robert Townshend. He was, you know, just down the road in Oyster Bay. And he's a, again, he's a half Quaker, half Anglican or Episcopalian, I think, merchant. But, you know, they had sort of known each other, but he was. Townsend was always a bit of the outsider here.

[Don Wildman]

They all come, as you're saying, from a place called Setauket, or at least the two guys, Abraham and Benjamin, come from Setauket, Long island, which confused me even when I was watching Turn. That's a long ways away in those days. You know, Long. Long Island's a massive place 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, this ring would be based. Why there?

[Dr. Alexander Rose]

That's where he had his friends.

[Podcast Advertisers/Hosts (Hayden and Stephen)]

Okay.

[Dr. Alexander Rose]

But they did expand. I mean, sir talk in oysterbury is about 50, 55 miles from New York. So, you know, it's a few days ride. It's not in the. Completely in the middle of nowhere. But they expanded. One of the reasons they needed Robert Townsend, the Quaker, is that he would stay in New York. He had a business in New York. Now he was a well established merchant there, so he's a very useful connection there.

[Don Wildman]

I see.

[Dr. Alexander Rose]

And secondly, Sutorket, though it is out a little bit, he's not downtown Manhattan. You know, it was that Long island was the granary and the bread basket. 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 to talk it. So it's very useful for notes. So, you know, they got their, the hay for their horses and cavalry. That's where they got it from Long Island. So it's a very important place to have it, especially when you're Washington and all you want is facts and figures. It was very useful.

[Don Wildman]

It was also very seagoing. And this was a center of privateering. Right. This was what Abraham Woodall had been up to.

[Dr. Alexander Rose]

Well, Woodall happened. Woodall was, this was a, you know, horny handed son of toil, farmer figure. The guy who was the, you know, the crazy action man figure. He's very entertaining is Caleb Brewster. He's one of these people who live in a kind of a gray zone 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. The polite word for it is privateering.

[Don Wildman]

Smuggling.

[Dr. Alexander Rose]

Well, yeah, that's a, 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 donated to the great cause.

[Don Wildman]

Right, Tax free.

[Dr. Alexander Rose]

Tax free, yes, exactly.

[Don Wildman]

Making a little money, no forms required. Right, so Talmage knows Woodall. Woodall then is turning to his friends as well. And this is how this network is established, this circle, the 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 this thing from the top. 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. These are codenames that will become very important in the way that they communicate.

[Dr. Alexander Rose]

They're a bit unoriginal. When it came to the codenames with the Junior and Senior, they could have done a little better there. I think.

[Don Wildman]

It certainly emerges in the series that Abraham Whittle 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?

[Dr. Alexander Rose]

Absolutely. I mean, what comes through in all of their letters is that they all have very distinct characters. You know, you have Woodhull, 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 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 in a huff when he didn't get what he wanted. Caleb Brewster didn't even bother using a code name. He just went under his own name because he thought he was the bee's knees. Kind of challenged the British to catch him. So they all have their own very distinct characters. And the point is that they had all sort of known each other. Again, Talmadge knew all of them. And Tallmadge could probably best be classified or categorized nowadays as the case officer. He very rarely. He was based in Connecticut, and he very rarely went to Long Island. It was very dangerous. And that's what. Well, made Abraham Wood also nervous. What they were doing was dangerous. They were spies. There's no sugar coating 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 sort of local scaffold, probably. 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.

[Don Wildman]

At some point, there is a very close call from Woodall because he's going into the city under the COVID 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. That's where Caleb Brewster becomes much More active. But they're getting their event, their. Their information eventually from this man named Robert Townsend, who has his own connections in town.

[Podcast Advertisers/Hosts (Hayden and Stephen)]

But.

[Don Wildman]

But often he's listening in on. On officers at a. At an inn. Right. At a. A drinking house.

[Dr. Alexander Rose]

Yeah. They. They all played their part in acquiring intelligence.

[Don Wildman]

Yeah.

[Dr. Alexander Rose]

Townshend 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, you know, of officers chatting to each other. I mean, he was 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 Woodhall, who would supply his own information. He watched British logistics or supply trains going by, wagons going past, and he would count how many haystacks there were or how many artillery pieces went by. Stuff that Townsend didn't do in a. 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'd be picked up by either Talmadge or one of his designated dragoons, and it would be speeded to Washington, whose headquarters were most of the time in sort of around White Plains.

[Don Wildman]

Right. So the Culpa 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.

[Dr. Alexander Rose]

Yeah. Remember, 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've read them all. He would fill his letters to Washington almost as you know, because he was speaking to the commander in chief of the Continental Army. And, you know, he's a very 18th century way of thinking, you know, he's a great man. I must respect him. And it was just full of these grand perorations about the importance of liberty and freedom and throwing off the oppressor's yoke and all this kind of stuff. And Washington just goes, could you just tell him. Just leave that stuff out. I just need the numbers. Just tell me how many artillery pieces they have. Tell me how many horses they have, which regiments are there, how many haystacks there are. Have they brought in the food yet? So, Abrams for a while, Woodall Learns and he compresses his reports and keeps it strictly to the facts, man kind of thing. So, you know, and again and over time, Washington supplies them with a kind of an invisible ink developed by, I always get his name, 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 because it was very difficult to find these chemicals.

[Podcast Advertisers/Hosts (Hayden and Stephen)]

Right.

[Dr. Alexander Rose]

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, I think it was. I think it was Woodall. And they would write between the lines a lot of the time or and of a regular letter in invisible ink. And one time, Woodall comes up with this brilliant idea. He gets a sheaf of blank paper and he writes the entire letter in invisible ink and he inserts it somewhere in the sheaf of paper. He sends it to Washington. Washington complains, okay, you know, which one is it? Because they forgot to mention where it was in the pile of paper. So they make mistakes, as does Washington.

[Don Wildman]

Tell me what the chemistry I. You know, when I was a kid, I used this. Some from little spy books. But what was the mixture that they used for this ink?

[Dr. Alexander Rose]

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 play. At the time it was very advanced. You know, they would use lemon juice and you could expose it over a flame.

[Don Wildman]

I see.

[Dr. Alexander Rose]

You know, some. I mean, if you were really in a pinch, you could use urine. Worked pretty well, apparently, though a bit. 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. That's sort of a recipe for it. It's kind of out of some sort of nut.

[Don Wildman]

It's called the Sympathetic Stain. A 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?

[Dr. Alexander Rose]

Well, the reason it's called a Sympathetic Stain, kind of catchy name for it. 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, is that Jay developed 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 the 18th century sense in that when you swabbed the chemical reagent over the letter with the invisible writing, the letters would suddenly appear.

[Don Wildman]

Oh, magical.

[Dr. Alexander Rose]

It was a very complex process, but that's what made it such a quite an astounding step forward. They probably used it in Europe before, but in the US or North America it had never been seen. And it took a lot, a long time to develop.

[Don Wildman]

I think of the sneaky Spanish and French as using all this stuff, not the honest English.

[Dr. Alexander Rose]

Well, that gets into a whole different 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.

[Don Wildman]

The code books also became more sophisticated, right?

[Dr. Alexander Rose]

Well, yes and no. They started off in plain English and they developed what's known as a code dictionary. This is essentially an, to use a little bit of jargon here, a mono alphabetic alphanumeric substitution system. That is a long phrase for what you have is you switch out a name or a word and you put a number in instead. It's something again, an 8 year old likes to do nowadays. And it was alphabetical, which was a big security flaw in it, by the way. So Rhode island would be 7:12 and Pennsylvania would be 4, 5, 6 kind of thing. And you would switch out the various numbers and you would try and mislead like that. You would use it for names, you would use it for numbers, you would use it for places, that kind of thing.

[Don Wildman]

George Washington was 7 11, right?

[Dr. Alexander Rose]

711 or 71 1. And they had a list of code names and so on and 712-713 and all this sort of stuff. Again, an experienced code breaker at the time would have broken it in about 15 seconds. It was so easy to do. 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 encrypt messages that take days to decrypt.

[Don Wildman]

Right.

[Dr. Alexander Rose]

They have to move fast and it would forestall just a casual cursory examination by someone.

[Don Wildman]

And they use dead drops and so forth, you know, familiar to all CIA people to pass on this information. Agreed upon locations, et cetera and this is how they kind of kept things. So at the height I'm just to review here, you've got Townsend gathering intelligence in New York City. A guy named Rowe, one of their other agents transporting this.

[Dr. Alexander Rose]

The courier?

[Don Wildman]

Yeah, the courier. Woodall compiling it as a talket. Caleb Brewster delivering. Talmad's receiving it. Washington considers. How fast did these messages travel through this network?

[Dr. Alexander Rose]

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, remember, you have to get it outside of 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 it, you know, they did it in at the height of their powers. It took about a week.

[Don Wildman]

Wow.

[Dr. Alexander Rose]

Which to Washington was amazingly fast. And that was regarded as extremely timely intelligence, which is why he valued them so highly.

[Don Wildman]

And over time I imagine they're more often being sent. So he's maybe getting them every few days as a result. Right.

[Dr. Alexander Rose]

At key crisis moments they would, it would come in quite regularly. Other times when there was nothing much going on, especially later in the war when a lot of the action moves to the south, the Culpas really aren't anywhere near as useful as they used to be. So they kind of. It becomes much more irregular at that point.

[Don Wildman]

Right. All right, let's take another break. When we come back, we'll discuss the Culpa rings biggest contributions to the war and how their efforts were uncovered. Years later,

[Dr. Alexander Rose]

We're lost.

[Don Wildman]

It feels like we're going round in circles. I'm gonna ask that man for directions. Hi there. We're trying to get to the state fairgrounds. Well, you're going to take a left at the old oak tree at this here road.

[Dr. Alexander Rose]

Nah, I'm just kidding. Let me get my phone out. How is their signal out here?

[Podcast Advertisers/Hosts (Hayden and Stephen)]

T Mobile and US Cellular are coming together.

[Don Wildman]

So the network out here is huge.

[Podcast Advertisers/Hosts (Hayden and Stephen)]

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[Don Wildman]

Okay, here's the turn. Actually, can you pull up the way to a T Mobile store?

[Podcast Advertisers/Hosts (Hayden and Stephen)]

America's best network just got bigger. Switch to T Mobile today and get built in benefits the other guys leave out plus our five year price guarantee. And now T Mobile is available at US Cellular stores in Hermiston. Best mobile network based on analysis by Ooklo Speed test intelligence data. Second half of 2025. Bigger network. The combination of T Mobile's and US Cellular's network footprints will enhance the T mobile network's coverage price guarantee on talk text and data exclusions like taxes and fees apply CT mobile.com for details. Howdy, howdy ho, and welcome to Fantasy Fan Fellas. I'm Hayden, producer of the Fantasy Fangirls podcast and your resident lover of all things Sanderson.

[Dr. Alexander Rose]

And I'm Stephen, your bookish Internet goofball. But you can call me the Smash Daddy.

[Podcast Advertisers/Hosts (Hayden and Stephen)]

And we are currently deep diving brief Brandon Sanderson's fantasy epic Mistborn. But here's the catch. Steven here has not read Mistborn before.

[Dr. Alexander Rose]

That's right. Hey. Hey. So each week you'll get my unfiltered raw reactions to every single chapter.

[Podcast Advertisers/Hosts (Hayden and Stephen)]

And along the way we'll do character deep dives, magic explainers, and Steven will even try to guess what's next. Spoiler alert. He'll be wrong.

[Dr. Alexander Rose]

News flash, I'm never wrong. Episodes come out every Wednesday, and you can find fantasy fanfellows wherever you get your podcasts.

[Don Wildman]

Alex, I want to talk about the impact and consequence of the Culpa 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 wheat from the chaff. What were the Culpring's biggest contributions to the war effort?

[Dr. Alexander Rose]

Oh, well, they had a couple of big ones. You know, the things that we would regard as the 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 York of troops, maybe I can launch a surprise attack and grab New York while he's not looking. Ha ha ha. Now, it doesn't come off. He decides not to do it. It's too dangerous. And Clinton calls it off because he gets delayed anyway. But it was a. You know, the Culpas had done sterling work there in getting this tip off to Washington. Second time is almost by accident. The Culpas didn't have that much to do with it. But Talmage did. In that Talmadge is the guy who realizes that John Andrew, the man who was handling the Benedict Arnold defection from West Point, that he's in Westchester county contacting Benedict Arnold, who's about to betray West Point. So Talmadge is the guy who puts it all together, mostly because he'd heard the aliases before and so on. So that's another important thing. But that stuff is actually not anywhere near as important as the continuity of the Culpa Ring. And that this was the only spy ring, 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, 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 gotta remember there were times when New York to 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 Townshend and Woodhall when he went into the city, actually providing information from inside this fortified stronghold was of, I mean, colossal value in Washington. That's why Washington spends so much time with the Culpas, 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 them right when they aired kind of thing. So there's a very close connection between Washington and these men on Long Island.

[Don Wildman]

Did they ever meet?

[Dr. Alexander Rose]

Not during the war. I mean, they, it. It again, you're getting into 18th century mentalities versus 21st or 20th century mentalities of. They were all regarded spying as. As dishonorable. They were embarrassed by it.

[Don Wildman]

Interesting.

[Dr. Alexander Rose]

They, it was something that was underhanded, it was sneaky, you know, below the salt.

[Don Wildman]

Yeah.

[Dr. Alexander Rose]

And so they, they never talked about it. 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. And it's something like. And during the war I undertook certain services for George Washington. And it continued throughout the war. 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 in chief of the army and these sort of obscure gentlemen on Long island and New York. So it's a, you know, it's an interesting. And so the stuff didn't really come out till many decades later. 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, of Long island and Woodhull or Brewster or someone, introduces himself and, you know, Washington remembers him. Oh, yes. Yeah. Great.

[Don Wildman]

Interesting.

[Dr. Alexander Rose]

Great work. Good work, boys.

[Don Wildman]

It's amazing. I mean, what a difference, you know, 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.

[Dr. Alexander Rose]

Well, they'd be on TikTok bragging about it.

[Don Wildman]

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 about Culper Jr. And Culper Sr. And start beginning to patch it together. But it was really your book that at least brought it to my intention, you know, in our age, which is pretty incredible.

[Dr. Alexander Rose]

That's the weird thing. The original work was done by a man called, with the immortal name of Morton Pennypacker, just a sort of a local amateur historian who did sterling work piecing together who exactly Robert Townshend was and the relationship with the Culver Ring. And he wrote a book in the early 30s called George Washington Spies. And it's a fantastical read in the sense of, you know, he made up most of it.

[Don Wildman]

Oh, really?

[Dr. Alexander Rose]

Pennypacker 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, reopen this cold case and try and just put the real story together. And there was, you know, there was actually a huge amount of information out there. It's just it hadn't really been put together in a history book with proper noting and references and so forth.

[Don Wildman]

Right. Well, you knocked it out of the park. It's an amazing book. Alexander Rose's book that we're discussing is called Washington 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 of course, as we've mentioned, led to the big, multi seasoned television drama Washington Spies, which I'm sure you can still watch online. It will become an addiction. 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.

[Dr. Alexander Rose]

Well, thanks for having me on.

[Don Wildman]

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, 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.

[Dr. Alexander Rose]

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