The Godfather of American Spying

Code names, dead drops, invisible ink, and secret ciphers were all part of the American Revolution. Historian Taylor Stoermer introduces Benjamin Tallmadge, George Washington’s chief intelligence officer.

Learn more: Spy Central


Harmony Hunter: Hi welcome to the podcast. I’m Harmony Hunter. History at its best is nothing more than a collection of great stories: stories of heroes, stories of villains, struggles for power, and stories of spies.

It’s that last type of story, the spy story, that we get to talk about today. Joining us now is historian Taylor Stoermer who stopped by to tell us about the grandfather of American spying, Benjamin Tallmadge.

Taylor, thank you for being here today.

Taylor Stoermer: Oh, it’s my pleasure Harmony.

Harmony: Benjamin Tallmadge turns out to be sort of the founder of spying in America during the American Revolution, but before we talk about the spy ring I want to think about who Benjamin Tallmadge is; where he’s born, what kind of family he grows up in. What do we know about his formative years?

Taylor: Well we know a lot about it because he wrote a rather nice autobiography which is always helpful when you’re talking about these kinds of figures, but Benjamin Tallmadge was born in 1754 on Long Island to a rather large family. His father was a pastor. When he was 15 he went to Yale in Connecticut where he became friends with Nathan Hale, who  was a fellow student of his at Yale, and they became very good friends.

In 1773 both he and Hale graduated from Yale and they both became schoolmasters in Connecticut and then when the Revolutionary War broke out in 1775 they did what everybody else did; they joined up. So they’re in their early 20s in 1775, they join Connecticut regiments and then they end up as officers in George Washington’s army.

Harmony: Tallmadge starts out with a brilliant educational career. I did the math. He’s nineteen when he becomes a school master?

Taylor: He’s 19 when he becomes a schoolmaster.

Harmony: Is he like a child prodigy or is that a common age?

Taylor: It’s pretty common.

Harmony: So he’s not exactly a child genius, but he is very distinguished in studies. I wonder if some of this early distinction academically helps inform what he is able to do in his career.

Taylor: I think absolutely. That one of the things that is very interesting about Tallmadge is that in his background, his academic pursuits, his academic qualifications, is that from a very early age he’s very good a languages. He’s very good at Latin and Greek and when you talk about Latin and Greek. It’s not learning a language that’s based upon a familiar set of grammar rules or even on the same alphabet when you’re talking about Greek. You’re talking about interpreting symbols and transforming those symbols into a language.

I think that it’s that kind of thing that his capacity for language, his capacity to understand these ancient languages that are so different in structure from anything that he’s familiar with. I mean his ability to really grasp symbols and meaning and being able to turn those into an effective form of communication, I think that that speaks volumes for the kind of student he was, the kind of mind that he has, and the kind of things that he’s able to achieve when he becomes in charge of George Washington’s intelligence.

Harmony: How does he climb up through the ranks in his early assignments?

Taylor: Well when he first starts the war he is in a Connecticut militia unit, but I think the turning point is that when he ends up transferring to a regiment of basically Calvary. The unit is called the Second Continental Light Dragoons, but it’s basically a Calvary regiment. And at the time, and we’re talking 17th and 18th century in warfare that the units that are charged with gathering intelligence, however crudely they do it, but the units that are in charge of doing that are the Calvary units.

So they’re the ones that are supposed to be going out and engaging in reconnaissance, finding out where the enemy is, reporting on their numbers, reporting back and he’s able to go as a part of that Calvary unit. He’s able to go out on missions, on individual missions, on larger missions, to go out and find out what the enemy is doing.

I think it is that experience that makes him recognize what, not only what a challenge that is and how important it is to know that, but also how it can be done better. That having a bunch of soldiers on horses go out looking for the enemy might not be the most effective way to also keep the enemy from knowing where you are, that there’s got to be a better way to do this and so I think that that is, that’s the big watershed in his career and in intelligence gathering because I think he starts thinking about it at that point.

Harmony: What is Tallmadge’s better way? How does he improve traditional recon?

Taylor: Well the first thing that he actually does, and he does this still while he’s part of the Continental Dragoons, is that he develops a network among his friends. Now at the time most of the fighting is going on around New York. It shifted from Boston down to the New York area. The British Army is in control of New York, but remember Benjamin Tallmadge is from Long Island and so he has all of these connections around New York and down Long Island where the British are and so he thinks that the best way to be able to communicate, to find out what the enemy is doing and to communicate that information accurately and quickly is to put together a network of those people.

Harmony: But this is a civilian network.

Taylor: It’s a civilian network. These are people who are not a part of the military and for the most part not known to each other. I mean, he starts off with them being his friends, but then builds on that as he expands it even further and he develops his own ideas about how to go about doing that.

He wasn’t the first person who was in charge of intelligence gathering for George Washington. That was a guy named Charles Scott. But Charles Scott wasn’t doing a terribly good job. So Washington did things like would go out and ask for volunteers from the Continental ranks, particularly from the Calvary units who would be interested in going on spying missions and that’s how Tallmadge’s friend Nathan Hale gets involved. That in late 1776 Washington does this. Goes out asks for volunteers for people who are willing to go on spying missions behind British lines in New York to find out what the enemy’s strength numbers are, what their locations are. And Nathan Hale steps up.

Nathan Hale has no training as a spy, obviously. I mean he’s almost exactly the same age as Benjamin Tallmadge. They’re both 22 at the time and, but his enthusiasm is such that he’s not going to let this opportunity go by to distinguish himself with the Commander in Chief and so in a very, what me might call an amateurish way if that’s not putting it too strongly, he goes behind enemy lines, he has a heart of an ox in doing this and nothing scares this guy, but he is quickly identified when he gets behind those lines on Long Island in Tallmadge’s backyard. He is openly, in a notebook writing down enemy strengths, enemy positions. People pegged him very quickly and then in a tavern one night a British officer basically gets him to confess that he gets him to admit that he’s actually behind the lines spying on the British for the Americans and that’s on September 21, 1776 and poor Nathan Hale, for all of his spirit, got himself into trouble very, very quickly and on September 22 he was hanged.

Harmony: This must have really been a searing shock to Tallmadge to see his childhood friend; his college friend caught spying this way and meeting this end. Do you think that that’s one of the influences that makes Tallmadge think, “How can we do this better?”

Taylor: To me one of the most interesting things about the American Revolution is how personal it is for so many of its participants that how the things that influence the course of their careers, the choices that they’re making are all so individual. They’re based upon personal relationships. And I think that what happens with Nathan Hale and also with his brother William are things that influence him enormously. That here is one of his best friends he went through his formative years with when they’re at college, they both follow the same pattern in their careers as school teachers and then their careers in the Army and what happens is that you have somebody who is inexperienced, you’re sending them behind the lines to do something dangerous that trained, experienced people should be doing and you’re just putting both them and your own cause at risk.

So what you need to do, and I think that this is how it really impacts Benjamin Tallmadge is that when the British not only find him so easily and they react so quickly and execute him right away that that makes Tallmadge think that what we need to do is have trained people do this. We need to come up with a clear system for gathering this information and we need to make sure we are dealing with people in a fair way when it comes to this. So asking for volunteers isn’t going to do it. If we want to really win this, then we need to be professional about how we’re gathering our intelligence. And in the back of his mind I think he always has the example of Nathan Hale as to why it’s so important to develop a professional intelligence gathering network that’s geared entirely to do that and not asking people to do things that they’re not trained to do because that’s just blatantly unfair to them and its detrimental to the cause.

Harmony: And thus begins the Culper Spy Ring. Tallmadge creates his spy ring and they initiate a lot of practices that are new to the American Revolution, maybe not new to the world. What are some of the techniques that Tallmadge institutes in his own spy ring?

Taylor: Well, a couple of things that are really interesting because he’s very creative as we talked about before in terms of his use of languages. I mean their use of codes, but also in terms of their practices, but everybody has a code name so that nobody knows actually who any other members of the spy ring are. So that the spy ring had dozens of people in it, but he thought that the best way to protect them and to protect the network that he built was to make sure that nobody knew who anybody else was, including George Washington. George Washington had no idea of the identity of the people who were in this spy ring. Only Benjamin Tallmadge and one of the other major figures in it knew who anybody else was and so that’s the first thing is keeping your identity secret.

Harmony: And how did they do that? They gave individuals numbers.

Taylor: Well they gave some individuals numbers so you would be 121, you’d be 242. One of the things that Tallmadge did was, he came up with his own cipher book that was basically a dictionary of numbers that were assigned to particular words and particular identities and particular places. So these people would not only have their own code names in this book so say John Culper who isn’t a real person but he would then have a number. And so when they were communicating back and forth to each other or even communicating between Tallmadge and Washington he would refer to them by number so that even if you had the cipher you would then just have this person’s code name and you still wouldn’t know who they were.

Some of the other things that they did in terms of practices, they would use dead drops in order to exchange information about troop movements and so what this network would do is it really was connecting dots that one person would find out the information and then they would take it to a dead drop for example so that would be in the case of the Culper Spy Ring the middle of a field on the Northern shore of Long Island that had a large rock in it, but under the rock the ground was dug out and so they would put the message into the hole, put the rock back over it, and then a woman right next door would put up on her wash line a white sheet, just like she was drying her sheets, but one sheet or two sheets or three sheets would mean different things to somebody who’s watching from the other side of the Long Island Sound. But these people wouldn’t know each other.

And so things like dead drops, things like code names and things like ciphers were hallmarks of the Culper Spy Ring. One of the things that made them so effective in giving George Washington the information he needed to keep the British Army bottled up in New York for as long as he could.

Harmony: And of course like all good spies they used a great quantity of invisible ink.

Taylor: They did. They had a whole bunch of different ways of doing it. Tallmadge was particularly…it was and now again this is another example of how Tallmadge’s mind worked. Tallmadge came up with a very complicated invisible ink. Some invisible inks are very easy; lemon juice works, milk works and all you have to do is write it in lemon juice for invisible ink, you expose it to a little bit of heat and then the message shows up on a piece of paper. It’s very easy.

But what Tallmadge came up with was one that was based upon a compound of chemicals and so you would use…you would write it in one form of chemical and then in order for it to appear you’d have to apply another chemical to do it. So it wasn’t quite so as easy all you’re doing is you’re using lemon juice and you just hold it up to a candle. You need both chemicals. Tallmadge used that a lot between himself and Washington. And so there are lots of examples of letters between him and Washington that are using this invisible ink compound.

Now other people would write using different kinds of codes so they wouldn’t have to worry about things like invisible ink, that they would use things like what’s called a book code and that’s what something John Andre and Benedict Arnold used to communicate and something that’s still used today. But that just depends upon two people having the exact same edition of a particular book and that’s just a set of numbers that’ll guide you to a page, a line and the word in that line.

Another way that was also a favorite of the British, the Americans didn’t use this one very often, was to use what’s called a Cardan grille, or a mask. And that is basically you write your message in a particular form. Henry Clinton, who was the Commander in Chief of the British Army, used an hourglass. So basically, you write your message in this, using the shape of an hourglass, so you write your message in the hourglass and then you take off the grill and then you actually write a letter around those words incorporating them. So when you read it just, on the face of it, it’s just an innocuous letter about supplies or something like that but then when you put the grill over it…

Harmony: Like a stencil?

Taylor: Exactly like a stencil. The real message will show up. And the British loved that one, and it actually got them into trouble because Clinton almost refused to use pretty much anything else. So during the Battle of Yorktown, a number of dispatches from Charles Cornwallis to Clinton are intercepted and the codes in them are easily broken by the Americans, because they know exactly what Cornwallis’s situation is.

And there’s one case that I think it’s very interesting to talk about when you’re talking about spying in the American Revolution and that is anybody can do it. This wasn’t, and I think this is something that was particularly important to Tallmadge too, about “let’s not use the likeliest candidate for this.” Really anybody needs to be doing it; young, old, male, female, free, enslaved.

Harmony: You said that anybody can be a spy and at Colonial Williamsburg we really mean that. We’ve got a program called Rev Quest that allows guests, parents, children, families, adults, everybody to come and be a spy. Tell us about that program and how it works and how it will draw you in to the world of Revolutionary spies.

Taylor: Well Rev Quest The Lion and the Unicorn is really about making sure that those who play the game understand that to protect your republic, to protect your country it requires the personal responsibility of every citizen. Everybody has this kind of responsibility and can play a role and so what we’ve done with the Lion and the Unicorn is that we have taken a very real historical figure, a double agent, and following his experience, people who play the game have to find out who he is, and also defend him from being identified by the British.

And to do that, they have to actually use 18th century documents, but also a number of these spying techniques that we’ve just been talking about. They have to decode a number of letters. They have to use things like the book code. They have to use things like the Cardan grille.

In doing so, they’re able to learn about the French alliance with America, they’re able to learn about British offers of freedom to slaves, they have to learn about what it means to be a double agent, how spying in the American Revolution because this is essentially a Civil War is particularly fraught, because you don’t know who your enemy or your friend is. You have to be very careful about these things because it could be very easy for you to take a misstep and then you end up not only endangering your cause but you end up endangering yourself.

Now of course nobody is going to be endangered playing Rev Quest Lion and the Unicorn at Colonial Williamsburg, you can learn a whole lot about what it meant to be a spy during the American Revolution and you can also have a whole lot of fun doing it.

Harmony: And listeners can start now. They can get their spy name for starters on your website. Taylor, where can people go to start learning about this game?

Taylor: The can go to and there they can get their spy name as they said and they can also begin to play the game by learning a whole lot about the kind of things that we’ve been talking about; what it means to be a spy. They can get messages from Benjamin Tallmadge, they can find out a lot more about him, they can find out a lot more about the techniques they need to know in order to be a spy before they every arrive here in Williamsburg so they’re ready to hit the ground running.

Harmony: Well Taylor, if that’s your real name, thank you so much for being our guest today.

Taylor: Thank you very much Harmony.


  1. This was really fascinating! My one regret about our recent trip to Colonial Williamsburg was that our son wasn’t interested in RevQuest… Maybe next time I will play this episode of the podcast for him first! Thanks for another great discussion.

  2. Well done history. Well done interview. Mr. Stoermer not only knows the subject well but draws valuable conclusions. Linking Benjamin Tallmadge to his friend Nathan Hale in the podcast was great for people to hear. I’ve enjoyed reading the messages between Tallmadge and George Washington on the LOC website.

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