Politics & Policy

George W’s Spooks

Inside the Culper Ring.

Alexander Rose: Thankfully, this isn’t a chicken-and-egg question, so the answer is a simple one: Washington’s spies, otherwise known as the Culper Ring. There were five primary members. First in seniority was Benjamin Tallmadge, a dragoons officer who acted as the Ring’s manager in American-held Connecticut and made sure their intelligence was passed on to Washington back at headquarters. The agent who sailed back and forth across Long Island Sound (I prefer the more colorful contemporary description of it, “the Devil’s Belt”), tussling with freebooters and dodging patrol-boats, was Caleb Brewster, a former whaleboatman who really, really liked fighting. Brewster’s contact in Setauket, Long Island, was the farmer Abraham Woodhull, the cell-leader and the man who collated the Ring’s reports for Tallmadge and Washington. Based in New York itself, then under British occupation, was Robert Townsend, a well-connected merchant and ostensibly impeccable Loyalist. The agent usually detailed to ride the perilous road between New York and Setauket was Austin Roe, who owned a tavern. Getting back to the question, the Culper Ring began operations in the summer of 1778 and continued its work until the end of the Revolutionary War. Tallmadge, incidentally, had performed some secret service as early as 1777, so I guess you could say he predated even the Culpers. By way of comparison, Arnold and Andre (his case-officer, Tallmadge’s equivalent in what might be called British Intelligence) only began working together in 1780.

Lopez: How did Washington’s differ from British spies?

Rose: There’s no easy warm-up questions with you, is there? O.K, I’ll try to summarise the general differences, but I’ll restrict myself to talking about the Culper Ring, if you don’t mind. The reason is, there were so many spies working on either side at various points and in different theaters that I couldn’t possibly consider all their individual cases. Basically, in the 18th century there were three classes of “spies.” First, there were the uniformed soldiers who ranged ahead of the armies, probed the enemy’s fortifications and strength, and reported back to base. This was all above board, of course, and was part of a tradition stretching back to at least Julius Caesar. Washington himself did a bit of this sort of thing during the French and Indian War. The second type of spying was a high-class affair in which diplomats spied on each other, steamed open the diplomatic mails, and tried to break each other’s codes. Again, all perfectly acceptable, and just part of the ancient and cynical game played by Great Powers. But then we come to the third type of spy. These were paid agents of no fixed loyalty who infiltrated the enemy in civilian dress and informed on Jacobins, Jacobites, and various other radicals. Their work was universally regarded as ignoble and embarrassing (though that never stopped European spymasters from hiring them en masse), and it was to them that Napoleon was referring when he said that the only true reward for a spy was gold. Now, all the members of the Culper Ring were members of the respectable New York/Long Island middle-class and were horrified at the thought of serving for money. Or worse still, that Washington, an aristocratic Virginia landowner, would assume they wanted payment. As they told Washington on numerous occasions, they worked strictly out of republican idealism and support for the American cause. So, in short, that was the major difference between the Culper Ring and most other spies at the time. Having said that, I must add that, being patriotic Americans of sound commercial mind, they did insist on having their expenses reimbursed.

Lopez: How did Washington pick these guys in particular? Some of them sound like, well, they’d be no general’s first choice.

Rose: Well, for the most part, it wasn’t a matter of Washington picking his agents, but more that they were picked for him by Tallmadge and Woodhull. In 1778, New York was dead, intelligence-wise, and Washington desperately needed eyes and ears in the city to give him inklings of what the British were up to. He told Tallmadge to find people, and he did . . . by approaching his childhood friends — Woodhull, Roe, and Brewster — all of whom were from Setauket. In the very nasty war that was going on, it was hard to know who was trustworthy, who was a collaborator, and who would betray you. At least with Woodhull and Co., Tallmadge could be certain of their loyalties. The downside was, none of them was James Bond, and they all had particular idiosyncrasies and flaws. Townsend, for instance, was a depressive insomniac; Woodhull spent much of the War close to nervous collapse; Roe turned up late for meetings; and Brewster was sometimes difficult to find because he was conducting his own private war against the Tories. But the key thing is, they were one-man dogs who insisted on working only for Tallmadge, and only together as a team. At the same time, they were subject to the same pressures that bear on everyone’s friends, siblings, and work colleagues, which meant that they, like everybody else, had tiffs, tantrums, fallings-out, and reconciliations. In other words, they weren’t superhumans, but they were very human — just like any spy, then and now.

Lopez: What got you interested in the topic? Not exactly the first one thinks of when he thinks of that first George W.

Rose: Hmm, let me cast my mind back. I think that the idea of writing about espionage during the American Revolution first occurred to me when I was reading two books at the same time (not literally, of course): a biography of Benedict Arnold and the memoirs of another traitor, the British mole, Kim Philby. Something clicked and I thought, if you look at the Arnold affair through the eyes of a British intelligence officer, getting a senior general of the opposing army to work for you was a major coup. In fact, in British terms, Arnold was less a traitor than a defector. I began sniffing around the local university library to see what else had been written on Revolutionary spying and, much to my surprise, barely anything had. And anything that had been written tended to suffer from the same flaw; that is, they fell victim to a kind of unrealistic romanticism about spooks and spookdom. I wanted to write a book that stripped away the encrusted myths about ruthless, rugged secret agents and omniscient spymasters and told the real story of a small group of ordinary men who performed extraordinary deeds. I wanted to relate how agents (and their managers) make mistakes, cross wires, and slip up occasionally. Nobody’s perfect. Washington himself erred on several occasions (he used Woodhull’s real name by mistake) and Tallmadge was careless enough to let a packet of intelligence be intercepted by the British. These things are natural in that line of work, but with any luck, they don’t lead to your agents twisting at the end of a noose. But even now, I can’t really explain why the subject of spying was almost completely passed over for so long. It might partly be because we have this stately one-dollar-bill image of Washington and nobody wanted to undermine it by linking him to such allegedly dubious pursuits as reading other people’s mail, or perhaps simply because, well, the subject is so obvious maybe everybody kind of assumed it had already been done to death.

Lopez: How does one research something that happened over 230 years ago and was never officially acknowledged by the U.S. government?

Rose: Well, I don’t know about the “never officially acknowledged” bit, but the role of spying in the Revolution was certainly kept very quiet. That’s the whole point about spying, I guess. As for the research on the Culper Ring, anybody can do as I did and go to the Library of Congress website, navigate to the George Washington Papers section, and type in the keyword, “Culper.” Most of their letters, and Washington’s letters to them, will pop up. Thanks to a grant by Reuters and the hard work of the LofC, virtually all of Washington’s papers have been digitized and are available gratis. Good luck, though, with reading Woodhull’s handwriting. In addition to that, I pored over eighteenth-century newspapers and dug through many volumes of now-gathering-dust collections of letters and memoirs left by participants in the secret war. I was very lucky, too, in my choice of spies to write about. Spies, owing to the risk of the job, rarely keep any incriminating documents lying around, and for that reason the Culpers naturally destroyed their letters to and from Washington. However, what they didn’t know was that Washington’s efficient aides (including Alexander Hamilton) duly filed the Culpers’ letters and, crucially, kept copies of Washington’s letters to them. So, if you read every single piece of the Culper correspondence in chronological order (I don’t recommend it), what you’ll end up with is the warts-and-all autobiography of George Washington’s private spy network. To find such a trove is a rare thing indeed in intelligence literature.

Lopez: So make your movie pitch here. (I expect a percentage when a deal is done . . . ) What’s so fascinating about Washington’s spy ring?

Rose: Here goes: George Washington. Spying. The Revolution. Think The Patriot mixed with The Spy Who Came In From The Cold. Tell you what, if a deal goes through, I’ll consider donating to NRO’s scandalously nonexistent Battlestar Galactica Fund. Can’t say fairer than that.

Lopez: Any idea of what of Washington’s spies lives on in present-day spy work?

Rose: Washington’s brilliance as a spymaster shines through in his instructions to his spies. In them, he nicely outlined the eternal verities of espionage. Well aware that espionage was a game often played by fantasists and adventurers, he insisted on strictly sober observations, solid reporting, value for money, an absence of speculation, and most importantly, he used to cross-reference one agent’s reports against others to cut down on the exaggeration and hyperbole that inevitably emerges. He inherently grasped that intelligence work consists of laboriously assembling together a myriad of random facts, collected by sources of varying quality and trustworthiness, in order to form a vague picture of what the enemy might do. But the key thing was that Washington (unlike the British secret service during the “Hiram” triple-agent fiasco, which I talk about in the book) never let this fuzzy hypothesis about the enemy’s capabilities and intentions become thought of as established, unchallenged fact and then base decisions on that assumption. Those are pretty good lessons, I think.

Lopez: Have you offered any reform proposals to the CIA yet based on what you’ve learned about George Washington’s men?

Rose: I keep calling Michael Hayden, but the guy, like, never picks up. It’s as if he’s too busy to talk to random authors or something.

Lopez: Did any of these dudes wind up with government positions or just fall into obscurity when their jobs changing history was done?

Rose: I could answer that, but I won’t because that would give the ending away. Let’s just say they were modest men.

Lopez: Did the Culper Ring really change the course of history?

Rose: Yes and no. They played an important role in the Revolution, but Washington will always remain the indispensable man. They acted as good and faithful servants, and they broke some important revelations, such as the British effort to subvert the Continental dollar by circulating counterfeits and Sir Henry Clinton’s bid to destroy the Franco-American alliance by surprising the newly landed French at Rhode Island. On a day-to-day basis, they provided Washington with accurate intelligence regarding troop embarkations, naval movements, army gossip, and supply levels.

Lopez: How well did you get to know George Washington while you were writing this book?

Rose: I got to know a devious side of Washington that he kept very well hidden. He positively enjoyed spying the daylights out of the British, and was quite ruthless about how he acquired information. There’s an incident I mention in the book about when a couple of Tory counterfeiters working undercover for the British were captured. They were interrogated and Washington ordered their execution — they were spies, after all, caught behind the lines — but suspected they might be holding something back. So he ordered the clergyman detailed to comfort them in their cells to coax a fuller confession from them during their final hours. There’s a lot more in Washington’s Spies about the secret world that you don’t read about in the history books: gun-running, smuggling, raiding, illegal trading with the enemy, privateering, kidnapping, assassinations, double-crosses, that sort of thing. In short, Washington was not only able to tell a lie, he told a great many of them, and smiled as he did so. But keep in mind that I think his appreciation of, and natural talent for, espionage only increases his already heroic stature. Commanders-in-chief are required to employ spies to discover the enemy’s motions and designs; to do anything less is a dereliction of duty.

Lopez: What’s the top question you’d love to ask one of these Culper dudes if he were around?

Rose: Not sure I’d have just one question. I got to know these wholly unknown men so well while I was writing the book that I’d prefer to have a quiet dinner. I’m very fond of all of them, but I guess, if forced, I’d plump for a chat with Benjamin Tallmadge. This is the guy, as I describe in the book, who was Nathan Hale’s dearest friend at Yale, who was close to Washington, who was acquainted with Benedict Arnold and came close to capturing him before he got to the British, and who escorted his doomed antagonist John Andre to the gallows. Along the way, he and Andre, both old hands in the secret war, had a rather touching discussion about the nature of their business. The secret world, back in those days, was a small one.

Lopez: Looking at other book topics?

Rose: Nothing right now, though I’m all “spied” out for the moment. In the meantime, if you’d like to know more about the Culpers, have a look at my website, www.rosewriter.com.

<em>Washington’s Spies</em>, by Alexander Rose


Alexander Rose


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