Syracuse University SURFACE Syracuse University Honors Program Capstone Syracuse University Honors Program Capstone Projects Projects Spring 5-2016 A Spy of His Own Confession: A Revolution in American Espionage Cole Ellenbogen Follow this and additional works at: https://surface.syr.edu/honors_capstone Part of the History Commons Recommended Citation Ellenbogen, Cole, "A Spy of His Own Confession: A Revolution in American Espionage" (2016). Syracuse University Honors Program Capstone Projects. 975. https://surface.syr.edu/honors_capstone/975 This Honors Capstone Project is brought to you for free and open access by the Syracuse University Honors Program Capstone Projects at SURFACE. It has been accepted for inclusion in Syracuse University Honors Program Capstone Projects by an authorized administrator of SURFACE. For more information, please contact [email protected]. Abstract: The most well known spies are usually the ones who were caught. But what about those who took their secret lives to the grave? In the summer of 1778, arguably one of the biggest players in the United States’ fight for independence was released from a rebel-controlled prison in Connecticut. Abraham Woodhull, arrested earlier in the year for smuggling, was offered his freedom in exchange for his loyalty to the continental army. His friend, Major Benjamin Tallmadge, was looking to replace the dated espionage methods employed by his superior officer and contentious rival. In just a few short years, the organization they created would change the tide of the war – and all of espionage – forever. Executive Summary: In the summer of 1778, the American Revolution was at an unusual stalemate. All of Britain’s supply ships were coming into New York City from Ireland, making the Island of Manhattan a critical stronghold. At the same time, Britain was ready to lead a campaign north to take West Point, which would cut the resistance in half, and separate the rebels from their supply lines in Connecticut. If the British left New York, Washington could sweep in, capture the city, and cut off the British soldiers from re- supplies. If Washington left the New York area, then the British could do the same to West point. General Washington needed information; if he knew which generals were staying in Manhattan, what supplies were coming in, and what defenses were being built, he could plan his actions accordingly and with little risk of losing the Hudson Valley. That’s where the Culper Ring came in. Earlier in the war military intelligence was carried out in short recon missions. Officers would sneak behind enemy lines to gather scraps of intelligence, knowing that if they were caught, they would have no reasonable excuse for being there. Nearly half of these missions ended in capture and execution. Because every minute in enemy territory was life threatening, spies could rarely stay in place long enough to learn anything useful. When it came to New York City, agents would need to find a way to pass closely monitored security checkpoints just to get onto the Island of Manhattan, which was swarming with British soldiers. 2 After a series of particularly bad missions in which then-spymaster Charles Scott lost all but two of his men, Washington decided to try something else. He allowed his favored Major, Benjamin Tallmadge of Setauket, to assemble a team of civilian operatives. Tallmadge believed that a spy network deep in enemy territory was the key to long term, high quality information. He set out recruiting his childhood friends who lived on Long Island and New York City to spy for him, and used whaleboat captain Caleb Brewster to smuggle the information across the Long Island sound, into friendly territory. Some of the Culper Agents, namely Robert Townsend, were able to gain the trust and confidence of prominent loyalists in New York City; which led to the thwarting of a counterfeit plot that would’ve destabilized the Continental Congress’s currency, the protection of the French Fleet from a full-scale British attack, the discovery of Benedict Arnold’s treason, and even the capture of British Spymaster John Andre. Despite these incredibly important feats pulled off by just a handful of patriots, the Culper Ring is an obscure piece of history. Every agent managed to take their secret well beyond their grave; the full extent of their accomplishments wasn’t known until more than 150 years after the American Revolution. Understanding the secretive yet effective nature of the Culper Ring is crucial in understanding the evolution and development of espionage, from brute force high-risk-low-reward spectacles, to long term and intricate organizations operating in deep cover. In my research, I started by reviewing secondary sources, and more general summaries of the Culper Ring’s activities. I read Alexander Rose’s book: Washington’s Secret Six. This gave me the broad overview of the Ring I needed to get started. Next, I wanted to learn about specific agents in the ring on a more personal level. I read 3 memoirs. Letters between agents helped fill in the remaining gaps in my information. Initially, I could spend a whole afternoon trying to make it through one letter, but after a lot of practice I was able to read through them much more quickly. After I had a good amount of knowledge about the events and the players involved, I wanted to learn about the locations where it all took place. I took a trip to Setauket, the town where Abraham Woodhull, Austin Roe, Caleb Brewster, and Anna Strong did most of their work for the Culper Ring. Most of the buildings of historic significance were destroyed in the early 20th century. A few survived, and the Three Village Historical Society was able to show me around the area. I was able to visit conscience bay, where the agents met to exchange information. After exploring Setauket, I went to Oyster Bay to visit the family home of Robert Townsend, one of the most important operatives. Unlike most of the other historic sites, the Townsend house was well preserved. I was able to visit the room where Colonel Simcoe and Major John Andre stayed while garrisoned on Long Island. Being able to immerse myself in the Culper Ring’s History allowed me to write a thorough and – what I hope to be a compelling – account of their actions and achievements. 4 Table of Contents: Abstract – 1 Executive Summary – 2 Table of Contents – 5 Acknowledgements – 6 Project Body – 7 Part I: Early Espionage / The One-Man Missions – 7 Part II: Establishing Connections / Founding the Culper Ring – 19 Part III: Unconventional Tactics / British Pushback – 114 Part IV: Exposing the Enemy / Complex Plans Uncovered – 209 Part V: The Spy Hunt / The Culpers’ Last Letters – 320 Sources Cited and Consulted – 324 Reflective Essay – 325 5 Acknowledgements: Special thanks to my advisor Mark Schmeller, and my reader Dympna Callaghan for helping shape my work; and for not only reading all 300 pages of the completed work, but providing insightful feedback that helped me grow as both a writer, and a student of history. I also wish to thank my high school English teachers, James Incorvia and Jessica LaMantia for giving me the grammatical and structural skills I needed, as well as the encouragement to pursue my love for writing. Finally, I am especially grateful to my parents, who provided me with the encouragement and resources I needed along the way. I could not have finished such a large body of work without them. 6 Project Body: I. 1776 Early Espionage: The One-Man Missions 7 September 21st The Weary Traveller Alehouse New York, New York A lanky blonde haired man sits at the bar rail; reading over a few small leafs of paper by candlelight. He takes a gulp from his tall glass, emptying it. “Another pint, please,” the man asks the barkeep. The grizzled man nods, taking the guest’s glass and walking over to a cask behind the bar. “What business do you have in New York?” The barkeep asks casually, opening the tap. “I am a schoolteacher,” the man replies quickly. The barkeep closes the tap and drops a fresh pint of ale before the patron. “Not quite what I was asking. What are you doing here? – I mean. I don’t recall seeing you around before.” Another customer sitting at a corner table looks up from his untouched beer. He pauses briefly to scratch at his beard before looking down again and swirling his mug pensively. “Oh yes, I’m only visiting,” The guest replies. Then he remarks, “It appears to be somewhat of a slow evening.” The barkeep nods. “Had some crowds earlier, but word came there was a fire spreading through the city, set by those bloody rebels. Regulars all left to try and help, I’d imagine. Of course, someone had to stay and look after the place.” He gestures to the nearly empty room. 8 The guest smiles approvingly. The bartender picks up a rag and throws it over his arm. “Excuse me sir, I have to do a bit of straightening up before closing.” He crosses the room and begins cleaning the tables of glassware, which had all been left in a hurry. Looking bored, the customer from the corner table crosses the room to sit at the bar. The out-of-towner hastily sweeps up his papers, folds them, and stuffs them into his coat pocket. “Relax,” the stranger says casually, “I think the both of us are here for the same purpose.” “I-I’m afraid I have no idea what you’re talking about,” the man answers. “My name is John Rogers,” he leans in, “I’m here to gather information on British troop movements,” he whispers.