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2020 EHFA Essay Contest Winner – The Culper Ring by Emily Matthews

© Emily Matthews

In 1616, Edward Howell married Frances Paxton and in 1620, the couple’s eldest daughter, Dorothy Howell was born. It is widely believed that Dorothy Howell married Richard Wodhull. “Wodhull” was the spelling used in England and it eventually became “Woodhull” after a few generations in the new English colonies. Dorothy and Richard settled in Setauket, New York where Richard became a prominent public official. Their eldest son, Richard Jr., married Temperance Topping. Their son, Richard III, married Mary Fordham and their son Richard IV married Margaret Smith. In 1750, their son, Abraham Woodhull was born. Edward Howell was the great-great-great-grandfather of Abraham Woodhull.

In the eighteenth century, spying was not seen as an honorable act or duty. Spies were often viewed as criminals, liars, and thieves, only gathering intelligence for their own personal interest. This was fairly accurate because most spies required some kind of reward for their services. Historically, the punishment for being caught as a spy was to be sent to the gibbet. One of the most famous early American spies was Nathan Hale. Nathan Hale was from a middling Connecticut family and attended Yale at the age of fourteen. While at Yale he met Benjamin Tallmadge and the two became very close friends and “if anything malign ever happened to one, the other would be merciless toward his assailants” (Rose, page 6). Hale enlisted in the Connecticut Seventh Regiment on July 6, 1775; however, Hale grew bored because he had been in battle, but he never got to fire his musket. He transferred to Knowlton’s Rangers, a new scouting group, where he would get a better chance at actually being able to fight and by September 1, 1776, Hale was a Captain. When Commander of the British army, William Howe, landed at Kip’s Bay. General George Washington wanted some spies to cross into Connecticut and then cross the sound to Long Island and eventually make their way to Brooklyn and then return to the army. Hale volunteered for this task because he felt that he had not really contributed to the cause because he had yet to fight in battle. On September 15, 1776, Hale arrived in Connecticut and found a ride across the Sound to Long Island. He was wearing civilian clothes and carrying only his Yale diploma to help convince others of his cover as a schoolmaster (which is what he did prior to enlisting). Robert Rogers caught wind of a suspected American spy on Long Island and tried to track him down. Rogers was in command of the “Independent Company of Rangers,” which was widely referred to as “Rogers Rangers.” Rogers had fought in the French and Indian War and was renowned for his ruthless tactics. He was described “as subtil & deep as Hell itself…a low cunning cheating back biting villain” (Rose, page 19). Rogers hunted Hale for days, watching him as took notes of British supplies and movements. Finally, Rogers convinced Hale that he was also a spy behind enemy lines and when Hale showed up to have dinner with Rogers, Hale was arrested and taken to Manhattan where Howe was. Hale had no formal trial because Rogers had witnesses to a confession, incriminating documents and Hale confessed to being an officer in the Continental army in front of Howe. Hale’s diploma was kept as a souvenir by William Cunningham, the provost marshal. On September 22, 1776 Nathan Hale was hung near present day Third Avenue and Sixty-sixth Street. In his diary, British Captain Frederick Mackenzie wrote “He behaved with great composure and resolution, saying he thought it the duty of every good man officer, to obey any orders given to him by his commander in chief; and desired the spectators to be at all times prepared to meet death in whatever shape it might appear.” (Rhodehamel, page 299). Lynching was actually a very complex procedure because the noose was not tied correctly around the victim’s neck resulting in a messy or prolonged execution. Nathan Hale’s “hangman was a former slave freed by the British who was unlikely to be familiar with the latest methods” (Rose, page 32). Therefore, it most likely took Hale several excruciating minutes to die because the noose was not tied correctly. Even though the mission failed, Washington learned from the mistakes he had made with Hale. After Washington’s retreat from the city, he understood the need for obtaining useful and reliable intelligence. However, Washington now was more interested in Civil spies, rather than military scouts like Nathan Hale. When soldiers went undercover, it was harder for them to blend in due to habits that were formed while drilling. Civilians blended in more easily because they never had to walk in perfect time or salute superiors. All Washington needed now was an officer to organize the civil spies and handle all of the logistics.

For the job, Washington secretly appointed Captain Benjamin Tallmadge of the Second Continental Light Dragoons. In early 1777, Tallmadge worked with Nathaniel Sackett to get agents on Long Island, however, in April 1777, Tallmadge was promoted to Major and his intelligence duties were neglected. During this time, Sackett was experimenting with different techniques for spies. The most important thing he learned was that he needed a spy that constantly stayed in enemy territory and would regularly communicate intelligence via letters. Sackett mysteriously left his post working with Tallmadge and was not heard from until after the war. After the Philadelphia Campaign, Howe resigned and was replaced by Sir Henry Clinton in May 1778. Clinton and the army moved back up to New York City and Washington surrounded Clinton “stretching from the New Jersey Highlands across the Hudson to Dobbs Ferry and then on to the Connecticut coast” (Rose, page 66). To know what the British were up to Washington needed intelligence from the city and Long Island. Washington attempted to send more one-time spies into the city, however, all of the missions failed due to strengthened British security. Tallmadge had the idea to create a chain of civilian agents that secretly moved intelligence between each other that eventually made its way to Washington. Washington was very skeptical of this idea because “if one member of the network was blown or flipped by the enemy’s counterespionage service, it rendered the rest of the chain useless” (Rose, page 77), however, Washington was willing to try it. The contact Tallmadge had in mind was Abraham Woodhull of Setauket. Woodhull was a farmer who participated in the New York black market called the “London Trade.” When the British took the city, they had access to the wide variety of fine imports from London, however, all of the rural areas surrounding the city were controlled by the Continental Army. This led to vegetables and meats being rationed and the prices rising dramatically on these commodities. “Woodhull would sail across the Sound and sell them for hard currency” (Rose, page 73). Congress tried to stop the London Trade and “during one of the periodic swoops urged by Congress” (Rose, page 74) Woodhull was caught and imprisoned in Connecticut. Tallmadge contacted Governor Jonathan Trumbull and asked him to release Woodhull. Trumbull granted the request and Woodhull was sent back to Setauket. However, before he left Connecticut, Tallmadge spoke to Woodhull about becoming a long-term spy for Washington and Woodhull agreed. In order to protect the members of the ring, Tallmadge created aliases for them. Tallmadge called himself “John Bolton” and Woodhull was called “Samuel Culper.” Samuel was the first name of Tallmadge’s younger brother who had helped with transporting intelligence on Long Island a year before. Washington named “Culper” after Culpeper County, Virginia whereas a teenager he surveyed land. Washington wanted Woodhull to be the chief agent of the new chain of secret agents that would be formed. When Woodhull returned to Setauket, his Tory neighbors were somewhat skeptical of his release. Tallmadge suggested that Woodhull take an oath of loyalty to the Crown, which helped convince his neighbors that he wasn’t a rebel sympathizer. On June 8, 1775, a local petition called the “List of Associators” was signed by about seventy men who pledged their loyalty to support Congress against the Crown. Woodhull, John Tallmadge (Benjamin’s little brother), and Caleb Brewster all signed this. Caleb Brewster was a close friend of Benjamin Tallmadge and helped him significantly with the agents on Long Island. Woodhull, Tallmadge, and Brewster had grown up together in Setauket, which is why they trusted each other so much. However, they were all inspired to fight for independence in different ways. Tallmadge despised the British because the Loyalist Colonel Richard Hewlett seized his father’s church and used the gravestones from the cemetery as outer defenses. Tallmadge’s older brother, William, was captured during the Battle of Long Island and starved in British prison. Brewster seems to have always been ready for an adventure. When Brewster was nineteen, he became a whaler on a ship that went all the way to Greenland. Whaling was a grueling job that was very physically demanding, so after a few years at that Brewster started to work as a guide for merchant ships. He would help merchants navigate their vessels through the dangerous “Devil’s Belt” at night with his years of experience sailing in the Sound. December 1775, Brewster joined the Suffolk County Militia as a Second Lieutenant and was promoted to a full Lieutenant in the Spring of 1776. Eventually he transferred to the Second Continental Artillery in Connecticut until 1778. Woodhull was outwardly a quiet farmer, however, inwardly he condemned the British and secretly enjoyed fooling them. For a brief time, he was a Lieutenant in the Suffolk County Militia in the fall of 1775. During his few months in the militia he learned to shoulder a musket but saw no action. He didn’t volunteer again and returned to Setauket to care for his elderly parents. It wasn’t until the Battle of Long Island that Woodhull truly felt compelled to make a significant contribution to the American cause. The specific action in the battle that caused the spark in Woodhull was the death of his cousin, General Nathaniel Woodhull. General Woodhull was a veteran of the French and Indian War who was brutally attacked by the British and “deprived of medical care and food and died in agony on September 20” (Rose, page 86). His cousin’s death compelled Woodhull to help take down the British, without them even knowing it.

In the early days of the Culper Ring, Woodhull had to venture into New York City every few weeks by himself to gather intelligence. While in the city he stayed at Amos and Mary Underhill’s inn. Mary was Abraham’s older sister, so he stayed there at a discounted price, but the prices in the city had inflated so much that they had to charge him 3£ a week. The cause of these inflated prices was the Great Fire and of course, the thousands of British soldiers that had flooded the city. The trip between Setauket and New York City was extremely dangerous for Woodhull because of the many British checkpoints. Woodhull had the cover story that he was selling his crops or visiting family, this worked initially, but soon the British were starting to get suspicious of how often he was entering the city. As if gathering intelligence in the city wasn’t enough, Woodhull also “performed double duty by acting as Brewster’s liaison in Setauket” (Rose, page 88). Once Woodhull had returned to Setauket Brewster would pick up the intelligence and bring it across the Sound to Tallmadge in Connecticut. As dangerous as Woodhull’s task was, Washington greatly appreciated Woodhull’s reports of troop numbers, troop movements, and things he had heard among officers. During his trips to the city, Woodhull kept a cash book in which he recorded “the costs incurred by his espionage: travel, lodging, and food, mostly” (Rose, page 95). Woodhull did not serve for pay, he only wanted to be reimbursed from the expenses he accumulated while spying for Washington. Washington tried to reimburse Woodhull with Continental money, however, because Woodhull was spending this money in British-held New York City he said that “Continental money will not serve me; It is much lower here” (Samuel Culper to Benjamin Tallmadge, 22 January 1779). There were some delays in the initial year of the Culper Ring, but Tallmadge made some improvements to help the speed of communication. Instead of Tallmadge himself waiting in Connecticut on Brewster to get across the Sound, Tallmadge ordered a chain of his Dragoons to be stationed at different checkpoints all the way to Washington’s headquarters so that the intelligence would constantly be moving. Then in December 1778, Tallmadge recruited Jonas Hawkins to transport the intelligence from Woodhull in the city to Brewster in Setauket. Later, Austin Roe would also be a courier between the city and Setauket. Roe owned a tavern in Setauket, so he entered the city under the cover story of picking up supplies. Having the couriers not only quickened the pace of transportation, but also took some of the suspicion off of Woodhull. By the end of January 1779, the Culper Ring could transport a letter from New York City to Washington’s headquarters in a week.

Many technical advancements were made after the first year of the Culper Ring that helped with the security of the intelligence and the protection of the ring members. One of the biggest contributions to the Culper Ring’s security was made by Sir James Jay. Sir James Jay was the older brother of John Jay and was a doctor in England who dabbled in chemistry. Jay wanted to create a type of ink that “might possibly be discovered for invisible writing, which would elude the generally known means of detection, and yet could be rendered visible by a suitable counterpart” (James Jay to Thomas Jefferson, 14 April 1806). Jay had created a new kind of invisible ink that required the use of two separate liquids. The “agent” was the actual invisible ink that the Culpers would write their dispatches in, and the other was the “reagent” which the recipient would lightly brush over the hidden message to make it visible. Washington called Jay’s ink “Sympathetic Stain” (George Washington to Elias Boudinot, 3 May 1779) and it was so important because only those with the reagent could read the messages, and only Jay knew the recipe. The most common invisible ink at the time was simply using acidic fruit juices which were made visible by applying heat. Acidic juices and common chemicals were the primary kinds of invisible ink used by the British, but these messages were extremely easy to uncover because everyone was aware of this tactic. Jay’s ink was highly secure, however, he had a difficult time creating a lot of it because when he moved back to America the chemicals were difficult to get from England. Woodhull first received a vial of the ink in April 1779 and because it there wasn’t a lot of it, he had a tendency to hoard it. Washington was irritated at Woodhull’s hoarding of the ink saying, “what I have sent for him at different times would have wrote fifty times what I have recd. from him” (George Washington to Benjamin Tallmadge, 5 February 1780). On July 2, 1779, the feared British Colonel Banastre Tarleton attacked Tallmadge’s camp in Connecticut. During this attack Tallmadge’s horse was stolen and in the saddlebags on the horse was a letter from Washington to Woodhull. From this letter, the British found out that a spy on Long Island went by the alias “C—–r” and that Tallmadge was the American head of intelligence. The significance of this attack was not only the fact that the British were closer to exposing the Culper Ring, but it also convinced Tallmadge that the intelligence letters needed to be encrypted. Tallmadge began working on a code for the ring to use and by the end of July 1779, Tallmadge had made a “full-scale Code Dictionary” (Rose, page 121). In his dictionary, Tallmadge replaced names, locations, military terms, etc. with numbers and he also had an alphabet for words that weren’t in the dictionary. One of the most important things Tallmadge did to protect the Culpers was that he never told anyone, not even Washington, their true identities. Washington said that “You will be pleased to observe the strictest silence with respect to C—–, as you are to be the only person intrusted with the knowledge or conveyance of his letters” (George Washington to Benjamin Tallmadge, 20 November 1778). Even with the improved security measures Tallmadge had taken Woodhull was getting jumpier due to the increase of British security and frequent attacks. There was one instance when Woodhull was writing a dispatch with the sympathetic stain and suddenly, two people burst into the room and Woodhull, thinking they were the British in the next room over, jumped up and tipped over the table, breaking the vial of stain. The two people were actually his nieces, who were attempting to surprise him. A few days after that scare, Woodhull “was mugged near Huntington and was glad to escape with his life” (Rose, page 128). On June 5, 1779, Woodhull wrote to Tallmadge that someone had “lodged information against me before Col. Simcoe of the Queens Rangers” (Samuel Culper to Benjamin Tallmadge, 5 June 1779). Simcoe had learned this information from a Long Island privateer named John Wolsey that was captured by the British. Simcoe went to Setauket hoping to find and capture Woodhull but Woodhull had “set out for N. York  the day before his arrival”(Samuel Culper to Benjamin Tallmadge, 5 June 1779) and said that “to make some compensation for his voyage he fell upon my father and plundered him in the most shocking manner” (Samuel Culper to Benjamin Tallmadge, 5 June 1779). When Woodhull returned to Setauket his friend Colonel Benjamin Floyd from a loyalist militia “contacted a general’s adjutant and stood guarantor for Woodhull’s Loyalist credentials” (Rose, page 129). Even though his “Loyalist credentials” were known, Woodhull said that “I am very obnoxious to them and think I am in continual danger” (Samuel Culper to Benjamin Tallmadge, 5 June 1779).

Eventually, traveling between Setauket and the city became too dangerous. At first, Woodhull considered joining the army in Connecticut because he still wanted to contribute to the war without the risks of spying. Woodhull went into the city in hopes of finding a replacement for himself, however, he found something even better. Woodhull found a man who worked in New York and was almost constantly surrounded by British officers who was willing to spy for Washington. Woodhull would now stay in the ring and “in Setauket to act as the new agent’s handler” (Rose, 131). Robert Townsend was the man in New York Woodhull had found and his code name was “Samuel Culper, Junior”. Townsend was from Oyster Bay which was about halfway between the city and Setauket. Townsend’s father was a Quaker and his mother was Episcopalian, which helped to hide him from suspicion because Quakers were generally neutral in terms of the war since they were pacificist. Townsend and Woodhull probably met at Amos Underhill’s boardinghouse since there were limited places to stay in the city. Woodhull knew that Robert was the son of the well-known Whig, Samuel Townsend. In June 1779, Woodhull approached Townsend about spying for Washington and Townsend agreed. Many factors inspired Townsend to help the ring. The biggest was the publication of Thomas Paine’s Common Sense, which Townsend read Paine’s view that Quakers could be Patriots without betraying their religion. Another contributing factor was in November 1778, when Colonel Simcoe and his Rangers settled in Oyster Bay for the winter and stripped the town (private homes and churches) of wood and supplies to build his small fortress. Simcoe and his staff officers took quarters at Raynham Hall, which was the home of the Townsend family. Townsend was a very valuable spy because he had his own dry goods business in the city and where British soldiers would buy supplies. The importance of British commercial purchases was that the purchase could identify “future British movements based upon the types of orders placed for provisions and equipment, reasons provided for particular delivery dates, and casual details provided regarding the purposes of the orders” (Daigler, page 180). Townsend also owned a share of James Rivington’s coffeehouse where a lot of British officers liked to gather and socialize. James Rivington was the founder and editor of the Royal Gazette which was an anti-American paper. Rivington may have possibly been spying for Washington, however, there is not enough evidence to fully support this theory. When the British occupied the city, they quartered a lot of their troops on Long Island because there were more resources to plunder. The civilians were placed under martial law and even the Loyalists were starting to resent the British for their abuses to people and property. This was why the journey between Setauket and the city was so dangerous. By mid 1779, Austin Roe was the sole courier for the ring because Hawkins had quit due to almost being captured. After Townsend started collecting the intelligence in the city, Woodhull rarely made the dangerous trip. However, Woodhull once wrote to Tallmadge that “Soon after I left Hempstead Plains and got into the woods I was attacked by four armed men, one of them I had frequently seen in N. York. They searched every pocket and lining of my clothes, shoes, and also my saddle, which the enclosed [Townsend’s letter] was in, but thank kind Providence they did not find it. I had but one dollar in money about me. It was so little they did not take it, and so came off clear” (Samuel Culper to Benjamin Tallmadge, 10 October 1779). Washington eventually instructed the Culpers to write their dispatches on “the blank leaves of a pamphlet; on the first second &c. pages of a common pocket book; on the blank leaves…of registers, almanacs, or any new publication or book of small value” (George Washington to Benjamin Tallmadge, 24 September 1779). Washington had the Culpers do this because books would not be suspicious if by chance the British got a hold of them and the paper quality was often better than regular parchment for the sympathetic stain. The ring now had very organized and relatively efficient channel of communication. First, Townsend would collect the intelligence in his store and Rivington’s coffeehouse. Then, Roe would ride to the city and pick up Townsend’s reports and bring them back to Setauket. When Roe arrived in Setauket he would deliver the reports to Woodhull “either giving it to him in person or, for safety’s sake, dead-dropping it in a buried container in one of Woodhull’s fields—who would add his own letter containing observations, as well as information given to him by Roe” (Rose, page 132). Then, Anna “Nancy” Strong would inform Brewster across the Sound when a report was ready and where to pick it up. When a report was ready, Anna Strong hung up a black petticoat on her laundry line with a certain number of handkerchiefs which “would indicate at which cove or inlet Brewster was to land to await the report” (Daigler, page 185). After Brewster carried the dispatch across the sound, he would give it to Tallmadge to be prepared for Washington. The ring was considerably fast given all of the circumstances, however, Washington wanted it to be faster. In the spring of 1780, Washington was considering cutting Woodhull out of the ring and just dealing directly with Townsend. Townsend sent his teenage cousin, James Townsend, through a route in New Jersey. The mission was a complete failure because James was caught by the Americans and accused of being a British spy and “it took the commander-in-chief’s personal intervention, and a great deal of trouble, to secure the teenager’s release” (Rose, page 187). This incident showed Townsend how easy it was to get caught and after this Townsend was reluctant to send any written reports and only transmitted intelligence verbally. This mission also showed Washington that the ring could not function securely without Woodhull. After 1780, the ring went through periods of inactivity, but when Washington heard that the comte de Rochambeau was supposed to be landing soon, he reactivated the ring.

There were three major contributions the Culper Ring made to help Washington along with all of the individual military intelligence they gathered. The first one was in July 1779 when they exposed Christopher Duychenik as a British spy posing as a Patriot. This report demonstrated “that the ring had access to internal information on the Tory intelligence system” (Daigler, page 191). The second major contribution was when the British attempted “to lessen the value of the Continental Congress monetary script by counterfeiting those notes and thus making it even more difficult for the Congress and the army to obtain supplies” (Daigler, page 192). Initially, the paper the British were using for the counterfeit money did not exactly match what the Congress used. In November 1779, the Culper Ring informed Washington that the British had gotten paper that matched the paper the Congress used. Washington informed the Congress of this and in March 1780, “Congress was forced to retire and recall all its bills in circulation, effectively declaring bankruptcy to save itself” (Rose, page 184). This was extremely important because it demonstrated how the ring was able to collect economic intelligence to help save the very fragile Continental economy. The third report was the most important. The Culper Ring informed Washington that Clinton was planning to attack the recently arrived French forces at Newport, Rhode Island with 8,000 men and twelve warships. The purpose of Clinton’s attack was to weaken the French forces while they were vulnerable “after a long period at sea and required some time to get organized and healthy prior to any combat (Daigler, page 193). Clinton was not supposed to know about the French arrival until the French actually landed. What Washington didn’t know was that Clinton had been expecting the French since mid-June. Clinton had spent the past month secretly preparing to attack and crush the French forces and hopefully end the Franco-American alliance. Clinton learned this crucial bit of information from the American Commander of West Point and the hero of Saratoga, Major general Benedict Arnold. Arnold had heard about the French from Washington and told Major John André (who was essentially the British Head of Intelligence) and André informed Clinton of this. When Washington learned from the ring that Clinton was planning to attack the French, he initially considered attacking New York City because the majority of the British army would be in Rhode Island. However, Washington and his staff officers decided that an attack on New York City was too risky. They agreed that even if they did recapture the city, they most likely would lose it again due to the British navy. In order to protect the French from a crushing defeat, Washington pretended that he was going to attack New York City. Washington sent in agents who brought false documents to Clinton and “Clinton was apparently convinced that the danger was real and recalled his troops to protect the city” (Daigler, page 193). This maneuver was so critical to the outcome of the war because the French were instrumental in the American victory at Yorktown. If Washington hadn’t learned from the Culpers that Clinton knew about the French ahead of time, the French troops and the alliance may have been lost, resulting in the possible British victory of the war.

After Benedict Arnold was discovered as a spy, he fled to New York City to see Clinton. Washington knew all of what Arnold had done because when André was captured and held in custody, he wrote a detailed letter to Washington explaining everything. Tallmadge gave the letter to Washington and André was sentenced to death for inciting Arnold to commit treason. André’s only request was that he have “an honorable soldier’s execution: by firing squad” (Rose, 212). At first, Washington agreed, but changed his mind because he wanted to make an example out of him and decided that André should be hung like a common spy. André was not told he was going to be hung and as he approached the gallows for a brief moment he looked “startled, and enquired with some emotion whether he was not to be shot” and he exclaimed “How hard is my fate!” but he ended with “It will soon be over” (Tallmadge, page 38). André stepped up into the wagon and “the victim, after taking off his hat and stock, bandaged his own eyes with perfect firmness…The rope being appended to the gallows, he slipped the noose over his head and adjusted it to his neck, without the assistance of the awkward executioner” (Thacher, page 274). Right before the wagon was removed from under him, he wished to the crowd “that you all bear witness that I meet my fate like a brave man” (Thacher, page 274). On October 2, 1780, André was executed. Tallmadge didn’t necessarily believe that André deserved to die, he said that he wished “Arnold had been in his place” (Hall, page 38). However, the execution of André was a form of “revenge” that Tallmadge got from the British for the death of his friend, Nathan Hale. Tallmadge said that André “who tho’ he dies lamented, falls justly” (Benjamin Tallmadge to Samuel Webb, 30 September, 1780). After André’s execution, Arnold appointed himself spyhunter-general and started imprisoning anyone that he thought was a spy in New York City and Long Island. Tallmadge worried about his agents, however he “never gave their names to him, [Arnold] he was not able to discover them, although I believe he tried hard to find them out” (Benjamin Tallmadge to Jared Sparks, 17 February 1834). Even though the Culpers were fine, they could not write or collect any intelligence because of the added dangers. Townsend was still in the city when Arnold imprisoned “one that hath been ever serviceable to this correspondence [Culper Ring]” (Samuel Culper to Benjamin Tallmadge, 26 October 1780). Townsend decided to temporarily leave New York City for fear of exposure. The man Arnold had imprisoned, who Woodhull alludes to have been involved with the ring, was Hercules Mulligan. Mulligan was an Irish tailor with a secret Patriot past. Mulligan was well acquainted with high ranking British officers and when they would come into his shop to get their clothes fitted, he would collect intelligence. Townsend’s father used Kortwright & Company to import and export goods to and from the West Indies, which Hugh Mulligan (the older brother of Hercules) bought in 1773. That is the same company that Alexander Hamilton worked for as a teenager in St. Croix and who sponsored his trip to New York City. Hercules “took the orphan under his wing” (Rose, 224) and helped him buy his commission in the army in 1776. Washington learned of Mulligan as a possible source of intelligence because Hamilton had told him. Woodhull mentions “an acquaintance of Hamilton’s” (Samuel Culper to Benjamin Tallmadge, 12 August 1779) in the summer of 1779. That is probably around the time that Mulligan became a subagent of the Culper Ring. Mulligan would not write the intelligence, but he would pass information verbally on to Townsend (who’s store was close to Mulligan’s). Mulligan was not imprisoned for very long because Arnold had no evidence that he was a spy. Even though he was released, Townsend refused to continue the Culper correspondence.

As the British plundering and raids became more and more severe, the members of the Culper Ring were forced to drop the correspondence. With the added violence in the Long Island Sound, Brewster could not risk crossing it. There were some attempts made by Tallmadge to decrease the plundering and piracy, but none proved to make any significant difference. The British started to become more suspicious of Woodhull and other members of the Culper Ring. Woodhull said that “You must acknowledge and readily conclude that have done all that I could, and stood by you when others have failed, and have not left you in the darkest hour but when our affairs appear as clear as the Sun in the Heavens, and promiseth a speedy and I hope a happy conclusion” (Samuel Culper to Benjamin Tallmadge, 4 June 1781). After Cornwallis surrendered at Yorktown, Clinton resigned, and Sir Guy Carleton was put in his place. Washington briefly reactivated the ring to find out if Carleton was going to make any last effort attack. When Washington learned that Carleton was not going to attempt anything like that, he lost interest in the ring because it now had no use. The most professional group of amateur spies during the Revolutionary War could finally rest easy now that the dangers that once infected Long Island and New York City were subsiding. Woodhull sent his last Culper letter on February 21, 1783. The Treaty of Paris in September 1783 officially ended the war and Carleton began the slow evacuation process out of New York City.

After the war, Caleb Brewster married Anne Lewis and Benjamin Tallmadge married Mary Floyd who was the daughter of William Floyd, a signer of the Declaration of Independence. John Graves Simcoe became the first Lieutenant governor of Canada in 1791. Robert Rogers resigned at Howe’s request and after that bounced around between Canada, England, and the colonies. He eventually returned to England after the war where he drank heavily and told people his war stories. Benedict Arnold moved to London at the end of the war, however, he learned that the British hated and distrusted him. John André’s memory of being a hero was everywhere, which deeply infuriated Arnold. Arnold’s economic schemes in Great Britain, the West Indies, and Canada had all failed. When Arnold was on his deathbed in 1801, “it is said that he dressed in his old Continental uniform and fearfully begged God to forgive him for ever donning another” (Rose, page 275). When Arnold died, the papers barely reported it. Robert Townsend remained a bachelor for the rest of his life. Out of all the ring members, only Townsend became bitter that Washington had not given him some reward or public office. For a brief time, Townsend went into business with his brother, but eventually they parted ways and Townsend moved back Oyster Bay where he died quietly on March 7, 1838. Austin Roe was married before his time as a spy and continued to run his tavern after the war. There was one time when President Washington came to visit Long Island and stayed at Roe’s inn and it is said that Roe was so excited to see George Washington that he fell off his horse and broke his leg. Caleb Brewster and his family moved to Fairfield, Connecticut and Brewster joined what became the Coast Guard in 1793. His job was to stop his former colleagues smuggling and eventually retired to his farm in Black Rock where he died on February 13, 1827. Abraham Woodhull became the first judge of Suffolk County and served from 1799-1810. He married Mary Smith in 1781 and they had three children, Elizabeth, Jesse, and Mary. His wife Mary died in 1806 and in 1824, Woodhull married Lydia Terry but they had no children. Woodhull died on January 23, 1826 and he never told anyone about his time as one of Washington’s spies. Benjamin Tallmadge and his family settled in Litchfield, Connecticut. Tallmadge became very wealthy due to his investments in the west and in 1801, he was voted to Congress on the Federalist ticket. He retired in 1817 and established “a training school for Native American and Asian missionaries” (Rose, page 278). Tallmadge died on March 7, 1835. Even though Tallmadge’s spy ring was responsible for critical intelligence getting to Washington, it was still perceived as a tainted job to be associated with. In his memoir, Tallmadge only said “This year I opened a private correspondence with some persons in New York which lasted through the war. How beneficial it was to the Commander-in-Chief is evidenced by his continuing the same to the close of the war. I kept one or more boats continually employed in crossing the Sound on this business” (Tallmadge, page 29).


Allen, Thomas. George Washington, Spymaster: How the Americans Outspied the British and Won the Revolutionary War. Illustrated, National Geographic Children’s Books, 2007.

Culper, Samuel. Letter to Benjamin Tallmadge. 22 January 1779. Papers of George Washington, University of Virginia Press, Charlottesville, Virginia. Manuscript.

Culper, Samuel. Letter to Benjamin Tallmadge. 5 June 1779. Papers of George Washington, Library of Congress, Washington D.C. Manuscript.

Culper, Samuel. Letter to Benjamin Tallmadge. 10 October 1779. Papers of George Washington, Library of Congress, Washington D.C. Manuscript.

Daigler, Kenneth. Spies, Patriots, and Traitors: American Intelligence in the Revolutionary War. Reprint, Georgetown University Press, 2015.

Hall, Charles Swain. Benjamin Tallmadge: Revolutionary Soldier and American Businessman. Columbia University Press, 1943.

Jay, James. Letter to Thomas Jefferson. 14 April 1804. Papers of Thomas Jefferson, Library of Congress, Washington D.C. Manuscript.

Rhodehamel, John. The American Revolution: Writings from the War of Independence (Library of America). Library of America, 2001.

Rose, Alexander. Washington’s Spies: The Story of America’s First Spy Ring. Illustrated, Bantam, 2007.

Tallmadge, Benjamin. Memoir of Colonel Benjamin Tallmadge. Paean Publishing, 2016.

Thacher, James. An Army Doctor’s American Revolution Journal, 1775–1783 (Dover Military History, Weapons, Armor). Dover Publications, 2019.

Washington, George. Letter to Benjamin Tallmadge. 20 November 1778. Papers of George Washington, University of Virginia Press, Charlottesville, Virginia. Manuscript.

Washington, George. Letter to Benjamin Tallmadge. 24 September 1779. Papers of George Washington, University of Virginia Press, Charlottesville, Virginia. Manuscript.

Washington, George. Letter to Benjamin Tallmadge. 5 February 1780. Papers of George Washington, University of Virginia Press, Charlottesville, Virginia. Manuscript.

Washington, George. Letter to Elias Boudinot. 3 May 1779. Papers of George Washington, University of Virginia Press, Charlottesville, Virginia. Manuscript.