Abraham Woodhull, spy for General George Washington, nearly got himself hanged on one of his first missions. It was in October 1778, when Woodhull toured British-held New York City and its environs, observing Crown military activities. At one point he neared an encampment of Loyalist soldiers commanded by General William Tryon. Woodhull was probably preparing to make careful mental notes of Tryon’s camp when he unluckily stumbled upon a group of soldiers who immediately detained him and demanded to know why he was wandering around. Woodhull wrote, “I received their threats for coming there that made me almost tremble knowing my situation and business.”[1] His statement only hinted at what he inwardly knew; that if the soldiers discovered his espionage mission, they would have hanged him without compunction. Woodhull somehow successfully answered the soldiers’ questions but the encounter still shook him to his bones. Yet he still completed his mission and submitted a valuable intelligence report to Washington. Woodhull became one of Washington’s best spies, knowing all the while that he was one step away from a noose.

Normally Woodhull was a farmer in the town of Setauket on Long Island’s north shore where he cared for his elderly parents. Woodhull was mildly supportive of the American cause but before 1778 the closest he came to the rebellion was an uneventful two-month stint in his county militia. Also, his cousin, Continental Brigadier-General Nathaniel Woodhull, died at the battle of Long Island in 1776. But the 27 year-old, unmarried Woodhull was also something of a risk-taker.

In mid-1778 he began sailing across Long Island Sound to British-held New York to sell his farm’s produce for hard currency. The Rebels considered the practice trading with the enemy and those caught in the act faced a jail sentence. In July 1778 Woodhull paid for his daring when a Continental naval patrol intercepted his boat and Rebel authorities threw him into a Connecticut jail. In late August, Woodhull received an unexpectedly early release from jail by order of Connecticut Governor Jonathan Trumbull. Before he left Connecticut, Woodhull was probably stunned when he received a visit from Benjamin Tallmadge, who he knew as a fellow Setauket native. Now Tallmadge wore the uniform of a major in the Second Continental Dragoons. Neither man recorded the details of their meeting but we can make some inferences by the result. Certainly they had an emotional reunion and talked about the rebellion. They likely discussed Woodhull’s activities trading with the British. Possibly after testing his old friend’s allegiance, Tallmadge probably dropped his bomb; it was he who secured his early release from Governor Trumbull, and would Woodhull be willing to spy for the American cause?

British forces on Manhattan obtained much of their supplies from the farms of Long Island, which meant that Woodhull could travel regularly to New York, ostensibly to sell his goods but really to observe military activities. It was an extraordinary and risky offer – both men knew that spying could be a short path to a hanging.

What leverage Tallmadge used to get Woodhull to consider the offer is unknown, but the major may have reminded Woodhull about the death of his cousin, General Nathaniel Woodhull, at British hands. The exact circumstances of Nathaniel’s death remain elusive but stories popular at the time held that he was wounded in action, captured, maltreated, and died miserably. The loss of his cousin deeply affected Woodhull, who was a somewhat introspective, sensitive character, and he secretly hated the British for what he believed was his cousin’s unnecessarily brutal demise. What better way to get back at the enemy, Tallmadge might have said, than by spying on the British under their own noses and helping the American cause? Whatever tactic the major used, Woodhull accepted the offer.[2]

Woodhull was to be a new type of American spy. For the first few years of the Revolution, Continental Army leaders preferred to sneak operatives into British territory where they skulked around for a few days, acquired information, and then slipped back out through the lines to report to American commanders. The tactic was sometimes effective but the information often lacked the detail, accuracy and timeliness that Washington needed. Nor had the Americans uniformly mastered the techniques of successfully moving in and out of enemy territory. To overcome these problems Washington and Tallmadge envisioned a permanent network of spies that lived behind British lines and communicated their information through coded messages. Tallmadge’s recruitment of Woodhull enabled them to put their plans into action.[3]

Woodhull returned to Setauket and began his spying in October. Under the system that Tallmadge designed, Woodhull travelled to New York every few weeks on “business,” mixed with Crown soldiers, listened for news, and observed activities. Then he wrote down his observations and hid them at a secluded cove near Setauket. Another of Tallmadge’s operatives was Caleb Brewster, a Continental artillery lieutenant and skilled mariner stationed on the Connecticut coast who previously supplied Washington with naval intelligence. It was Brewster’s job to sail across the Sound, retrieve Woodhull’s communications from their hiding spot, and return the missives to Tallmadge in Rebel-held Connecticut. Tallmadge and his commander, Brig. Gen. Charles Scott, added their own comments and couriers then sped the messages to Washington at Continental Army headquarters in New Jersey. To protect their identities Tallmadge assigned aliases for their correspondence; Tallmadge went by “John Bolton” and Woodhull used the name “Samuel Culper.” It was the beginning of what became known as “the Culper Ring.”

Woodhull was good at the espionage business. To appear as a devoted subject of King George III he publically took an oath of loyalty in Setauket. By the end of October he recruited his brother-in-law Amos Underhill, owner of a Manhattan boarding house, to gather information from his British Army lodgers. Eventually operating from Underhill’s boarding house, Woodhull so successfully played the part of a loyal but inquisitive farmer that he gained all of the information he needed, and more. His first intelligence in October addressed British troop strengths and their shortages in provisions.[4] In November he reported how Loyalist units were scouring local farms for wood and livestock.[5] In February 1779 he sent information on troop movements, supply problems, naval matters, the total strength of enemy forces around New York, the possibility of reinforcements, and other military plans; the report was seven pages long.[6] In March Woodhull sent intelligence on British plans to raid the port of New London, Connecticut.[7] Tallmadge added two couriers to the operation to speed the reports from New York City to Setauket. In early 1779 it took about a week for Woodhull’s letters to reach Washington, which was a substantial improvement to the pre-Culper Ring espionage efforts in New York City.[8]

Yet for all of his success, the pressure of spying and leading a double life severely strained Woodhull. Early on, Woodhull had urged General Scott to “destroy every letter after reading for fear of some unforeseen accident that may befall you and the letter get into the enemies hands and probably find me out and take me before I have any warning.”[9] A month later Tallmadge told Washington that Woodhull used “extreme caution and even timidity.”[10] Woodhull particularly hated traveling the 50 miles to New York City because every trip put him at risk of questioning and discovery at military checkpoints. Highwaymen on the road near the town of Huntington robbed him of all of his money in early April 1779, and Woodhull told Tallmadge that he felt “a life of anxiety to be within . . . the lines of a cruel and mistrustful enemy.”[11] Tallmadge had Brewster sail him to Setauket – an exceptionally dangerous move itself – so he could meet with Woodhull and allay his spy’s concerns. Unfortunately, several British officers decided to billet at Woodhull’s farm at the same time and a violent storm prevented Brewster from retrieving Tallmadge. For five days Tallmadge hid in the woods while Woodhull sneaked him food. But Tallmadge secured Woodhull’s continued service and gave him a new tool for his trade – a vial of disappearing ink, which would lessen the chance of their letters, if ever confiscated, being identified as intelligence reports. One night Woodhull was drafting a report with the new ink while British officers were still in his house and Tallmadge hid in the woods. Suddenly the door to his room flung open and two people burst into his room. Startled, Woodhull sprang to his feet and snatched up his writing paper, breaking the vial of special ink on the floor. Moments later he realized that the intruders were his nieces, playing a game to surprise their uncle, and successfully so. Washington sent another vial of ink.[12]

In early May 1779 Woodhull’s worst fears almost came true. A Loyalist named John Wolsey returned to Long Island after a stint in a Connecticut prison for privateering and reported a rumor that Woodhull was working for the Rebels. Colonel John Graves Simcoe, commander of the Loyalist Queen’s American Rangers, promptly launched a raid to grab the spy. Woodhull was in New York City when the Loyalist troops came to his house, but he later reported how his 66 year-old father was home, and that Simcoe “plundered him in a most shocking manner.” Woodhull escaped Simcoe’s wrath by arranging for a prominent local Loyalist to vouch for his character. But the event convinced the spy of his “constant danger” and he curtailed operations.[13] The respite was ill-timed; Woodhull missed most of the signs that the British were beginning an offensive to seize control of the Hudson River, and the campaign of 1779 began with Washington unaware of Clinton’s plans.

Still dedicated to his mission, in June Woodhull expanded the operation by recruiting 25 year-old Robert Townsend, a former lodger at the Underhill boarding house, as an additional agent.[14] Like Woodhull, Townsend played the part of a devoted Loyalist but he was a secret Patriot who had served briefly as a commissary to General Nathaniel Woodhull, Abraham’s cousin. His position as a merchant in New York City put him in an excellent position to learn British plans from his Crown business contacts. Townsend also owned a share of a coffee house popular with British officers operated by James Rivington, printer of the Loyalist Royal Gazette. Townsend may have dabbled in journalism himself, which gave him a perfect excuse to spend long hours picking up information.[15] Tallmadge assigned Townsend the alias “Samuel Culper Junior.”

With the new spy permanently in place in New York City, Woodhull assumed the role of the leader of the operation, passing on instructions from Tallmadge and occasionally meeting Townsend in New York. Working together, Woodhull and Townsend warned Washington about British activities as the 1779 campaign developed and they discovered British plans to wreck American finances by counterfeiting Continental currency.

What General Washington, the ultimate consumer of Culper Ring intelligence, thought of the operation is unclear. The correspondence between the general and Tallmadge shows that Washington often relied heavily on Culper Ring information during times of crisis. One example is from October 1779, when the Americans anticipated the arrival of a French fleet. Washington planned a naval attack on New York City and pressed Tallmadge for Woodhull to “at all times keep his attention on changes of situation, or the new positions which may be taken by the enemy. He will inform me what new works are erected on Long Island besides those at Brooklyn, and where, and of what nature. I wish also to know where their shipping lies, and if they appear to be taking measures and what measures for their security in case of a French fleet’s entering the harbor.”[16] However as a commander who needed timely and accurate intelligence, Washington sometimes found Woodhull’s skittishness irritating, as he wrote to Tallmadge in September 1779, “I have been expecting for some time past a communication from Culper. . . . That he has gone so far beyond his promise makes me rather uneasy on his account.”[17] And the ever-frugal general often testily reminded his spies not to waste the expensive disappearing ink and to find ways to communicate their intelligence faster.

In the spring of 1780 the strain of spying was wearing on both Woodhull and Townsend, and Tallmadge told Washington that Townsend had become less active, and “even Culper Senior grows timid and thinks that intercourse had better be dropped for the present.”[18] Washington agreed to shut the Culper Ring down, only to reactivate it in July to gain information that would support operations of another French fleet expected later that summer. If Woodhull and Townsend were exhausted they remained dedicated and efficient. In late July the agents reported that the British knew about the expected fleet and were moving naval forces to counter a planned French attack on Rhode Island. The Culper intelligence allowed Washington to arrange countermoves, and the episode was one of the Ring’s greatest successes.[19]

But on the heels of this victory came a threat to their security. Soon after Benedict Arnold defected to the British, he directed the arrest of people in New York and Long Island that he suspected as American spies, based on his knowledge of Continental Army intelligence. Tallmadge wrote Washington on October 11, 1780 that Arnold knew “not a single link in the chain of my correspondence,” but that the Culper operatives were “too apprehensive of danger to give their immediate usual intelligence.”[20] Woodhull and Townsend laid low but returned to providing information.[21]

In 1781 British and Loyalist units still patrolled Long Island and though Woodhull continued reporting, he remained concerned about his safety. “We live in daily fear of death and destruction, this added to my usual anxiety hath almost unmanned me,” Woodhull wrote to Tallmadge in June. [22] In the same letter he finally bowed out of the spy business. Woodhull’s marriage to Mary Smith in November may have reinforced his decision; as a family man, he had more to lose than his own life. By that time Washington and Tallmadge had developed other agents in New York City and the Culper Ring’s role diminished. But there can be no doubt of Woodhull’s dedication. Even after resigning he sent seven more letters about British activities. He filed his last intelligence report, not written in code but still signed with the alias “Samuel Culper,” on February 21, 1783, while the British planned the war’s closing act, the evacuation of New York City.[23] Woodhull’s expense report submitted in July was the final curtain on his clandestine service.[24]

After the war ended in December 1783, Woodhull stayed in Setauket. He had three children with his wife Mary, lived prosperously as a Suffolk County judge, and died in 1826. Woodhull never spoke of his spying activities to anyone. But he probably never forgot that day in 1778 when he came very close to being hanged.