"If men were angels, no government would be necessary. If angels were to govern men… [no] controls on government would be necessary." — James Madison

Benjamin Tallmadge and the Culper Spy Ring

While serving as an officer in the French and Indian War, George Washington became acutely aware of the importance of accurate intelligence in the successful prosecution of a campaign. Washington would later go on to oversee the creation of the United States’ first espionage organization—the Culper Spy Ring.

Patriots of the American Revolution is proud to present the following look at the Ring and its leader, Benjamin Tallmadge, by Richard F. Welch. The author teaches history at Long Island University and Farmingdale State College.

In August of 1776, as the British began landing on Long Island in preparation for an attack on Patriot forces dug in around Brooklyn, Washington dispatched an untrained volunteer spy behind British lines.

Connecticut schoolteacher Nathan Hale was quickly detected by the British and subsequently tried and executed. In the ensuing weeks, the Redcoats drove Washington and his army from Brooklyn, then from Manhattan, then from New York, and then across New Jersey during what might have been the darkest hour for both Washington and the Patriot cause. Yet the general recovered the initiative, and kept his soldiers’ morale alive with December victories at Trenton and Princeton. In the meantime, the British settled into New York City, which would become their major base of operations throughout most of the war. Long Island also fell under British occupation and was used as a source of supplies and quarters for the British, German, and Loyalist troops aligned against the Continentals.

The failure of Nathan Hale’s mission did not deter Washington from pursuing other intelligence venues, and he had success in deploying other agents in New Jersey. But his most significant progress in conducting intelligence operations began after he was contacted by Caleb Brewster, a resident of Setauket, Long Island, who—like many Patriots—fled to Connecticut following the Continental Amy’s defeat at Brooklyn. Although he served in the Continental Army, Brewster was most often on detached duty, crossing Long Island Sound to raid the British occupying his native shores. This combination of raid and counter-raid became known as the “Whaleboat War” after the long, double-bowed whaleboats in which the raids were ordinarily carried out. Equipped with a sail, and usually a swivel gun, whaleboats were large enough to carry twelve men and maneuverable enough to put into the myriad coves and harbors that dotted the North Shore of Long Island, which Brewster knew well. He also perceived that he could use his forays on the island to gather information about British troop dispositions, fortifications, supplies, numbers, and possibly plans.

Brewster wrote directly to Washington, suggesting that he engage in precisely such information-gathering activities. Hungry for information about British designs, Washington agreed—but he saw Brewster’s activities as only a beginning. What he wanted was a network of focused agents in Manhattan who could pass their reports back to Washington by way of Long Island and the whaleboat raiders. The first step was to find a suitable officer to organize and run the operation. By necessity this had to be a person in whom Washington had total trust, possessing both the intelligence and diligence to create and maintain such a system. He also had to be well acquainted with Long Island. Fortunately for Washington, he knew such a man.

Benjamin Tallmadge

Benjamin Tallmadge was a native of Setauket who had graduated with Nathan Hale from Yale University in 1773. Later, Tallmadge had enlisted in a Connecticut regiment that became the 2nd Connecticut Continental Dragoons and rose in rank from lieutenant to major. His intelligence, daring, and unswerving commitment to the cause of American Independence soon placed him among the circle of Washington’s favored young officers.

Tallmadge’s support for American liberty and independence came naturally. His father was minister of the Setauket Presbyterian Church, a denomination that backed the movements of resistance and revolution and had strong ties to the Whiggish Presbyterians and Puritans in New England. Indeed, during the British occupation of Long Island, Puritan and Presbyterian churches were frequently desecrated, damaged, and sometimes destroyed by the British and their Loyalist allies. Furthermore, his older brother, who also enlisted in the Continental Army, had been captured at the Battle of Long Island and died of abuse and neglect on one of the notorious British prison ships anchored in the East River. Having served with distinction in the major battles around New York and Philadelphia from 1776-1777, Tallmadge—with his deep Long Island connections and proven abilities—was an obvious choice to run Washington’s spy network. As he would later obliquely write in his memoirs:

“This year (1778) I opened a private correspondence with some persons in New York (for Gen. Washington) which lasted through the war.”1

The Agents

Tallmadge carefully recruited agents he knew and trusted for his nascent network, relying on Setauket friends, neighbors, and members of his father’s congregation. In addition to Brewster (a boyhood friend), Tallmadge tapped Abraham Woodhull, a local farmer whom he had known since childhood. Woodhull’s political leanings were probably influenced by his Presbyterian faith, but he was also the cousin of American General Nathaniel Woodhull, who had been captured after the Battle of Long Island and died of wounds that many people believed were inflicted after Woodhull had surrendered. This no doubt had an effect on Abraham Woodhull as well.

Because Woodhull made trips to Manhattan to sell his produce at markets, he could collect information for Tallmadge. Yet these journeys were highly dangerous—Woodhull had to pass through various British checkpoints at which he might be detected as a spy, or he might have been robbed along the way; the war and British occupation of Long Island had unleashed a wave of brigandage with criminal gangs stealing from Patriots and Loyalists alike. Consequently, Woodhull was often stressed and anxiety-ridden, and he feared that too frequent trips into the city would arouse suspicion.

Setauket men also served as couriers, taking information collected by Woodhull in Manhattan and carrying it back to Setauket when Woodhull himself was unable to leave. Austin Roe and Josiah Hawkins, friends and fellow Presbyterians, were the most frequently employed riders. Once intelligence was collected in Setauket, usually with Woodhull serving as the “clearinghouse,” it was necessary to wait for Brewster to make one of his frequent trips across Long Island Sound. Local legend had it that Anna Strong—wife of Patriot Selah Strong, who was forced to flee Long Island for Connecticut—would signal Brewster when intelligence was ready for pick-up and in which cove to land his boat to avoid detection. She did this by using a code based on the color and placement of the laundry drying on her clothesline. Though the story is unverifiable, the British learned that a woman was involved in “disloyal” activities in Setauket, and Anna fits the bill.

Robert Townsend, who became the Ring’s key Manhattan operative, was the anomaly in the organization. A member of a prominent family in Oyster Bay in Queens County, Townsend sprang from a Quaker-Anglican background. In contrast to Suffolk County on eastern Long Island, the western Kings and Queens Counties (present-day Nassau and Queens) were home to large numbers of Loyalists and neutrals. Townsend’s father, Solomon, was one of the few well-known outspoken pro-independence leaders, but he had been forced to submit to the British after the American defeat in Brooklyn. Townsend spent much of his time in New York City where he operated a merchant business at Peck Slip. Though he had acted as a commissary officer for the Continental Army before August of 1776, he—like his father—submitted to the British as they occupied Long Island, and may have even served briefly in a Loyalist militia unit. Although his business interests required him to overtly cooperate with the British, his personal proclivities leaned towards the cause of American independence.

In the fall of 1778, Oyster Bay was occupied by Colonel John Graves Simcoe’s Queens Rangers, one of the most effective Loyalist units raised during the war. Simcoe’s men constructed a bastion on land owned by the Townsends just south of the family residence, destroying an orchard in the process. Additionally, the occupiers “requisitioned” indiscriminately, and frequently ruined property for policy or sport. Residential activity was constrained by a curfew. Moreover, Simcoe chose the Townsend residence, later dubbed Raynham Hall, for his personal quarters. Townsend was forced to watch as the overbearing British officers used his family homestead as they saw fit and treated the Townsends as servants. He was further offended by Simcoe’s efforts to woo his attractive sister, Sally. Back in Manhattan, Townsend made the acquaintance of Abraham Woodhull, who was scouting for someone with a legitimate reason to stay in the city to serve as the network’s Manhattan agent. Exactly what was said between the two men remains a mystery, but Townsend joined the Ring. The timing of Townsend’s service, coming just after Simcoe’s occupation of Oyster Bay and Raynham Hall, suggests that for Townsend—like Tallmadge and Woodhull—the war was both ideological and personal.

Codes, Invisible Ink, and Strategies

As he organized the Ring, Tallmadge took pains to develop what later became known as “tradecraft.” For example, he devised a numerical code system, and created over 710 specially coded words: Long Island was 728, Manhattan 727. Agents were assigned both numbers and codes. Woodhull was both 722 and “Culper, Sr.” while Townsend was 723 and “Culper, Jr.” It was this use of the Culper pseudonyms that later led historians to dub Tallmadge’s network the “Culper Spy Ring.” Tallmadge himself assumed the nom de guerre “John Bolton” or 721. Only Brewster, who was already famous (or infamous) as a whaleboat captain, declined to adopt an alias or code.

As a further precaution, Tallmadge and Washington secured a supply of a specially concocted invisible ink that they called the “sympathetic stain” with which reports from Townsend in New York to Woodhull in Setauket were often written.

Secrecy was, of course, vital. In fact only Tallmadge knew the true identity of the “Culpers.” Washington never requested their identities from Tallmadge, and the information was not offered. It seemed that the fewer people who knew the names, the better.

Townsend became the key agent in the espionage network. His merchant activities in Manhattan provided the perfect cover for him to spend lengthy periods in the occupied city, while his close friendship and partnership with James Rivington, an ostensible Loyalist who published the pro-British Rivington’s Gazette (later the New York Gazette), provided the perfect cover for gaining the confidence of the British officers who frequented the coffee shop adjoining Rivington’s newspaper office. In actuality, Rivington was a double agent, or at least he played to both sides and supplied Washington with information. Interestingly, there is no indication that either he or Townsend was aware of each other’s activities.

Though Washington was content to let Tallmadge run the Ring, he demonstrated a consistent interest in the network and offered advice to Tallmadge: the commander-in-chief requested that Tallmadge pass on his suggestion that the man he knew only as “Culper, Jr.” (Townsend) write his reports on the blank pages of pamphlets that “…he may forward without risqué of search or the scrutiny of the enemy as this is chiefly directed against paper made up in the form of letters.”2

Alternatively, Washington proposed that Townsend/“Culper, Jr.”

“…may write a familiar letter…to his friend in Satuket [sic] or elsewhere, interlining with the stain, his secret intelligence or writing it on the opposite blank side of the letter. But that his friend may know how to distinguish these from letter addressed solely to himself, he may always leave such as contain secret information without date or place; (dating it with the stain) or fold them up in a particular manner, which may be concerted between the parties.” 3

Washington was also explicit in the intelligence he required. In another letter, he instructed Tallmadge to inform Townsend/“Culper, Jr.” that he wanted to know

“The quantity and quality of the provisions in New-York, comprehending their whole stock whether in magazines or on ship-board. He will be particular as to the kind and size of the works that are lately formed, or that may be erected. And 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 lyes, and if they appear to be taking measures for their security in case of a french [sic] fleet’s entering the harbor.”4

Townsend did his best to comply, and forwarded a steady stream of intelligence reports throughout the period from 1778-1780. The following is a decoded excerpt from a typical letter reporting on British deployments in New York and on Long Island from early 1779:

“[There is one] Hessian Regt near Jones and Delancy’s land and the other near the Water Works. The number on Staten Island I do not know. On Long Island the number is as mentioned a Regt of Horse about Flushing, a guard of about 30 men of the 3rd Battalion of DeLancy’s Brigade with a party of Militia Horse are at Jamaica as a guard for the General. He might have been taken off with much ease sometime ago, but it would now be very difficult as the Queens Rangers are at Oyster Bay. Their number is about 120 men, 100 of whom are mounted. The 3rd Battalion of Delancy’s Brigade are at Lloyd’s Neck. From [near] the vicinity of the Queens Rangers who can be there by means of an alarm gun in two hours. I think it would by no means be advisable to attack them—They were alarmed on Thursday night last and was there [Lloyd’s Neck] in one and a half hours after the alarm….”5

Achievements and Legacy

The importance of Culper Spy Ring activities to the Continental cause is impossible to assess. Intelligence regarding British dispositions, strength, order of battle, forage and supplies, morale, and even intentions no doubt played a significant role in Washington’s calculations. Messages from Townsend clearly helped Washington forestall a British attack on the French during their initial landing at Newport, Rhode Island, before they had the chance to secure their positions. Warned of the British expedition, Washington deceived the British into believing that he was planning a major attack to capture New York. This tactic led the British to drop their plans to descend on Newport and prepare for a non-existent offensive.

The Culper Spy Ring also revealed British intentions to counterfeit Continental currency, but such money was already so devalued that the actual effect of unleashing counterfeits is hard to ascertain.

Tallmadge’s achievement in organizing and operating the Ring seems more remarkable when it is remembered that he was simultaneously engaged in full-time military service. Not only did he help protect the pro-Patriot inhabitants of the Lower Hudson Valley from British raids and incursions, but he worked to suppress Loyalist guerrillas as well. He also convinced Washington to allow him to conduct raids against British fortifications on Long Island. In September of 1779, he cleaned out a nest of Loyalist whaleboat men adjoining Fort Franklin on Lloyds’s Neck, and by 1780 he began formulating a “…plan of breaking up the whole system” of British strongholds on Long Island through a series of commando-like strikes.6 Washington’s confidence in Tallmadge’s ability to execute this campaign led him to give the young major a separate command consisting of dismounted dragoons from his regiment, which would function as light infantry, plus horses.

Tallmadge’s most spectacular raid occurred on November 21-22, 1780, when he led about 100 men across the Sound, marched them from the north to the south shores of Long Island and, shouting “Washington and Glory,” they captured Fort St. George. Only one of Tallmadge’s men was wounded during the attack, while the British suffered seven men killed and had over fifty taken prisoner. On his return to the boats on the Sound, Tallmadge torched a large supply of provisions that the British had accumulated at Coram for winter use.7

On October 2, 1781, he dispatched another raid against the British at Fort Slongo, which was also destroyed and its garrison captured. In addition, Tallmadge directed his friend Caleb Brewster and other American whaleboat raiders in their attacks on British and Loyalist shipping in the Sound, sometimes joining in the action himself.

Tallmadge also became a key player in the unraveling of Benedict Arnold’s plot to turn over West Point to the British. On September 23, 1780, Tallmadge returned from picket duty in Westchester County and was presented with a prisoner recently captured by American guerrillas who called himself John Anderson. Observing Anderson’s demeanor, Tallmadge concluded that he had been “bred to arms,” and shortly afterwards Anderson confessed to Tallmadge that he was Major John André, Adjutant General of the British Army, who had been serving as a conduit between the British and Arnold.8 Arnold’s treason was unmasked, and although he escaped capture, West Point was saved and André sent to the gallows.

The capture of British Major John André and the revelations of Arnold’s treason filled Woodhull and Townsend with anxiety. Arnold knew Washington had established an intelligence operation centered on Long Island and New York, though he did not know the true identities of the agents. Nevertheless, Arnold’s knowledge—combined with other intelligence the British had secured—led the Redcoats to redouble their attempts to stop the Ring, and British and Loyalist patrols increased their efforts across Long Island. Fearful they would be found out, the Culper agents “went dark”—silent—at the end of 1780 and into 1781. This was not as serious a reversal as it could have been because the main current of the war shifted southward to Virginia. Washington’s army soon joined Rochambeau’s French troops in forcing the British to surrender at Yorktown.

Although this capitulation ended the major fighting of the American Revolution, raids and skirmishes continued, and the Culper agents resumed their operations. Indeed, intelligence from the Ring gave Washington the first confirmed reports that a peace treaty based on the principle of American independence had been concluded between American and British diplomats. The Revolution was coming to an end, and so were the operations of the Culper Spy Ring.

Postscript

Once the hostilities concluded, the members of the Setauket-Oyster Bay-New York spy network resumed their peacetime pursuits. None of them ever revealed their wartime activities. Even Tallmadge, who moved to Litchfield, Connecticut—where he commenced a successful career as a Federalist Congressman and land speculator—confined his remarks about the organization to two vague sentences in his memoirs. Robert Townsend continued his mercantile activities and died a bachelor in Oyster Bay in 1837. Abraham Woodhull devoted himself to local concerns, primarily his farm and his role as first Judge of Suffolk County after independence. Caleb Brewster remained in Connecticut and pursued a successful career as a ship owner along the Sound. In the 20th century, Long Island historian Morton Pennypacker noticed the similarities between the writing in Townsend’s account books and the letter signed “Culper Jr.” Using handwriting analysis, he revealed Townsend as the New York spy. This provided the key in discovering the full extent and importance of the Revolution’s most significant espionage organization.

References

Alexander Rose, Washington’s Spies: The Story of America’s First Spy Ring (Bantam, 2006).

Barnet Schecter, The Battle for New York (Walker & Company, 2002).

Benjamin Tallmadge, Memoir of Colonel Benjamin Tallmadge (New York: Thomas Holman, 1858).

Culper Correspondence, Pennypacker Papers, East Hampton Public Library.

George Washington to Benjamin Tallmadge, September 24, 1779. Electronic Text Center, University of Virginia Library.

Joseph S. Tiedemann and Eugene R. Fingerhut, The Other New York (State University of New York Press, June 2006).

Notes

1 Benjamin Tallmadge, Memoir of Colonel Benjamin Tallmadge (New York: Thomas Holman, 1858), 29.

2 George Washington to Benjamin Tallmadge, September 24, 1779. Electronic Text Center, University of Virginia Library.

3 Ibid.

4 Ibid., October 6, 1779.

5 Culper Correspondence, Pennypacker Papers, East Hampton Public Library.

6 Benjamin Tallmadge, Memoir of Colonel Benjamin Tallmadge (New York: Thomas Holman, 1858), 33.

7 Ibid., 42.

8 Ibid., 36.