10 Significant Things About The Culper Ring, George Washington’s Most Important Spy Network

George Washington Ordered the Creation of the Culper Ring in 1778 to Gather Intelligence on British Activities in New York

When the British occupied New York in 1776, general Washington realized the importance of gathering information about his enemies’ troop movements and intentions. After he was defeated and forced to evacuate the city in the summer of 1776, Washington directed that a “channel of information” be established on Long Island. It was an ad hoc and poorly run affair, without permanent agents on the ground. It came to grief with the capture of Nathan Hale, a young captain who volunteered for an intelligence gathering mission behind British lines, only to get caught and hanged as a spy.

The Hale fiasco convinced Washington that civilians would make less conspicuous spies than military officers. So in February of 1777, he requested the aid of a Nathaniel Sackett to spy on the British, and appointed a major Benjamin Tallmadge (1754 – 1835), a New York native and Yale graduate, as military liaison and point of contact. Sackett’s information was hit and miss, accurate at times, and inaccurate at others. But even the accurate intelligence was lacking in both quantity and timeliness to satisfy Washington, so he sacked Sackett.

The general was disappointed with other intelligence operations that were established in 1777, and his frustration with the inability to set up a reliable intelligence pipeline continued into 1778. Then in August of 1778, a Connecticut lieutenant named Caleb Brewster offered to furnish intelligence from behind enemy lines, and Washington accepted the offer. By the end of the month, Brewster had sent in accurate reports about British troops movements, as well as the condition of Royal Navy ships after a storm and battles with the French.

Encouraged by Brewster’s success, Washington tasked a general Charles Scott with handling the new intelligence pipeline, and assigned him major Tallmadge as an assistant. General Scott had a full plate, however, and was uninterested in intelligence gathering anyhow, so Tallmadge ended up as the de facto spy master in charge of Brewster’s intelligence gathering. Tallmadge’s remit expanded when Washington tasked him with recruiting spies to gather intelligence from New York and the surrounding areas.

Tallmadge recruited Abraham Woodhull, a friend and neighbor with whom he had grown up in Setauket, a small community in Long Island. Woodhull would gather the intelligence and deliver it to Brewster, who would then deliver it to Tallmadge and thus to George Washington. Washington, who was exceptionally hands on for a general when it came overseeing espionage activities, gave Woodhull the codename “Samuel Culper” – a play on Culpeper County, Virginia. With its key players in place and its tasks defined, the Culper Ring was now operational and ready to shape events and make history.

Abraham Woodhull – the ‘Culper’ of the Culper Ring

Abraham Woodhull (1750 – 1826), a key figure of the Culper Ring, was born into a prosperous family in Setauket, a small agricultural community on the north shore of Long Island, New York. His father was a judge, and he was a cousin of Nathaniel Woodhull, leader of a New York Patriot legislature set up as an alternative to the Loyalist New York Assembly, and a militia general. The family owned prime farmland in Setauket, and Abraham became a farmer.

Abraham joined the militia in 1775, but his heart was not really into it, so he quit after a few months. However, his patriotic zeal flared anew after his cousin, general Nathaniel Woodhull, was captured by the British in 1776, then slashed by sabers for refusing to say “God save the King”. Abraham’s cousin was then denied medical care and food, and died an agonizing death while in British captivity in September of 1776.

In 1778, Woodhull was caught smuggling contraband across the Long Island Sound and imprisoned in Patriot-held Connecticut. His childhood friend and neighbor Benjamin Tallmadge, now an intelligence officer in the Continental Army, put in a good word with Connecticut’s governor and got him released. He then asked him to spy on the British, and Woodhull accepted. After swearing a loyalty oath to king George III to establish his cover as a trusted Loyalist, Woodhull headed into Manhattan for his first foray into the world of espionage.

The British obtained much of their food from the farmlands surrounding New York, particularly Long Island and communities such as Setauket. That meant Woodhull had a good excuse – selling his farm produce – for regularly travelling the 55 miles separating Setauket from New York City without arousing suspicion. While in the city, he observed British military activities, and mingled with people in taverns frequented by the British and Loyalists to pick up gossip and news. He collected information from various contacts, including British officers, and recruited additional spies from amongst those whom he trusted.

Woodhull would then return to Setauket, where he would write down detailed reports of the intelligence gathered, and hide it in secluded coves nearby. The reports were collected by Caleb Brewster, who regularly crossed the 18 mile stretch of the Long Island Sound from Patriot held Connecticut to British held Long Island in a whaleboat. Brewster would deliver the reports to Benjamin Tallmadge, who would then pass them on to George Washington. Instructions and requests for additional or specific information were passed down the same chain from Washington to Tallmadge to Brewster to Woodhull.

Later in the war, Woodhull stopped going into New York personally, and relied instead on a courier, Austin Roe, who operated under the guise of a merchant to travel back and forth between Setauket and New York City. Having collected information from New York, Roe would convey it via dead drop in a box buried in land he rented from Woodhull.

The Spy Ring’s Methodology: Scouting Missions vs Embedded Spies

From early on, there was a difference of opinions between general Charles Scott, whom Washington had appointed to oversee intelligence gathering, and his subordinate, major Benjamin Tallmadge, who actually ran day to day operations. Scott believed in sending scouts in single shot missions, sneaking across enemy lines into British held territory to gather information and return with their findings.

Tallmadge thought that was inefficient and too risky, as illustrated by the fate of lieutenant Nathan Hale, who had been caught and hanged as a spy without accomplishing anything. Instead, Tallmadge wanted to recruit spies who were already living behind lines, who would not arouse suspicion by their mere presence. Those spies would remain embedded in place, and rather than risk sneaking back and forth across enemy lines, transmit their information to base via secure lines of communications, such as couriers experienced in slipping through the lines.

In September of 1778, Scott’s methodology led to the capture of 3 out of 5 spies sent on missions to New York City, and that convinced Washington to give Tallmadge’s methodology a try. In late October, Scott was pushed out and made to resign his position as head of intelligence, and Tallmadge was appointed in his place as chief spymaster.

Tallmadge abandoned Scott’s strategy of dispatching scouts into enemy territory, and he and Abraham Woodhull set up a network of embedded agents, operating from their homes in New York City, Long Island, and Connecticut. They collected intelligence, then waited for couriers to collect what they had gathered and deliver it to the Patriots. The contrast between the effectiveness of Scott’s and Tallmadge’s methodologies was stark: while numerous scouts had been captured during Scott’s single shot missions, not a single one of Tallmadge’s embedded spies was captured during the war.

The Spy Ring’s Methodology: Tactics and Information Gathered

In the Culper Ring’s early days, Abraham Woodhull frequently travelled to New York City under the cover of his occupation as a farmer delivering produce, or to visit his sister, who lived in the city. While in New York, he gathered information about the units in the city, their dispositions, and any news he overheard from talkative Loyalists and British officers.

It was valuable information, but close questioning by inquisitive British soldiers during one of those visits drove home the dangerousness of what he was doing, and how a single slip, wrong move, or simple bad luck, could send him to the gallows. So to reduce his exposure and the frequency of his travel from Long Island to New York and back, Woodhull began leaning more on recruiting spies in the city, and using their reports instead of his personal observations. An early recruit was his sister’s husband in New York, but his brother in law’s reports were often so vague as to be useless.

Initially, Woodhull would gather the information from New York City, return with it to Setauket, Long Island, then deliver it to Caleb Brewster, who delivered it to Benjamin Tallmadge, who delivered it to George Washington. It was a time consuming process that was eventually shortened by using couriers to collect the information in New York and speedily get it to Setauket, 55 miles away. The process was further shortened by the use of express riders to transmit the intelligence from Tallmadge to Washington.

A neighbor and friend of Woodhull in Setauket, Anna Strong, used her laundry as a code to coordinate between Brewster and Woodhull as to when intelligence was ready to gather, and where it should be collected. When Brewster was in the area, ready to pick up Woodhull’s reports, Anna would hang a black petticoat in her laundry as a signal to Woodhull. Woodhull would then finish compiling a report, and stash it in a prearranged hiding spot in one of six coves near Setauket. Anna would then hang up white handkerchiefs to dry, their number corresponding to the number of the cove where Woodhull had stashed the report. Brewster would then go to the correct cove, pick up the report, and deliver it across the Long Island Sound to Tallmadge in Connecticut.

Close Calls and Brushes With Disaster Led to the Emergence of the Culper Ring’s Most Valuable Agent

In June of 1779, a smalltime Long Island pirate was captured by the British, and to secure his release, he snitched on Abraham Woodhull by telling the British that the Setauket farmer was up to something iffy. Acting on the tip, a British detachment was sent to look in on Abraham, but he was away in New York City at the time, so they beat up his father, the local magistrate. Abraham only escaped arrest after another British officer vouched for him, but the close brush with disaster frightened him into laying low.

Things only got worse when a letter from Washington to Tallmadge, coded but still offering clues to the identities of some Culper Ring members, plus other telling information, was intercepted by the British. In early July of 1779, a British cavalry raid on Tallmadge’s camp seized documents mentioning an agent C___, who was reporting to Tallmadge from New York City.

Abraham Woodhull was already jittery, and news of the raid on Tallmadge’s camp heightened his anxieties. So he informed Tallmadge that things were too hot for him to keep venturing into New York City, as he was under suspicion from the British. However, he added that he had recruited an agent who lived in the city, who could do the intelligence gathering for him.

That agent, Robert Townsend (1753 – 1838), was given the codename “Samuel Culper, Jr.” (Abraham Woodhull was “Culper, Sr.”). He was a storekeeper with Patriot political leanings, who lived and worked in New York’s red light district, catering to a clientele of soldiers and the working class. His political inclinations were solidified by British mistreatment of colonists in his hometown of Oyster Bay, Long Island, and the seizure of the Townsend home to quarter British soldiers.

Balanced against Townsend’s Patriot inclinations was his upbringing as a liberal Quaker. His faith and its pacifist ethos, as well as his personality, kept him from taking up arms. When Woodhull asked him to spy on the British, it gave Townsend a means of helping the Patriot cause without personally engaging in acts of violence prohibited by his religious upbringing. He would prove to be the most valuable and productive agent of the Culper Ring, and the most valuable American spy throughout the entire war.

Robert Townsend: America’s Most Important Spy

The Culper Ring’s Robert Townsend might have been the single most important spy in America’s history. His espionage activities probably had a greater and longer lasting historical impact than that of any other single clandestine operative from the country’s founding to the present. For somebody whose actions played such a great role, he is remarkably little known, and does not get anywhere near the recognition his historical contributions warrant. That was how he wanted it. Townsend never sought recognition during the war, insisting that his identity be kept secret even from George Washington. After the conflict, the few who knew his identity – whose numbers by then included Washington – respected his wish to remain anonymous.

George Washington personally spelled out Townsend’s tasks. In a letter with detailed instructions, the Continental Army’s commander in chief directed Townsend to remain in New York City and: “… collect all the useful information he can – to do this he should mix as much as possible among the officers and refugees, visit the coffee houses, and all public places. He is to pay particular attention to the movements by land and water in and about the city especially“.

Washington went on to add that Townsend was to report on the number of troops operating in New York and its environs; identify their units; the defensive fortifications; the security measures in place to protect transports; the state of supplies and provisions; and the morale of the military and civilians. He closed by noting: “There can be scarcely any need of recommending the greatest caution and secrecy in a business so critical and dangerous. The following seem to be the best general rules: To entrust none but the persons fixed upon to transmit the business. To deliver the dispatches to none upon our side but those who shall be pitched upon for the purpose of receiving them and to transmit them and any intelligence that may be obtained to no one but the Commander-in-Chief“. Little did Washington know just how well Townsend would perform, or how well positioned he was to come across some of the most sensitive information of the entire war.

After gathering information, Townsend wrote his reports using invisible ink on seemingly blank reams of paper. He then handed them to a courier who delivered them to Abraham Woodhull in Setauket, and from there they made their way to Washington. The general read the reports after developing the invisible ink with a chemical agent, and often responded to Townsend with invisible ink messages of his own.

Townsend did a lot of valuable legwork gathering intelligence and fulfilling the tasks assigned him by George Washington. He got a gig as a columnist for a Loyalist newspaper, and visited coffeehouses to hobnob with British officers, many of whom opened to him in the hopes of seeing their name in print. That was how Townsend got wind of a British plot to wreck the American economy by flooding the country with counterfeit dollars. His warning enabled the Continental Congress to avert disaster in the nick of time by recalling all bills then in circulation, and issuing new ones.

Townsend also discovered that the British had learned that the French, who had joined the war on America’s side, were sending a fleet to land French troops in Rhode Island. The British and their more powerful Royal Navy planned to intercept and capture or sink the French at the sea before they disembarked their troops. Townsend’s timely warning enabled George Washington to bluff the British into staying put in New York, by feeding them false information about a nonexistent plan to attack New York. So the British prepared to defend New York against an attack that never came, while the French safely landed their troops in Rhode Island. That link up between French and American armies would ultimately doom the British. The allied Franco-American forces would effectively decide the war in 1781 by trapping a British army in Yorktown, Virginia, and forcing its surrender.

One of Townsend’s greatest coups resulted from the unwelcome, but as it turned out fortuitous, quartering of British officers in the Townsend family home in Oyster Bay. During the British stay, one of Townsend’s sisters overheard a visiting officer, John Andre -Benjamin Tallmadge’s British counterpart in charge of intelligence gathering – discussing the defection of a high ranking American hero. She passed that on to her brother, and from there it worked its way through the Culper Ring to Tallmadge. It eventually contributed to the unmasking of Benedict Arnold as a traitor.

The Culper Ring Played a Key Role in Unearthing Benedict Arnold’s Treason: the Capture of John Andre

One of the Culper Ring’s greatest contribution to the Patriot war effort was its enterprising spy work in the fall of 1780. The ring’s skullduggery led first to the capture of British intelligence officer John Andre, and Andre’s capture in turn led to unraveling Benedict Arnold’s treason. It spared the American side from what would have been a dramatic espionage coup that might have altered the war’s outcome and the course of history.

John Andre (1750 – 1780) joined the British Army in 1771, and was posted to Canada in 1774, on the eve of the American Revolutionary War. He was captured and made prisoner early in the war, before regaining his freedom in December of 1776 in a prisoner exchange. A likeable character, he was popular in colonial society in New York as well as Philadelphia, where he was posted for a time after that city’s capture by the British in September of 1777. He lived in Benjamin Franklin’s house during the British occupation of Philadelphia, and upon leaving when the British were forced to decamp from the city, he looted the famous Founding Father’s home of valuables.

In 1778, Andre was made an adjutant to the British commander in chief, Henry Clinton. The following year he was promoted to the rank of major and placed in charge of British Secret Service, tasked with intelligence gathering. At the time, the war in the northern colonies had entered a stalemate, following the collapse of the British campaign of 1777, which had aimed to split New England from New York and Pennsylvania. Instead, the campaign ended in the defeat of general John Burgoyne and the capture of his army at Saratoga in upstate New York.

The plan to split New England from the other colonies remained viable, however, provided the British could control the Hudson River. Were that to happen, the British would be able to sail northward from their base of operations in New York City, deep into upstate New York. From there, the British could interdict communications with New England, or even launch an invasion into that region.

The Patriots were aware of that threat, however, and dealt with it by constructing strong fortifications on bluffs overlooking the Hudson upstream from New York City, at West Point. That choked off the river to enemy navigation, and capturing West Point thus became a Holy Grail for the British. In 1780, Andre entered into communications with American general Benedict Arnold, who held the American command at West Point. The go between was Arnold’s wife, Peggy Shippen, a Philadelphia socialite from a Loyalist family, with whom Andre was rumored to have had a romantic affair during the British occupation of that city.

Arnold agreed to turn coat and betray West Point to the British in exchange for £20,000 – about $3.7 million in 2018 US dollars. Spymaster and would-be traitor met secretly in September of 1780, and Arnold gave Andre the plans for West Point, along with civilian clothes and a passport to get him through American lines. Andre aroused suspicions, however, and was detained by an American patrol. On him were found the incriminating documents.

Andre was sent back to the Continental Army headquarters, where he almost bluffed his way out of it. He convinced his captors to send him to Benedict Arnold, whose treason had not yet been suspected, when the Culper Ring doomed him. Major Benjamin Tallmadge had received word from the ring that a high ranking American officer had turned traitor, and upon hearing of Andre’s capture, he halted the plans to send him on to Benedict Arnold.

Cross checking the documents found on Andre with the intelligence gathered from the Culper Ring unraveled the plot. During interrogation, Andre asked Tallmadge how he would be treated, and Tallmadge, a friend of Nathan Hale who had been hanged by the British as spy, apprised his prisoner of Hale’s fate. When Andre asked if the situations were similar, Tallmadge replied: “Yes, precisely similar, and similar shall be your fate“. He was right. Andre was tried, convicted, and hanged as a spy on October 2nd, 1780.

Benedict Arnold’s Treason

John Andre’s partner in crime was American Revolutionary War general Benedict Arnold (1741 – 1801), the United States’ most infamous traitor, and one whose name has become an epithet, synonymous with treason and betrayal. It was shocking at the time, because Arnold had been a leading Patriot in the fight against the British, and was perhaps the most capable combat leader on the rebels’ side. However, a combination of resentments over slights, real and imagined, coupled with financial distress, soured him on the American cause and led him to sell out to the enemy.

Arnold had provided valuable service to the American side before turning traitor, and played a leading role early in the war in 1775, in the capture of Fort Ticonderoga in northern New York. It was the Patriots’ first major victory, and the cannon captured at Ticonderoga, which were then dragged over hundreds of miles of rough terrain to the rebels then besieging Boston, forced the British to evacuate that city.

Afterwards, Arnold led an expedition through extremely inhospitable terrain in an attempt to capture Quebec. It failed in its ultimate aim, but he exhibited remarkable leadership in getting his men to the outskirts of Quebec. An enterprising Arnold further added to his laurels in 1776, when he constructed a fleet from scratch at Lake Champlain, and used it to defeat a vastly superior British fleet.

While lionized as a hero by the public, Arnold’s successes, rash courage, and driving style aroused the jealousy and resentment of other officers, who backbit and schemed against him. When Congress created five new major generals in 1777, Arnold was stung when he was bypassed in favor of some of his juniors. Oly George Washington’s personal entreaties prevented the prickly Arnold’s resignation.

Soon thereafter, Arnold repelled a British attack in Connecticut, and was finally promoted to major general. However, his seniority was not restored, and that became another slight that ate at him. He sought to resign once more, but was prevailed upon to remain. Arnold then performed brilliantly in halting the British advance into upstate New York in 1777. He was instrumental in bringing about its defeat, culminating in the British surrender at Saratoga, where Arnold fought courageously and was severely injured.

Crippled by his wounds, he was put in charge of Philadelphia, where he took to socializing with Loyalist families, as well as to extravagant living, which he financed with iffy dealings that led to scandal. He also married a much younger woman of loyalist sympathies, Peggy Shippen – rumored to have been British intelligence officer John Andre’s mistress during the Redcoats’ occupation of Philadelphia. Arnold’s new wife had spendthrift habits that soon drove her husband deep into debt, and between resentments and financial difficulties, he secretly approached the British to offer his services. They accepted, and assigned major John Andre to be his spy handler.

Arnold had been placed in command of the American fortifications at West Point on the Hudson River, upstream from British-occupied New York City and barring the Redcoats from sailing upriver. Arnold plotted to sell the British West Point’s plans, and deliver them the fortifications for £20,000. However, John Andre was captured, along with documents given him by Arnold. The Culper Ring had developed intelligence that a high ranking American hero was about to defect, and between that information and the documents found on Andre, Arnold’s treason was unmasked. The American general fled just in time to evade arrest and the fate of Andre, who was hanged.

The Postwar Lives of Key Members of the Culper Ring

As the war in the northern colonies settled into a stalemate, the British adopted a southern strategy, and shifted their military focus to the southern colonies in hopes of reviving their fortunes. With the war’s center of gravity shifting to the south, and especially after Washington and his French allies’ decisive victory at Yorktown in October of 1781, New York City, and with it the Culper Ring, became less important. The ring closed shop and ceased activities soon thereafter.

However, although Yorktown proved to be the last major battle of the Revolutionary War, the war did not officially end until Congress accepted the terms of the 1783 Paris Peace Treaty, and formally ratified it in January of 1784. Until then, George Washington remained skeptical of the British – who held on to New York City until November of 1783 – and their intentions. Accordingly, he ordered the Culper Ring reactivated in September of 1782, but there was not much to report. As Robert Townsend wrote on September 19th, 1782, the British had truly thrown in the towel, accepted American independence, and were just waiting for peace negotiations to conclude so they could leave.

After the war, Townsend withdrew into anonymity, and his wishes to remain anonymous were respected by those who knew of his espionage. He wrapped up his business activities in New York City, and returned to the family home in Oyster Bay, Long Island. He never married, although he fathered an illegitimate son upon a housemaid. Robert Townsend lived with his sister in Oyster Bay until he died of old age in 1838.

Abraham Woodhull got married in 1781, as the war was winding down. He had three children with his wife before she died in 1806. He remarried late in life, in 1824, before dying two years later in Setauket, in 1826. By then, he had become a man of stature in local politics, having served as magistrate of Setauket, judge of the Court of Common Pleas, and first judge of Suffolk County.

After the war, Caleb Brewster married a woman from Fairfield, Connecticut, and settled there with her, where the couple raised a family of eight children. He made a living as a blacksmith and a farmer until 1793, when he joined the United States Revenue Cutter Service – forerunner of today’s Coast Guard. He eventually retired to a farm in Black Rock, Connecticut, and died in 1827.

Benjamin Tallmadge served in the Continental Army until it was disbanded in 1783. He then returned to civilian life, and settled down to raise a family of seven children with his wife in Connecticut. He became a businessman and entered into a variety of business ventures, including serving as a bank president, and speculating in land in Ohio. When George Washington was elected president, he appointed Tallmadge as postmaster for Litchfield, Connecticut. In 1800, he was elected to Congress as a Federalist, and served in the House of Representatives until 1817. He died in 1835.

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Where Did We Find This Stuff? Some Sources & Further Reading

Biography – Abraham Woodhull

Connecticut History – Caleb Brewster and the Culper Spy Ring

Encyclopedia Britannica – Benjamin Tallmadge: American Continental Army Officer

Encyclopedia Britannica – Culper Spy Ring

Mount Vernon Online – Benjamin Tallmadge

Mount Vernon Online – John Andre

New England Historical Society – A Spy For a Spy: John Andre Hanged

New York Times, December 15th, 1985 – Remembering a Master Spy at Home

New York Times, November 13th, 2017 – When New York City Was a (Literal) Battlefield

Study.Com – The Role of New York in the American Revolution

Wikipedia – Culper Spy Ring

Wikipedia – Robert Townsend (Spy)