The Culper Ring: How Espionage Won the American Revolution

For millennia, from the bloody campaigns waged by the students of Sun Tzu to the cat-and-mouse game between the CIA and the KGB during the Cold War, military intelligence has played a crucial role in the success or failure of armies, campaigns, and entire nations.

Unfortunately, that shadowy game, played by ordinary men and women, free and enslaved, has gone unrecorded in the annals of history, including in the American Revolutionary War.

This is one of those stories.

The Commander-in-Chief of the Continental Army, George Washington, wasn’t a professional soldier before the American Revolution began. But he knew the importance of knowing one’s enemy.

“There is nothing more necessary than good intelligence to frustrate a designing enemy, & nothing requires greater pains to obtain,” Washington would later remark.

But Washington’s intricate knowledge of military intelligence hadn’t come from books, nor had he gleaned the concept from discussing with professional British officers back in the French and Indian War. Washington had been a spy himself.

In 1753, the 21-year-old Washington had been hired as a surveyor in the Ohio Territory for the British government. But that was just a cover story.

Relations between France and Great Britain had always been tense; indeed, the French and Indian War would break out a year later. Washington was really there to observe troop movements, take note of the relations between France and her Native American allies in the region, and painstakingly choreograph French fortifications.

And he did well. Indeed, the CIA later wrote that “one of the things he did particularly well was to exploit the social environment of drinking sessions and meals with French officers to acquire useful intelligence.”

When Washington took over the reins of the Continental Army, he quickly tried to establish an effective intelligence network, hiring the New York merchant Nathaniel Sackett, who had a rudimentary knowledge of ciphers, to be his first of intelligence in February 1777. It is interesting to note that Washington himself paid Sackett’s salary, and he remained a private man, never joining the Continental Army.

However, creating an intelligence network from scratch was a Herculean task. It was a task for which neither Washington nor Sackett were well-suited. Though Washington had been a successful spy during his youth and Sackett could devise an effective communications system, neither knew how to organize a wartime spy ring deep in enemy territory.

Worse, they could barely find volunteers willing to enter enemy territory. Spying was dangerous and seen as dishonorable, according to Alexander Rose, author of Washington’s Spies: The Story of America’s First Spy Ring (2006); it was something beneath the average man.

For example, neither Washington nor Sackett ever spoke about their espionage activities during the war, and Sackett’s eventual successor, Benjamin Tallmadge, only vaguely hints at his eventual role as Washington’s spymaster in his autobiography:

“[In 1778,] 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.”

Eventually, though, Washington found his volunteer.

Captain Nathan Hale was boated across the Long Island Sound on September 8, 1776, to report on British troop movements.

Two weeks later, Hale was dead, dangling from a tree after being caught by the British and executed.

Hale’s fate wasn’t unique. After a string of disappointing failures, Washington fired Sackett and replaced him with the unproven Major Benjamin Tallmadge.

A New Leader, A New Plan 

Though Tallmadge had never been involved with espionage, he was well-educated, young, and, perhaps most importantly, motivated by revenge.

Nathan Hale had been one of Tallmadge’s best friends at Yale College, and his death on one of Sackett’s first missions had left him bitter. He quickly began rebuilding the Continental Army’s intelligence apparatus from the ground up.

Sackett believed operating a network behind enemy lines was impossible for a prolonged period. As a result, he preferred sending agents on one-time intelligence-gathering missions when Washington thought it prudent.

Tallmadge thought Sackett’s system was a disaster. Sending in agents one at a time was foolish. Not only were the infiltration and exfiltration incredibly dangerous, but an itinerant wanderer with no ties to the local community would draw far more attention than a well-known resident. Wouldn’t it be better to have someone on the inside who could submit reports when the opportunity arose?

Taking this in stride, Tallmadge asked Washington to release one of his childhood friends, Abraham Woodhull, from prison. Woodhull, wanting to get out of a hellish Continental Army prison for smuggling, agreed to serve the patriot cause.

Woodhull also had a personal motive; his cousin, Nathaniel Woodhull, had been an officer in the Continental Army, was wounded in battle, and died in British captivity. Spying granted him his immediate freedom and let him get some measure of revenge.

Woodhull, ​​given the codename “Samuel Culper” by Washington himself, was an excellent agent. He lived in the small village of Setauket, around sixty miles from New York City. His father was a respected judge who was loyal to the British cause.

Even better, his sister ran the Underhill boarding house in New York City, allowing him to blend in and observe the city in relative obscurity. How was the morale of the enemy garrison? The local populace? Were supplies being stockpiled for an operation? What was the latest talk of the town?

Woodhull then combined his observations into reports, which, after he arrived back in Setauket, he passed to his friend, Caleb Brewster. Brewster was a whaleboat captain who regularly sailed the Long Island Sound. He’d drop the information off at Tallmadge’s camp in Fairfield, Connecticut.

Tallmadge would, after analyzing the information, submit a report to Washington.

Despite the smooth start, Woodhull’s monthly trips to New York started raising suspicion. What was he doing, coming to New York City every month when he had elderly parents at home?

The straw that broke the camel’s back came when John Wolsey, a Loyalist smuggler whom the Continental Army had detained, returned home and informed the British that Woodhull was working for the rebels. He didn’t know the specifics, but it was enough to draw the ire of the British.

When Samuel Culper/Woodhull returned from a trip to New York in early May 1779,     he found his father beaten by members of the Queen’s American Rangers, a Loyalist light infantry unit. The soldiers had beaten the elder Woodhull in hopes he would betray his son.

It’s unclear whether Abraham’s father genuinely didn’t know his son was a Continental spy or whether he had a change of heart, knew of his activities, and protected his secret. Regardless, the Rangers failed to beat a confession out of him.

The men immediately seized the junior Woodhull and hauled them before their commander, Colonel John Graves Simcoe. Simcoe began berating Abraham, asking him question after question.

Why was he traveling to New York every month? What was he doing in the city? Was he spying for the rebellion?

There is no account of the exchange between Simcoe and Woodhull/Culper, though the officer must have found the young man’s responses wanting. He prepared to hang Woodhull as a spy.

At this moment, Woodhull’s life was saved by an unlikely hero, Captain Benjamin Floyd. Floyd, a lifetime Setauket resident and well-known Loyalist, pleaded with Simcoe, insisting that the Woodhulls were loyal to the Crown. His men had already beaten his father without cause. Were they really to murder his son, at his orders no less?

Simcoe’s anger abated, and he relented. Woodhull lived to tell the tale. However, his time as an agent was over. He was a marked man. Luckily for the American cause, Woodhull had recruited another agent in British-occupied New York City during his visits: Robert Townsend. He was given the codename Samuel Culper Jr.

With Culper Sr. unavailable, Culper Jr. got to work. Townsend was an alcohol merchant. In a city inundated with thousands of soldiers and sailors, Townsend dealt primarily with soldiers and sailors of all ranks and stations. When his clients came to purchase their spirits, Townsend could gently probe for information by asking harmless questions.

The big break came when James Rivington, a business partner, dedicated Loyalist, and printer of the pro-British Royal Gazette, asked him for help. Directing the day-to-day affairs of the coffee house they co-owned prevented Rivington from conducting interviews with British civil and military officials. Would Townsend be willing to do the interviews so Rivington could reprint them in the Royal Gazette?

Townsend couldn’t believe his luck. He accepted Rivington’s proposal and swiftly threw himself into his work, his journalistic career gaining him access to the highest levels of the British administration. Better yet, his status as a news reporter for a pro-Loyalist paper insulated him from suspicion. He was merely a journalist asking questions and taking statements for the faithful British subjects of New York City.

Townsend gathered a wide array of invaluable intelligence for the rest of the war. Here are just two examples.

In early 1780, Townsend learned of a British plot to undermine the colonial economy. The American economy had always been precarious, and the British plan to flood the market with counterfeit bills very well could have led to total economic collapse.

With prompt warning from Townsend, Washington informed the Continental Congress of the impending danger. Congress acted quickly, recalling all the bills in circulation and reprinting them on new paper.

The British plan had been successfully killed in the crib.

In July of that same year, when the British learned from spies of their own that a French fleet under the Comte de Rochambeau was sailing for Rhode Island, the British prepared a daring interception.

They’d catch the French convoy off the coast and send it to the bottom of the Atlantic. With any luck, the destruction of such a large fleet could torpedo the alliance between France and the rebellious colonies.

Townsend dutifully reported on the British plan. In response, Washington ordered immediate preparations for an attack on New York City. The ever-cautious commander of British forces in North America, Lieutenant General Sir Henry Clinton, decided to keep the fleet in port for artillery support and order the garrison on high alert.

The attack was a feint; after the French embarked on American soil, Washington called off the assault.

The Culper Ring would continue to expand and remain active until the end of the war, submitting its last report on September 19, 1782.

Their contribution to American Independence would only be publicized in the 1930s when a historian researching the Townsend family discovered several of Culper Jr’s long-lost letters.

Woodhull, Townsend, and Brewster were hardly the only spies in the employ of the Continental Army during the American Revolution.

Hercules Mulligan and Cato Howe, enslaved by Mulligan, jointly ran a tailor shop in British-occupied New York City throughout the war and passed on information to the American cause. In April 1777, Cato traveled across the Hudson River to inform Washington about the impending British summer offensive aimed at Pennsylvania. This was hardly their only contribution to the cause. The two saved Washington’s life on at least two occasions, in late 1779 and early 1781.

In late 1780, James Armistead Lafayette, an enslaved African American man in the service of the Marquis de Lafayette, infiltrated the camp of Lord Cornwallis shortly after the disastrous Battle of Camden. James was a master at his craft. He had Lord Cornwallis’ trust completely and successfully embedded himself as a double agent, promising to report rebel troop movements and plans to the British. Instead, James routinely sent Cornwallis false or misleading information regarding rebel intentions and disposition. All the while, he provided the Marquis with accurate, timely, and vital intelligence on the British.

And when Cornwallis decided, in large part due to James’ false intelligence, to withdraw to Yorktown and abandon the southern campaign, James swiftly informed the Marquis of the British plan. The young Frenchman wrote to Washington. Washington immediately broke camp and hurried south at a breakneck pace, arriving and besieging Yorktown. The French fleet soon arrived and cut off any escape by sea.

Cut off, surrounded, outgunned, and outnumbered, defeat for Cornwallis was now only a matter of time.

Though the sacrifices of James, Cato, Mulligan, Woodhull, Brewster, Hale, and so many others are often forgotten, we’d do well to remember the unsung heroes of the American Revolution.

Too often, we remember only those who fought by more conventional means, such as the legendary minutemen who risked life and limb for their country, dropping everything to fight the invader.

But a spy’s life is fraught with far more danger than a soldier’s. Soldiers go on leave; they rest in camp, far behind the frontlines. They do not need to look over their shoulder constantly, and they don’t need to pretend to be someone (and something) they aren’t.

A spy doesn’t get a moment of respite. They spend every waking moment in sheer terror, always knowing the slightest mistake in the most mundane daily task could see them ripped from their homes and strung up from the nearest tree, abandoning their families to an uncertain fate.

A soldier risked life and limb; a spy risked everything.