Learn About America's First Spies, the Culper Ring

How Civilian Agents Changed the American Revolution

New York Map, 1776
During the American Revolution, George Washington needed spies in New York City. New York Library Digital Collection, public domain image, via Wikimedia Commons

In July 1776, colonial delegates wrote and signed the Declaration of Independence, effectively announcing that they intended to separate from the British Empire, and soon, war was underway. However, by the end of the year, things weren’t looking so good for General George Washington and the Continental Army. He and his troops had been forced to abandon their position in New York City and flee across New Jersey. To make matters worse, the spy Washington sent to gather intelligence, Nathan Hale, had been captured by the British and hanged for treason.

Washington was in a tough spot, and had no way to learn about his enemies’ movements. Over the next few months, he organized several different groups to collect information, operating under the theory that civilians would attract less attention than military personnel, but by 1778, he still lacked a network of agents in New York.

The Culper Ring was thus formed out of sheer necessity. Washington's director of military intelligence, Benjamin Tallmadge—who had been Nathan Hale's roommate at Yale—managed to recruit a small group of friends from his hometown; each of them brought other sources of information into the spy network. Working together, they organized a complex system of gathering and relaying intelligence to Washington, risking their own lives in the process. 

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Key Members of the Culper Ring

Benjamin Tallmadge
Benjamin Tallmadge was the spymaster of the Culper ring. Hulton Archive / Getty Images

Benjamin Tallmadge was a dashing young major in Washington’s army, and his director of military intelligence. Originally from Setauket, on Long Island, Tallmadge initiated a series of correspondences with friends in his hometown, who formed the key members of the ring. By sending his civilian agents out on reconnaissance missions, and creating an elaborate method of passing information back to Washington’s camp in secret, Tallmadge was effectively America’s first spymaster. 

Farmer Abraham Woodhull made regular trips into Manhattan to deliver goods, and stayed at a boarding house run by his sister Mary Underhill and her husband Amos. The boarding house was a residence for a number of British officers, so Woodhull and the Underhills obtained significant information about troop movements and supply chains.

Robert Townsend was both a journalist and merchant, and owned a coffeehouse that was popular with British soldiers, placing him in a perfect position to gather intelligence. Townsend was one of the last of the Culper members to be identified by modern researchers. In 1929, historian Morton Pennypacker made the connection by matching handwriting on some of Townsend's letters to those sent to Washington by the spy known only as "Culper Junior."

The descendant of one of the original Mayflower passengers, Caleb Brewster worked as a courier for the Culper Ring. A skilled boat captain, he navigated through hard-to-reach coves and channels to pick up information gathered by the other members, and deliver it to Tallmadge. During the war, Brewster also ran smuggling missions from a whaling ship.

Austin Roe worked as a merchant during the Revolution, and served as a courier for the ring. Riding on horseback, he regularly made the 55-mile trip between Setauket and Manhattan. In 2015, a letter was discovered that revealed Roe’s brothers Phillips and Nathaniel were also involved in espionage.

Agent 355 was the only known female member of the original spy network, and historians have been unable to confirm who she was. It is possible that she was Anna Strong, a neighbor of Woodhull’s, who sent signals to Brewster via her laundry line. Strong was the wife of Selah Strong, a judge who had been arrested in 1778 on suspicion of seditious activity. Selah was confined on a British prison ship in New York harbor for “surreptitious correspondence with the enemy.

It is more likely that Agent 355 was not Anna Strong, but a woman of some social prominence living in New York, possibly even a member of a Loyalist family. Correspondence indicates that she had regular contact with Major John Andre, the chief of British intelligence, and Benedict Arnold, both of whom were stationed in the city.

In addition to these primary members of the ring, there was an extensive network of other civilians relaying messages regularly, including tailor Hercules Mulligan, journalist James Rivington, and a number of relatives of Woodhull and Tallmadge.

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Codes, Invisible Ink, Pseudonyms, and a Clothesline

George Washingtons retreat to Long Island, August 27, 1776, American Revolutionary War, United States of America, 18th century
In 1776, Washington retreated to Long Island, where the Culper ring became active two years later. De Agostini Picture Library / Getty Images

Tallmadge created several complex methods of writing coded messages, so that if any correspondence was intercepted, there would be no hint of espionage. One system he employed was that of using numbers instead of common words, names, and places. He provided a key to Washington, Woodhull, and Townsend, so that messages could be written and translated quickly.

Washington provided members of the ring with invisible ink, as well, which was cutting edge technology at the time. Although it isn’t known how many messages were sent employing this method, there must have been a significant number; in 1779 Washington wrote to Tallmadge that he had run out of the ink, and would attempt to procure more.

Tallmadge also insisted that members of the ring use pseudonyms. Woodhull was known as Samuel Culper; his name was devised by Washington as a play on Culpeper County, Virginia. Tallmadge himself went by the alias John Bolton, and Townsend was Culper Junior. Secrecy was so important that Washington himself did not know the true identities of some of his agents. Washington was referred to simply as 711.

The delivery process for intelligence was fairly complex as well. According to historians at Washington’s Mount Vernon, Austin Roe rode into New York from Setauket. When he got there, he visited Townsend's shop and dropped off a note signed by John Bolton–Tallmadge's code name. Coded messages were cached away in trade goods from Townsend, and transported by Roe back to Setauket. These intelligence dispatches were then hidden

“... on a farm belonging to Abraham Woodhull, who would later retrieve the messages. Anna Strong, who owned a farm near to Woodhull's barn, would then hang a black petticoat on her clothesline that Caleb Brewster could see in order to signal him to retrieve the documents. Strong indicated which cove Brewster should land at by hanging up handkerchiefs to designate the specific cove.”

Once Brewster collected the messages, he delivered them to Tallmadge, in Washington's camp.

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Successful Interventions

John Andre
Culper agents were instrumental in the capture of Major John Andre. MPI / Getty Images

Culper agents learned in 1780 that British troops, commanded by General Henry Clinton, were about to advance into Rhode Island. Had they arrived as planned, they would have caused considerable problems for the Marquis de Lafayette and Comte de Rochambeau, Washington's French allies, who intended to land with 6,000 troops of their own near Newport. 

Tallmadge passed the information along to Washington, who then moved his own troops into place. Once Clinton learned of the Continental Army’s offensive position, he cancelled the attack and stayed out of Rhode Island.

In addition, they discovered a plan by the British to create counterfeit Continental money. The intention was for the currency to be printed on the same paper as American money and to undermine the war efforts, the economy, and trust in the acting government. Stuart Hatfield at Journal of the American Revolution says,

"Perhaps if people lost faith in the Congress, they would realize that war could not be won, and they would all return to the fold."

Perhaps even more importantly, the members of group are believed to have been instrumental in the exposure of Benedict Arnold, who had been conspiring with Major John Andre. Arnold, a general in the Continental Army, planned to turn over the American fort at West Point to Andre and the British, and eventually defected to their side. Andre was captured and hanged for his role as a British spy.

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After the War

US Constitution
The members of the Culper ring returned to normal lives after the Revolution. doublediamondphoto / Getty Images

Following the end of the American Revolution, the members of the Culper Ring returned to normal lives. Benjamin Tallmadge and his wife, Mary Floyd, moved to Connecticut with their seven children; Tallmadge became a successful banker, land investor, and postmaster. In 1800, he was elected to Congress, and remained there for seventeen years.

Abraham Woodhull remained on his farm in Setauket. In 1781, he married his second wife, Mary Smith, and they had three children. Woodhull became a magistrate, and in his later years was the first judge in Suffolk County.

Anna Strong, who may or may not have been Agent 355, but certainly was involved in the ring’s clandestine activities, was reunited with her husband Selah after the war. With their nine children, they stayed in Setauket. Anna died in 1812, and Selah three years later.

After the war, Caleb Brewster worked as a blacksmith, a cutter captain, and for the last two decades of his life, a farmer. He married Anna Lewis of Fairfield, Connecticut, and had eight children. Brewster served as an officer in the Revenue Cutter Service, which was the predecessor of today’s US Coast Guard. During the War of 1812, his cutter Active provided “the best maritime intelligence to authorities in New York and to Commodore Stephen Decatur, whose warships were trapped by the Royal Navy up the Thames River.” Brewster remained in Fairfield until his death in 1827.

Austin Roe, the merchant and tavern keeper who regularly rode a 110-mile round trip to deliver information, continued to operate Roe’s Tavern in East Setauket after the war. He died in 1830.

Robert Townsend moved back to his home in Oyster Bay, New York, after the Revolution ended. He never married, and lived quietly with his sister until his death in 1838. His involvement in the Culper ring was a secret he took to his grave; Townsend’s identity was never discovered until historian Morton Pennypacker made the connection in 1930.

These six individuals, along with their network of family members, friends, and business associates, managed to leverage a complex system of intelligence methods during America’s early years. Together, they changed the course of history.

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Key Takeaways

Two sergeants of 4th Massachusetts Regiment, one wearing wool cap and holding ax, and other wearing tricorn hat and blue uniform, American Revolutionary War, 18th century, Historical reenactment
De Agostini / C. Balossini / Getty Images
  • A group of civilian spies recruited during the American Revolution gathered intelligence which was then passed along to George Washington.
  • Members of the group used a numbered code book, false names, invisible ink, and a complex delivery method to get information back to Washington's staff.
  • Culper agents prevented an attack on Rhode Island, uncovered a plot to counterfeit Continental money, and were instrumental in the exposure of Benedict Arnold.
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Selected Sources

Founding Fathers presenting their draft of Declaration of Independence to Congress, June 28, 1776, by John Trumbull (1756-1843), 1819, Declaration of Independence of United States of America, United States, 18th century
DEA PICTURE LIBRARY / Getty Images