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The Culper Spy Ring - Facts, Code and Importance

The Culper Spy Ring - Facts, Code and Importance

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British forces occupied New York in August 1776, and the city would remain a British stronghold and a major naval base for the duration of the Revolutionary War. Though getting information from New York on British troop movements and other plans was critical to General George Washington, commander of the Continental Army, there was simply no reliable intelligence network that existed on the Patriot side at that time. That changed in 1778, when a young cavalry officer named Benjamin Tallmadge established a small group of trustworthy men and women from his hometown of Setauket, Long Island. Known as the Culper Spy Ring, Tallmadge’s homegrown network would become the most effective of any intelligence-gathering operation on either side during the Revolutionary War.

The Dangers of Spying

In mid-September 1776, the American officer Nathan Hale was hanged without trial in New York City. British authorities had caught Hale when he was on his way back to his regiment after having penetrated the British lines to gather information. Hale’s death illustrated the grave dangers inherent in spying for the rebels during the Revolutionary War, especially in the British stronghold of New York. Meanwhile, Benjamin Tallmadge, a young cavalry officer from Setauket, had enlisted in the Continental Army when the American Revolution began in 1775 and was soon awarded the rank of major. In mid-1778, General George Washington appointed Tallmadge the head of the Continental Army’s secret service; he was charged with establishing a permanent spy network that would operate behind enemy lines on Long Island.

Tallmadge recruited only those whom he could absolutely trust, beginning with his childhood friend, the farmer Abraham Woodhull, and Caleb Brewster, whose main task during the Revolution was commanding a fleet of whaleboats against British and Tory shipping on Long Island Sound. Brewster, one of the most daring of the group, was also the only member whom the British had definitely identified as a spy. Tallmadge went by the code name John Bolton, while Woodhull went by the name of Samuel Culper.

Workings of the Culper Spy Ring

Woodhull, who began running the group’s day-to-day operations on Long Island, also personally traveled back and forth to New York collecting information and observing naval maneuvers there. He would evaluate reports and determine what information would be taken to Washington. Dispatches would then be given to Brewster, who would carry them across the Sound to Fairfield, Connecticut, and Tallmadge would then pass them on to Washington. Woodhull lived in constant anxiety of being discovered, and by the summer of 1779 he had recruited another man, the well-connected New York merchant Robert Townsend, to serve as the ring’s primary source in the city. Townsend wrote his reports as “Samuel Culper, Jr.” and Woodhull went by “Samuel Culper, Sr.”

Austin Roe, a tavernkeeper in Setauket who acted as a courier for the Culper ring traveled to Manhattan with the excuse of buying supplies for his business. A local Setauket woman and Woodhull’s neighbor, Anna Smith Strong, was also said to have aided in the spy ring’s activities. Her husband, the local Patriot judge Selah Strong, had been confined on the British prison ship HMS Jersey in 1778, and Anna Strong lived alone for much of the war. She reportedly used the laundry on her clothesline to leave signals regarding Brewster’s location for meetings with Woodhull.

Achievements of the Culper Spy Ring

Despite some strained relations within the group and constant pressure from Washington to send more information, the Culper Spy Ring achieved more than any other American or British intelligence network during the war. The information collected and passed on by the ring from 1778 to war’s end in 1783 concerned key British troop movements, fortifications and plans in New York and the surrounding region. Perhaps the group’s greatest achievement came in 1780, when it uncovered British plans to ambush the newly arrived French army in Rhode Island. Without the spy ring’s warnings to Washington, the Franco-American alliance may well have been damaged or destroyed by this surprise attack.

The Culper Spy Ring has also been credited with uncovering information involving the treasonous correspondence between Benedict Arnold and John Andre, chief intelligence officer under General Henry Clinton, commander of the British forces in New York, who were conspiring to give the British control over the army fort at West Point. Major Andre was captured and hung as a spy in October 1780, on Washington’s orders.

The Culper Spy Ring - Facts, Code and Importance - HISTORY

  • Invisible Ink - The Americans used an invisible ink called a "stain" that was developed by Doctor James Jay. It took a special chemical (known only to the Americans) to reveal the writing.
  • Secret Codes - Secret codes were also used in combination with a cipher to keep messages safe. In many cases, however, the enemy was able to decipher the codes.
  • Mask Letters - A final way to hide a message used a specific mask on what seemed to be a normal letter. The mask would reveal a secret message hidden within the letter.

Spies often used covers and disguises to get the enemy to trust them. They would pretend to be peddlers or local farmers. Loyalists would pretend to be patriots to get into groups like the Sons of Liberty. Patriots would do the same thing to find out what the loyalists were doing.

One of the largest spy operations of the Revolutionary War was the Culper Spy Ring. The ring was organized by George Washington's spymaster Benjamin Tallmadge. The goal of the ring was to provide Washington with information about the British army in New York City. The two main secret agents in the ring were Abraham Woodhull and Robert Townshend.

The Culper Spy Ring provided lots of valuable information to George Washington including British troop movements, strategic plans, and that American officer Benedict Arnold was going to turn traitor.

Nathan Hale - Hale was an American spy who was caught while gathering information in New York City. He was hung by the British, but is remembered for his famous last words which were "I only regret that I have but one life to give for my country."

Benjamin Tallmadge - Tallmadge ran the American spy network under George Washington. He organized the famous Culper Spy Ring in New York City.

Abraham Woodhull - Abraham was a key member of the Culper Spy Ring. He used the alias Samuel Culper when sending messages and working as a spy.

Lydia Darragh - Lydia spied on British officers who met in her home to discuss battle plans. She then passed on the information to American soldiers.

Benedict Arnold - Benedict Arnold was a general with the Continental Army when he decided to switch sides. He planned to turn over Fort West Point to the British before his plans were exposed and he fled to the British.

Hercules Mulligan - Mulligan owned a clothing store in New York City where many British officers shopped. He would gather information by talking to the officers and then pass it on to George Washington.

Daniel Bissell - Bissell pretended to desert the Continental Army and join the British. He worked for the British for over a year, gathering all sorts of detailed information.

Nancy Hart - There are many stories about the exploits of Nancy Hart during the war. They include her dressing up as a man to infiltrate British camps as well as capturing a number of British soldiers in her house.

The Spy Ring&rsquos Methodology: Tactics and Information Gathered

In the Culper Ring&rsquos 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&rsquos husband in New York, but his brother in law&rsquos 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&rsquos 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.

Culper Spy Ring

The Culper Spy Ring was an American spy network operating during the War of American Independence that provided George Washington with information on British troop movements. In November 1778, George Washington appointed Major Benjamin Tallmadge as director of military intelligence, charged with creating a spy ring in New York City, the site of British headquarters.

This network became known as the Culper Spy Ring and operated successfully in and around New York City for five years, during which time no spy was ever unmasked. Indeed even Washington was ignorant of the spies' identities. Tallmadge's informants consisted of friends he made at school on Long Island, including Austin Roe, Caleb Brewster, Abraham Woodhull, and Anna Strong.

Though Woodhull was Tallmadge's chief agent, Robert Townsend was an important informant who posed as a Loyalist coffee-shop owner and merchant while working as a society journalist. As a reporter Townsend was able to obtain information from the British at society gatherings.

In order to safeguard the identity of his spies, Tallmadge utilized a number of protective measures. Tallmadge gave his informants pseudonyms and invented a numerical substitution system to identify his informants rather than use names. Seven hundred and sixty-three numbers were used, with 711 denoting General Washington, 745 representing England, and 727 for New York. Tallmadge and his associates also wrote in invisible ink.

The spy ring established a sophisticated method of conveying information to Washington, who was based at New Windsor in New York. As a result, all information sent to Washington had to be transported through British-held territory. Austin Roe rode from Setauket, Long Island to New York City, where he entered Townsend's establishment. There Roe placed an order from Tallmadge who signed under his code name John Bolton.

Contained in this message were prearranged code words from Washington to Tallmadge to which Tallmadge responded in code. The messages were then hidden in goods that Roe took back to Setauket and hid 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. Brewster would then deliver the messages to Tallmadge.

The spy ring played an important role in the Revolutionary War. For instance, in 1780 the group learned that the British under the command of General Henry Clinton were about to launch an expedition in Rhode Island. Tallmadge contacted Washington who immediately ordered his army into an offensive position causing Clinton to cancel the attack. The group was also responsible for the apprehension of the British spy Major John André.


Crowdy, Terry. The Enemy Within: A History of Espionage. Oxford: Osprey Publishing, 2006.

Nagy, John A. Invisible Ink: Spycraft of the American Revolution. Yardley, PA: Westholme Publishing, 2009.

Rose, Alexander. Washington's Spies: The Story of America's First Spy Ring. New York: Bantam Books, 2007.

Spy Letters of the American Revolution (Clements Library, University of Michigan)

Book offers an authentic history of the Culper Spy Ring

Spies and spying have been a fascination among even the most conventional among us for generations. The intrigue has no boundaries of timeline or locale: Witness the popularity of Bond movies, the FX series &ldquoThe Americans,&rdquo &ldquoMission Impossible&rdquo &mdash the TV series and the movies &mdash and more recently, &ldquoTurn: Washington&rsquos Spies.&rdquo But it is rare that viewers can say they live where Revolutionary War spying took place, except in the case of &ldquoTurn,&rdquo in which some members of the Culper Spy Ring lived in the hamlet of Oyster Bay and Setauket.

Historians say there are many inaccuracies in the story depicted in &ldquoTurn,&rdquo as well as the roughly dozen books written about the Culper Spy Ring. This prompted Bill Bleyer, a Pulitzer Prize-winning retired Newsday journalist and author, to write &ldquoGeorge Washington&rsquos Long Island Spy Ring: A History and Tour Guide,&rdquo which he describes as an &ldquoanalytical comparative story.&rdquo

&ldquoThere was so much misinformation and conflicting information,&rdquo said Bleyer, who lives in Bayville. &ldquoA lot of them took their information from earlier [book] versions. I picked through what the others said, went through every piece with the historians and pointed out what other authors said and included the historians&rsquo comments explaining why that couldn&rsquot have happened. I fact-checked all of it.&rdquo

The debunked theories began with Suffolk County historian Morton Pennypacker&rsquos 1939 book, &ldquoGeneral Washington Spies on Long Island and in New York,&rdquo and continued in subsequent books about the spy ring, including the New York Times bestseller, &ldquoGeorge Washington&rsquos Secret Six,&rdquo by Brian Kilmeade, Bleyer said.

His book, released this month, clarifies and corrects the &ldquounsubstantiated speculation&rdquo by including comments from Oyster Bay historian Claire Bellerjeau, from Raynham Hall Museum and from Beverly Tyler, the historian at the Three Village Historical Society in Suffolk County. Bleyer sets the record straight on who the spies were, how they did their spying and what they accomplished. He also examines the Culper Spy Ring&rsquos impact on history, and includes a tour guide of Long Island&rsquos Revolutionary War sites at the end of the book.

As for AMC&rsquos &ldquoTurn,&rdquo Bleyer said he couldn&rsquot watch much of it. The series drew his ire from the beginning, when it incorrectly stated that the Culper Spy Ring formed in 1776, instead of 1778. So many inaccuracies followed, Bleyer said.

&ldquoIt&rsquos a series about spying, but they don&rsquot talk about it for the first 40 minutes,&rdquo he said. &ldquoThey turned [Abraham] Woodhull&rsquos very patriotic father [Richard Woodhull] into a Tory sympathizer, even though he was almost beaten to death by Simcoe&rsquos Queen&rsquos Rangers. In &lsquoTurn,&rsquo Richard badmouths the Revolution and is shown enjoying tea with Simcoe and the other Queen&rsquos Rangers.&rdquo

Raynham Hall Museum hosted a virtual book discussion of Bleyer&rsquos book this month. Harriett Gerard, executive director at the Oyster Bay house museum, said that everyone at Raynham Hall, once the home of Culper Spy Robert Townsend, was in awe of Bleyer&rsquos book.

&ldquoIt takes a certain kind of courage to write a book like this,&rdquo Gerard said. &ldquoBill brings the same amazing commitment to history as he always does to unearthing and presenting the truth, whatever it may be.&rdquo

Christopher Judge, an educator at Raynham Hall, agreed. &ldquoThis book is the story of truth,&rdquo he said. &ldquoIt is important to our museum&rsquos central story.&rdquo

A passion for history

Bleyer has been an avid reader all his life, and always loved history. Born and raised in Little Neck, Queens, until he turned 13, he read history books written for children, finishing the Landmark Book series before he started kindergarten.

Moving to Bayville in 1966, he found more history, visiting Sagamore Hill and President Theodore Roosevelt&rsquos gravesite at Youngs Memorial Cemetery. A 1970 graduate of Locust Valley High School, Bleyer attended Hofstra University. After graduating, he was the editor of the Oyster Bay Guardian from 1974 to 1975. He began his 33-year career at Newsday in 1981, where he sometimes wrote about Raynham Hall. When he retired in 2014, he began writing books. &ldquoGeorge Washington&rsquos Long Island Spy Ring&rdquo is his fourth book.

&ldquoPeople kept saying to me that I should write a book on the American Revolution,&rdquo Bleyer said. &ldquoWhen &lsquoTurn&rsquo came out, my publisher, The History Press, asked me to write a book about the Culper Spy Ring, because the television show was so popular. At first I said no.&rdquo

His reason, he said, was because there were so many other books out there about the spy ring. He wondered what he could do differently. Then he came up with the idea of including a tour guide, and was green-lighted right away.

Finding the truth

He read most of the letters about the spy ring. But when he read the books, he realized that much of the information was inaccurate. All of it, he said, was historical fiction.

Bleyer&rsquos journalism experience was helpful. &ldquoIt helped me to juggle all of the conflicting accounts, and I was on the phone every day with Beverly or Claire,&rdquo he said. &ldquoWe&rsquod talk out what I found. Sometimes I&rsquod change their minds, or they would change mine.&rdquo

He found the process satisfying. &ldquoWhat I enjoyed most was picking through the different book versions and debunking them,&rdquo he said. &ldquoIt did take a lot of work playing sleuth to untangle all of this.&rdquo

Pennypacker&rsquos book lacked footnotes, and he transformed anecdotal information and legend into fact. Writers who followed him repeated the inaccurate information without researching or questioning it, Bleyer said.

He learned that Kilmeade had met with historians from Setauket and Oyster Bay who gave him information on the spy ring, but he ignored it. There were many inaccuracies instead, Bleyer said. Worse, Kilmeade included fictitious dialogue in his book, without identifying it as such.

&ldquoWhy invent secret agents and all this other crap to hype up the story,&rdquo Bleyer said, &ldquowhen the real story is so good?&rdquo

What&rsquos in the book?

&ldquoGeorge Washington&rsquos Long Island Spy Ring: A History and Tour Guide&rdquo covers the period 1776 to 1790, beginning with an introduction, which corrects the inaccuracies of previous works.

The book continues with the Battle of Long Island in 1776, followed by the British occupation of Long Island, Nathan Hale&rsquos attempt at spying, other early spying efforts and how the Culper Spy Ring operated. There is also a section on each of the Long Island spies, with an analysis of all of their letters from 1778 through the end of the Revolutionary War, the importance of the spy ring and what it accomplished. The book has comments from Bellerjeau and Tyler throughout on the authenticity of the story, as well as explanations of what some of the historical information could mean.

The last third of the book focuses on New York state&rsquos George Washington Spy Trail, which includes a treasure trove of 47 pages of photographs and explanations of what happened at each location.

Personal after-effects

Bleyer said that writing the book did not change him in any way, instead cementing beliefs he already had. &ldquoIt made me more skeptical of what other people write, how things get amplified, all without critical analysis,&rdquo he said. &ldquoYou get a historical rush when reading a story of people risking their lives, thinking in codes, coming up with invisible ink. Why check off all the boxes for entertainment?&rdquo

Bleyer said he&rsquod like to think he would have joined the Culper Spy Ring given the opportunity, but said he wasn&rsquot sure. &ldquoIt was a pretty dangerous occupation, considering the first spy on Long Island was Nathan Hale,&rdquo he said, &ldquoand we all know he didn&rsquot end up too well.&rdquo

His book will never get the kind of exposure that &ldquoTurn&rdquo received, Bleyer said, but he&rsquos OK with that. It&rsquos more important to him to continue with lectures promoting the book. It will quench his authorial thirst, he said, to continue correcting the record.

Why was spying important in the Revolutionary War?

Rest of the in-depth answer is here. Then, how did spies impact the Revolutionary War?

Spies. Information during the Revolutionary War was passed along using handwritten letters. Spies used various methods to protect their messages in case they were intercepted by the enemy. Secret Codes - Secret codes were also used in combination with a cipher to keep messages safe.

Secondly, who was a spy in the American Revolution? Nathan Hale Hale was captured by the British army and executed as a spy on September 22, 1776. Hale remains part of popular lore connected with the American Revolution for his purported last words, &ldquoI only regret that I have but one life to give for my country."

Thereof, why are spies important?

Spies help agencies uncover secret information. Any individual or spy ring (a cooperating group of spies), in the service of a government, company or independent operation, can commit espionage.

Why was the Culper spy ring important?

The Culper Spy Ring enabled the Continental Army to gather intelligence in an efficient and unconventional manner in British-occupied New York City during the American Revolution. Among its most notable accomplishments was gathering intelligence that saved French troops from a British ambush in July 1780.

The Culper Spy Ring - Facts, Code and Importance - HISTORY

In August 2020 the Long Island Museum discovered an uncatalogued Culper Spy Ring letter in its collections. Acquired by the museum in December 1951, the handwritten double-sided letter measures 9 3/16” x 7 5/8”, is dated November 8, 1779, and is from Benjamin Tallmadge (using his alias, John Bolton) to Robert Townsend (alias, Samuel Culper Jr.).

The men were part of a spy network during the American Revolution which supplied George Washington with information on the activities of British troops then occupying the city of New York and Long Island. In the summer of 1778 George Washington tasked Major Benjamin Tallmadge with gathering military intelligence on the British headquartered in New York City. Born in 1754 on Long Island in the village of Setauket, Tallmadge recruited childhood friends and neighbors for his spy ring, including Caleb Brewster, Abraham Woodhull, and Austin Roe. In the ring’s most frequent movements, intelligence gathered in New York City would be sent by written message via courier to Setauket, then across Long Island Sound to Connecticut, and on to Washington’s headquarters. Reply messages would return by the same route.

Tallmadge took additional actions to maintain secrecy. The spies were assigned pseudonyms, with the network named after the ones for Abraham Woodhull (Samuel Culper Sr.) and Robert Townsend (Samuel Culper Jr.). Tallmadge created a numerical code book of 763 numbers that substituted for words. “George Washington,” for instance, was 711, “New York” was 634, and “doctor” was 126. Individual letters and numbers could also be swapped for other letters, with a word such as “silk” being disguised as “umco.” Lastly, correspondence could eventually also be written in invisible ink.

Despite the constant threat of being uncovered and several near misses, the spy ring operated successfully for five years, with no agents’ identities revealed or correspondence intercepted. One important example of the intelligence it provided Washington was when British General Clinton in July 1780 planned to send a force from New York City to attack French forces that had just arrived in Newport, Rhode Island. Once a Culper message and other intelligence reached Washington, he pretended to send troops to attack New York City, thereby forcing Clinton to cancel the plan and remain in the city to defend it.

Upon this letter’s August 2020 discovery, it was shared with Beverly Tyler, Historian at the Three Village Historical Society (which has documented and commemorated the spy ring through scholarship, an exhibition, and an annual Culper Spy Day) Kristen Nyitray, Director of Special Collections and University Archives at Stony Brook University (which owns two Culper letters authored by George Washington) Claire Bellerjeau, Director of Education at the Raynham Hall Museum (the former home of Culper Spy Robert Townsend, and home to Townsend family archives) and Bill Bleyer, freelance journalist, author, and retired Newsday reporter (who has a new book on the Culper Spy Ring). With an initial transcription and analysis by Bellerjeau and Nyitray, the group discussed how the letter fit with other surviving Culper correspondence and compared the handwriting.

Tallmadge wrote this letter to Robert Townsend on November 8, 1779, from Bedford, New York, where his Second Regiment of Continental Light Dragoons was based. A “No. 16” in the letter’s top left corner labels it as the sixteenth letter between the two men. Robert Townsend had joined the spy ring by the summer of 1779, and sent his first report to Washington that June. His position as a merchant importing goods into Manhattan allowed his to visit coffee houses, shops, and the waterfront without attracting suspicion. Townsend listened and observed the British, collecting information on fortifications, military plans, and the numbers, health, and movement of troops. Townsend (as Samuel Culper Junior) typically sent his letters via courier to Abraham Woodhull (as Samuel Culper Senior) in Setauket, who handed them to Caleb Brewster for transport across Long Island Sound.

In this coded letter, Tallmadge (as John Bolton) asks that Townsend refrain from using invisible ink for private conversations between them that do not need to go onto George Washington, as Tallmadge currently doesn’t have any of the “counterpart to decipher it”. Tallmadge says instead to use their numerical codes for future personal correspondence. Tallmadge also asks whether Townsend can transport “silks, gauzes, and such costly articles from New York to Setauket without danger,” and how the war has affected their values.

Tallmadge ends the letter with a request that “you would give some distinguishing mark to the Sheet which is the true Letter to Washington when it comes in a Quire, as I may send the wrong one to Washington.” A “quire” is a unit of paper quantity, of about twenty-five pages in modern usage. This detail reveals Townsend’s practice of writing letters to Washington using invisible ink and inserting the page into a new pack of paper (among the merchandise he sold at his Manhattan business), which he then provided to one of the spy ring’s couriers to take to Woodhull in Setauket.

The largest significance of this document is that it is the only surviving Culper Spy Ring letter from Benjamin Tallmadge to Robert Townsend. Abraham Woodhull was supposed to deliver it to Townsend, but subsequent Culper letters reveal that the intended November 10 meeting between the two did not take place. Undelivered and unread, it was nonetheless saved. Although it’s a private letter between two spies instead of conveying important intelligence up the chain of command, it’s noteworthy for mentioning the challenges of using invisible ink, showing how Townsend submitted his reports, and uses the Culper code (the “Dictionary”) to make it incomprehensible to outsiders.

After its discovery, the Long Island Museum decided to ensure the letter’s authenticity. To that end, the letter was inspected in November 2020 by Peter Klarnet, Senior Specialist in Americana in the Books and Manuscripts Department of the New York office of Christie’s. He concluded that based on the handwriting and paper that the letter is indeed genuine.

Both sides of the letter had been “silked,” an early 20th century preservation practice by which a fine silk mesh is applied to old paper to give extra support. The silk naturally degrades over time, however, voiding its effectiveness in addition, it decreases the document’s legibility. In December 2020 the Long Island Museum sent the letter to Reba Fishman Snyder, paper conservator at the Morgan Library, in New York, to remove the silking. The process ensured the long-term preservation of the letter, as well as improved its readability.

In September 2021 the Long Island Museum will display the letter to the public, as part of Culper Spy Day (September 18) events in the Three Village area.

A transcription of the letter:

Some time ago I proposed a certain affair to you, & directed
you not to write me an answer with the Stain, as it
might possibly expose us, I having none of the Coun-
terpart then on hand. Not long since I rec’d a line from
you written with the Stain, which I luckily discovered to
be of a private nature, having a little of the counterpart
on hand.
What I wish to know of you is whether 707 [you] can 640 [transport]. 1 [a] few
Umcou [silks], Aewtiu [gauzes], 5 [and] such costly articles from 727 [New York]. 634 [to]. 729 [Setauket]
without 132 [danger]. I also wish to know what relation 625 [the]. 75 [cost].
of such articles bears now 634 [to]. their 75 [cost] before 625 [the]. 680 [war].
As soon as you resolve me in these Questions I will
write you more fully on the Subject. I write this in
plain Style as I am informed C–– Sen’r is to have an interview
with you & can deliver it himself. I should be glad
of an answer by the Return of the Bearer.
I must again remind you not to write to me on
private business with the Stain, as I have none of the

Counterpart to decipher it & of course it must go on to 711 [Washington].
I have the Stain & can write you with that, but your private
Letters to me must be wrote for the present with the Dic-
I wish in future you would give some distinguishing
mark to the Sheet which is the true Letter to 711 [Washington].when it
comes in a Quire, as I may possibly send the wrong
one to 711 [Washington].
Let what I have wrote here be a profound
Secret with yourself & C – Senior.

Key Members of the Culper Ring

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.

Never Enough History

With the Culper Ring now established, the network of spies spread across the New York City area. Now, Tallmadge and Hale were both well known patriots, so they entrusted Abraham Woodhull, a friend of Tallmadge, and Robert Townsend a well known merchant in Manhattan. It was through these two men that the network reported to Washington.Woodhull was the first to start spying on the British. He would travel into Manhattan and pretend to visit his sister. However, it was pretty obvious he wasn't visiting his sister and was just wandering around like a lost tourist looking for British troop movements and just plain snooping around. It was after the British tried to arrest him that Woodhull knew he needed an inside man. That inside man was Robert Townsend. Townsend was able to more easily find out about British troop movements and about British supply ships coming in to the port. It was then between the these two that the Culper Ring gets it's name. For some reason Woodhull signed a letter to Townsend as "Samuel Culper Sr." which Townsend's response letter was signed "Samuel Culper Jr." It was in these letters that the two communicated in a coded language described as "gibberish." Now what pushed these two to help in the fight for Independence? Well Woodhull is believed to have started spying as a form of probation for illegal trading on the black market. As for Townsend, he was inspired by the words of Thomas Paine's Common Sense, the mistreatment against his family and friends by the British and lastly was his relationship with Woodhull. Together these two men gathered much need information and played a key roll in the fight for American Independence.

So how did Woodhull and Townsend pull it off? Was it just the two of them? How did they get the information around? Well they had free range to do whatever they wanted since they were spies. The first step was to grow the network and gather as much information as possible. They needed a link between Woodhull, in Connecticut, and Townsend, in Manhattan, so they employed Austin Roe as a courier, another friend of Woodhull's. Roe's cousin's Phillip and Nathan also acted as couriers depending on the location of Washington headquarters. Townsend also used his own sister Sarah and cousin James to wander New York and take notes on the British. They also used other local business owners to report on movements and just general gossip. One of their key spies was James Rivington. He was so because he worked as a publisher for the Royal Gazzette which was the pro British newspaper in New York City. It was through these spies that intel on the British was gathered and relayed back to Washington himself. But how? Well the information gathered in the city was given to Austin Roe. Roe would then take the information back to Long Island with the "supplies" he was picking up. Then a signal from Woodhull's neighbor Anna Strong would give an alert to Caleb Brewster to come collect the information from Roe. From there the intel was taken across the Long Island Sound and then onto Washington through American controlled Connecticut. Sounds complicated right? Well it was, but they pulled it off and you won't believe some of the events that would have taken place in the Culper Ring wasn't there to foil the British plans.

Now what is the Culper Ring's biggest claim to fame? Foiling the plan of America's most famous bad guy, Benedict Arnold. For my faithful reads, mainly my mom, will know that I am a staunch defender of Mr. Arnold and his actions in the cause of American Liberty. Now with that said I will put my personal views on Arnold aside and tell how the Culper Ring saved West Point from falling into the hands of the British. Major Andre, Arnold's contact with the British, was stopped at a checkpoint in Tarrytown, New York. When Andre was stopped he had not only the plans to West Point but a letter written by Arnold on how he planned to hand over West Point. As word spread through the American ranks Major Benjamin Tallmadge, aka "Samuel Culper Jr.," found out and demanded that Andre be turned over to Washington, instead the commanding officer had Andre turned over to, Colonel Jameson, who then turned Andre over to Benedict Arnold. smart move right? So as we know Arnold then switched sides and became known as America's greatest traitor, even though I strongly disagree and think Jane Fonda should take that spot. That may be the Culper Ring's biggest and most bad ass part of the Revolutionary War, but without the work they did behind enemy lines and without the information gathered in New York City the cause may have been lost and Washington and his forces may have never been as successful as they were.

Yes, the legend of 355 lives on. For those comic fanatics, you may be familiar with the name 355 from the DC Comic line of Y:The Last Man. Now, 355 in the comic mirrors the 355 in real life. 355 was a "bodyguard who works for a mysterious US government agency," according to Wikipedia. But little is known about the actual 355, so little even a name is unknown. Most historian believe the 355 was a woman from a Loyalist family which would explain how the the amount of information was gathered out of New York City. The reason for that belief is that information about Major Andre when he was stationed in New York flowed like water from a faucet, but when Andre was out of the city the well basically dried up. Aside from her link to New York, there is only one other mention of 355 in any Culper Ring letters. The identity and value of 355 has never been found. Some believe that 355 was Anna Strong, a link in the spy chain. Others feel that 355 was inside the city, mingling with the British officers and officials and that 355 was code for "lady." Some say that 355 was found out to be a spy, imprisoned and died on The Jersey, a British prison ship. Then there are some that say 355 never even existed and that the mention of 355 was in reference to something else. One thing is for sure, when dealing with a spy ring, nothing will ever be truly known. However, if 355 was real, the information she obtained would make her a hero, right up there with Molly Pitcher and Nancey Hart. Without the work of an agent like 355, the American fight could have taken longer and cost greater.

What do we learn from the Culper Ring? Well we learn that without them, the American cause for Independence may have not happened. We can look back and see that without the work they did the British may have had much more success against the Americans. The information gathered on British movements, forts, shipments and plans was proven to be key to Continental Army. The Culper Ring spoiled the plans of Benedict Arnold and stopped countless attacks on unsuspecting American regulars and militia. The Culper Ring is full of mystery which makes it alluring. However, the little that is known about them makes them harder to study and even harder to understand. What we do know is that the Culper Ring set the standard for how America would gather intelligence. They and they alone risked their and their families lives every time they walked the streets of New York. It was the one weakness that the British never saw coming, spies within their own stronghold. Not knowing who your enemy is will only ensure your defeat, and the Culper Ring was that enemy. Today, there are no monuments to the work of the spy ring, no mention in American History classes, just talks amongst history buffs like myself and the occasional History Chanel show. But they must be looked into more, for the simple reason that without them Washington would not have some of the success that makes him the hero he is today.

The Revolutionary War’s Best Kept Secret

One of Washington’s worst intelligence failures concerned his friend of many years, Benedict Arnold. Arnold, a brigadier general in the American Army, became a British agent. It was the Culper Ring that first discovered that he was working for the enemy when British Major John André paid a visit to the home of Robert Townsend’s father in Oyster Bay, Long Island.

Townsend’s sister Sarah saw a stranger leave a note addressed to “John Anderson” and later heard André talking to another British officer about the fortifications at West Point, saying how easy it would be to capture the fort. Sarah told her brother about the mysterious man in their father’s home. Townsend quickly sent a message to Benjamin Tallmadge who found out that André-Anderson had been picked up with information about West Point stashed in his boot. Tallmadge remembered that Arnold had issued orders that André be allowed through the American lines. Townsend immediately sent word of Arnold’s treason to Washington’s headquarters.

Unfortunately, before Arnold could be captured, he fled to a waiting British warship and returned to British-occupied New York where he worked openly for the British. Washington planned a covert operation to capture Arnold and bring him back for trial, but before the plan could be carried out Arnold and his unit were sent to the Chesapeake Bay area. As for John André, he suffered the ultimate fate. After a short hearing by a number of American military officers, he was found guilty and hanged as a spy.

Fleeing the colonies, Arnold made his way to England in 1781 and eventually ended up in Canada. He later served in the British military in the West Indies in 1794-1795. He died in England on June 14, 1801, a man forgotten by his contemporaries.
After the war of independence was won, Tallmadge married Mary Floyd and moved to Litchfield, Conn., where he operated a prosperous dry goods store. He was elected to Congress in 1800 and served eight terms. He died in 1835, aged 81.

The Culper Ring adequately proved its worth during the Revolution and was one of the war’s best-kept secrets.

Watch the video: The Culper Ring Explained in 11 Minutes (July 2022).


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