By the fall of 1778, it seemed clear that the British garrisons at New York City and Newport, Rhode Island were going to remain where they were for the foreseeable future. The Continentals maintained armies nearby both garrisons in case they ventured out for any reasons. But the Continentals could not take either garrison while the British navy controlled the waters around them.
Washington had hoped that the arrival of the French fleet under Admiral d’Estaing would assist in the recapture of these cities. But as I’ve already discussed, d’Estaing declined to attack at New York and ended a planned coordinated attack on Newport after the British fleet arrived and a storm damaged both fleets. After that, d’Estaing went to Boston for repairs. In November 1778, per his instruction from Versailles, d’Estaing took the French fleet down to the West Indies, where the winter was the prime fighting season.
As a result, Washington knew the standoff would remain in place at least over the winter. He had to wait for another opportunity to fight in coordination with the French Navy.
Early Espionage Efforts
To keep tabs on the British in New York, Washington realized he needed a better intelligence system, so that he could respond to British raids, or any military builds ups or redeployments. This was not Washington’s first attempt at intelligence. The Continentals had made attempts to deploy spies and build spy networks since the war began. Their lack of experience in such matters , meant that they had trouble getting intelligence, or agents, such as Nathan Hale, ended up hanging from a tree.
In the early years of the war, Sackett had served in the New York Provincial Congress’ Committee for Detecting and Defeating Conspiracies, which tried to reveal British spies, collect intelligence, and out any loyalists trying to keep a low profile. As part of his work, Sackett had developed some experience in writing in cyphers and using secret codes. His work on that committee with William Duer and John Jay led them to recommend him to Washington.
In early 1777, Washington paid Sackett to develop a civilian network in and around the city. Sackett recruited a number of people, but never really got Washington the intelligence that he needed. After getting frustratingly little information about General Howe’s decision to begin the Philadelphia campaign in the summer of 1777, Washington terminated Sackett that fall. Sacket returned to his real life’s work as a merchant, serving as a sutler for the Continental Army.
Over the fall and winter, Washington’s focus was not on New York but on Philadelphia. New York intelligence became less of a priority. After the British abandoned Philadelphia and Washington moved his army back to northern New Jersey, intelligence from New York City became more of a priority again in the spring of 1778.
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| Charles Scott |
Rather than turning to another civilian for help, Washington turned to his officers. He made General Charles Scott his new chief of intelligence. Scott had been commissioned as a brigadier in the spring of 1777. Since then, his career seems to have been, to put it charitably, mixed. General Scott had served under General Adam Stephen at Germantown. His troops got out of position and ended up firing on another Continental unit. Scott placed the blame on General Stephen, who ended up being kicked out of the army. Again, at Monmouth, Scott precipitated the retreat that infuriated General Washington, but once again blamed his superior, General Charles Lee, who also was removed from command following a court martial.
Washington, however, still had faith in Scott, and put him in a key position out in front of the Continental Army. Scott’s brigade would deploy in West Chester, just north of the enemy lines. In addition to acting as the front line of defense for the Continentals, Scott was assigned the task of collecting intelligence. Some of this would be sending out scouts or interrogating deserters or other prisoners. It also involved use of civilian agents. It was under Scott’s command that the Culper Spy Ring was created.
Scott, however, was not keen on use of civilian agents, especially when he could not confirm their identity or how they got their information. He was concerned about the validity of their reports, and often refrained from providing timely information to Washington while he tried to confirm intelligence.
Washington sent Scott several letters critical of the lack of good intelligence. It was during this time that the British surprised the Continentals with the Kingsbridge and Old Tappan raids, as well as the massive foraging offensive into Bergen county that I discussed a couple of weeks ago. In that same episode, I mentioned that British Spy Ann Bates had been identified as a British spy. When caught, she appealed directly to General Scott, fed him a lie, and got the general to write her a pass, allowing her to return to the British lines. Scott also sent at least three undercover scouts behind enemy lines in September, all of whom were captured and hanged.
Scott was also fighting with Washington about what to do with a large portion of his army that had enlistments expiring on December 1. Scott wanted to let them return home for the winter so that they would be more inclined to rejoin the army in the spring. Washington wanted Scott to pressure them to remain in the field.
As a result, Scott was not happy with his position and in October, requested to resign. In addition to his problems, Scott was complaining about some sort of illness that had been afflicting him for some time. Washington responded that only the Continental Congress could accept his resignation. Rather than go to Congress, Scott instead requested a furlough to return home to Virginia. In November, Washington granted Scott his requested furlough and turned over his much reduced command to Colonel William Russell.
Benjamin Tallmadge
Although Russell took over command of the front lines in the army, the take over the military intelligence aspect of Scott’s work, Washington turned to Major Benjamin Tallmadge. Major Tallmadge was the son of the Reverend Benjamin Tallmadge, a minister in Setauket on Long Island. After growing up on Long Island Tallmadge graduated from Yale College in 1773, and took a job as the superintendent of Wethersfield High School in Connecticut.
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| Benjamin Tallmadge & Son |
Part of Major Tallmadge’s duty as a dragoon was to gather enemy intelligence, in part by just riding out toward enemy lines to observe the enemy. Officers, of course, were encouraged to find intelligence by whatever means they could. In his memoirs, Tallmadge recounts entering a tavern to meet with a woman who had just been to British-occupied Philadelphia and wished to pass along some information. The tavern was close enough that the enemy saw him enter the tavern in uniform. The British attempted to capture him, but he jumped on his horse with the women and rode away, galloping for several miles while exchanging shots with his pursuers.
After the British evacuation, Tallmadge found himself back near New York City under the command of General Scott. In his memoirs, Tallmadge notes that he “opened a private correspondence with some persons in New York.” Tallmadge does not really talk about his espionage activities in his memoirs, but it was at this time, in the summer of 1778 that he began to run what would become known as the Culper Ring.
Abraham Woodhull
Tallmadge had quite a few friends from his time growing up in Setauket, Long Island. Many of these people were still living there behind enemy lines. One of the problems that Tallmadge observed with earlier intelligence efforts was that a person crossing between lines would be subject to scrutiny by the enemy, making the gathering of more information more difficult. Tallmadge realized it would make sense to have one group of people gather the intelligence, then pass it off the trusted couriers to get it where it needed to go. That way, the spies could act in perfectly normal ways and not raise any suspicion when they observed British movements or spoke with British soldiers.
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| Page from Culper Code Book |
Woodhull was the only son of Judge Richard Woodhull. Although Abraham supported the patriot cause, he did not enlist because his parents needed help with the family cabbage farm. In 1778, Woodhull attempted to bring some of his crops to New York to sell for specie. A patriot ship intercepted him on Long Island sound and arrested him for attempting to trade with the enemy. Tallmadge met with Woodhull and agreed to get him released and returned to Setauket so that he could begin gathering intelligence.
Initially, Washington was skeptical. He saw Woodhull as a smuggler. It had been Washington’s experience that smugglers liked to use espionage as a cover for their smuggling activities so that they had a get out of jail free card when caught. Their primarily focus was on making money, not providing intelligence. Tallmadge vouched for Woodhull and said he would be a good agent.
At the same time, Woodhull was concerned for his own safety. He really did not want to end up hanging from a tree. Tallmadge had to assure Woodhull that his identity would only be known to himself and a courier, someone who was also an old mutual friend. Even Washington himself would not know Woodhull's true identity. He gave Woodhull the code name “Samuel Culper.” Samuel was the name of Tallmadge’s father. Culper was a shortened version of “Culpepper, Virginia” where Washington had spent time as a young man.
Since Woodhull lived in Setauket, miles from the city, he would develop agents who lived in New York to keep their eyes and ears open, make note of troop movements, and listen in on tavern conversations.
Initially, Woodhull would take cabbages into the city for sale, as cover to make contact with his agents. In order to reduce the suspicion of pickets about a military age man travelling into the main British camp, Woodhull would take along an older woman with him on his trips.
Anna Strong lived on a nearby farm with her ten children. Her husband was a British prisoner, by some accounts aboard the prison ship Jersey. Woodhull and Strong would travel to New York, sell their cabbages, and collect the information, then bring it back to Setauket. After several trips, Woodhull got skittish about traveling into the city. He recruited a courier named Austin Roe to carry the messages between New York and Setauket.
Caleb Brewster
Once he had intelligence, Woodhull needed another courier to bring the information from Long Island to the Continental Army in Connecticut. A man named Caleb Brewster took on that difficult role.
Before the war, Brewster worked as a seaman, mostly aboard local ships in Long Island Sound that transported goods around the area. He had been a member of the patriot militia. During the first year of the war, he played a prominent role in the militia and had signed an oath to resist British authority. When the British captured Long Island, that made him a target.
Brewster fled his home in Setauket to become a war refugee in Connecticut. There, he helped other refugees, transport their families and possessions from Long Island to Connecticut. During much of the war, the area of Long Island Sound became a dangerous area, full of smugglers and criminals who took advantage of the no man’s land where neither the British nor the Continentals had secure control.
Brewster obtained a lieutenant’s commission in the Continental Army, but seems to have spent most of his time running whaling boats across Long Island Sound. Tallmadge recruited his old friend as part of his spy network. He actually recruited Brewster before Woodhull. At first, Brewster just kept his eyes open while sailing around Long Island Sound and reported anything noteworthy. Later, he became the courier between Woodhull and Tallmadge.
Passing Messages
According to local lore, Anna Strong acted as a messenger between Woodhull and Brewster. She would hang a large black petticoat on her clothesline whenever either man needed to make contact. That she would hang between one and six handkerchiefs on the line to indicate which of six coves the meeting should take place.
Woodhull would sometimes write out intelligence for Brewster to collect. Other times, he would simply pass it along orally. Brewster would then carry the information to Connecticut to Major Tallmadge. If Tallmadge received written intelligence, he would rewrite it in his own handwriting in order to ensure it could not be traced back to Woodhull. Tallmadge would then brief Washington about any useful intelligence.
Woodhull recruited other agents as well. Most of these were ordinary people in New York who might just come across some helpful information. Many of them are only known by their code names to this day, and have never been identified.
The British became aware that there was some spying going on around Setauket. Once, a British officer discovered Brewster hanging around on Strong’s farm. Brewster knocked the man unconscious and robbed him in order to convince the officer he was a common criminal and not a spy. On another occasion, the British intercepted a letter from Washington to Culper, but could not identify the real name of the recipient.
Even so, the British did identify Brewster as a likely Continental agent, probably from local Tories who knew him. They knew Brewster was working with others, but never identified Woodhull’s role in the ring.
The agents used coded messages and invisible ink to hide communications. They also used a series of dead drops to avoid meetings that might arouse suspicion. Very quickly, Washington was pleased with the level of information that he received. It was specific and accurate.
Despite their efforts at secrecy. The British came to suspect Woodhall’s involvement in the ring. At one point, Colonel John Graves Simcoe of the Queen’s Rangers came looking for Woodhull at his farm. Woodhull was in New York at the time, but Simcoe roughed up his father, trying to get information out of him. It was after that incident that Woodhull decided to lay low for a while and his dispatches fell off.
Successes
Sometimes Washington would request that the ring investigate specific questions that he had. Other times, the ring would simply report information that it happened upon. Much of the information was fairly routine, the size, location, and movements of troops. It might include build up of supplies, or other facts that might indicate planning for an upcoming action. Washington was able to keep a better picture of British activity in New York as a result of this intelligence.
Other times the information was of more immediate importance. In 1780, the ring learned that the British intended to ambush the French fleet at Newport. In response, Washington made it appear that he was planning an offensive against New York. This forced the British to cancel deployments of soldiers from New York to Newport, so that they would be available to defend the city.
On another occasion the ring learned that a top American officer was in discussions with the British leadership about defecting. They did not learn until too late the identity of that officer as Benedict Arnold. Late in the war, the ring obtained a copy of the British Navy’s flag signals. That information allowed the French fleet to read British signals and anticipate their moves, which became a critical element just before Yorktown.
The Culper Ring remained active until the end of the war. It largely remained a secret, even after the war ended. Washington developed spy rings in other times and places as well, but the Culper ring was the largest and longest running of the war. Over the course of the war, his appreciation for the value of such intelligence grew. The commander spent more time focusing on obtaining it, and also developed better experience in running an intelligence agency.
Next week: we return to Philadelphia where local patriots recovering from British occupation look to provide some payback on the loyalists who remained behind.
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Next Episode 201 Treason in Philadelphia
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Further Reading
Websites
The Founding Fathers of US Counterintelligence: https://www.intelligence.gov/index.php/wall-of-spies/john-jay
Nathaniel Sackett: https://sackettfamily.info/g5/p5383.htm
American Spies of the Revolution: https://www.mountvernon.org/george-washington/the-revolutionary-war/spying-and-espionage/american-spies-of-the-revolution
Benjamin Tallmadge: https://www.mountvernon.org/library/digitalhistory/digital-encyclopedia/article/benjamin-tallmadge
The Culper Spy Ring: https://www.history.com/topics/american-revolution/culper-spy-ring
Culper Spy Ring: https://www.mountvernon.org/library/digitalhistory/digital-encyclopedia/article/culper-spy-ring
Schellhammer, Michael “Abraham Woodhull: The Spy Named Samuel Culper” Journal of the American Revolution, May 19, 2014: https://allthingsliberty.com/2014/05/abraham-woodhull-the-spy-named-samuel-culper
Foley, Robert Caleb Brewster in the Revolutionary War: https://bportlibrary.org/hc/historical-accounts/caleb-brewster-in-the-revolutionary-war
Caleb Brewster and the Culper Spy Ring: https://connecticuthistory.org/caleb-brewster-and-the-culper-spy-ring
Anna Smith Strong: https://www.womenhistoryblog.com/2011/07/anna-smith-strong.html
Based on a True Story Podcast: A look at AMC’s Turn! and the Culper Spy Ring: https://www.basedonatruestorypodcast.com/139-turn-washingtons-spies-with-michael-troy
Free eBooks
(from archive.org unless noted)
Prather, Michael S. George Washington, America's first director of military intelligence, Monterey: Dudley Knox Library, 2002.
Simcoe, John G. Simcoe's Military Journal: a history of the operations of a partisan corps, called the Queen's Rangers, commanded by Lieut Col. J.G. Simcoe, during the war of the American Revolution, New York: Bartlett & Welford, 1844.
Tallmadge, Benjamin Memoir of Col. Benjamin Tallmadge, New York: T. Holman, 1858.
Books Worth Buying
(links to Amazon.com unless otherwise noted)*
Daigler, Kenneth Spies, Patriots, and Traitors: American Intelligence in the Revolutionary War, Georgetown Univ. Press, 2014.
Kilmeade, Brian & Don Yaeger George Washington's Secret Six: The Spy Ring That Saved the American Revolution, Sentinel, 2013. ng, Bantam, 2006.
Ward, Harry M. Charles Scott and the "Spirit of '76", Univ of Virginia Press, 1988.
Welch, Richard F. General Washington's Commando: Benjamin Tallmadge in the Revolutionary War, McFarland, 2014.
* As an Amazon Associate I earn from qualifying purchases.
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