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By John A Burke and Andrea Meyer
By 1779, the Revolutionary War had reached a stalemate outside New York City. Many states were no longer sending their allotted shares of money, men, and supplies. The British, headquartered in Manhattan, controlled the lower gate to the Hudson, but the American controlled fortress at West Point kept them from sweeping up the Hudson to accomplish the most important strategic goal of the war for both sides: control of the Hudson Valley. If the British gained it, they could divide the colonies in two, conquering New England and the South separately.
One way to break the stalemate was for one side to gain an intelligence advantage over the other, and the Americans did just that. A group of citizen-spies known as the Culper Spy Ring (from its code name, “Samuel Culper”) operated from 1778 to 1780 in an intricate network from New York City to Setauket, Long Island, north to Connecticut, and then back west to George Washington’s headquarters at Newburgh, New York and Morristown, New Jersey. They also uncovered the biggest plot of the Revolution: Major General Benedict Arnold’s scheme to “sell” West Point to the British.
At the beginning of the war, Benedict Arnold was a wealthy, self-made merchant. During the brutal 1775 campaign to attack Québec, and the Battle of Valcour Island in 1776, Arnold built a fleet of boats to escape the British and used his personal fortune to supplement the lack of funds from Congress. But conflicts with members of Congress, and loss of receipts during the heat of battle, combined to deny him reimbursement. By 1776 he was ruined financially, and by 1780 he was still petitioning Congress for repayment— and still being denied. Even his salary was withheld because Congress maintained he was accountable for the expenditure of original funds for which he lacked proof of payment. Ironically, modern historians eventually located Arnold’s receipts in Canadian archives and discovered that he had been scrupulous in his record keeping.
By the summer of 1780, Arnold, now a major general, had gained command of West Point—and was also preparing to surrender it to the British Army, commanded by General Sir Henry Clinton, in return for money. This disaster would have occurred if American intelligence had not uncovered the developing plot and reported it to General George Washington.
Arnold’s full intentions were worse than previously recognized. He intended to surrender the fort with Washington and the French leadership inside—a blow General Clinton referred to as a coup manqué, which he was sure would end the war. Today’s history books state that the plot was foiled by a lucky accident, in which three highwaymen strip-searched Arnold’s British cohort, Major John André, and discovered incriminating documents about the plot. But information in several archives shows this tale to be a fabrication, possibly intended as a cover story to protect the rest of the Culper spies still in place.
An Elaborate Network
In 1778, Benjamin Tallmadge, a young American officer who was about to become General Washington’s new intelligence chief, organized an ingenious top-secret network of spies. Washington ordered that not even he himself should know who they were. For recruits, Tallmadge turned to old friends and acquaintances in his hometown of Setauket, Long Island. One of these, Abraham Woodhull, was chosen as his agent. But Woodhull (code-named “Culper Senior”) soon fell under suspicion of British counterintelligence due to his frequent trips to Manhattan. So Woodhull recruited a relative living in his sister’s Manhattan boardinghouse, a dry goods merchant and society reporter, Robert Townsend of Oyster Bay. Code-named “Culper Junior” and the ring’s central figure, Townsend gathered information on British forces and passed it on to Setauket tavern keeper Austin Roe, who rode the 110 miles into New York ostensibly to buy supplies but who also carried these dispatches (often written in invisible ink and code) from Townsend’s New York store back to Setauket.
In Setauket, Caleb Brewster, another ring member and a childhood friend of Tallmadge’s, was captain of a whaleboat that raided British shipping on Long Island Sound. Every few weeks he would slip into one of Setauket Harbor’s coves to receive dispatches. According to British counterintelligence reports and a report from Brewster to Tallmadge, Anna Strong, who lived nearby on Strong’s Neck, would signal Brewster’s exact location, probably using her clothesline and a certain number of handkerchiefs hanging out to dry. At the signaled location, Abraham Woodhull would then pass the dispatches to Brewster. Revisionists today challenge these stories as family lore, but careful inspection of letters and ledgers provides evidence to support them.
Robert Townsend’s early reports to Tallmadge indicated that he could get good information on the British Navy, but little on the British Army. This situation continued for months until Woodhull mentioned in a letter to Tallmadge that he was on his way to Manhattan to visit a woman of his acquaintance, with whose help he expected to “outwit them all.” Within two months, detailed headquarters-level intelligence on the British Army flowed to Washington in Newburgh from Townsend’s reports. Who was this woman, and was she recruited by Woodhull as an official member of the Culper Spy Ring? We may never know. We do know, however, that not long before going to meet her, Woodhull had a near miss when British Colonel Simcoe and his Queen’s Rangers rode to Setauket to arrest him— and he was not at home. Woodhull subsequently sent a report that he had been saved only by the intervention of a “friend of the Gen’l Aide”— the “aide” being none other than John André, Adjutant General of the British Army and head of British intelligence. Evidently this person’s friendship with André was crucial to the spy ring’s future success: while they continued to suspect Woodhull of spying, the British never again attempted to arrest him.
John André was considered the most eligible bachelor in New York. Handsome and extremely cultured, he was constantly surrounded by beautiful women. But they were also his weak point. In 1777, when the British occupied Philadelphia, André held a secret meeting in the Darragh house where he was quartered. Housewife Lydia Darragh simply sneaked up to the closed door, listened in, and subsequently warned General Washington of an impending surprise attack on his army at White Marsh. When the British Army took to the field, it became obvious that Washington had been warned. During André’s investigation of the leak, he questioned everyone in the Darragh house except Lydia—since he believed that eighteenth-century women all held the same political views as their husbands.
The Culpers’ secret reports all but ceased when André left New York in December 1779 for the siege of Charleston, and Washington was soon complaining to his aide, Alexander Hamilton, that the ring’s information had become useless. However, within a few weeks of André’s return to New York in May 1780, the Culper Ring was reporting the biggest scoop of the war: an American general was “in compact with the enemy.” Washington’s staff warned their other spies, and Benjamin Tallmadge wrote the governor of Connecticut, who was in charge of supplying West Point, to expect “some sudden and unexpected stroke” and that “the enemy would know well American forces and disposition.” Tallmadge added, “And for God’s sake be guarded against such a movement.”
Was Tallmadge’s female acquaintance, with whose help he expected to “outwit them all,” the friend of John André who had intervened on behalf of Woodhull? Since Woodhull did not indicate the gender of “the friend of the Gen’l Aide” (André) who saved him, we cannot be certain. However, if they were the same person, this might explain why the spy ring’s reports ceased when André left New York, and resumed when he returned.
André as Unwitting Source
Obviously, covert British plans to use an American general to capture the most important fort on the continent were shared only on a need-to-know basis. André himself handled the correspondence-based negotiations with Arnold, originally making contact through Arnold’s wife—who happened to be André’s old Philadelphia theater friend, Peggy Shippen. Meanwhile, at Washington’s headquarters, Benjamin Tallmadge and Alexander Hamilton took charge of tracking the developments. A view of these ongoing machinations can be seen in Hamilton’s letter to his best friend, fellow aide, and recently exchanged prisoner John Laurens. Written after the September 1780 arrest of André, the letter shared some aspects of the plot that could never have come to Laurens through public sources. Hamilton wrote that the scheme traced back to June 1780 (coinciding with André’s return to New York), and noted that the Americans had intercepted some of the letters between the conspirators. While neither Hamilton nor Tallmadge ever explicitly credited a source, ringleader Robert Townsend’s ledgers and other Culper letters show that a pattern of action occurred whenever Arnold and André corresponded. During these same months, the Culper Ring provided enormously important counterintelligence about information that Arnold leaked to the British in his correspondence, including news of the arrival of the vulnerable French fleet at Newport.
Arnold began to suspect that his mail was being intercepted. Soon after, André received a letter from Arnold that no one at British headquarters could decode; it appeared to be gibberish. Then Arnold and André attempted to meet in the dead of night at West Point, but for reasons unknown they missed each other. Another meeting was scheduled, but General Henry Clinton ordered André not to leave the ship that would take him upriver without the company of experienced field agent Colonel Beverly Robinson, and under no circumstances was André to carry documents back or remove his uniform. As history has recorded, despite these instructions all three events transpired: André was captured alone, in civilian dress, with maps of West Point and a pass signed by Arnold in his possession. Benjamin Tallmadge’s memoirs reveal that when he heard the news, he immediately recognized both André and the situation. The memoirs also detail a struggle to prevent the news of André’s capture from reaching Arnold, who ultimately escaped. André confessed and was hanged as a spy.
The Unknown Spy
General Clinton went into mourning, and Arnold began a hunt for the spies who had obviously warned the Americans of his plans. Since the plot’s discovery had been reported as an accidental encounter involving highway-men who just happened to intercept André on his ride back to headquarters, perhaps details from public reports of André’s capture and trial revealed discrepancies that made Arnold suspicious and tipped him off that spies had forewarned the Americans. During this period, Abraham Woodhull’s correspondence indicates that Robert Townsend and other Culper ring members fled New York City and went into hiding. After about two weeks, sensing a decline in tempers, they returned. But then disaster struck: Woodhull informed Tallmadge of the arrest of “several of our dear friends,” including “one who hath been ever serviceable to this correspondence.”
Townsend’s powerfully emotional reaction to this news is evident through his own ledgers and in Woodhull’s letters. He traveled to Setauket and arrived at Woodhull’s home in a state of extreme depression. According to Woodhull, Townsend swore to stop spying, and according to Townsend’s own business ledgers he proceeded to steal large sums of money from every business with which he was connected, including his father’s, for a total of over 600 pounds in ten days—a veritable fortune at the time. No evidence reveals what the money was for, but ring member Anna Strong had ransomed her husband’s freedom from a New York prison earlier in the war. Could the now-arrested “one who hath been ever serviceable” be the same “friend of the Gen’l Aide” who had saved Woodhull from arrest, and the same woman of Tallmadge’s acquaintance whom he expected to “outwit them all”? And might Townsend have formed a powerful emotional attachment to her, and tried to ransom her freedom? No letter describes the release of this arrested individual. Conditions in New York prisons were so horrific that life expectancy was a few months; recent scholarship suggests that more Americans died in such confinement than were killed in all the battles of the American Revolution combined. Could this have been the fate of the anonymous ring member?
Certainly the quality of the Culper Ring’s intelligence peaked after Woodhull’s narrow escape and when ladies’ man John André was in town. After André’s hanging and the unknown ring member’s arrest, Culper reports decayed significantly, even after Robert Townsend eventually resumed spying. According to family correspondence, Townsend lived out his days depressed, unmarried, and drinking heavily until his death at age eighty-five.
Because of the nature of espionage, good spies leave little documentary information behind. But enough information remains in archival collections to suggest that the Culper Spy Ring played a significant role during a dark period in Revolutionary War history––and that much more of this role remains to be discovered. Both the evidence and history show, however, that this band of citizen-spies scored one of the most important intelligence coups in American history.