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Spies of the Revolution Volume 9 • Number 2 Fall 2009 $4.95 Bringing Down Benedict Arnold Confederate Prisoners Speak • The Photography of Berenice Abbott New York Cleans Up Its Streets • Seaway Celebrates Fifty Years 9 John André Benedict Arnold SpiesAn ingeniousof theRevolution ring of citizen-spies based in New York City and Long Island helped the Americans gain the advantage in the Revolution—and also scored the biggest intelligence coup of the war. BY JohN a. BuRKE aND aNDREa MEYER y 1779, the One way to break the Revolutionary War stalemate was for one side to had reached a stale- gain an intelligence advantage mate outside New over the other, and the BYork City. Many states were Americans did just that. A no longer sending their allot- group of citizen-spies known as ted shares of money, men, the Culper Spy Ring (from its and supplies. The British, code name, “Samuel Culper”) headquartered in Manhattan, operated from 1778 to 1780 controlled the lower gate to in an intricate network from the Hudson, but the American- New York City to Setauket, controlled fortress at West Long Island, north to Connec- Point kept them from sweeping ticut, and then back west to up the Hudson to accomplish George Washington’s head- the most important strategic quarters at Newburgh, New goal of the war for both sides: York and Morristown, New control of the Hudson Valley. Jersey. They also uncovered the If the British gained it, they biggest plot of the Revolution: could divide the colonies in Major General Benedict two, conquering New England Arnold’s scheme to “sell” ANDRE:NEW YORK STATE LIBRARY/MANUSCRIPTS AND SPECIAL COLLECTIONS’. ARNOLD: NEW YORK STATE ARCHIVES and the South separately. West Point to the British. www.nysarchivestrust.org 10 4 5 To avoid the British in Manhattan and the lower Hudson Valley, spies for George Washington took a 3 circuitous route from New York City (1) to Setauket (2), across Long Island Sound to Fairfield, Connecticut 2 (3), then northwest through the wilderness to his headquarters near Newburgh (4). 1 West Point (5), which Benedict Arnold planned to turn over to the British, is just twenty miles south of Newburgh. Target: Treason Arnold, now a major general, story to protect the rest of At the beginning of the war, had gained command of West the Culper spies still in place. Benedict Arnold was a wealthy, Point—and was also preparing self-made merchant. During to surrender it to the British an Elaborate Network the brutal 1775 campaign to Army, commanded by General In 1778, Benjamin Tallmadge, attack Québec, and the Battle Sir Henry Clinton, in return a young American officer of Valcour Island in 1776, for money. This disaster would who was about to become Arnold built a fleet of boats have occurred if American General Washington’s new to escape the British and used intelligence had not uncovered intelligence chief, organized an his personal fortune to supple- the developing plot and ingenious top-secret network ment the lack of funds from reported it to General George of spies. Washington ordered Congress. But conflicts with Washington. that not even he himself members of Congress, and Arnold’s full intentions should know who they were. loss of receipts during the heat were worse than previously For recruits, Tallmadge turned of battle, combined to deny recognized. He intended to to old friends and acquain- Anna Strong would him reimbursement. By 1776 surrender the fort with tances in his hometown of he was ruined financially, and Washington and the French Setauket, Long Island. One of signal Brewster’s exact by 1780 he was still petition- leadership inside—a blow these, Abraham Woodhull, location, probably ing Congress for repayment— General Clinton referred to as was chosen as his agent. But and still being denied. Even his a coup manqué, which he Woodhull (code-named using her clothesline salary was withheld because was sure would end the war. “Culper Senior”) soon fell Congress maintained he was Today’s history books state under suspicion of British and a certain number accountable for the expenditure that the plot was foiled by a counterintelligence due to his of handkerchiefs of original funds for which lucky accident, in which three frequent trips to Manhattan. he lacked proof of payment. highwaymen strip-searched So Woodhull recruited a hanging out to dry. Ironically, modern historians Arnold’s British cohort, Major relative living in his sister’s eventually located Arnold’s John André, and discovered Manhattan boardinghouse, receipts in Canadian archives incriminating documents a dry goods merchant and and discovered that he had about the plot. But informa- society reporter, Robert been scrupulous in his record tion in several archives shows Townsend of Oyster Bay. keeping. this tale to be a fabrication, Code-named “Culper Junior” By the summer of 1780, possibly intended as a cover and the ring’s central figure, NEW YORK archives • FALL 2009 11 Townsend gathered informa- help he expected to “outwit General Washington of an tion on British forces and them all.” Within two months, impending surprise attack on Handsome and passed it on to Setauket detailed headquarters-level his army at White Marsh. When tavern keeper Austin Roe, intelligence on the British Army the British Army took to the extremely cultured, NEW YORK STATE LIBRARY/MANUSCRIPTS AND SPECIAL COLLECTIONS who rode the 110 miles into flowed to Washington in field, it became obvious that New York ostensibly to buy Newburgh from Townsend’s Washington had been warned. André was supplies but who also carried reports. Who was this woman, During André’s investigation constantly surrounded these dispatches (often written and was she recruited by of the leak, he questioned in invisible ink and code) Woodhull as an official mem- everyone in the Darragh house by beautiful women. from Townsend’s New York ber of the Culper Spy Ring? except Lydia—since he believed store back to Setauket. We may never know. We do that eighteenth-century But they were also In Setauket, Caleb Brewster, know, however, that not long women all held the same his weak point. another ring member and a before going to meet her, political views as their husbands. childhood friend of Tallmadge’s, Woodhull had a near miss The Culpers’ secret reports was captain of a whaleboat when British Colonel Simcoe all but ceased when André left that raided British shipping on and his Queen’s Rangers rode New York in December 1779 Long Island Sound. Every few to Setauket to arrest him— for the siege of Charleston, weeks he would slip into one and he was not at home. and Washington was soon of Setauket Harbor’s coves to Woodhull subsequently sent a complaining to his aide, receive dispatches. According report that he had been saved Alexander Hamilton, that the to British counterintelligence only by the intervention of a ring’s information had become reports and a report from “friend of the Gen’l Aide”— useless. However, within a Brewster to Tallmadge, Anna the “aide” being none other few weeks of André’s return Strong, who lived nearby on than John André, Adjutant to New York in May 1780, Strong’s Neck, would signal General of the British Army the Culper Ring was reporting Brewster’s exact location, and head of British intelli- the biggest scoop of the war: probably using her clothesline gence. Evidently this person’s an American general was “in and a certain number of friendship with André was compact with the enemy.” handkerchiefs hanging out to crucial to the spy ring’s future Washington’s staff warned dry. At the signaled location, success: while they continued their other spies, and Benjamin Abraham Woodhull would then to suspect Woodhull of Tallmadge wrote the governor pass the dispatches to Brewster. spying, the British never again of Connecticut, who was in John André’s self-portrait, sketched the Revisionists today challenge attempted to arrest him. charge of supplying West day before he was hanged as a spy. these stories as family lore, Point, to expect “some sudden but careful inspection of ladies’ Man and unexpected stroke” and letters and ledgers provides John André was considered that “the enemy would know evidence to support them. the most eligible bachelor in well American forces and dis- New York. Handsome and position.” Tallmadge added, important Friends extremely cultured, he was “And for God’s sake be guard- Robert Townsend’s early constantly surrounded by ed against such a movement.” reports to Tallmadge indicated beautiful women. But they Was Tallmadge’s female that he could get good infor- were also his weak point. acquaintance, mation on the British Navy, In 1777, when the British with whose but little on the British Army. occupied Philadelphia, André help he NEW YORK STATE ARCHIVES This situation continued for held a secret meeting in the months until Woodhull men- Darragh house where he was tioned in a letter to Tallmadge quartered. Housewife Lydia that he was on his way to Darragh simply sneaked up Manhattan to visit a woman of to the closed door, listened his acquaintance, with whose in, and subsequently warned www.nysarchivestrust.org 12 This print shows British Major John André being captured near Tarrytown, New York. The men are examining papers that detailed the fortifications at West Point, which André had hidden in his boot. cepted. Soon after, André received a letter from Arnold that no one at British head- quarters could decode; it LIBRARY OF CONGRESS appeared to be gibberish. Then Arnold and André attempted to meet in the dead of night at West Point, but for reasons unknown they Tallmadge and Alexander missed each other.
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