Volume 9 • Number 2

Fall 2009

$4.95

Bringing Down 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 and 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 , 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 ’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.

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5 To avoid the British in Manhattan and the lower Hudson Valley, spies for took a 3 circuitous route from New York City (1) to Setauket (2), across Long Island Sound to Fairfield, 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, , 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, , 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,

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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 SPECIAL AND LIBRARY/MANUSCRIPTS STATE YORK NEW 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, , 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 , 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 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- ’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 , André help he NEW YORK STATE ARCHIVES STATE YORK NEW 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 OF LIBRARY 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. Another Hamilton took charge of meeting was scheduled, tracking the developments. but General Henry Clinton A view of these ongoing ordered André not to leave machinations can be seen in

NEW YORK STATE ARCHIVES STATE YORK NEW the ship that would take him

Hamilton’s letter to his best upriver without the company friend, fellow aide, and of experienced field agent recently exchanged prisoner Colonel Beverly Robinson, John Laurens. Written after and under no circumstances the September 1780 arrest of was André to carry docu- André, the letter shared some ments back or remove his This pass, signed by Benedict Arnold, expected to “outwit them all,” aspects of the plot that could uniform. As history has would have allowed Mr. John Anderson (André’s alias) to pass “to the friend of John André never have come to Laurens recorded, despite these the White Plains or below if he chus- who had intervened on behalf through public sources. instructions all three events es. He being on Public Business by of Woodhull? Since Woodhull Hamilton wrote that the transpired: André was my Direction.” did not indicate the gender of scheme traced back to June captured alone, in civilian “the friend of the Gen’l Aide” 1780 (coinciding with André’s dress, with maps of West (André) who saved him, we return to New York), and Point and a pass signed by cannot be certain. However, noted that the Americans had Arnold in his possession. if they were the same person, intercepted some of the letters Benjamin Tallmadge’s this might explain why the between the conspirators. memoirs reveal that when spy ring’s reports ceased when While neither Hamilton nor he heard the news, he imme- André left New York, and Tallmadge ever explicitly diately recognized both resumed when he returned. credited a source, ringleader André and the situation. The Robert Townsend’s ledgers memoirs also detail a struggle andré as unwitting Source and other Culper letters to prevent the news of André was captured Obviously, covert British plans show that a pattern of action André’s capture from reach- to use an American general to occurred whenever Arnold ing Arnold, who ultimately alone, in civilian capture the most important fort and André corresponded. escaped. André confessed dress, with maps of on the continent were shared During these same months, and was hanged as a spy. only on a need-to-know basis. the Culper Ring provided West Point and a pass André himself handled the enormously important coun- The unknown Spy correspondence-based negotia- terintelligence about informa- General Clinton went into signed by Arnold in tions with Arnold, originally tion that Arnold leaked to the mourning, and Arnold began his possession. making contact through British in his correspondence, a hunt for the spies who Arnold’s wife—who happened including news of the arrival had obviously warned the to be André’s old Philadelphia of the vulnerable French fleet Americans of his plans. Since theater friend, Peggy Shippen. at Newport. the plot’s discovery had been Meanwhile, at Washington’s Arnold began to suspect reported as an accidental headquarters, Benjamin that his mail was being inter- encounter involving highway-

NEW YORK archives • FALL 2009 Among the papers found in André’s 13 boot was this list of the number of men necessary to “man the works” at West Point––important information for the British who were planning to capture the fort. men who just happened T h E a R C h i V E S to intercept André on his CoNNECTioN ride back to headquarters, perhaps details from public aterial exists on the reports of André’s capture Culpers in the East and trial revealed discrepancies M Hampton Library’s Long that made Arnold suspicious Island Collection and the and tipped him off that New York Public Library’s spies had forewarned the Emmet Collection, including Americans. During this period, Robert Townsend’s business Abraham Woodhull’s ledgers and the Alexander correspondence indicates Hamilton-John Laurens

that Robert Townsend and ARCHIVES STATE YORK NEW letter. The New York State other Culper ring members Archives holds the docu- fled New York City and went ments found on John André, into hiding. After about and the Library of Congress’ two weeks, sensing a decline George Washington in tempers, they returned. Papers contain most of the But then disaster struck: correspondence between Woodhull informed Could the now-arrested “one ladies’ man John André was the Culper members. Other Tallmadge of the arrest of who hath been ever service- in town. After André’s hang- collections hold smaller “several of our dear friends,” able” be the same “friend ing and the unknown ring gems, such as Benjamin including “one who hath of the Gen’l Aide” who had member’s arrest, Culper Tallmadge’s memoirs at the been ever serviceable to this saved Woodhull from arrest, reports decayed significantly, collections correspondence.” and the same woman of even after Robert Townsend in New York; the Townsend Townsend’s powerfully Tallmadge’s acquaintance eventually resumed spying. Family Papers at the emotional reaction to this whom he expected to “out- According to family corre- New-York Historical Society, news is evident through his wit them all”? And might spondence, Townsend the Oyster Bay Historical own ledgers and in Woodhull’s Townsend have formed a lived out his days depressed, Society, and Raynham Hall letters. He traveled to Setauket powerful emotional attach- unmarried, and drinking in Oyster Bay, Long Island; and arrived at Woodhull’s ment to her, and tried to heavily until his death at age and Benedict Arnold’s home in a state of extreme ransom her freedom? No eighty-five. receipts at Laval University depression. According to letter describes the release Because of the nature of in Québec City. Most of Woodhull, Townsend swore of this arrested individual. , good spies leave the correspondence that to stop spying, and according Conditions in New York little documentary information negotiated Arnold’s treason to Townsend’s own business prisons were so horrific that behind. But enough informa- is contained in the Sir ledgers he proceeded to steal life expectancy was a few tion remains in archival Henry Clinton Papers at the large sums of money from months; recent scholarship collections to suggest that University of Michigan’s every business with which he suggests that more Americans the Culper Spy Ring played a Clement Library. was connected, including his died in such confinement significant role during a dark father’s, for a total of over than were killed in all the period in Revolutionary War 600 pounds in ten days—a battles of the American history––and that much more veritable fortune at the time. Revolution combined. Could of this role remains to be No evidence reveals what this have been the fate of the discovered. Both the evidence the money was for, but ring anonymous ring member? and history show, however, member Anna Strong had Certainly the quality of that this band of citizen-spies ransomed her husband’s the Culper Ring’s intelligence scored one of the most freedom from a New York peaked after Woodhull’s important intelligence coups prison earlier in the war. narrow escape and when in American history. n

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