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Washington's Eyes and Ears: Based on Long Island, the Culper spies give the Americans a valuable edge

A rendering by Allyn Cox, for a mosaic

A rendering by Allyn Cox, for a mosaic at Ward Melville High School, shows Austin Roe delivering a message to Caleb Brewster on the shore at Crane Neck Bend in Old Field. The message would be carried across the Long Island Sound by whaleboat to Fairfield Connecticut to be handed over to Maj. Benjamin Tallmadge. Credit: Newsday / Newsday File Photo

This story first appeared in 1998 as part of "Long Island: Our Story"

Spying was risky business. Gen. George Washington wanted the newly recruited Culper Spy Ring to be aware of just how risky it was.

"There can be scarcely any need of recommending the greatest caution and secrecy in a business so critical and dangerous," Washington wrote from his New Jersey headquarters to his chief of intelligence, Maj. Benjamin Tallmadge, on July 10, 1779.

With the British controlling New York City, there was much that the commander in chief needed to know: The sizes and numbers of vessels in the harbor, and how they were protected; the number of men guarding the city, and how they were deployed; descriptions of forts and redoubts that had been built by the British, and whether pits had been dug in front of them "in which sharp pointed stakes are fixed"; and last, "The state of the provisions, forage and fuel to be attended to, as also the health and spirits of the army, navy and City."

The spy ring had begun its activities on a small scale in 1778, with Abraham Woodhull of Setauket, alias Samuel Culper, doing much of the snooping in New York. But his absences in Setauket started to become noticeable. In the fall he found Robert Townsend of Oyster Bay, who was his father's purchasing agent in New York, to take over that job. Townsend exacted a promise that no one, not even Washington, would ever know his real name. He took the spy name Culper Jr., making Woodhull Culper Sr. Townsend's real name was not learned until 1930, when Suffolk historian Morton Pennypacker, aided by a handwriting expert, matched Culper Jr.'s handwriting with Townsend's.

As Culper Jr., Townsend dug out most of the important information needed by Washington. He was not only a merchant, he also worked part time, without pay, as a journalist for Rivington's Gazette, a pro-British New York newspaper. And he became a silent partner in a nearby Wall Street coffeehouse run by the paper's owner, James Rivington. It was frequented by British officers eager to get their name in the paper, so they talked freely to Townsend.

Here is how the spy ring worked: Imagine a communications loop running from Washington's headquarters somewhere in New Jersey, across Westchester County, then Connecticut, then across Long Island Sound to Setauket. From there the loop would make its way into New York City, where British headquarters lay.

Sometimes, Washington would have a specific request, which would be sent around the loop into the city. Once gathered, the information would return in the reverse direction. At other times, Townsend in New York would come up with some vital information on his own, and send it on its roundabout way to the general.

Austin Roe, the Setauket tavern-keeper, made the 55-mile ride into New York at least once a week, sometimes more often. His cover story was that he needed to purchase supplies for his business. He would meet Townsend, and when the papers were ready, return to Setauket, where he would deposit the information in a box in the corner of one of Abraham Woodhull's farm fields.

After checking the drop-box, Woodhull would use a spyglass to keep a close watch on the clothesline of his neighbor across Little Bay. That was Anna Smith Strong, better known as Nancy, whose husband, Judge Selah Strong, had been imprisoned by the British in New York for "surreptitious correspondence with the enemy."

Woodhull was looking for Nancy Strong's black petticoat, which she would hang out only when she knew that Agent 725, Caleb Brewster, had arrived from Connecticut in his whaleboat. She would add to the line one to six white handkerchiefs, indicating in which of six coves Brewster was hiding. No one has ever figured out how Anna Strong knew when Brewster was in town, or where he was hiding.

Under the cover of night, Brewster would sneak through the British boats guarding the nearby waters and make his way across Long Island Sound to Fairfield, Conn., which was still controlled by the Americans. A courier would take the papers to Tallmadge, and Tallmadge would send them to Washington.

Toward the end of the war, Washington got impatient with waiting for a response to his questions. And British counterintelligence raised suspicions about the Setauket connection. The route was eventually shortened to go across the Sound near Cow Neck, the modern Port Washington.

From the very start, the general made clear that his standards were high. In a June 27, 1779, letter to Tallmadge, Washington enclosed 10 guineas to reimburse Culper Sr. for expenses, and then commented somewhat sharply -- not an unusual trait for Washington -- on his expectations for Culper Sr.'s successor in New York, Culper Jr.:

His successor (whose name I have no desire to be informed of provided his intelligence is good, and seasonably transmitted) should endeavor to hit upon some certain mode of conveying his information quickly, for it is of little avail to be told of things after they have become matter of public notoriety, and known to every body.

Even the respected Tallmadge was not immune from the general's tongue. Within a week, Tallmadge's camp was attacked by the British, and in the ensuing battle, he lost his horse, most of his baggage, Washington's letter and the 10 guineas. Washington wrote to Tallmadge on July 5:

The loss of your papers was certainly a most unlucky accident, and shows how dangerous it is to keep papers of any consequence at an advanced post. I beg you will take care to guard against the like in the future. If you will send me a trusty person, I will replace the guineas.

LEGACY: ANNA STRONG'S GRAVE

Spy ring member Anna Smith (Nancy) Strong is buried with her husband, Selah Strong, in the St. George's Manor Cemetery on Strong's Neck, Setauket. First used for the burial of William Smith in 1705, the small, private family cemetery is on Cemetery Lane, off Dyke Road. It can be visited by the public.

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