The Siege of Yorktown had everything: Cannon fire, sea battles, death, destruction, sickness, victory— and spies. So it’s odd when people ask, “Was Yorktown important?” In the summer of 1778, George Washington authorized the formation of a secret chain of agents known as the Culper Ring to operate in British-occupied New York. The following excerpt from Alexander Rose’s, “Washington’s Spies: The Story of America’s First Spy Ring,” describes the ring and the risks involved with early espionage. Courtesy of the Museum of the American Revolution, opening in Philadelphia next year.

Washington's Spies“[Benjamin] Tallmadge had learned from Nathaniel Sackett how to disguise agents as enemy sympathizers using realistic cover stories, and from John Parke that a spy could nestle within the beast of an unsuspecting foe for months, perhaps years. So Tallmadge ambitiously envisioned combining these two approaches to create a network of agents-in-place permanently embedded in occupied New York and running to Long Island, then across the Sound to his headquarters in Connecticut, where the intel would be digested and passed upstairs to the commander-in-chief-with Tallmadge’s summary and analysis attached.”

Washington’s Spies a Chain of Agents 

“[Washington] now wanted a chain of agents stationed permanently in enemy territory. His choice of chief agent was Tallmadge’s recruit, ‘Mr. C——.’ Becasue if he ‘could be engaged in a work of this sort, his discernment, and means of information, would enable him to give important advices.'”

“Invigorated by this unexpected support, Tallmadge intended to forge [Abraham] Woodhull and [Caleb] Brewster. They became the nucleus of a network-what would become known as the Culper Ring….”

“Tallmadge adopted a set of aliases. Tallmadge became the anodyne ‘John Bolton,’ and Woodhull, ‘Samuel Culper.’ To be sure, Tallmadge was from coastal Setauket, in Suffolk County, the small town in which Woodhull still lived and whence Brewster had left in the years before the war. Earlier, the three of them had grown up together. And everyone knew each other. This complex web of personal relationships, continuing down through generations and concentrated in one compact locality, was key to the Culper Ring’s later success.”

Fear of being found out

“After having sworn his oath of loyalty to His Majesty, Woodhull dispatched his first ‘Samuel Culper’ letter. Hitherto he had passed on intelligence verbally. He feared incriminating documents falling into the enemy’s hands. So Tallmadge had assured him that none but he and Brewster knew his real name. And that if captured, they would destroy the letters before surrendering. For safety’s sake, Tallmadge did destroy Woodhull’s original letter. First, he copied it verbatim in his own handwriting and passed that version to headquarters. There remained nothing left now to trace it back to Woodhull. Yet the experience of transcribing Woodhull’s epistles must have bored the busy Tallmadge. He soon resorted to just sending on the originals without telling his trusting correspondent.”

“Woodhull performed double duty. He acted as Brewster’s liaison in Setauket and traveled to New York every few weeks to pick up news. Woodhull hated making that trip. It was by far the riskiest aspect of his job. Not only did villains, Tory plunderers, and British patrols infest the 55-mile road to New York. But he had to leave his aged parents for several days at a time, stay in expensive inns on the way, and travel by himself .”

Innate Caution Prevailed

“At one British checkpoint where he was routinely questioned, Woodhull ‘received their threats for coming there that make me almost tremble knowing…my business.’ After that little scare, Woodhull’s innate caution prompted him to tell his chiefs to ‘destroy every letter instantly after reading for fear of some unforeseen accident that may befall you and the letter get into the enemies [sic] hands and probably find me out and take me before I have any warning.’ (Woodhull would have suffered an apoplexy had he discovered that Washington’s staff actually kept his letters for administrative reasons.)”

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