In the eighteenth century, spying was considered an unsuitable job for a gentleman. Nonetheless, 21-year-old Nathan Hale volunteered to gather information behind British lines, perhaps because he hadn’t seen military action yet. He was fully aware of the danger; a spy was considered an enemy combatant and quickly executed.
In fact, his spy career lasted less than a week. On Sept 22, 1776, Nathan (“I regret that I have but one life to give to my country”) Hale was hanged by the British.
George Washington realized that besides forming an army, he also need a better method of obtaining intelligence. The man he entrusted with the task was Maj. Benjamin Tallmadge (1754-1835,) former teacher, Yale graduate, and veteran of several Revolutionary War battles. In 1777, he was instrumental in organizing a spy ring to relay information to George Washington.The ring was tasked with the mission of spying on the British Army and reporting on troop movements, positions, fortifications and plans in the New York area. The ring continued to operate until the end of the war in 1783.
In order to cloak his identity, Tallmadge assumed the name of “John Bolton.”
The ring used elaborate codes and aliases as well as dead drops and invisible ink in the course of their activities. Tallmadge tapped two men for the task, Abraham Woodhull (1750-1826,) a farmer from Setauket, New York and Robert Townsend (1753-1838,) a dry goods merchant from Manhattan Tallmadge started the New York City operation with Woodhull making trips into New York, ostensibly to visit his sister, Mary Underhill, who operated a boarding house with her husband Amos Underhill Woodhull sent his messages under the alias “Samuel Culper,” later as “Samuel Culper, Sr.” Townsend’s was Samuel Culper, Jr. (The ring eventually became known as The Culper Ring.)
Tavern keeper Austin Roe (1748-1830) served as a courier. using the excuse of buying supplies for his tavern as the reason for his frequent trips to Manhattan, and ferryboat captain Caleb Brewster(1747-1827) took the information on his ferry across the Long Island Sound where it was taken to General Washington. Anna Strong (1740-1812,) the wife of a Long Island Patriot judge, would use her laundry as a way of signaling times and locations for the spies to meet. She would hang a black petticoat on the clothesline to indicated that Brewster was in town and available to ferry messages. She would then hang between one and six handkerchiefs on the line next to the petticoat in order to indicate the particular spot in which Brewster could be found. Another unidentified member of the ring was referred to as 355. 355 was believed to have passed along information garnered from Major John Andre and Benedict Arnold and she was believed to have been arrested and taken to the HMS Jersey where she was questioned and would later die after giving birth to a child.
The manner in which the ring operated was ingenious according to the conventions and limitations of the day. It was operated in such secrecy that even General Washington did not know the identity of many of the key players. Besides selling dry goods, Townsend was the society reporter for a local American newspaper. His job as a reporter gave him access to British soldiers and functions without arousing suspicion. Roe would often drop by Townsend store to purchase goods as well as drop off a special order from a Mr. Bolton.
The Culper Ring is credited with a number of successful operations, including the notifying Gen. Washington that the British planned a surprise attack on the newly allied French forces under Lieutenant General Rochambeau at Newport, Rhode Island, before the French could fully recover and set up defenses after their arduous sea journey to America. They also reported that the British planned to counterfeit American currency on the actual paper used for the Continental dollars, in enough time for the Continental Congress to retire the bills. And they discovered that a high-ranking American officer (subsequently shown to be Benedict Arnold) had been plotting with British Major John Andre to surrender the garrison at West Point to the British.
At the outbreak of the war, Gen. Benedict Arnold participated in the capture of the British garrison of Fort Ticonderoga. In 1776, he hindered a British invasion of New York at the Battle of Lake Champlain, and the following year, he played a crucial role in bringing about the surrender of British General John Burgoyne’s army at Saratoga. But Arnold never received the recognition he thought he deserved, and in 1779, he entered into secret negotiations with the British, agreeing to turn over the U.S. post at West Point in return for money and a command in the British army. The plot was discovered, Maj. Andre was hanged, and Benedict Arnold escaped to England.
After the war, the Culper Ring dissolved, and the principals went back to their previous professions.
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