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Historically Speaking

Historically Speaking: Washington’s Spy Ring – Key to the Revolution

By Tom Morrow

If you’ve been watching the television series, “Turn – Washington’s Spies,” the episodes have closely portrayed reality.

In the summer of 1778, the Culper Ring was a spy group organized by Continental Army Major Benjamin Tallmadge under orders from General George Washington. It began during British occupation of New York City at the height of the American Revolutionary War.

The “Culper” name was suggested by Washington, who devised it from Culpeper County, Virginia where he had been a surveyor as a young man. The two main members of the Ring were Abraham Woodhull and Robert Townsend, who used “Samuel Culper, Sr.” and “Samuel Culper, Jr.” respectively as aliases. Tallmadge was in direct contact with and control of the Ring, but Washington often directed its operations. Major Tallmadge was referred to by the alias of “John Bolton.”

The Ring’s task was to send messages to Washington about the activities of the British in New York City. The members of the Ring operated mostly in New York City, Long Island, and Connecticut. The Ring’s covert operations started in late October 1778 and continued through the British retreat from New York in 1783, but its primary activities were between 1778 and 1781.

The spies discovered a high-ranking American officer, Benedict Arnold, had been plotting with British Major John Andre to surrender the garrison to the British and to turn over the vitally important American fort on the Hudson River known as West Point.

Tallmadge recommended Abraham Woodhull of Setauket on Long Island as a contact for Brewster. Woodhull was a childhood friend of both Lt. Caleb Brewster and Major Tallmadge. Before Woodhull left Connecticut, Tallmadge spoke with him about joining Washington’s secret service. In a dinner with Washington and Scott on Aug. 25, Tallmadge convinced Washington that Woodhull was trustworthy. At that dinner, the officers devised the alias “Samuel Culper” for Woodhull. Washington agreed with Tallmadge’s method of embedding a spy in the middle of British-held territory should be used. He was communicating directly with Tallmadge about setting up a network with Woodhull and Brewster.

As depicted in the TV series, Anna Strong, a friend and neighbor of Abraham Woodhull, helped pass along messages from the spy ring by posting pre-arranged signals to indicate when one of the spies was ready to submit intelligence. If Strong hung a black petticoat on her clothesline, it meant Brewster had arrived in town in his whaleboat.

While Woodhull was away in New York City, Colonel John Graves Simcoe, commander of the Queen’s Rangers, came to Setauket to look for him.[86] Not finding Woodhull at home, Simcoe’s men attacked and beat Woodhull’s father Judge Richard Woodhull. Abraham Woodhull escaped arrest because Loyalist militia officer Colonel Benjamin Floyd vouched for him. (Floyd had married his distant relative Ruth Woodhull, a sister or cousin of New York militia Brig. Gen. Nathaniel Woodhull. Simcoe was every bit as vicious as portrayed in the TV series.

Abraham Woodhull reported that after the Simcoe incident at Setauket, he could not continue to operate in New York City because he was still under suspicion, but he had a new agent for New York City lined up and would go to New York to finalize arrangements with him.

In June 1779, Woodhull engaged Robert Townsend to gather intelligence in New York City, using the alias “Samuel Culper, Jr. Townsend owned part-interest in a pub where British officers gathered. He also had access to the British through several channels, including his own tailoring business. He also wrote a society column in a Loyalist newspaper.

Secrecy was so strict that Washington did not know the identity of all the operatives. Townsend was recruited by Woodhull and was especially insistent that his identity not be revealed.

Among the techniques the Ring used to relay messages were coded messages published in newspapers and invisible ink, called a sympathetic stain, to write between the lines of what appeared to be typical letters. And, you thought those techniques were modern-day spy tricks.

Washington made sure the Culper Ring spies had more support and operated in greater secrecy than previous Continental spies, perhaps with Nathan Hale in mind. Through Tallmadge, he provided them with codes, dead drops, and aliases. Tallmadge, Woodhull, and Townsend were given code names. George Washington’s was 711.

The spy ring’s primary years of operation was from 1778 through 1783, when Clinton’s British troops abandoned New York City. Ironically, the American public was unaware of the spy ring’s existence until the late 1930s. Robert Townsend’s identity as “Culper, Jr.” was discovered in 1929, with the examination of old letters written by Townsend in his family’s home.

The Culper Ring is a fascinating chapter from the history of the United States’ founding – one of the many episodes of heroism in that war.

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