Espionage and the Culper Ring

For viewers of television’s new Revolutionary War espionage series TURN, the adventures of Anna Strong, Abraham Woodhull, Caleb Brewster and Benjamin Tallmadge are intriguing and entertaining.  The focus of TURN is the Culper spy ring that operated throughout most of the war. Who were the real people who inspired the characters?

In 1778 British commander General Howe made the decision to re-establish British headquarters in New York, where they remained until 1783. General George Washington had no organized intelligence network there, a major weakness in his disastrous campaigns in the area in 1776.   He assigned General Charles Scott to develop intelligence sources. Scott stuck to the traditional practice of sending soldiers out to scout enemy positions.  Continental Army Major Benjamin Tallmadge offered to develop a spy ring to gather intelligence against the British forces occupying New York City and Long Island. When several  men spying for Scott were captured and executed, Washington moved toward Tallmadge’s plan and put him in charge of intelligence. Tallmadge organized a ring of civilians, known to us as the Culper ring, that provided critical intelligence using methods we would recognize today – dead drops, code names, number substitution codes and invisible ink.

Tallmadge already had a good informant, Caleb Brewster, a childhood friend from Setauket, Long Island.  Brewster was a lieutenant in the Continental Army and owned a whaleboat that allowed him to travel between Connecticut and Long Island by water.  Abraham Woodhull, another friend from Setauket, was also recruited about this time.  Woodhull was unmarried and lived with his father, a local magistrate.  Tallmadge gave Woodhull the code name Samuel Culper and later Samuel Culper, Sr., a reference to Culpepper County, Virginia where Washington had surveyed as a young man.  Washington, Woodhull, Brewster, Tallmadge and others also were assigned numbers.  Woodhull’s number was 722.

In the initial phase of the ring’s operations Abraham made trips to New York City to visit his married sister, Mary Underhill, at her boardinghouse in the city.   Once there, he gathered whatever information he could, then traveled back to Setauket and conveyed the information to Brewster.  Brewster picked up the information at Setauket, rowed across Long Island Sound, and delivered the information to Tallmadge in Connecticut, who then carried the message to Washington.

Woodhull’s frequent trips into the city caught the attention of the British guards at local checkpoints. Within a few months Woodhull was stopped and searched.  Despite their best efforts the British did not discover the letter concealed in his saddle.  This close call and perhaps others led to a change in strategy.

Woodhull talked a distant relation, Robert Townsend, into joining the ring.  Townsend was given the code name Samuel Culper Jr.  Townsend was a tailor and silent partner in a coffee house in New York City who mingled daily with British officers. Townsend harbored a secret hatred of the British because of atrocities they committed against civilians. Woodhull now stayed home while Townsend gathered information in the course of his business in the city, then encoded it and sent it via courier to Setauket.  The courier buried it in a pre-arranged location on land owned by Woodhull, who collected and evaluated it.  This is where Anna Strong may have come into the story.  According to some sources Strong, another childhood friend, hung a black petticoat and one to six handkerchiefs from her clothesline.  This signaled Caleb Brewster, patrolling the sound nearby, that a message was ready and in which of six coves he should land his boat. Once Brewster had the message in hand, he carried it in his boat to Tallmadge in Connecticut, and the message was then carried by courier to General Washington.

Many of these communications survive today, and give us a wonderful window into the secrets the ring uncovered, and the methods and mindsets of Woodhull, Townsend, the couriers and others who undertook these dangerous duties from 1778 to 1780.  Woodhull, Townsend, Brewster, Tallmadge and Strong all survived the war, and lived to see the United States established as an independent nation.

The spying that the Culper ring undertook was risky business. Other spies and spy rings  aided the patriot cause in Phildelphia, Boston and Yorktown. The penalty for spying was death.  What motivated Tallmadge, Woodhull, Townsend and others to take the risk?  Were their actions heroic? Would you be willing to do what they did?

Recently published books on this topic include Alexander Rose’s Washington’s Spies: The Story of America’s First Spy Ring, 2007, and Brian Kilmeade and Don Yaeger’s George Washington’s Secret Six: The Spy Ring that Saved the American Revolution (2013).