The Culper Ring was a network of spies active during the American Revolutionary War, organized by Major Benjamin Tallmadge and General George Washington in 1778 during the British occupation of New York City. The name "Culper" was suggested by George Washington and taken from Culpeper County, Virginia. The leaders of the spy ring were Abraham Woodhull and Robert Townsend, using the aliases of "Samuel Culper Sr." and "Samuel Culper Jr.", respectively; Tallmadge was referred to as "John Bolton".
While Tallmadge was the spies' direct contact, Washington often directed their operations. The ring was tasked to provide Washington information on British Army operations in New York City, the British headquarters. Its members operated mostly in New York City, Long Island, and Connecticut between late October 1778 and the British evacuation of New York in 1783.
The information supplied by the spy ring included details of a surprise attack on the newly arrived French forces under Lieutenant General Rochambeau at Newport, Rhode Island, before they had recovered from their arduous sea voyage, as well as a British plan to counterfeit American currency on the actual paper used for Continental dollars, which prompted the Continental Congress to retire the bills.
The ring also informed Washington that Tryon's raid of July 1779 was intended to divide his forces and allow Lieutenant General Sir Henry Clinton to attack them piecemeal. In 1780, the Culper Ring discovered that a high-ranking American officer, subsequently identified as Benedict Arnold, was plotting with British Major John André to turn over the vitally important American fort at West Point, New York on the Hudson River and surrender its garrison to the British forces.
Background
Before British Major General William Howe's move from Staten Island, George Washington had received information of varying utility from individual spies working independently and without significant direction, such as Lawrence Mascoll. After evacuating the Continental Army from Brooklyn Heights, Washington asked William Heath and George Clinton to set up "a channel of information" on Long Island, but he did not yet try to establish permanent agents behind enemy lines.
Instead, he sought volunteers for espionage missions. Among them was Captain Nathan Hale, who went to New York City under a false identity but was quickly captured by the British and executed on September 22, 1776. This made Washington realize that a more discreet and well-organized espionage system would be necessary to infiltrate British operations. He decided that civilians would attract less attention than soldiers, and he asked William Duer to recommend a suitable agent. Duer recommended Nathaniel Sackett; his army contact was Hale's former classmate, then Captain Benjamin Tallmadge.
Sackett had some success, for example, the discovery that the British were building flat-bottomed boats for a campaign against Philadelphia; however, Washington felt he did not produce enough correct intelligence fast enough, and Sackett was soon paid off. Early in 1777, American Colonel Elias Dayton set up a spy network on Staten Island, which worked with an established network known as the Mersereau Ring.
The British victory at the Battle of Brandywine on September 11, 1777, led to the capture of Philadelphia on September 26, which became a new focus of intelligence gathering. Washington assigned this task to Major John Clark. Recently returned to service after being wounded before Brandywine, Clark set up a successful network, but poor health forced him to take up a desk job.
Establishment Initial formation: Tallmadge and Brewster In August 1778, Washington accepted an offer from Lieutenant Caleb Brewster, based at Norwalk, Connecticut, to provide intelligence. His first report included details on the condition of British warships before the Battle of Rhode Island, and the dispatching of several regiments to Newport, Rhode Island.
Washington asked General Charles Scott to handle Brewster and find additional agents, assisted by Tallmadge. Scott delegated most of the work to Tallmadge, and Washington asked him to recruit reliable intelligence agents in New York City. As a contact for Brewster, Tallmadge recommended a mutual childhood friend, Abraham Woodhull of Setauket on Long Island. Washington may have suggested the alias "Samuel Culper" after Culpeper County, Virginia, where he had worked as a surveyor in his youth.
Tallmadge and Scott had different approaches. Scott preferred single-mission agents, who returned to base after each completion; Tallmadge favored embedding agents and establishing a secure line of communication. Since Scott lost three out of five agents sent into New York City in early September, Washington decided that Tallmadge's method should be used. He opened discussions on setting up an embedded network with Woodhull and Brewster. Scott resigned on October 29, and Tallmadge replaced him as intelligence chief.
Early operations: Woodhull and Anna Strong
Woodhull traveled to New York City every few weeks to gather intelligence.Rose, 2007, p. 88. His married sister, Mary Underhill, lived there and gave him a valid reason to visit.Rose, 2007, p. 90.Kilmeade, 2013, p. 46. He was questioned at a British checkpoint on October 31, 1778, which increased his anxiety about the dangerous mission, but he returned to Setauket with valuable information about the British supply fleet.Rose, 2007, p. 89. He provided a precise report on November 23 with the identity of British units and the numbers of troops and dispositions in New York City, which proved his worth as a spy.Rose, 2007, pp. 93–94.Kilmeade, 2013, p. 59. Woodhull soon recruited his brother-in-law, Amos Underhill, to gather intelligence; the latter ran a boarding house in the city with his wife, Mary, but Underhill's reports were often too vague to be of much value.Rose, 2007, p. 92.
At first, Woodhull had to return to Setauket to pass messages to Caleb Brewster, which Brewster would take to Tallmadge or to receive messages from Tallmadge via Brewster. Tallmadge set up couriers in December who would take messages the between New York and Setauket, initially Jonas Hawkins then mainly Austin Roe beginning in the early summer. The courier's task was to get the letters to Brewster, who would pick up messages at one of six secluded coves near Setauket and take them across Long Island Sound with his rotating whaleboat crews to Tallmadge at Fairfield, Connecticut.Rose, 2007, p. 101.Nelson, David Paul. Culper Ring in Hastedt, Glenn, P., ed. Spies, Wiretaps, and Secret Operations: A-J. Santa Barbara, CA: ABC-CLIO, 2011. . p. 217. Tallmadge would then take them to Washington's headquarters. The time-consuming task was replaced in January 1779 by the assignment of express riders to take the messages from Tallmadge to Washington.Rose, 2007, p. 102.
Local tradition claims that Anna Strong, a resident of Setauket and a friend and neighbor of Abraham Woodhull, helped pass along messages from the spy ring by posting prearranged signals to indicate when one of the spies was ready to submit intelligence. If she hung a black petticoat on her clothesline, it meant that Brewster had arrived in town in his whaleboat. Also, she would hang a quantity of white handkerchiefs to indicate which of the six hiding places he was in. Woodhull used her signals to meet Brewster or to drop messages at one of the meeting places.Mahoney, 1999, p. 309.Naylor, Natalie A. Women in Long Island's Past: A History of Eminent Ladies and Everyday Lives. Charleston, SC: The History Press, 2012. . Retrieved May 1, 2014. p. 38.Kilmeade, 2013, pp.93–94, doubts that the laundry signals took place.Naylor, 2012, p. 38 attributes the story to oral folklore The historian Richard Welch writes that the tradition of the clothesline signal is unverifiable, but it is known that the British suspected a Setauket woman who fit Anna's profile of Patriot activities.Welch, Richard F. General Washington's Commando: Benjamin Tallmadge in the Revolutionary War. Jefferson, NC: McFarland & Company, Inc., 2014. . p. 37.
Brewster occasionally would add his own report to the Culper messages. In a January 1779 report received by Washington in early February, Brewster sent some information about naval matters and boat building at New York City and warned that Loyalists were outfitting privateers for operations on Long Island Sound.Rose, 2007, p. 103. That was delivered with a message from Woodhull that precisely described the British regiments and commanders at the northern tip of Manhattan, totaling about 8,500 men. Woodhull also reported on British boatbuilding, confirming Brewster's report. Tallmadge and Washington thought that the boats might be planned for transport for an attack against Connecticut from Major General William Tryon, who had conducted a raid during the winter.Rose, 2007, p. 106.
Woodhull became increasingly anxious about being discovered and did little in May and June 1779. John Wolsey was a Long Island privateer who was captured by the British. To secure parole, he told British officers on June 5 that Woodhull was up to something dubious.Rose, 2007, p. 129. Colonel John Graves Simcoe, the commander of the Queen's Rangers, came to Setauket to look for Woodhull, but he was away, in New York City. 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 was married to a member of the Woodhull family. Woodhull reported that he could not continue to operate in New York City after the visit from Simcoe in June because of suspicion, but Woodhull had a new agent lined up and would go to New York to finalize arrangements with him.Rose, 2007, p. 131.
In late June, Washington sent a letter to Tallmadge in which he identified George Higday as a possible operative to relieve Woodhull in New York City. The British had intercepted a June 13 letter from Washington that referred to "C_____" and Tallmadge. On July 2, British cavalry under the command of Colonel Banastre Tarleton attacked Tallmadge's camp and captured his horse and some papers, including the letter mentioning Higday.Rose, 2007, p. 112. They were trying to capture Tallmadge himself because they knew that he was head of Washington's intelligence operation. The second letter confirmed that the agent C______ was operating in New York City and that Tallmadge was the chief intelligence officer for Washington.Rose, 2007, p. 113. Higday escaped execution but was of no use as a spy to Washington or to Clinton, who tried to recruit him as a double agent.
Expansion: Townsend, Hawkins, and Roe In June 1779, Woodhull engaged Robert Townsend to gather intelligence in New York City by using the alias "Samuel Culper Jr."Rose, 2007, p. 132. Townsend was involved in business there, and his presence would arouse less suspicion than Woodhull's visits. He had access to British officers through several channels, including his own tailoring business. He also wrote a society column in a Loyalist newspaper and owned an interest in a coffeehouse with the newspaper's owner, James Rivington, who was also a secret member of the Culper Ring.Nelson, David Paul. Robert Townsend in Hastedt, Glenn, P., ed. Spies, Wiretaps, and Secret Operations: A-J. Santa Barbara, CA: ABC-CLIO, 2011. . p. 763.Rose, 2007, pp. 150–154.