Culper Ring

The Culper Ring was an American Revolutionary War spy ring, organized by Major Benjamin Tallmadge, set up in 1778 during the British occupation of New York City. The name "Culper" was suggested by George Washington, taken from Culpeper County, Virginia. The two leaders 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."

Culper Spy Ring
Colonel Benjamin Tallmadge, leader of the Culper Ring, in a 1790 portrait with his son William
Formation1778
FounderGeorge Washington
Extinction1783
Typemilitary spy ring
Purposeto provide military intelligence from British-occupied New York
HeadquartersSetauket and New York City
leader
Colonel Benjamin Tallmadge
Key people
Abraham Woodhull, Robert Townsend, Caleb Brewster, Austin Roe, Anna Strong, Agent 355

While Tallmadge was their direct contact, Washington often directed its operations. Their task was 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, beginning in late October 1778, until the British evacuation of New York in 1783.

The information they supplied 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. Another was a plan to counterfeit American currency on the actual paper used for the Continental dollars, prompting 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, it discovered 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
Washington became convinced that well-organized intelligence was a necessity after several intelligence failures, including the capture and execution of Nathan Hale.

Prior to Howe's move from Staten Island, Washington received information of varying utility from individual agents such as Lawrence Mascoll.[1] After evacuating 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.[2]

Instead, he employed Captain Nathan Hale, who was captured in New York City, and executed by the British on September 22, 1776.[3] This made Washington decide civilians would attract less attention, 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.[4]

Sackett had some success, for example the discovery 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 he was soon paid off.[5] Early in 1777, American Colonel Elias Dayton set up a spy network on Staten Island, which worked with an established network, the Mersereau Ring.[6]

British victory at the Battle of Brandywine on September 11, 1777, led to the capture of Philadelphia on September 26, which became the new focus of intelligence gathering. Washington assigned this task to Major John Clark, recently returned to service after being wounded before Brandywine; he set up a successful network, but poor health forced him to take up a desk job.[7]

Establishment of the Culper Ring

Initial formation

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 prior to the Battle of Rhode Island, and the despatch of several regiments to Newport, Rhode Island.[8]

Washington asked General Charles Scott to handle Brewster and find additional agents, assisted by Tallmadge. As Scott delegated most of the work to Tallmadge, Washington asked him to recruit reliable intelligence agents in New York City.[9] [10] [11] [12] As a contact for Brewster, Tallmadge recommended a mutual childhood friend, Abraham Woodhull of Setauket on Long Island as a contact for Brewster.[13]

A few months earlier, Woodhull had been arrested for illegal trading, of which he was in fact guilty, and was being held in a Connecticut prison. Tallmadge arranged his release through Governor Jonathan Trumbull, and obtained approval by Washington and Scott to recruit him as an intelligence agent. Washington suggested the alias "Samuel Culper" after Culpeper County, Virginia, where he had worked as a surveyor in his youth.[10]

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.[14] Since Scott lost three out of five agents sent into New York City in early September, Washington decided 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.[15]

Early operations
Historic Marker for the former Roe Tavern on New York State Route 25A in East Setauket, New York. It reads: ROE TAVERN / Stood here 1703–1936 / Washington spent the night here April 22, 1790 / Austin Roe, Inn Keeper, was / one of Washington's spies / State Education / Department, 1938

Woodhull would go to New York City every few weeks to gather intelligence.[16] His married sister Mary Underhill lived there, giving him a reason to visit.[17][18] He was questioned at a British checkpoint on October 31, 1778, increasing his anxiety about the dangerous mission,[16] but he returned to Setauket with valuable information about the British supply fleet.[19] 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, proving his worth as a spy.[20][21] Woodhull soon recruited his brother-in-law Amos Underhill to gather intelligence, who ran a boarding house in the city with his wife Mary,[17] but Underhill's reports were often too vague to be of much value.[22]

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.[23] Tallmadge set up couriers in December who would take messages the 55 miles (89 km) between New York and Setauket, initially Jonas Hawkins then mainly Austin Roe beginning in the early summer.[24] 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.[23][25] Tallmadge would then take them to Washington's headquarters.[23] This time-consuming task was replaced in January 1779 by the assignment of express riders to take the messages from Tallmadge to Washington.[24]

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 pre-arranged 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. Next to that, 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.[25][26][27][28] Historian Richard Welch writes that the tradition of the clothesline signal is unverifiable, but it is known that the British suspected a woman at Setauket of Patriot activities who fits Anna's profile.[29]

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.[30] This was with a message from Woodhull which precisely described the British regiments and commanders at the northern tip of Manhattan, totaling about 8,500 men.[30] Woodhull also reported on British boat-building, confirming Brewster's report.[30] Tallmadge and Washington thought that the boats might be planned transport for an attack against Connecticut from Major General William Tryon, who had conducted a raid during the winter.[31]

Woodhull became increasingly anxious about being discovered and did little in May and June 1779.[32] John Wolsey was a Long Island privateer who was captured by the British. In order to secure parole, he told British officers on June 5 that Woodhull was up to something dubious.[33] Colonel John Graves Simcoe, commander of the Queen's Rangers, came to Setauket to look for Woodhull, but he was in New York City,[33] so Simcoe's men attacked and beat Woodhull's father Judge Richard Woodhull.[33] Abraham Woodhull escaped arrest because Loyalist militia officer Colonel Benjamin Floyd vouched for him. Floyd was married to a member of the Woodhull family.[33]

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.[34] The British had intercepted a June 13 letter from Washington referring 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.[34] They were trying to capture Tallmadge himself because they knew that he was head of Washington's intelligence operation.[34] The second letter confirmed that an agent C______ was operating in New York City and that Tallmadge was the chief intelligence officer for Washington.[32] 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.[32]

Woodhull reported that he could not continue to operate in New York City after the visit from Simcoe in June because he was under suspicion, but he had a new agent lined up and would go to New York to finalize arrangements with him.[35]

Expansion of the Ring

In June 1779, Woodhull engaged Robert Townsend to gather intelligence in New York City, using the alias "Samuel Culper, Jr."[36] Townsend was engaged in business there, and his presence would arouse less suspicion than Woodhull's visits. He also had access to British officers through several channels, including his own tailoring business. He wrote a society column in a Loyalist newspaper, and he owned an interest in a coffeehouse with Loyalist newspaper owner James Rivington, who also was a secret member of the Ring.[37][38]

The only known portrait of instrumental spy Robert Townsend, sketched in the early 1800s[39]

Once Townsend began his intelligence activities in New York City, Woodhull operated almost exclusively from Setauket, and he revised the communications network. Townsend would pass intelligence to a courier—initially Hawkins, then Hawkins and Roe, and exclusively Roe after September 1779—who would take it to Setauket and pass it to Woodhull, usually via dead drop in a box hidden in a field which Roe rented from Woodhull.[36] Woodhull would evaluate and comment on it and pass it to Brewster, who would take it across Long Island Sound, occasionally adding an intelligence note of his own, and pass it to Tallmadge.[30] Tallmadge would usually add a cover letter with comments,[25] and he sent and received messages by a relay of dragoons acting as couriers.[24][25]

Raynham Hall, the Oyster Bay, New York home of Robert Townsend, now a museum

Hawkins was bold at first, but he became increasingly anxious about British patrols. His role was reduced between April and July, when Tallmadge assigned a code number to Roe in his code directory but not to Hawkins.[40] Woodhull wrote in a coded message on August 15 that Hawkins had to destroy a letter from Culper, Jr. or be captured.[40][41][42] He also wrote that Hawkins insisted that his next meeting with Townsend be in an out of the way location.[40]

Townsend did not like taking the additional risk and was beginning to doubt Hawkins' reliability and to regret the destroyed messages.[40] Hawkins finally stopped his courier services for the Ring in September 1779, as Townsend refused to deal with him any longer.[40] Woodhull acted as courier on September 11 so that he could explain to Townsend the loss of the earlier letters,[43] and Roe became the sole permanent courier for the Ring.[40]

Secrecy
A page from the Culper Ring's code book, with noteworthy people and place names listed side-by-side with numerical representations

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, although Austin Roe and Jonas Hawkins needed to know him.

Among the techniques that the Ring used to relay information were coded messages published in newspapers and invisible ink,[44] called a sympathetic stain, to write between the lines of what appeared to be typical letters. In the first months of the Ring's operations, they were forced to rely on crude tactics to conceal their information before a complex web of codes and invisible ink were accessible, so they relied on a small number of codes for memory. Woodhull used the codes 10 (New York), 30 and 40 (Post Riders), and 20 (Setauket) in his first letter of correspondence.[45]

Tallmadge realized the significance of creating a code book to increase their vocabulary. By July 1779, he had completed pocket dictionaries with lists of verbs, nouns, people, and places with their corresponding code number. These dictionaries were given to General Washington, Woodhull, Townsend, and Tallmadge himself, to ensure that it did not get into enemy hands.[45] With the use of the codes, the letters were very complex and required much effort to write and comprehend. The code book was a way that Washington made sure that the Culper Ring spies had more support and operated in greater secrecy than previous Continental spies, perhaps with Nathan Hale in mind. Tallmadge, Woodhull, and Townsend were given code names and code numbers, along with Washington, Brewster, Roe, and Rivington. George Washington's code number was 711.[46]

Hercules Mulligan and Cato

Hercules Mulligan[47] was recruited to spy for the Continental Army in New York City by Alexander Hamilton.[48][49] He was born in 1740, was a friend of Townsend's father,[50] and was an active member of the Sons of Liberty. He had taken in Alexander Hamilton when Hamilton arrived in New York as an orphan in 1773 to attend King's College, and he had helped Hamilton obtain a commission in the army.[51] He was married to Elizabeth Sanders, daughter of a Royal Navy admiral, and he also had a fashionable clothing business near Robert Townsend's establishment—and these things gave him access to officers who would talk to him about military matters.[52]

Mulligan began his activities in late 1776 or early 1777, well before formation of the Culper Ring.[53] Historian Stephen Knott says that Mulligan cooperated with the Culper Ring, but mostly operated as a lone agent.[53] Alexander Rose states that Mulligan gave Townsend information which Townsend added to his reports.[50]

Mulligan's slave Cato was his "faithful accomplice" in his intelligence activities.[54] In January 1779, Cato delivered a message from Mulligan to George Washington's aide Alexander Hamilton that the British planned to kidnap or kill American leaders, including Washington and New Jersey Governor William Livingston.[55] Mulligan had received the information from his brother Hugh, who was with Kortright and Company, a contractor for the British Army.[55]

The British arrested Mulligan on suspicion of espionage after Benedict Arnold defected in New York. Townsend ceased his activities for a time for fear that he, also, would be discovered.[51] Woodhull passed on the information concerning Townsend's dejection and concern over the arrest of "one that hath been ever serviceable to this correspondence."[51] Arnold did not have any hard evidence against Mulligan, so he was released, but he may have spent as many as five months in prison, until February 1781,[50][56] and he continued to pick up intelligence after his release.[56] He discovered that the British planned to ambush Washington while he was on his way to a meeting with Rochambeau on March 5, 1781.[56] Mulligan and Cato remained under suspicion and could not communicate directly with Washington's headquarters, so Mulligan gave the information to Townsend, who sent it to Washington via the Culper Ring network.[56] The message arrived in time for Washington to avoid the trap and travel to the meeting by another route.[56]

Other persons identified as informants

The members of the ring gathered information from a variety of sources, including persons other than unwitting British officers. Some of those informants or associates included Joseph Lawrence, a Long Island resident; Captain Nathan Woodhull, Woodhull's uncle who served as a Loyalist militia officer but provided information to Abraham Woodhull; Nathaniel Ruggles, a schoolmaster and physician born in 1713; Joshua Davis, a Brewster deputy and occasional substitute; George Smith, a whaleboat man who filled in for Brewster near the end of the war; and William T. Robinson, a merchant.[57][58]

Alexander Rose writes that John Cork was a code name for an unidentified informant.[59] Harry Thayer Mahoney writes that John Corke of Groton, New York posed as a Tory and could travel back and forth to New York City because he was "exceedingly intimate at British headquarters."[60] Corke wrote intelligence reports to Tallmadge in invisible ink or reported verbally to him.[60] Mahoney states that Washington and Tallmadge considered Corke a valuable recruit for the Culper Ring.[60]

A letter by loyalist soldier Nehemia Marks was uncovered in 2015 which identifies brothers Nathaniel and Phillip Roe as supporters of the spy ring, with Nathaniel providing intelligence and Phillip material aid. The letter also provides evidence that the Culper ring operated in Drowned Meadow beyond Setauket and Oyster Bay, as previously believed. The letter is housed in the William L. Clements library at the University of Michigan, where it was discovered by a former resident of Port Jefferson researching the Culper Ring.[61][62]

Women in the Ring

Some sources note a female member of the ring known only as Agent 355, while others believe that this code number referred to Anna Strong or was simply a misunderstanding of a cryptic reference in one of Abraham Woodhull's letters.[63] Other women were informants for the Culper Ring, such as Robert Townsend's sister Sarah (Sally) Townsend[64] and Abraham Woodhull's sister Mary Underhill, who provided important information about Major John Andre and his alias of John Anderson,[65] according to some sources.

Twentieth-century disclosure of the Ring

The general public was unaware of the Ring's existence until the 1930s. Robert Townsend's identity as "Culper, Jr." was discovered in 1929, with the examination of old letters written by Townsend in the Townsend family home. Historian Morton Pennypacker reviewed the letters and noticed that the handwriting in letters from the trunk, written by Robert Townsend, was similar to handwriting in letters written by "Samuel Culper, Jr." in George Washington's collection.[66] Other evidence later corroborated Townsend's identity.[66] James Rivington was confirmed by scholars to be a member of the ring only in the 1950s.[67]

  • James Fenimore Cooper's novel The Spy (1821) may have been based on the Culper Ring, and Woodhull and Townsend (as the combined Samuel Culper) specifically[68]
  • Roseanna M. White's Ring of Secrets features the Culper Ring and continues with conjecture on possible later actions in Whispers from the Shadows and Circle of Spies[69]
  • The AMC television series Turn: Washington's Spies (2014–2017) is based on Alexander Rose's Washington's Spies: The Story of America's First Spy Ring (2006) and tells a fictionalized version of the story of the Culper Ring, with a focus on Abe Woodhull and his correspondence with Washington during the war.
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See also

References
  1. Rose 2007, p. 14.
  2. Rose 2007, pp. 15-16.
  3. Rose 2007, pp. 18,27,32.
  4. Rose 2007, p. 43.
  5. Rose 2007, pp. 50-51.
  6. Mahoney & Mahoney 1999, p. 126.
  7. Rose 2007, p. 62.
  8. Rose 2007, pp. 70-71.
  9. Tallmadge 1858, p. 68.
  10. Kilmeade & Yaegar 2013, p. 52.
  11. Schellhammer 2012, p. 45..
  12. Sharp 2012, p. 240.
  13. Rose 2007, pp. 72,79.
  14. Rose 2007, pp. 76-77.
  15. Rose 2007, pp. 78-79.
  16. Rose, 2007, p. 88.
  17. Rose, 2007, p. 90.
  18. Kilmeade, 2013, p. 46.
  19. Rose, 2007, p. 89.
  20. Rose, 2007, pp. 93–94.
  21. Kilmeade, 2013, p. 59.
  22. Rose, 2007, p. 92.
  23. Rose, 2007, p. 101.
  24. Rose, 2007, p. 102.
  25. Nelson, David Paul. Culper Ring in Hastedt, Glenn, P., ed. Spies, Wiretaps, and Secret Operations: A-J. Santa Barbara, CA: ABC-CLIO, 2011. ISBN 978-1-85109-807-1. p. 217.
  26. Mahoney, 1999, p. 309.
  27. Naylor, Natalie A. Women in Long Island's Past: A History of Eminent Ladies and Everyday Lives. Charleston, SC: The History Press, 2012. ISBN 978-1-60949-499-5. Retrieved May 1, 2014. p. 38.
  28. Kilmeade, 2013, pp.93–94, doubts that the laundry signals took place.
  29. Welch, Richard F. General Washington's Commando: Benjamin Tallmadge in the Revolutionary War. Jefferson, NC: McFarland & Company, Inc., 2014. ISBN 978-0-7864-7963-4. p. 37.
  30. Rose, 2007, p. 103.
  31. Rose, 2007, p. 106.
  32. Rose, 2007, p. 113.
  33. Rose, 2007, p. 129.
  34. Rose, 2007, p. 112.
  35. Rose, 2007, p. 131.
  36. Rose, 2007, p. 132.
  37. Nelson, David Paul. Robert Townsend in Hastedt, Glenn, P., ed. Spies, Wiretaps, and Secret Operations: A-J. Santa Barbara, CA: ABC-CLIO, 2011. ISBN 978-1-85109-807-1. p. 763.
  38. Rose, 2007, pp. 150–154.
  39. "Raynham Hall Museum". raynhamhallmuseum.org. Retrieved 2016-05-31.
  40. Rose, 2007, p. 172.
  41. Kahn, David. The Codebreakers: The Comprehensive History of Secret Communication from Ancient Times to the Internet. New York, Simon and Schuster, 1996. ISBN 978-1-4391-0355-5. p. 179.
  42. Kilmeade says that Hawkins destroyed Culper letters on two occasions for fear of being caught. Kilmeade, 2013, p. 100.
  43. Kilmeade, 2013, P. 100.
  44. Rose, 2007, pp. 106–110.
  45. Pennypacker, Morton, General Washington's Spies on Long Island and in New York (Long Island Historical Society, 1939), 209.
  46. Rose, 2007, p. 121.
  47. Rose, 2007, pp. 224–226.
  48. Mahoney, 1999, p. 253.
  49. Bakeless, John. Turncoats, Traitors & Heroes. New York: Da Capo Press, 1998. Originally published New York: J. B. Lippincott, 1959. ISBN 978-0-306-80843-2. p. 240.
  50. Rose, 2007, p. 226.
  51. Rose, 2007, p. 224.
  52. Rose, 2007, p. 225.
  53. Knott, Stephen. Secret and Sanctioned: Covert Operations and the American Presidency. New York: Oxford University Press, 1996. ISBN 978-0-19-510098-3. Retrieved May 22, 2014. p. 40.
  54. Misencik, Paul R. The Original American Spies: Seven Covert Agents of the Revolutionary War. Jefferson, NC: McFarland, 2013. ISBN 978-0-7864-7794-4. p. 116.
  55. Misencik, 2013, p. 117.
  56. Misencik, 2013, p. 122.
  57. Mahoney, 1999, pp. 284–285, 308
  58. Rose, 2007, pp. 173, 255–256, 265.
  59. Rose, 2007, p. 255.
  60. Mahoney, 1999, p. 111.
  61. Leuzzi, Linda "A letter of Significance” Long Island Advance, October 22, 2015
  62. William L. Clements Library "The Sir Henry Clinton Collection" retrieved October 27, 2015
  63. Rose, 2007, p. 173 identifies Agent 355 as Anna Strong, but notes on p. 277 that she died in 1812, which is inconsistent with other accounts of 355's fate. Kilmeade, 2013, pp. 93–94 doubts that Anna Strong was Agent 355. He believes that Agent 355 was more likely to have been a younger woman living with a Loyalist family in New York and acquainted with British spymaster John André. Mahoney, 1999, p. 304 agrees that Agent 355 had access to British headquarters but identifies her as the mistress and common law wife of Robert Townsend, who died in childbirth in 1780 while confined on a British prison ship.
  64. Misencik, Paul R. (2016). Sally Townsend, George Washington's teenage spy. Jefferson, North Carolina: McFarland & Company, Inc. ISBN 9780786499878. OCLC 910334343.CS1 maint: ref=harv (link) Misencik provides an extensive account of Sally Townsend's role as a spy.
  65. Weigold, Marilyn E. (2004). The Long Island Sound: A History of Its People, Places, and Environment. New York: NYU Press. ISBN 978-0-8147-9400-5.
  66. Kilmeade, 2013, pp. xvi–xvii.
  67. Mahl, Tom E. Espionage's Most Wanted: The Top 10 Book of Malicious Moles, Blown Covers, and Intelligence Oddities. Potomac Books, Inc., 2003. ISBN 978-1-61234-038-8. Retrieved May 1, 2014. p. 43.
  68. Walker, Warren S. "The Prototype of Harvey Birch". oneonta.edu. Retrieved April 27, 2014.
  69. White, Roseanna M. "The Culper Ring Series". RoseannaWhite.com. Archived from the original on 2014-05-31.

Sources
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