The Culper Ring

Sources

Significance. The code name for an American spy network during the Revolutionary War, the Culper Ring, proved to be the most effective espionage service employed by either side during the whole conflict. The ring successfully operated in the New York City area for almost six years, sustaining only one major reversal in 1780. Its history entails many hair-raising episodes, and James Fenimore Cooper used the ring as a basis for his 1821 novel The Spy.

Origins. Early in the war George Washington recognized the need for good intelligence concerning enemy troop dispositions and movements. In 1776 Nathan Hale was captured in New York City and hanged as a spy. During the Pennsylvania campaign of 1777 and subsequent British occupation of Philadelphia, various individuals supplied American forces with information. However, not until after the Battle of Monmouth Court-house in June 1778, when the British reestablished their headquarters in New York City, was the American commander in chief able to construct a reliable, systematic intelligence service.

Tallmadge. Washington preferred to act as his own head of the secret service. He alone determined policy and paid his spies with hard specie derived from a special fund provided by Congress. However, in late 1778 he needed a new deputy intelligence chief because the current one, Brig. Gen. Charles Scott, was in poor health and requested to be relieved of duty. Scott suggested one John Bolton, a man highly recommended by Maj. Benjamin Tallmadge. (Little did Scott know that John Bolton was the code name for none other than Tallmadge.) A dedicated dragoon officer, Tallmadge had once lived in Brookhaven, Long Island, a fact that made him invaluable to Washington.

Chain of Correspondence. The young officer was entrusted with the correspondence of an individual named

Samuel Culper. Tallmadge apparently utilized his Long Island connections to establish a viable secret service. All the initial members of the Culper Ring were Tallmadge’s friends or neighbors prior to the war. Caleb Brewster, a blacksmith and lieutenant in the Continental Army; Austin Roe, a tavern keeper; and Abraham Woodhull (alias Samuel Culper), a prosperous farmer, all hailed from Setauket, Long Island. At this time, the British not only occupied Manhattan, but Staten Island, Westchester County, and Long Island as well. The chain of correspondence that developed was as follows: Woodhull would pay frequent visits to his sister, Mary, who with her husband ran the Underbill Boardinghouse on Queen Street in New York City. There, Woodhull would gather information concerning enemy troop movements, shipping, and supplies. When Roe came into the city on the pretense of buying goods for his tavern, Woodhull would pass him this information. When Roe returned to Setauket, he would give the dispatches to Brewster. In 1779 Woodhull returned to his Long Island farm; his place in New York was taken by Robert Townsend, alias Samuel Culper, Junior. Townsend would pass the information to Roe, who would bury the secret messages in a meadow near Woodhull’s home. They were hidden there until Woodhull observed a black petticoat hanging on the clothesline of Anna Strong (whose sister was Tallmadge’s stepmother). The Strong residence commanded a panoramic view of nearby Setauket Harbor, and the black petticoat indicated that Brewster had crossed Long Island Sound from Connecticut in a whaleboat. The number of handkerchiefs hanging next to the petticoat indicated at which inlet Brewster waited. Woodhull

would then retrieve the intelligence and bring it to the lieutenant, who would recross the Sound, land at Fair-field, Connecticut, and deliver the information to Tallmadge, who would dispatch dragoon couriers to carry the news to Washington.

Frayed Nerves. This undercover operation worked in absolute secrecy, supplying the American commander in chief with accurate intelligence. Nevertheless, Samuel Culper, Senior feared capture on a daily basis, and in April 1779 he had a severe fright when two female relatives burst into his room while he was composing a secret message. (British officers occupied the adjacent quarters.) Tallmadge reported to Washington that “such an excessive fright and so great a turbulence of passions so wrought on poor C. that he has hardly been in tolerable health since.”

Culper Junior. In June, Woodhull requested to be relieved of his duties in the city; he found a trustworthy replacement in Townsend. A young Quaker merchant from Oyster Bay, Long Island, he made Woodhull pledge to never reveal his identity. (Apparently Wood-hull did tell Tallmadge.) Culper Junior proved to be a most enterprising spy. In order to conceal his activities, he opened a dry goods business with Henry Oakman and occasionally contributed articles to James Rivington’s Tory newspaper, the Royal Gazette. Rivington’s printing house and coffee shop afforded Townsend the opportunity to mingle with British officers, especially Maj. John Andre. As the newly appointed adjutant general to General Sir Henry Clinton, Andre coordinated British intelligence-gathering efforts.

More Contacts. By October 1779 the Culpers employed a whole crew of seemingly innocent civilians. Joseph Lawrence, whose son married Townsend’s niece, helped the spies on several occasions. James Townsend, a younger cousin of Culper Junior, once carried a message across the Hudson River to Washington’s headquarters. Sarah Townsend frequently provided her brother Robert with information obtained from conversations with enemy officers staying at the Townsend house. Meanwhile, Hercules Mulligan, a prominent tailor, sent reports on troop movements. An unidentified woman simply known as 355 also supplied the Culpers with information.

Code. In order to transmit messages, Tallmadge in July 1779 devised a code based on John Entick’s New Latin and English Dictionary (1771). He made only four copies of the code book, keeping one for himself and giving the others to Washington and the Culpers. Words that were most apt to be utilized in secret correspondence were assigned numbers. However, Tallmadge inadvertently numbered the words in nearly alphabetical order and with little variation (they, 629; there, 630; thing, 631). As a result, words beginning with a, b, or c had low numbers while words beginning with x, y or z had high numbers. The code could have been easily broken but fortunately this never occurred. Proper names also received numbers: 711 (Washington), 712 (Clinton), 721 (Bolton), 722 (Culper Senior), 723 (Culper Junior), 724 (Roe), 725 (Brewster), and 726 (Rivington).

Invisible Ink. More important than the code was an invisible ink developed by James and John (future chief justice of the U.S. Supreme Court) Jay before the war. Called “white ink” or “stain,” its exact composition is un-known. James Jay claimed that “if one writes on the whitest paper, the letters immediately become invisible.” In order to become legible the writing needed to be brushed with a “sympathetic” developer. The Culpers wrote invisible dispatches on preselected sheets in a ream of paper and on the leaves of pamphlets, registers, and almanacs. Even private correspondence was a practical vehicle for secret information: stained messages were written between the lines, at the end of the letter, or on the reverse side.

Valuable Information. The Culper network may have passed along valuable information to the American army, but it was usually a slow process. The distance from Manhattan to Setauket is fifty miles. In summer 1779 Culper Junior warned of an imminent attack upon the French army at Newport, Rhode Island. Information supplied through Culper Senior enabled Tallmadge and one hundred dragoons to raid Fort St. George on South Bay, Long Island, in November 1780.

The Arnold Conspiracy. The treason of American general Benedict Arnold and the subsequent execution of Andre involve the most perplexing secrets of the Culper espionage network. Tallmadge in his Memoir (1858) stated that he purposely omitted “some things relating to the detention of André.” What these “things” are will never be known, but evidence suggests Sarah Townsend had overheard Andre at her house mention West Point (a post commanded by Arnold) in a conversation with another officer. On 23 September 1780 an American patrol captured Andre in Westchester County with the plans of West Point. After Arnold fled to the enemy, the members of the ring scattered for several weeks, but in November several of them were imprisoned and questioned by British authorities.

Other Close Calls. Aside from the Arnold-Andre affair, the Culper Ring was almost exposed on several other occasions. In a skirmish with enemy cavalry Tallin adge lost some Washington missives addressed to the Culpers. British sentries searched Woodhull at the Brooklyn ferry in May 1781 because “some villain” was carrying messages out of the city and to the American army. Brewster’s frequent trips across Long Island Sound attracted the attention of the enemy from the start, but all attempts to capture him proved fruitless.

End of Service. When hostilities ceased in 1783, the need for the Culper Ring came to an end. Washington had a high opinion of the Culpers but never met either man. Although he knew Culper Senior’s real name, Tallin adge and Woodhull kept Culper Junior’s identity a secret. In fact, Culper Junior’s identity was not revealed until 1939, when the Long Island historian Morton Pennypacker noticed a fascinating resemblance between the handwriting of Culper Junior and Robert Townsend. Tallmadge and the Culpers had no desire for public recognition and never publicly discussed their activities during the war.

Sources

Corey Ford, A Peculiar Service (Boston: Little, Brown, 1965);

Memoir of Colonel Benjamin Tallmadge (New York: Thomas Holman, 1858);

Morton Pennypacker, General Washington’s Spies on Long Island and in New York, 2 volumes (Volume 1, Brooklyn, N.Y.: Long Island Historical Society, 1939; Volume 2, East Hampton, N.Y.: East Hampton Free Library, 1948);

Carl Van Doren, Secret History of the American Revolution (New York: Viking, 1941).