Who Was Agent 355?

Historians have tried to figure out the identity of a key member of Washington’s spy ring

George Washington well understood the need for spies. He learned firsthand during the run-up to the Seven Years’ War when the royal governor of Virginia sent the young major into French territory amid mounting tensions. British forces — with Washington among them — suffered a devastating defeat in that territory in 1754, in part because of insufficient knowledge of the enemy’s forces.

In 1776, eager to know more about British troops and plans, Washington sent Nathan Hale behind British lines in New York. Hale, though brave, was a terrible spy. He was captured by the British as he tried to return to his regiment and was hanged the following day without trial.

Washington’s next major foray into the spy business was much more successful: the Culper Ring, possibly named after an area of Virginia where Washington had done some surveying work. In one instance, the network tipped off Washington about British plans to counterfeit American money. Based on the information, Congress recalled currency that would have otherwise been devalued.

The Culpers also informed Washington of British plans to send troops from New York to Rhode Island to attack French forces there. And the Culpers played a role (though exactly what role is disputed) in foiling Benedict Arnold’s plan to turn over the fort at West Point to the British.

The American spies who gathered key intelligence from behind British lines in New York City and Long Island were understandably worried about keeping their identities secret. Most did not know more than one or two other members of the ring, and they referred to themselves by code names and numbers.

Maj. Benjamin Tallmadge, who was in charge of the operation and who reported directly to Washington, took the name John Bolton and the number 721. Abraham Woodhull, a Long Island businessman who used his regular business trips to Manhattan as cover, was Samuel Culper Sr. and 722. Robert Townsend, a partner in a coffee shop popular with British officers, was Samuel Culper Jr. and 723. Other members of the ring have also been identified.

The identity of one member remains a mystery. Woodhull referred to this person in an August 15, 1779, letter to Tallmadge. Woodhull was worried that British counterintelligence agents had learned of the ring’s activities and British soldiers might stop and search the American spies. But, Woodhull assured Tallmadge, “by the assistance of a 355 of my acquaintance,” they would “out wit them all.”

One clue as to the spy’s identity was the ring’s code book. It translated 355 not as a specific person but as “lady.” Perhaps “355” simply stood for “lady,” any lady. But that has not stopped historians from trying to identify a particular woman.

Some historians have made a case that 355 was Townsend’s lover and that she was arrested and imprisoned on a British prison ship. The key evidence, albeit circumstantial, is a November 1780 letter from Woodhull to Tallmadge. Woodhull informed Washington’s spy chief about the imprisonment of “one that hath been ever serviceable to this correspondence.” He added that this news left Townsend “dejected.”

In his 1948 book, the second volume of General Washington’s Spies on Long Island and in New York, Morton Pennypacker noted that Townsend’s son had lobbied in 1808 for a monument honoring the patriots who had died aboard British prison ships. This limited evidence was enough to convince Pennypacker that Townsend had been in love with 355.

Corey Ford, in his 1965 book, A Peculiar Service: A Narrative of Espionage in and Around New York During the American Revolution, waxed poetic about the love story and the spy story: “I like to picture 355 as the opposite of the reserved and sober young [Townsend]: small, pert, vivacious, clever enough to outwit the enemy, but feminine enough to give Townsend a brief interlude of happiness that he would never know again.”

Also speculative, though not quite so much so, is a 2009 article by John A. Burke and Andrea Meyer in New York Archives magazine. Burke and Meyer noted that the flow of Culper reports slowed when John André, the British spymaster, left New York in December 1779 for the siege of Charleston, and it picked up again in May 1780 when André returned. Burke and Meyer concluded 355 was a friend of André — or rather pretended to be a friend — in order to get information from him.

Part of the case for 355 being a friend of André is based on a careful reading of Woodhull’s letter about the “assistance of a 355.” In their 2013 book, George Washington’s Secret Six: The Spy Ring That Saved the American Revolution, Brian Kilmeade and Don Yaeger noted that Woodhull’s letter referred to “a 355,” or a lady. Kilmeade and Yaeger inferred Woodhull used “lady” rather than “woman” because 355 was from a prominent and probably Loyalist family in New York City. Her status would have enabled her to insinuate herself into British society and gain the trust of British officers like André.

Alexander Rose approached the mystery very differently in his 2006 book, Washington’s Spies: The Story of America’s First Spy Ring. Rose’s 355 was a Long Island woman named Anna Strong.

Strong had clear ties to the Culper Ring. Woodhull was Strong’s neighbor and a relative of her husband. Moreover, Strong’s husband was a known patriot.

Rose noted that in the August 1779 letter Woodhull mentioned 355 in the context of his worry about British soldiers stopping and searching suspected spies. Perhaps, Rose surmised, 355 had posed as Woodhull’s wife since the British might be less likely to suspect and search a woman, or a man traveling with a woman. Perhaps that was how she managed to “out wit them all.”

Rose was not the first historian to tie Strong to the Culpers. Pennypacker did not think Strong was 355, but he did credit her with playing a communication key role — hanging out the laundry. A black petticoat on the laundry line (which was visible to a boat on the Long Island Sound) signaled that Woodhull had information ready to be picked up. The number of handkerchiefs on the line signaled which landing place was safe.

Another member of the spy ring would then ferry the information across the sound to Tallmadge’s courier in Connecticut.

Rose’s position is satisfyingly concrete: his 355 was a real and specific person. Kenneth A. Daigler, in his 2014 book, Spies, Patriots, and Traitors: American Intelligence in the Revolutionary War, also posited that 355 was Strong.

Kilmeade and Yaeger initially dismissed Strong as a candidate since she had no ties to the British elite in Manhattan. Besides, her husband’s known patriot allegiance would have made her suspect in British eyes. But in the paperback edition of George Washington’s Secret Six, published in 2014, Kilmeade and Yaeger gave her a closer look and concluded, partly on the basis of persistent oral traditions, that Strong was a possibility.

A possibility is not, of course, a certainty. Kilmeade and Yaeger set forth six other possibilities besides Strong, of whom the most surprising was Benedict Arnold’s wife, Peggy Shippen Arnold (who certainly had connections to British society).

Maybe one day new evidence will emerge to identify 355 with certainty. Or maybe several women were part of the Culper Ring.

But, Kilmeade and Yaeger noted, even if 355 wasn’t one woman, several risked their lives, one was imprisoned, and “that heroism deserves to be honored.” 

Morton Pennypacker. General Washington’s Spies on Long Island and in New York. Brooklyn, New York: The Long Island Historical Society, 1939. This first volume of Pennypacker’s history includes his discovery that Culper Jr. was Townsend.

Morton Pennypacker. General Washington’s Spies on Long Island and in New York. East Hampton, New York: East Hampton Free Library, 1948. This second volume of Pennypacker’s history includes his speculation about 355 having Townsend’s child while on a British prison ship.

Corey Ford. A Peculiar Service. Boston: Little, Brown, 1965. Ford’s tendency to add elements of fiction renders his version of the story dubious (but entertaining).

Alexander Rose. Washington’s Spies: The Story of America’s First Spy Ring. New York: Bantam, 2006. The basis for AMC’s TURN, as well as the best documented study of the Culpers.

Kenneth A. Daigler. Spies, Patriots, and Traitors: American Intelligence in the Revolutionary War. Washington, D.C.: Georgetown University Press, 2014. As a CIA officer, Daigler had written a pamphlet for the agency about the founding fathers of American intelligence, so perhaps his support for Strong makes it a semi-official position.

Brian Kilmeade and Don Yaeger. George Washington’s Secret Six: The Spy Ring That Saved the American Revolution. New York: Sentinel, 2013. The paperback, published in 2014, includes a new afterword analyzing the case for seven possible women.