During the Battle of Long Island in August 1776, Washington, then commander-in-chief of the Continental Army, was repeatedly surprised by the British. He only escaped the destruction of his army thanks to fog, adverse winds that blocked the British fleet from cutting him off and the caution of British commander William Howe. Fresh off his near-defeat, the future president realized that his underdog army needed an intelligence operation to have any chance of successfully fighting one of the largest military powers in the world. After several fumbled attempts—most notably the fatal effort by the first American spy, Nathan Hale—Washington and his director of military intelligence, 24-year-old Major Benjamin Tallmadge, finally got it right in fall 1778 with the formation of the Culper Spy Ring.
Tallmadge recruited farmer Abraham Woodhull, his neighbor in the Long Island hamlet of Setauket, as the chief spy tasked with gathering intelligence in Manhattan. (Woodhull often traveled to the city to sell produce.) Setauket whaleboat captain Caleb Brewster, meanwhile, carried messages across Long Island Sound, between Setauket and Connecticut. From there, Tallmadge would convey them to Washington’s headquarters north of the city or in New Jersey. Later, when Woodhull became fearful of capture due to his frequent trips to the city, he asked Townsend, purchasing agent for a family mercantile business, to take over spying in Manhattan.
Significant people in the Culper Ring were not given names but rather numbers. This included people whose identities were not to be known by the enemy, especially spies. In the centuries since the American Revolution, authors have identified more than a dozen ongoing members of the spy ring. No evidence suggests that any of these individuals were women, though women would have certainly helped the spies out. Of the 193 surviving letters written by members of the ring, only one contains a reference to any woman. A coded letter from chief spy Woodhull to Washington, dated August 15, 1779, includes this sentence: “I intend to visit 727 [Culper code for New York] before long and think by the assistance of a 355 [lady in the code] of my acquaintance, shall be able to outwit them all.”
Alexander Rose, author of Washington’s Spies, the basis for the highly fictionalized AMC series “Turn,” is among several historians who believe that the 355 referenced in the letter was Anna Strong, a neighbor of Woodhull and the wife of Selah Strong, a patriot leader in Setauket. The problem is that there is no actual proof of 355’s existence beyond the one letter. While Anna Strong was clearly a supporter of and occasional participant in the espionage ring, in one case using her petticoats to communicate between Woodhull and Brewster, there is no indication that she actually participated in espionage or any other acts of war. In fact, there is no evidence that 355 is a real person. The only mention of her in the historical record simply states that she was a lady—not necessarily a spy—who could help the Patriots “outwit them all.”
However, the legend of 355 is a good story and continues to resonate today. Women took part in the struggle for freedom. In the past, too many times authors created romantic legends to represent women’s contributions. We don’t really need to make up and embellish women’s stories. We need to research and find the real stories that are out there waiting to be discovered.