According to popular lore, a woman spy known only as Agent 355 helped George Washington win the American Revolution, serving as a key member of the Manhattan-Long Island intelligence network later dubbed the Culper Spy Ring.
There’s just one problem with this story: No proof of 355’s adventures in espionage actually exists. The sole 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.” Unfortunately, this lack of evidence hasn’t stopped authors and television and movie producers from inventing tales of her exploits. From a pair of 1930s books by historian Morton Pennypacker to the recent Jessica Chastain movie The 355, the legend of the woman agent represents a cautionary tale of how speculation and myth can permeate American history and become almost impossible to eradicate.
Historians may never be able to “determine the name of the lady mentioned or how much assistance she provided, but just knowing she existed, and that a woman could possess such indispensable skills, sets everyone’s imagination on fire,” says Claire Bellerjeau, the former historian at the Raynham Hall Museum—onetime home of Culper spy Robert Townsend—in Oyster Bay, Long Island.
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.