The Myth of Agent 355, the Woman Spy Who Supposedly Helped Win the Revolutionary War

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.

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. But that didn’t stop Pennypacker, the first person to fully identify the Culper spies and how they operated, from stating that one woman was a member. Some subsequent writers have followed Pennypacker’s lead, unquestioningly repeating the story and turning his unnamed female spy into Agent 355—a problematic framing not only due to the lack of evidence but also because the term agent wasn’t routinely applied to intelligence gatherers in that era. (Spy was the preferred name during the American Revolution.)

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.”

That one vague reference to a woman (371 is the code for man) has spawned a whole subgenre of the spy ring story. It started with Pennypacker, who proposed the existence of a female Culper spy, codenamed 355, who was also Townsend’s mistress. He suggested that she’d been arrested, imprisoned on the infamous British prison ship Jersey and given birth to Townsend’s illegitimate son onboard before dying.

Other writers picked up the story and further embellished it. Chief among them is Fox News co-host Brian Kilmeade, who lives on Long Island. In George Washington’s Secret Six: The Spy Ring That Saved The American Revolution, the 2013 bestseller he wrote with Don Yaeger, he names 355 as one of six members of the spy ring. (Kilmeade offers no explanation for his exclusion of widely accepted members like Brewster.)

Without documentation—Secret Six is not footnoted but does include a list of selected sources—Kilmeade places 355 in the social circle of British spymaster and legendary party-thrower John André. “One agent remains unidentified,” the book states. “Though her name cannot be verified, and many details about her life are unclear, her presence and her courage undoubtedly made a difference.”

In Kilmeade’s telling, 355 was “a young woman living a fashionable life in New York” who was somehow connected to Townsend. “Though of pro-American sentiments herself, she almost certainly would have been attached to a prominent Loyalist family,” the author argues. “... It is therefore possible that 355 was part of the glittering, giggling cluster of coquettes who flocked around [André] as he moved around the city.” According to Kilmeade, 355 even helped uncover Benedict Arnold’s treasonous plot to switch sides and turn over West Point to the British.

Why Pennypacker and Kilmeade attach their female spy to Townsend when the letters’ only mention of a lady is in connection with Woodhull is unclear. In both writers’ accounts, 355 is imprisoned on the Jersey. While Pennypacker has her dying there, Kilmeade gives her a chance of surviving the ordeal.

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. While she clearly would have been a supporter of and occasional participant in the espionage ring, Rose and like-minded historians do not turn Strong—the subject of another famous Culper myth, in which she signals Woodhull where to meet with Brewster by arranging a petticoat and handkerchiefs on her clothesline—into a spy.

Many current historians lend little weight to the Agent 355 theories. Former CIA case officer Kenneth Daigler, in his 2014 book Spies, Patriots, and Traitors: American Intelligence in the Revolutionary War, called it “a romantic myth” discredited in the mid-1990s.

Beverly Tyler, the historian at the Three Village Historical Society in Setauket, has studied the spy ring for decades. He emphasizes that the letters contain only one reference to a lady: “That is it. Everything else is made up—the whole business of Agent 355 and Robert Townsend.”

Tyler is fully convinced that Strong was 355. “She had relatives who were Loyalists in New York City and she portrayed herself as a Loyalist,” he explains. “During the war, as far as we can tell ... she accompanied Woodhull into New York City on occasion. Anna Strong was 355. She wasn’t Agent 355.”

Members of the spy ring “didn’t refer to each other as agents,” the historian adds, and the spies who did have code names were all numbered in the 700s. “Making up the word agent and tying it to the number 355 has no validity whatsoever.”

Bellerjeau disagrees that the woman helping Woodhull was Strong or anyone else in Setauket.

“There is actually no documentation of Anna Strong being involved with the Culpers. It’s just a myth. But even if it were true, what would be the special ability of a woman living in Setauket?” she asks. “All the valuable information was coming out of Manhattan.”

Instead, Bellerjeau suggests another possibility. Her research points to a woman named Elizabeth, or Liss, who was enslaved by Townsend’s family on Long Island. In May 1779, Liss escaped with the help of an abolitionist British colonel, but she was subsequently enslaved again in the city by an unknown individual. Around that same time, Townsend became the ring’s chief spy in Manhattan.

Based on archival research, Bellerjeau, who detailed her findings in the 2021 book Espionage and Enslavement in the Revolution: The True Story of Robert Townsend and Elizabeth, suggests that Liss may have been a mole in a British officer’s household. “Being enslaved gave Liss a real way to outwit the British,” says the historian. “She could move about unnoticed, and pass intelligence to Townsend.”

As to why Liss would want to help someone from the family that had enslaved her, Bellerjeau says that she and Townsend clearly had a connection. When Liss was sold to a brutal owner in Charleston, Townsend arranged to purchase her and return her to his family on Long Island, where she was eventually freed.

Reflecting on why the legend of 355 continues to resonate today, Bellerjeau says, “Women took part in the struggle for freedom. In the past, too many times authors created romantic legends to represent women’s contributions.”

Tyler adds, “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.”

Bill Bleyer | READ MORE

Retired Newsday reporter Bill Bleyer is the author of five books on Long Island history, including George Washington’s Long Island Spy Ring.