Did an Enslaved Woman Try to Warn the Americans of Benedict Arnold’s Treason?

New research sheds light on Liss, who was enslaved by the family of a Culper Spy Ring leader and had ties to British spymaster John André

Illustration of Liss
As recent archival finds and reappraisals of well-known documents show, Liss forged her own path to freedom—and may have even spied on the British while doing so. Illustration by Lindsey Levine / Collection of Claire Bellerjeau

In the early morning hours of September 23, 1780, three American militiamen captured the dashing British spymaster John André near Tarrytown, New York. They searched the major, finding maps and incriminating papers in his boots. The plot—a conspiracy by André and American Major General Benedict Arnold, commander of Fort West Point, to surrender the military garrison to the British—quickly unraveled from there, with Arnold abandoning his command to flee to the British side and the Patriots maintaining control of this key fort along the Hudson River.

According to legend, Sally Townsend, the younger sister of Robert Townsend, a member of the Culper Spy Ring, foiled the plot after overhearing André and British commander John Graves Simcoe discussing it at her family’s house in Oyster Bay, Long Island. (At the time, Long Island was under British control, and many families, including the Townsends, were forced to host enemy soldiers in their homes.) The earliest accounts naming Sally can all be traced to local historian Morton Pennypacker, who wrote about the Patriot intelligence network in the 1930s. But the actual historical record bears no evidence of the story whatsoever. In fact, André wasn’t even in Oyster Bay at the time of the alleged reveal.

Nonetheless, two historical markers corroborate the tale: one outside the Townsend home, which claims that “information from here [led] to Major André’s capture,” and another near Sally’s grave describing her role as “instrumental.”

The Raynham Hall Museum
Today, the Townsend family's Oyster Bay home is known as the Raynham Hall Museum. Idoysterbay via Wikimedia Commons under CC BY 3.0

“Pennypacker did groundbreaking research, providing us with most of what we know about the participants and operation of the Culper Spy Ring,” says Bill Bleyer, author of George Washington’s Long Island Spy Ring. “Unfortunately, his books, which lack footnotes, include unsubstantiated legends recounted as fact, and those myths have proven difficult to eradicate.”

Pennypacker and later historians promoted the fabricated narrative in books, some of which are still used in classrooms today. Like most legends, the story appears to contain a grain of truth. But the actual events are far more compelling, and even more relevant to modern discussions about reexamining the historical record. While Sally was certainly acquainted with Simcoe, so were several other young women in the Townsend household, including Liss, an enslaved Black woman then about 17 years old. As recent archival finds and reappraisals of well-known documents show, Liss forged her own path to freedom—and may have even spied on the British while doing so.

On September 29, barely one week after André’s arrest, Congress ordered the publication of a pamphlet containing letters that laid out the evidence against him and explained why it was necessary to hang him for espionage. André was so admired, by the British and the Americans alike, that the government felt the need to publish a document justifying its capture and execution of a high-ranking enemy officer.

Housed at the East Hampton Library in New York, a surviving copy of this pamphlet features marginalia added in 1798 by John Lyon Gardiner, who as a child witnessed an August 20, 1780, meeting between André, Simcoe and Henry Clinton (the British commander-in-chief in America). His eyewitness accountnow transcribed accurately for the first time—served as the basis for Pennypacker’s connection of Sally to the treason plot and adds an interesting coda to the official accounts printed in the document.

Self-portrait by John André, drawn on the eve of his execution in 1780
Self-portrait by John André, drawn on the eve of his execution in 1780 Public domain via Wikimedia Commons

The meeting took place at Colonel Abraham Gardiner’s house, which served as the British headquarters in the town of East Hampton. The colonel had served in the British army before the war but sided with the Americans when the revolution began. Ultimately, however, he signed an oath to the king in order to protect his estate. Much of Abraham’s household had been evacuated to Connecticut following the British takeover of Long Island four years earlier, but his nephew John, the 10-year-old heir to Gardiners Island and his family’s vast fortune, lived at the estate in relative isolation, under the care of his aunt and uncle and several people enslaved by the family.

Gardiner’s recollections describe how a “woman who lived at [Abraham’s house] heard (in passing through a room) Major André say that if he must go he would, but he did not expect ever to return. It was supposed to refer to his going to West Point.” (Zell, the only enslaved woman listed in Abraham’s ownership in his 1782 will, is a promising candidate for this first eavesdropper.) A second woman then passed the news on to Gardiner’s aunt: “A woman, waitress or perhaps Mistress to Col. Simcoe said to told Mrs. G[ardiner], the Col.’s wife, that one of your ‘forts is to be delivered up to us soon by one of your Generals’ & that it was not N[ew] London nor _______.’” (He leaves a blank in his account here.)

A few days later, Abraham’s wife, Mary Smith Gardiner, had the opportunity to share this news with one of George Washington’s officers, Major John Davis, who had secretly come into town. Gardiner notes that his aunt “was on the point of mentioning to Major Davis what the woman told her but by some means or other, did not. She thought it might be only the woman’s foolish talk.”

Several details stand out in this account. The first is that the two women, identified by both Gardiner’s descendants and Pennypacker as “servants,” were almost certainly enslaved women of color. The woman who initially overheard the discussion is described as “passing through a room.” That the conference carried on as she did so indicates she wasn’t an individual of social standing, but rather someone who entered the room and was deemed unimportant enough for the conversation to come to a halt. Neither of the women who knew of the plot are named in the narrative, as is often the case in the rare instances when enslaved people are cited in the historical record at all.

Benedict Arnold (left) and John Graves Simcoe (right)
Benedict Arnold (left) and John Graves Simcoe (right) Public domain via Wikimedia Commons

When Pennypacker transcribed Gardiner’s marginalia, he quoted it incompletely, leaving out the word “waitress ” in describing the second woman who warned Mary. Conversely, in Gardiner family transcriptions, “Mistress” is omitted. By keeping in the word “Mistress,” Pennypacker may have wanted to emphasize a romantic link between Simcoe and Sally, whom he’d given a Valentine’s Day poem in 1779, while he was billeting at her house. Because Sally would never have been identified as a “waitress,” Pennypacker conveniently dropped the word. On the other hand, the Gardiners, who never attempted to identify the woman, may have chosen to omit the word “Mistress” out of a sense of propriety.

“The note on this pamphlet is really a lesson on the unreliable nature of transcriptions,” says Andrea Meyer, head of the Long Island Collection at the East Hampton Library, “since each transcription left out an important word used to identify Mrs. Gardiner’s source.”

Pennypacker’s impulse to acknowledge the contribution of a woman in the American story is laudable. Unfortunately, in doing so, he seems to have overlooked—or even intentionally ignored—clues that hinted the heroines of the story were likely two enslaved Black women. Instead, he aligned the story with an already familiar cast of characters, choosing to remain within the traditional mold of wealthy white landowners.

This story illustrates a pattern that is beginning to emerge as historical documents are reexamined with a fresh lens and a broader scope of considering who else was part of the narrative. For over 90 years, Pennypacker’s interpretation served as the basis for elevating Sally as an early American hero, despite the fact that she could not possibly have been either of the women involved. Now, the probable identification of these unsung heroes as enslaved Black women offers yet another reminder that diversity has been part of the complex tapestry of American history from the very beginning.

May 26, 1779 letter from Robert Townsend to his father, Samuel Townsend
May 26, 1779, letter from Robert Townsend to his father, Samuel Townsend Collection of the Friends of Raynham Hall Museum

A similar realigning of a long-accepted historical narrative took place in 2005, when Claire Bellerjeau, one of the co-authors of this article, was conducting research for an exhibition about slavery at Raynham Hall Museum, as the Townsend family home is known today. She realized that a letter in the collection referred not to a stolen cow, as had been believed for nearly 60 years, but to an enslaved woman named Liss, who escaped from the Townsends in 1779 with Simcoe’s help. (After the war, the British officer, who was morally opposed to slavery, served as lieutenant governor of Upper Canada and enacted the first laws ending the brutal institution in the colony.)

Written by Robert eight days after Simcoe left the Townsends’ home, the missive mentions the British regiment’s departure with the enigmatic Liss. “If I see any of the officers, will make inquiry for Liss – Tho’ I think there is no probability of your getting her again,” Robert told his father, adding, “I am surprised that Col. Simcoe would permit her to go.” Since earlier historians had no record of an individual of that name associated with the household and had yet to acknowledge the presence of enslaved people at the site, they simply assumed the letter referred a large, valuable female farm animal, probably a cow.

As part of her research, Bellerjeau asked staff at the East Hampton Library if they had any Townsend documents related to slavery in their collection. Sure enough, in a series of 1787 letters written to merchants in Charleston, South Carolina, Robert “request[ed] the favor of you to purchase a Wench named Elizabeth, sent from this place.” He described how the enslaved woman had been brought up in his father’s family and noted that during the war, she was “too fond of the British officers.” Elizabeth was later sold south without his knowledge, Robert added, before asking if the merchants would be willing to assist in repurchasing her so she could return to New York. Further research into family records confirmed Bellerjeau’s hunch that Liss was actually a nickname for Elizabeth.

This one simple shift in understanding introduced an entirely new story, unlocking a wealth of documents that chronicled Liss’ extraordinary life. Unraveling her struggle for freedom also led to a much fuller understanding of Robert, who joined an early anti-slavery movement after the war and is now known to be the “Culper, Jr.” of the famed spy ring.

Simcoe used the Townsend home as his headquarters in the winter of 1778 to 1779, while the elite regiment he commanded encamped in the town. In March 1779, his good friend André spent several weeks at the house, where he encountered the teenaged Liss as she performed her household duties. When the regiment departed Oyster Bay in May, Liss ran away with them. But she didn’t simply disappear.

The Townsends never ran a runaway ad about Liss in a New York newspaper. Indeed, Robert appears to have known exactly where she was. Not only did he write to his father to count her among “your other dead losses,” he also appears to have had some contact with her during the later war years, when she was enslaved in the household of an unnamed British officer in Manhattan. (Enslaved people who joined the Loyalist cause only gained their freedom at the end of the conflict.) Her name shows up several times in the logbooks for Robert’s store, with the spy apparently making various small purchases for her; it’s possible that he actually helped Liss escape in order to embed her as a mole in a British household. What’s more, Liss was in Manhattan during the same period in which the alleged “355”—a mysterious woman mentioned in a Culper spy letter whose identity has been the subject of more than 200 years of speculation—was supposedly helping the Culper spies, with a special ability to “outwit them all.”

The only known likeness of Robert Townsend
The only known likeness of Robert Townsend, sketched by his nephew Peter Townsend in 1813, when Robert was 60 years old, and pasted into Peter’s sketchbook Collection of the Friends of Raynham Hall Museum

Late in the spring of 1782, approximately 21 months after André’s capture, a pregnant Liss petitioned Robert to buy her so she wouldn’t have to leave with the evacuating British army. Robert agreed, paying his father £70 in compensation. Now living in Robert’s apartment, Liss gave birth to a son, Harry, whom Robert later described as biracial. Though impossible to know for sure, it’s plausible that Robert was the infant’s father.

When Harry was six months old, Robert, with Liss’ consent, sold them both to a recently widowed woman they knew, with the understanding that Liss and her son would never be resold to anyone other than Robert. In 1785, however, the widow married a man whose behavior toward Liss created conflict. After that marriage quickly dissolved, the husband resold Liss without Robert’s knowledge—and without her child—to Richard Palmes, a violent Charleston resident who was actually one of the instigators of the 1770 Boston Massacre. When Robert discovered Liss’ plight, he launched a monthslong quest to locate her, buy her back again and smuggle her home to New York—a move made necessary by recent legislation prohibiting the sale of enslaved people across state lines. Liss appears to have lived as a freewoman on Long Island upon her return and was counted as a paid servant in the 1790 census.

Sixteen years of research about Liss culminated in the 2021 book Espionage and Enslavement in the Revolution: The True Story of Robert Townsend and Elizabeth. But it was the 17th year that yielded even more knowledge of her life. Bellerjeau discovered her manumission (legal freedom) certificate from 1803 and the name of her mother (Pender). Additionally, Edward Blessing, head of user services and curator of published materials at the South Caroliniana Library, found a signed copy of an anti-slavery pamphlet that Robert gave to his father in 1787. “The fact that he presented it to his father—who was about to vote on legislation regarding manumission—provides insight into social and family dynamics, the use of the written word to stimulate and supplement discourse, and the shaping of anti-slavery sentiments in the Townsend household at a critical time in Liss’ story,” says Blessing.

Espionage and Enslavement in the Revolution: The True Story of Robert Townsend and Elizabeth

The inside story of Liss, an enslaved woman who may have spied on the British during the American Revolution

The other significant new puzzle piece was a reexamination of Gardiner’s account. Evidence, albeit highly circumstantial, points to the possibility that Liss might have been the “waitress, or perhaps Mistress,” of Simcoe, acting as a double agent and passing on crucial intelligence about the brewing treason plot, though the information was ultimately dismissed as “foolish talk.” Familiar with both Simcoe and André, Liss was living with a British officer in Manhattan when André made his quick trip to East Hampton. Could André have invited her to join him and see the man who had helped her escape the year before? Could Simcoe and Liss’ reunion have been affectionate enough to make her appear as a “Mistress” in the eyes of a child? And why would this unnamed woman in Gardiner’s account—an individual seemingly embedded with the British—have shared vital information of a possible treason plot that could change the course of the war? Whatever the case, Robert eventually went to great lengths to protect Liss, who was legally considered a fugitive from his family’s household.

Though the stories of the Arnold plot and Liss’ life may not be connected in characters, they are linked by the inescapable fact that they were both misunderstood and misinterpreted for decades by historians who failed to recognize the contributions of people of color. How many other familiar narratives might yield similar shifts in understanding upon reexamination? In many cases, the evidence is there. It’s just a matter of reconsideration. Expanding the canon of Founding Figures does not diminish the legacy of those already celebrated; instead, it recognizes the fact that even more brave individuals were willing to risk their lives, fortunes, and sacred honor for the great American experiment.

Claire Bellerjeau and Tiffany Yecke Brooks are the co-authors of Espionage and Enslavement in the Revolution: The True Story of Robert Townsend and Elizabeth (Lyons Press, 2021), as well as the upcoming middle-grades book Remember Liss, which they hope will find its way into classrooms across America to begin introducing a more inclusive interpretation of our country’s birth.

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