New Research

This Connecticut Teenager Spied on the British During the American Revolution, Succeeding Where Nathan Hale Failed

Newly uncovered documents reveal the story of David Maltbie, who relayed intelligence to the patriots in 1776, narrowly avoiding execution as a spy

Claire Bellerjeau and Tiffany Yecke Brooks

August 17, 2026 7:45 a.m.

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Nathan Hale, the young man from Connecticut who famously volunteered to spy for George Washington in September 1776, has gone down in history for his supposed final words: “I only regret that I have but one life to lose for my country.” Captured and hanged just days into his mission, Hale serves as an example of both the bravery and the tragedy of patriotic sacrifice, despite the fact that he probably never said the line famously attributed to him.

But few Americans know that a second spy from Connecticut, David Maltbie, took on the same mission as Hale around the very same time, succeeding where his better-known counterpart failed.

Letters uncovered at the Center for Brooklyn History by one of the authors of this article, historian Claire Bellerjeau, brought to light this lost story. The missives came to light in the course of researching the connection between a different spy, Robert Townsend, and an enslaved woman named Liss, or Elizabeth. In 1846, Townsend’s brother-in-law Ebenezer Seeley, acting on behalf of historian Henry Onderdonk Jr., interviewed an elderly woman who’d known Maltbie as a young girl. Onderdonk’s papers contained a letter detailing the long-overlooked narrative.

Alexander Rose, author of Washington’s Spies: The Story of America’s First Spy Ring, says that Maltbie’s story is significant “because it helps reveal the extent of Washington’s intelligence efforts in the early stages of the war.” Lesser-known spies like Maltbie, “almost without exception … were untrained volunteers lacking any support or logistics structure when they were behind enemy lines,” Rose adds. Their collective experiences and repeated failures “vividly demonstrated to Washington that he needed to somehow build a long-term, viable network of civilian agents in New York and on Long Island.”

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After the Continental Army suffered a demoralizing defeat at the Battle of Brooklyn in late August 1776, both New York City and Long Island fell under British control. They would remain in enemy hands for the rest of the war. Locals now carried out their daily business in occupied territory, with strict checkpoints in and out of town.

As the commander in chief of the Continental Army, Washington felt the blow keenly. Although the Americans controlled much of the upper Hudson River Valley, the Port of New York, with its strategic access to both inland waterways and Atlantic shipping routes, was one of the biggest prizes of the conflict. What was more, the dense forests and farmland of Long Island meant that the British Army had access to resources that would keep its soldiers well fed and well supplied for as long as they held the region.

From across Long Island Sound in Connecticut, patriot forces could just make out the New York shoreline—tantalizingly close but seemingly impossible to recapture.

That was why, less than a month after Washington evacuated his forces from Brookyln, the general commissioned a new unit under Colonel Thomas Knowlton. Known as Knowlton’s Rangers, these men sought to disguise themselves as ordinary citizens, collect intelligence and smuggle it across enemy lines without detection. Their ranks included Hale, who had served in the Seventh Connecticut Regiment under Colonel Charles Webb before being placed in command of his own regiment.

As 21-year-old Hale ventured into the Huntington area of Long Island, posing as a Dutch schoolteacher in search of work, 17-year-old Maltbie crossed the sound, arriving about seven miles west, in Oyster Bay. Using the same cover story as Hale, Maltbie sought employment as a teacher.

Under the guise of writing to friends back home, Maltbie sent letters outlining troop numbers and movements, gleaned from his own observations and conversations with locals. None of his letters have survived, so exactly how Maltbie was recruited and the manner in which his intelligence was delivered to Washington remain a mystery.

One interesting connection to Hale’s mission may, however, provide some insight. Hale’s onetime commander, Webb, was from Stamford, Connecticut, just like Maltbie. The Webb and Maltbie families were deeply connected through marriage: Maltbie’s stepfather was Webb’s cousin, and the spy’s wife, whom he married after the war, was Webb’s niece. Could Washington’s call for volunteer spies have reached Webb via Knowlton and sparked Maltbie’s recruitment? Perhaps the intelligence flowed through the Webb family connection and ultimately back to Washington.

Whatever the case, Maltbie managed to maintain a low profile in Oyster Bay, even as Hale blew his cover almost immediately. As autumn inched toward winter and the troops stationed on Long Island began making billeting plans for the coming months, Maltbie grew more confident in an American invasion’s chances of success, if only Washington could spare enough soldiers. As Seeley wrote in his 1846 letter to Onderdonk, Maltbie apparently suggested that “500 men could easily dislodge the British here.”

With growing frequency, Maltbie handed off his letters to an old man by the name of Seely (whether he was related to Townsend’s brother-in-law is unclear), who delivered mail by rowing across the sound between Stamford and Oyster Bay. Seely eventually became suspicious of the sheer volume of one-way correspondence and decided to open one of Maltbie’s letters. He immediately recognized the note’s significance, as it contained clear, undeniable statements outlining the British position.

Unfortunately for Maltbie, Seely was a staunch loyalist. The old man took the dispatches straight to the British, who promptly ordered Maltbie’s arrest as a spy. The teenager tried to escape by boat before the authorities arrived, but he was captured on his way across the sound and inevitably found guilty in a swift trial.

Imprisoned in a makeshift guardhouse in the middle of Oyster Bay (located in an old building used to bake bread), Maltbie waited for his sentence of death by hanging to be carried out. In the days before his scheduled execution, he received regular visits from a 10- or 11-year-old girl named Elizabeth Wooden, whose father had been a friend of Maltbie’s before the war.

Because the jailers considered her too young to be of any concern, Wooden was able to bring food to the condemned spy. Seventy years later, she recounted these visits in response to inquiries about Hale, whose exploits would be discussed in an 1849 book by Onderdonk. Although Seeley found Wooden to be “entirely ignorant of [Hale’s] character and fate,” she offered to share her memories of a different spy: Maltbie.

According to Seeley’s letter to Onderdonk, Maltbie “broke out of his prison and escaped” a short time before he was due to be hanged. “He had been reprieved, though he knew not of it at the time of his escape,” Seeley wrote.

With Hale dead, Maltbie on the run and Knowlton killed in action at the Battle of Harlem Heights, Washington was once again faced with an intelligence vacuum in the region. He decided to create a network of agents, ensuring that one lost link wouldn’t doom the entire endeavor to failure. The Culper Spy Ring operated successfully on Long Island and in Manhattan between 1778 and 1783. Its agent in Manhattan, code-named “Samuel Culper Jr.,” was Townsend, a merchant originally from Oyster Bay, whose parents lived just around the corner from where Maltbie had been held prisoner.

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Maltbie’s efforts for the patriot cause didn’t end with his first spying expedition. On December 18, 1776, he joined the Continental Army’s Ninth Connecticut Regiment, although he only served for one month and five days. By 1781, Maltbie was the captain of a whaleboat crew, participating in daring raids that captured British vessels and seized valuable goods from Long Island loyalists.

Toward the war’s end, Maltbie apparently began collecting intelligence again in New York. On New Year’s Day in 1783, he was captured in Manhattan by the British “for robbery and on suspicion of being a spy.” The alleged theft involved Maltbie and Libbey Stigney, a female accomplice who had yet to be caught. The pair were accused of stealing goods from two Long Island men “in a violation of a solemn promise and breach of trust by collusion and under false pretenses,” according to court transcripts.

This time, Maltbie was locked in the infamous Provost, a British prison in lower Manhattan, to await his fate. Inmates held there were often beaten and shackled in crowded, unsanitary conditions, surviving on rations of spoiled food and filthy water.

Maltbie’s trial that February focused solely on the accusation of robbery. (The specifics of the espionage charge, as well as why it was dismissed before trial, remain unknown.) The 23-year-old testified in his own defense. Although his words don’t survive today, he must have been quite persuasive because he was acquitted and released. The Revolution ended six and a half months later, with the signing of the Treaty of Paris in September 1783.

Back in Connecticut in 1784, Maltbie sold an 80-ton schooner at auction, although it’s unclear how he obtained it in the first place. He married Nancy Davenport in 1786; together, they had at least seven children between 1789 and 1802.

By 1791, Maltbie had established himself as a seller of animal skins and furs. In 1795, he was elected to represent Stamford in the Connecticut legislature. Two years later, he served as a justice of the peace for the city alongside Colonel Webb. Maltbie died in 1807 at age 48 and is buried in Stamford’s North Street Cemetery.

Despite his success as a spy on a mission that is more famous for its failure, Maltbie’s name and story haven’t been memorialized in the same way as Hale’s. Margo Williams, Maltbie’s fifth-great-great-niece, only learned of her ancestor’s wartime mission while conducting research for her application to the Daughters of the American Revolution. After finding a mention of Maltbie in our 2021 book, Espionage and Enslavement in the Revolution: The True Story of Robert Townsend and Elizabeth, she emailed us directly.

Makematic - The Culper Spy Ring

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Williams says that the resurfacing of Maltbie’s story is “nothing short of electrifying.” Even within her own family, she notes, knowledge of his espionage during the Revolution “had been lost over time and was unknown.”

Maltbie’s “story can teach us all about the values this nation was founded on and self-sacrifice for a cause greater than us,” Williams adds. “It is important to celebrate stories like his and remember that this nation was founded on the backs of everyday men and women to whom we owe a great debt.”

Bill Bleyer, author of George Washington’s Long Island Spy Ring, agrees that the new research is significant. As he says, “New information about the Revolution and the actions of Nathan Hale and the lesser-known but luckier Long Island spy David Maltbie broadens our understanding of the conflict and its implications.”

Just as William Dawes and Samuel Prescott, two patriots who sounded the alarm on the same night as Paul Revere, aren’t household names, Maltbie is a figure whose achievements have been overshadowed by a more famous but ironically less successful spy. Yet his is a name that should be known as a model of courage, patriotism and just enough derring-do to represent the very best of what launched the great American experiment 250 years ago.

Once forgotten, except in the recollections of a young girl, Maltbie’s wartime espionage reminds us that more founding figures are waiting to be restored to the annals of history.

Claire Bellerjeau is the co-author of Espionage and Enslavement in the Revolution: The True Story of Robert Townsend and Elizabeth, published in May 2021. In 2022, she co-founded a nonprofit organization called Remember Liss, with the mission of educating the community about Liss’ extraordinary life and times. Through the nonprofit, she co-wrote and published a student version of Liss’ story, titled Remember Liss, in March 2023. She has been researching the Townsend family and those they enslaved for over 20 years and works with teachers to develop curriculums to share Liss’ story, using primary documents from her research.

Tiffany Yecke Brooks  holds a PhD in American and dramatic literature from Florida State University and has spoken and published widely on early portrayals of race in trans-Atlantic performance, as well as the emerging American identity in the late 18th and early 19th centuries. She currently teaches nonfiction writing at the Gaylord College of Journalism and Mass Communication at the University of Oklahoma and has written or co-written a number of books, including Espionage and Enslavement in the Revolution and Remember Liss.