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

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.” 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.