Benjamin Tallmadge was a hero of the Revolution credited with establishing a sophisticated spy ring that was critical in America’s fight for independence. He exemplified an unspoken spycraft ethos of courageousness and honor that is still upheld today.
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Benjamin Tallmadge was born in 1754 on Long Island, New York, which was then still a British colony. He entered Yale College at the age of 15, where he befriended classmate and future spy volunteer Nathan Hale.
After graduating in 1773, Tallmadge served as superintendent of a high school in Wethersfield, Connecticut. Around this time, colonists’ disagreements with the British government had gone from strong words to acts of defiance, culminating in the opening gunfire of the Battles of Lexington and Concord on April 19, 1775—the start of the Revolutionary War.
The initial battles and the British oppression Tallmadge witnessed galvanized him with patriotic zeal to fight for his homeland’s independence. When a friend and Colonel in the local militia in Wethersfield offered him the position of aide-de-camp, he wrote, “I was gratified by this offer from my friend, and decided at once to lay aside my books.” He was commissioned on June 20, 1776.
Taking up arms against the most powerful country in the world was not for the faint of heart. The battles Tallmadge fought were brutal, and he experienced deep personal losses. That August, his brother starved to death on a British prison ship in New York Harbor after being captured in Brooklyn. A month later, the British caught and executed Hale for spying.
Artwork that depicts Nathan Hale on September 22, 1776 giving his last words. [Yale University Art Gallery]
By the end of 1776, General George Washington appointed Tallmadge to the 2nd Regiment of Light Dragoons, which was composed of the Continental Army’s premier cavalrymen. His orders were to go to the outskirts of the colonies’ then-capital of Philadelphia—which was occupied by the British—to lead a unit in conducting reconnaissance and intelligence collection.
Tallmadge quickly began recruiting and managing assets who were sympathetic to the American cause. In 1777, he was meeting with a young informant who had recently traveled from Philadelphia when Tallmadge saw the enemy advancing toward them on horseback at full-speed. He mounted his horse to escape, later recalling: “I found the young damsel close by my side, entreating that I would protect her. Having not a moment to reflect, I desired her to mount behind me, and in this way I brought her off more than three miles.”
During their sprint to safety, Tallmadge returned pistol fire, demonstrating that an intelligence officer’s solemn responsibility to protect a clandestine source was just as important as collecting information.
An illustration depicting Benjamin Tallmadge rescuing “the country girl,” his clandestine source, from British soldiers in close pursuit. Their dramatic horseback escape covered several miles before he brought her to safety.
Perhaps Tallmadge’s greatest challenge came in 1778 when General Washington appointed him to be his new intelligence chief. His task was to organize a spy network to operate in and around New York City—where the British military was headquartered—because Washington had little to no insight into the enemy’s plans or intentions.
Tallmadge understood that security and counterintelligence were paramount to achieving his mission. He reached out to childhood friends on Long Island and recruited them to work together, covertly, against the British. None had spied before, but they had known each other a long time and enjoyed a circle of trust. They became known as the Culper Ring—a crucial spy network during the war for independence that remains largely unknown to this day.
In addition to his intelligence role, Tallmadge was accomplished in his military service. On November 23, 1780, he led a raid behind enemy lines on Long Island to destroy Fort St. George, which served as a refuge for colonists loyal to British rule. He and 80 members of his military unit moved so quietly across the island that they took the Fort’s sentry by surprise. After a brief firefight, Tallmadge’s force seized the Fort, destroyed the structure and its stores, and captured 54 prisoners. The British suffered seven dead in the battle while only one of Tallmadge’s men was wounded.
In 1783, Britain was ready for peace and agreed to recognize America’s sovereignty. Once the war was over, Tallmadge rode into New York with the Dragoons to publicly restore the reputation of his spies and arrange for their protection. After all, this clandestine network was vulnerable to both sides. The spies were so successful pretending to be loyal to the British Crown in order to extract intelligence during the war effort that their fellow patriots viewed them with suspicion; meanwhile the actual Loyalists wanted vengeance for their side’s loss.
Tallmadge looked after his spy network, as always.
Benjamin Tallmadge portrait in his later years
In his later years, he reflected on the "Divine protection" bestowed upon him throughout his life. Despite all of the dangers he faced in military battles, gathering intelligence, and engaging in counterintelligence operations, he was never seriously wounded. Just as importantly, he wrote that, “I am not conscious that any man ever thought me to be a coward.”
Tallmadge passed away in his home in Litchfield, Connecticut in 1835. He was 82 years old.
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For more information on Benjamin’s Tallmadge’s life and work, his memoir (published after his death) is available digitally, here.