Tallmadge, André, and the Treachery of Benedict Arnold
“André was a most delectable Companion. It often drew tears from my Eyes to find him so pleasant & agreeable in Conversation on different Subjects, when I reflected on his future fate, & that too, as I believed, so near at hand.”
With those words, Setauket native Benjamin Tallmadge recalled his conflicted emotions during the final days of British officer and captured spy Major John André.
Early Life on Long Island
From the North Shore of Brookhaven, Benjamin Tallmadge was the oldest of five sons born to Rev. Benjamin Tallmadge and his wife, Susannah. Schooled in Latin and Greek by his father, young Benjamin was sent to Yale University at the age of fifteen. There, he became close friends with classmate Nathan Hale, later immortalized as one of the first American martyrs of the Revolutionary War.
Tallmadge graduated from Yale in 1773 and for a short period worked as head schoolmaster in Wethersfield, Connecticut. But the gunfire at Lexington and Concord in 1775 ended his teaching career. Like so many of his generation, he answered the call to arms, joining the Continental Army as a junior officer.
This young man, who had grown up along the shores of Long Island Sound, would go on to emerge as one of General George Washington’s most trusted operatives.
Family Sacrifice
The Tallmadge family bore heavy burdens for the cause of independence. Benjamin fought at the disastrous Battle of Long Island in August 1776, narrowly escaping capture as Washington’s army retreated. His older brother William also served in the Continental ranks, but his fate was darker: he was captured and died aboard a British prison ship, one of thousands of Americans who succumbed to starvation and disease on the infamous hulks anchored in New York Harbor.
Tallmadge distinguished himself as a cavalry officer and was repeatedly promoted. One Connecticut soldier described him as “a large, strong, and powerful man, who rode a large bay horse which he took from the British. He was a brave officer, and there was no flinch in him. A man of few words, but determined and energetic, and what he said was to the purpose.”
He saw action at Brandywine and Germantown, and he helped guard Washington’s army at Valley Forge by patrolling with his dragoons.
The Birth of American Intelligence
In 1778, Washington appointed Tallmadge as head of his intelligence operations. Out of this grew the Culper Spy Ring, centered in Setauket and New York City. Abraham Woodhull, Caleb Brewster, Anna Strong, and Austin Roe formed the backbone of this clandestine network. Their mission: to blend into everyday colonial life, gather information in occupied New York, and relay it across Long Island Sound to Tallmadge in Connecticut.
Tallmadge operated under the code name “John Bolton,” while Woodhull assumed the identity of “Samuel Culper.” Reports were encoded with numbers, phrases, and invisible ink. To the outside world, these men and women were ordinary civilians. In reality, they were risking their lives to feed Washington intelligence that often shaped the course of campaigns.
Tallmadge later admitted, in understated fashion, that his wartime role was simply to “open a private correspondence with some person in New York (for General Washington) which lasted through the war.” In truth, he had pioneered one of the first organized espionage systems in American history.
Arnold’s Treachery and André’s Capture
By the late 1770s, British strategy focused on seizing the Hudson River corridor, hoping to cut off New England from the rest of the colonies. Into this context stepped Benedict Arnold. Though once one of Washington’s most celebrated commanders, Arnold had grown resentful over perceived slights and financial troubles. For more than a year, he negotiated with the British, demanding 20,000 pounds and a senior command in exchange for treason. Ultimately, he received only 6,000 pounds and the rank of colonel.
On September 21, 1780, Arnold met secretly with Major John André to finalize the betrayal of West Point, the crucial American fortress on the Hudson. But fate intervened. As André attempted to return to British lines, he was intercepted by militia and later delivered to Tallmadge’s 2nd Regiment of Light Dragoons.
Though André initially claimed to be “John Anderson,” Tallmadge suspected otherwise. He withheld him from Arnold’s reach, fearing that the traitor might contrive André’s release. Soon André confessed: he was indeed a British intelligence officer working directly under General Henry Clinton.
Meanwhile, Arnold, realizing his plot had unraveled, fled to the British ship Vulture. He urged the American soldiers accompanying him to defect, offering commissions in the British army. They refused and were taken prisoner instead.
Tallmadge and André: A Human Bond
Tallmadge, hardened by years of war and the loss of his brother, nonetheless felt conflicted. André was cultured, charming, and by all appearances a man of honor. As the two spent time together, Tallmadge began to see him as more than just an enemy.
Riding toward Tappan, New York, Tallmadge reminded André of Nathan Hale, his college friend executed by the British for spying. André rejected the comparison, but Tallmadge replied bluntly: “Precisely similar, and so will be your fate.”
Yet, privately, he admitted his sympathy: “Head was at fault, & not his heart.”
Washington’s Dilemma
Washington faced a grave choice. He proposed exchanging André for Arnold, but Clinton refused, unwilling to surrender the man who had betrayed his country. Clinton threatened reprisals if André were executed, but Washington doubted the British would follow through, especially since the Americans held numerous prisoners.
For two days, Washington’s senior generals debated. Led by Nathanael Greene, they unanimously declared André guilty of espionage. André requested to die by firing squad, the death of a soldier, but Washington refused. On October 2, 1780, before a grieving crowd, Major John André was hanged as a spy.
Tallmadge escorted him from Mabie’s Tavern to the gallows. “I walked with him to the place of execution,” he later recalled, “and parted with him under the gallows, entirely overwhelmed with Grief, that so gallant an officer, & so accomplished a Gentleman should come to such an ignominious End.”
Alexander Hamilton, too, mourned. Writing anonymously, he insisted that while André’s execution was justified, “never perhaps did any man suffer death with more justice or deserve it less.”
André was first buried at Tappan, near West Point. In 1821, his remains were returned to England.
Arnold the Outcast
Arnold’s fate was far less noble. Though granted a commission in the British army, he was never fully trusted. He led destructive raids on Richmond, Virginia, and New London, Connecticut, burning towns and slaughtering defenders.
After the war, he and his wife Peggy Shippen moved between London and Canada. His business ventures failed, his reputation never recovered, and he died in London in 1801, reviled on both sides of the Atlantic.
Tallmadge After the War
Tallmadge returned to Connecticut, marrying Mary Floyd of Mastic, Long Island, and raising seven children. He entered politics, serving as a Federalist congressman from 1800 to 1817. He later became postmaster and president of the Phoenix Bank. Despite his prominence, he rarely spoke publicly of his espionage work, preferring to let his deeds rest in secrecy.
Legacy
The intertwined fates of Tallmadge, André, and Arnold reveal much about the Revolutionary era. Tallmadge embodied loyalty, discipline, and sacrifice; André, charm and tragedy; Arnold, ambition turned treachery. Their story continues to fascinate because it reminds us that war is not only a clash of armies but also of choices—some heroic, some dishonorable, and some profoundly human.
Tallmadge, who once confessed he wept for an enemy, reminds us that even in a brutal war, compassion and grief found a place alongside duty.