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Long IslandHistory

Leading the Charge: Benjamin Tallmadge, the revolutionary spy, soldier and hero from Setauket

Maj. Benjamin Tallmadge, who is pictured in this

Maj. Benjamin Tallmadge, who is pictured in this 1790 portrait with his son, William Smith Tallmadge, was chief of Gen. George Washington's secret service, leading the activities of Long Island's Culper Spy Ring. He also led a number of important whaleboat raids from Connecticut to Long Island.

This story first appeared in 1998 as part of "Long Island: Our Story"

Here is how William Patchin, a 19-year-old foot soldier from Connecticut, saw his commanding officer, Maj. Benjamin Tallmadge of Setauket:

He was a large, strong, and powerful man and rode a large bay horse which he took from the British. He was a brave officer, and there was no flinch in him. He was a man of few words, but decided and energetic, and what he said was to the purpose.

A confidant of Gen. George Washington, Benjamin Tallmadge was one of the most exceptional Long Islanders to come out of the Revolutionary War. Not only did he lead a number of important whaleboat raids from Connecticut to Long Island, he was chief of Washington's secret service. Also, his name will be forever linked with the British spy, Maj. John Andre, who was captured and hanged in connection with Benedict Arnold's treason.

This is quite a load to carry for a man who was only 22 when the Declaration of Independence was signed in 1776.

Descended from a line of Tallmadges who had their roots in England, he was born in Setauket Feb. 25, 1754, the son of a minister. By the time he entered Yale College at age 15, he already had learned Greek and Latin from private tutors. He was a classmate and friend of Nathan Hale's, and, like Hale, he became a schoolteacher in Connecticut. On June 20, 1776, he was appointed a lieutenant in the Connecticut militia.

Tallmadge was at the Battle of Long Island on Aug. 27, where his brother William was captured, later to die of starvation in a British prison. By the following April, Tallmadge had risen to the rank of major. He was, as he later put it, "full of ambition and panting for glory."

After one battle near Philadelphia in late 1777, the handsome 23-year-old major rescued a damsel in distress whom he had met at a roadside tavern called the "Rising Sun." He relates the story in his "Memoir of Colonel Benjamin Tallmadge":

After we had made ourselves known to each other, and while she was communicating some intelligence to me, I was informed that the British light horse were advancing. Stepping to the door, I saw them at full speed chasing in my patrols, one of whom they took. I immediately mounted, when 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 up to Germantown, where she dismounted. During the whole ride, although there was considerable firing of pistols, and not a little wheeling and charging, she remained unmoved, and never once complained of fear after she mounted my horse. I was delighted with this transaction, and received many compliments from those who became acquainted with it.

But Tallmadge had more serious business ahead of him. Washington chose him as his chief of secret service, and as such he led the activities of Long Island's Culper Spy Ring. At the same time, he led attacks on Fort Franklin at Lloyd's Neck, Fort St. George at Mastic, and Fort Slongo at what is now Fort Salonga.

Tallmadge played a key role in the capture of the 30-year-old Maj. Andre in the affair of the turncoat Benedict Arnold in 1780. Arnold, who had taken command of West Point, conspired to surrender it to the British. The London-born Andre, a charming and personable man to whom both men and women were attracted, was chief of intelligence for the British, and an excellent officer. Tallmadge, too, would come under his spell.

On Sept. 23, 1780, after a secret meeting with Arnold behind American lines in Westchester County, Andre -- who was using the alias "John Anderson" -- was captured by three militiamen. He was taken to North Castle, where Lt. Col. John Jameson was in command of American troops. After Andre produced papers signed by Arnold, Jameson sent him on his way to West Point.

Tallmadge, who was operating out of North Castle, arrived later in the day and suspected foul play. Though he was Jameson's subordinate, he managed to have troops go out and bring "John Anderson" back. Andre revealed his true identity. Although Arnold got away, Andre, after a trial, was hanged as a spy at Tappan, N.Y., on Oct. 2, 1780.

In the days following Andre's capture and leading up to his execution, Tallmadge found himself drawn closer and closer to the major, finding him "a most elegant and accomplished gentleman." In his memoir, he explained his feelings further:

For the few days of intimate intercourse I had with him ... I became so deeply attached to Major Andre, that I can remember no instance where my affections were so fully absorbed in any man. When I saw him swirling under the gibbet, it seemed for a time as if I could not support it. All the spectators seemed to be overwhelmed by the affecting spectacle, and many were suffused in tears.

But quickly, Tallmadge was thrust back into the turmoil of war, and three years later it was officially over. In 1784 Tallmadge married Mary Floyd, daughter of William Floyd of Mastic. He became a businessman in Litchfield, Conn., and then served from 1801 to 1817 in Congress. He married Maria Hallet of New York after the death of his first wife, and he died in 1835.

At age 23, Tallmadge was panting for glory. When he died at age 81, he was covered in it.


It was not just damsels in distress that Benjamin Tallmadge liked to rescue when the bullets began to fly. His horse got the same treatment.

One of the last men to escape on the boats that ferried the Americans safely across the East River after the failed Battle of Long Island in August, 1776, Tallmadge had left his horse tied to a post at the ferry in Brooklyn. But then he had second thoughts, as he related in his memoir:

The troops having now all safely reached New York, and the fog continuing as thick as ever, I began to think of my favorite horse, and requested leave to return and bring him off. Having obtained permission, I called for a crew of volunteers to go with me, and guiding the boat myself, I obtained my horse and got off some distance into the river before the enemy appeared in Brooklyn. As soon as they reached the ferry we were saluted merrily from their musketry, and finally by their field pieces; but we returned in safety.

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