Major Benjamin Tallmadge
Benjamin Tallmadge was born on February 5th 1754, and he grew up in or near Setauket, New York. His father was the pastor of a local church, and he was closely related to the families of all the members of the Culper Spy Ring. Like most upper middle class New England men of his time, he was well-educated, and attended Yale, where he became close friends with Nathan Hale. Both Hale and Tallmadge became school teachers upon graduation in 1773. In 1775, Tallmadge joined the local militia.
Tallmadge joined the Continental Army in July of 1776, serving with the cavalry. Cavalry was in charge of intelligence gathering, and Tallmadge was active in the Battles around New York in 1776. During one of the retreats, his brother William was captured and imprisoned. Tallmadge advanced rapidly, becoming a captain in the mounted light dragoons under Elisha Sheldon, working mainly in New York, to the North of Manhattan. Tallmadge's duties with Sheldon's troop mainly consisted of reconnaissance, although he did see action at Brandywine.
By 1778, Tallmadge was "engaged" in correspondence "with some persons in New York" as he wrote in his memoirs. This was probably the Culper Ring, although Alexander Rose recorded some of Tallmadge's earliest attempts at playing spymaster. Tallmadge's superior, General Charles Scott, served as Washington's Chief of Intelligence, and Tallmadge was permitted some experimental leeway to try a new method involving a chain of agents with the creation of the Culper Spy Ring. Tallmadge returned to his hometown, visiting his closest friends and family members to enlist their help with his plan.
Benjamin Tallmadge Circa 1800
The Culper Spy Ring initially was not reporting news fast enough to be particularly useful, but since the network system was working, and consistently reporting, Washington felt it had great promise. Supposedly General Scott did not appreciate Tallmadge's spies' reports going directly to Washington and felt his young officer was a bit insubordinate. Tallmadge, however, managed to become one of Washington's favorite young officers during this period, and Scott soon found himself resigning to make way for Tallmadge and the future of American Intelligence.
From 1778 until the end of the war, Tallmadge worked with the Culper Spy Ring, serving as their main handler. Early in Tallmadge's espionage career, he was posted close to enemy lines and when his post was raided, he lost papers relating to the secret service, compromising the situation of a possible future spy named George Higday. After that event, Tallmadge was exceptionally careful. Even Washington did not know the identities of Tallmadge's spies. Following Arnold's treason, Tallmadge wrote to reassure Townsend that no one knew his name or identity.
Tallmadge wrote a cryptic note in his memoirs regarding Arnold's treason--that only he and four other officers in the American Army knew the full story of the events that unfolded. When American Intelligence was obviously intercepting the Arnold-Andre correspondence in August and September of 1780, Tallmadge would have known about it. Tallmadge seems to have had some advance warning of at Arnold's treason, since he wrote to warn Governor Trumbull to expect an attack, and he was immediately suspicious enough of both Arnold and Andre to challenge the decisions of his commanding officer.
Tallmadge and Hamilton shared exclusive guard duty of Major Andre, suggesting some need for secrecy. His denunciation of Andre's captors in Congress in 1817 also suggests Tallmadge knew or planned something else.
While the Culpers were a very successful effort from 1779 to 1780, after 1780 their intelligence was lacking at best. Tallmadge engaged several other agents, although none of these efforts had the success of the Culper Spy Ring at it's prime.Tallmadge's constant correspondence with Washington after Yorktown is a testament both to the uncertainty of the British surrender and to the close bonds between Washington and Tallmadge. Tallmadge was present for Washington's farewell.
Immediately following the war, Tallmadge married Mary, the daughter of Congressman and Declaration Signer William Floyd of Mastic, Long Island. Tallmadge moved to Connecticut, settling in Litchfield in 1783. He served as a leader in the Society of the Cincinnati, and as Litchfield's postmaster in 1792.
In 1801, he was elected to Congress, where he remained until 1817, always aligned with the minority Federalist Party. Before departing Congress, he denounced one of the captors of Major Andre who sought to augment his pension. Benjamin died on March 7th 1835 aged 81 years old.
Benjamin Tallmadge and his son George Washington Tallmadge, painted in 1790 by Ralph Earl.