Benjamin Tallmadge – Head of Washington’s Spies in New York

Benjamin Tallmadge (1754-1835) was an American continental army officer and head of George Washington’s secret service. His Culper Spy Ring provided Washington with crucial information on the British Army which was headquartered in NYC and is credited with significant contributions to the patriot war effort and success.

He was born in Setauket, Long Island, NY, on February 25, 1754, as the second of five children to Susannah and Rev. Benjamin Tallmadge Sr., who put great emphasis on young Benjamin’s education. He enrolled at Yale University in 1769 at age 15 – although according to his memoir, he was deemed qualified already when he was 12 or 13 years old. One of his classmates and friends in Yale was the future spy and martyr Nathan Hale. After graduating in 1773, he took on a position as a high school teacher and headmaster in Wethersfield, Connecticut.

However, after the first battles between American and British troops in Lexington and Concord in April 1776, he enlisted into the Connecticut militia in a short-term (6-months) regiment under Col. John Chester as a lieutenant in June 1776. His regiment joined Washington’s Continental Army encampment in New York City, he was in helping to train the new army. Tallmadge participated in the battles of Long Island in August and White Plains in October. In the former, his brother was taken prisoner and starved to death in a British prison. The Continental Army was driven from NYC.

Before his assignment expired in December, he was promoted to captain of the 2nd Continental Light Dragoons regiment, and in April 1777 to major. He fought in the battles of the Brandywine in (September) Germantown (October) and spent the winter of 1777-1778 in Washington’s encampment in Valley Forge. He was in charge of picketing the Schuylkill River with his dragoons, impressing Washington with his leadership skills and resourcefulness. In 1778, George Washington’s appointed Tallmadge as director of military intelligence and tasked him to secure information on the British in New York City.

Benjamin Tallmadge established the Culper Spy Ring in June 1778. It consisted of old childhood friends from Setauket, with Abraham Woodhull as lead agent. They began to operate in October, providing Tallmadge with information on British troop strengths in the NY area, defenses, morale, state, transport of supplies and provisions, and other activities.

All spies all had pseudonyms (Tallmadge operated under the name “John Bolton”)and not even Washington was aware of their true identities. In addition to invisible ink, a number system was used in messages. Tallmadge’s codebook consisted of 763 numbers representing names, places, nouns, verbs, and adjectives. For example, General Washington was 711, Abe Woodhull 722, Tallmadge 721, New York 727, reinforcement 584, defense 143, request 561.

enclosed is a Scheme for carrying on the Correspondence in future with C——.Some directions how to use sd Dictionary may be found annexed. Any proper Names, which your Excellency or C—— may wish to add, can at any time be set down—The haste with which I have been obliged to compleat this (as Capt. Belden goes off early in the morning), must apologize for its imperfections, tho’ I doubt not but it Will be sufficient to render the Correspondence safe, & put it out of the power of any one to decypher our letters, (in Case of accident) who is not furnished with a duplicate of the enclosed; a Copy of the same will be forwarded to C—— immediately. By the 29th inst. I expect to hear further from C——; his Dispatches shall be duly forwarded. I would take the liberty to observe that a safe Conveyance may be had, by the bearer, for the ink which your Excellency proposed sending to C——. A line informing that the enclosed comes safe to hand will much oblige your Excellencys most obedt Servt

Woodhull (codename “Samuel Culper”), a cabbage farmer, traveled to NYC under the pretext of selling his produce and visiting his sister. While he was in the city, he gathered information, wrote it down, and hid it on his way back home in a secret cove. Caleb Brewster, a fellow Setauket native, whaleboat operator, and Continental Army officer, picked it up and brought the intel across the Long Island Sound to Connecticut to Tallmadge, who then passed it on to Washington in New Jersey. Another childhood friend, Setauket tavern keeper Anna Strong, is believed to have served as a signal between Caleb Brewster and Abraham Woodhull to by hanging specific clothes on her line.

To reduce the frequency of his travels, Woodhall recruited a local spy – Robert Townsend (“Samuel Culper Jr.”). He was a merchant with British business contacts, co-owned a tavern frequented by British soldiers, and also worked with his tavern partner James Rivington, who published a Loyalist newspaper. All of these activities were perfect covers and opportunities to gather valuable information. After Woodhull stopped going to NYC, Austin Roe, a Port Jefferson (Long Island) native and tavern owner in Setauket became the Spy Ring’s main courier. Roe rented a pasture on Woodhull’s property where they used a dead drop (a buried box) to pass on information.

The Culper Spy Ring is credited with uncovering Benedict Arnold‘s treason and the capture of Tallmadge’s British counterpart, Major John André, preventing an attack against 6,000 French soldiers in Rhode Island, plots against George Washington, a plot of the British to counterfeit and weaken American currency, and obtaining the British naval codes.

Despite some close calls, none of the Culper Spy ring members were ever discovered. Even after the war, Benjamin Tallmadge never spoke openly about his activity. In his memoir, he wrote only that “[he] opened a private correspondence with some persons in New York (for Gen. Washington) which lasted through the war.” The existence of the Spy Ring and the identities of its members were only revealed in 1929 through correspondence.

Tallmadge was promoted to lieutenant colonel in 1783 and served in the Continental Army until it was disbanded in the same year. He married Mary Floyd in 1784 with whom he had 7 children and moved to Litchfield, Connecticut, where he became a businessman and president of the Phoenix bank.

Col. Benjamin Tallmadge with his son William, 1790 (Ralph Earl)

In 1792, Tallmadge was appointed postmaster of Litchfield, and in 1800 he was elected to Congress as a Federalist. After his wife Mary died in 1805, he remarried Maria Hallett in 1808. He served in the House of Representatives until 1817 when he did not seek re-election but returned to Litchfield and continued to be a successful merchant and import.

Benjamin Tallmadge died on March 7, 1835, at the age of 81. His son Frederick published his father’s memoir in 1858.

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