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George Washington Asks Spymaster Benjamin Tallmadge about British Movements in New York
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Benjamin Tallmadge had formed the Culper Spy Ring in 1778 to observe British activities during their occupation of New York City. His spies, merchants Abraham Woodhull and Robert Townsend using the aliases Samuel Culper (Sr. and Jr.) lived on Long Island and made frequent visits to New York City, where they mingled among British officers.

Just weeks after the discovery of the treason of Benedict Arnold and the hanging of his accomplice John André as a spy, General Washington on October 20 sent a letter to to his chief of intelligence asking for detailed reports. Having not heard back two weeks later, Washington sent this important letter to Tallmadge, from Washington’s headquarters in Wayne, New Jersey, 20 miles northwest of New York City.

GEORGE WASHINGTON. Autograph Letter Signed, to Benjamin Tallmadge, November 4, 1780, Headquarters [Wayne, New Jersey]. Endorsement at the bottom of the second page by the recipient’s son, Frederick A. Tallmadge. 2 pp., 7½ x 8⅞ in.

Inventory #26256       Price: $165,000

Complete Transcript

                                                                        Hd-Qrs Novr 4th 1780.

Dear Sir,

            You would oblige me by ascertaining as soon as possible the following things.—

            The number of Troops and different Corps that composed the last detachment which is supposed to have gone to the southwd

            The truth of the present report of another Imbarkation taking place—when it will happen & to what amount in men & Corps—and who is to commd the detachment.

            The present disposition of the remaining Troops on Long Island and York Island and the number at each place

You cannot be too expeditious in your communications on these <2> heads—distinguishing between things certain and matters of mere report.

I am – Dr Sir
Yr Obedt Servt
Go Washington

This letter was addressed to Maj Benj Tallmadge 2 Regt Dragoons.  F. A Tallmadge


Benjamin Tallmadge(1754-1835) was born on Long Island, and in 1773 graduated from Yale College where he was a classmate of Nathan Hale. He served as superintendent of a school in Wethersfield, Connecticut before joining the army. He received a commission as a major in the 2nd Continental Light Dragoons in June 1776 and soon became George Washington’s director of military intelligence. Tallmadge assembled the Culper Spy Ring, which operated in British-occupied New York City from 1778 to 1783.

In 1779, the ring informed Washington that Tryon's raid in July was intended to divide his forces and allow Lt. General Sir Henry Clinton to attack the American forces piecemeal. The Ring also uncovered a British plan to print counterfeit American currency on the actual paper used for Continental dollars.

The next year, the Culper Ring uncovered British plans to ambush Lt. General Rochambeau’s French army at Newport, Rhode Island, soon after their arrival in mid-July. Alexander Hamilton, one of Washington’s young aides, received the message of an impending British attack from the Culper Ring on July 21. Without the Ring’s warnings to Washington, the Franco-American alliance might have been damaged or destroyed.[1]

Also in 1780, the Culper Ring discovered that a high-ranking American officer was plotting with British Major John André to turn over West Point to the British forces and informed Tallmadge. Though they did not identify Benedict Arnold in time to prevent his escape, André was captured and hung as a spy in October 1780, on Washington’s orders.

Following this Letter
Tallmadge responded to Washington from Bedford, New York, on November 7, enclosing a letter from Abraham Woodhull (“Samuel Culper”) and another from Caleb Brewster about hay stockpiled by the British at Coram on Long Island. Tallmadge wrote:

I expect in a day or two to have a more perfect account of the situation of the Enemy, & their late Embarkation. I have had no certain Accounts from New York, via Kingsbridge, since my Return from Head Quarters. I have however recd a second hand report, that the Troops said to have lately embarked at N.Y. have actually sailed, & that it consisted nearly of the Corps mentioned in Col. Jameson’s Letter to Your Excellency. There are Reports from the same authority, that another Detachment of Recruits, supposed to be about 2000 men, with some of the Cork fleet, have arrived within a few Days, at N.York—this is but Report —C—’s next Letter will be more particular.

With Respect to the information contained in Lt Brewster’s letter, I would observe, that the Place at which the hay is said to be collected is about nine miles from the Sound, & southeast from Setauket, alias Brookhaven—the Detachment of Refugees, mentioned in C—’s letter, to be posted at Mr Smith’s house, is about 8 miles beyond Corum, where the hay lies, & the same Course further on—They are about 40 in number. If your Excellency wishes to have the hay destroyed, or the Corps taken, I don’t doubt of its practicability, & with abut 40 or 50 of our dismounted Dragoons, I would undertake it.[2]

Four days later, Washington approved Tallmadge’s plan for a raid on Long Island, including permission to attempt an assault on the Loyalist refugees at Manor St. George, the estate of State Senator William Smith, if not too risky:

The destruction of the Forage collected for the use of the British Army at Coram, is of so much consequence that I should advise the attempt to be made. I have written to Colo. Sheldon to furnish a Detachment of dismounted Dragoons, and will commit the execution to you… If the party of Refugees at Smith’s house can be attempted without frustrating the other design, or running too great a hazard, I have no objection. But you must remember this is only a secondary object, and in all cases, you will take the most prudent means to secure a retreat.[3]

On November 14, Tallmadge forwarded another letter from “Samuel Culper,” dated November 12, in which “Culper”/Woodhull wrote,

In answer to your first question, I again informe you, That I was at New York—about the 20 of last Month, I there with the advice of C— Jur and others, transmitted you the most accurate account of the embarcation under Genl Mathews,[4] That could possibly obtain, And assured you of their going to Virginia, As also of another embarcation bound to the Southward, then Just in embryo—Which were possitively to Sail three days ago Said to amount to 1300 Men, I then informed you of the severity And watchfullness of the Enemy Several of our dear friends, were imprisoned, In particular one that hath bene ever Servicable to this corespondence, This Step So dejected the Spirits of C. Jur that he resolved to leave New Yorkfor a time, I earnestly endevourd to prevent it but Could not, So that I have no person there now that I can Send the Experess to that can rely upon—In respect—to the different Corps and numbers that have embarked—and those within these Lines, I cannot ascertain nither do I think it can possibly be done perfectly—for this reason: The Enemy make it a rule to Supply every embarcation almostt with draughts from every Regt in their Army, The before mentiond reasons together with some other dificulties that Attend me at this time, prevents me from makeing the attempt to give you a returne of the Enemy—And hope youll excuse my non compliance.[5]

On November 21, Tallmadge led his dragoons by boat eighteen miles across Long Island Sound from Fairfield, Connecticut, to Cedar Beach, in Mount Sinai, New York. The following day, they marched across Long Island to the southern shore, where they captured and burned the British fort at Manor St. George and a ship with supplies directly off the coast on November 23. They burned 300 tons of hay stockpiled by the British in Coram, New York, before returning to Connecticut with their prisoners.

On November 28, General Washington wrote to Tallmadge from Morristown, New Jersey,

I received with much pleasure the report of your successful enterprise upon Fort St George and the Vessel with Stores in the Harbour—and was particularly well pleased with the destruction of the Hay; which must, I should conceive, be severely felt by the Enemy at this time. I beg of you to accept my thanks for your judicious planning, and spirited execution of this business—and that you will offer them to the Officers and Men who shared the honors of the enterprize with you.[6]

After the war, Tallmadge held several offices in the Connecticut branch of the Society of the Cincinnati. He served as postmaster of Litchfield from 1792 to 1801, and from then to 1817 served as a Federalist member of the U.S. House of Representatives. He also established a successful mercantile and importing business and was the first president of the Phoenix Branch Bank from 1814 to 1826.

Benjamin Tallmadge, by descent to — Frederick A. Tallmadge, given to — William Frederick Havemeyer, mayor of New York (per presentation letter, November 26, 1845, of “the last & onlyletter that I possess written entirelyby Genl Washington to my venerable parent”). By descent through successive generations (accompanied by correspondence between Havemeyer’s great-granddaughter Sarah C. A. Potter and John Fitzgerald re the letter’s publication), until sold at Swann, November 7, 2017, lot 7, to Ira Lipman. Sold by his estate, Sotheby’s April 14, 2021, lot 503.

[1]In response to the British threat against Rochambeau’s army, Washington planned a diversionary attack outside New York City, at Kingsbridge, in the hope of forcing British General Henry Clinton to call off the expedition against Rochambeau at Newport. Meanwhile, Hamilton sent a courier to the Marquis de Lafayette at Newport, warning him of the planned attack. Hamilton later sent a second dispatch to Rochambeau based on additional information on the British embarkation at New York, as did Benjamin Tallmadge from his vantage on the northern side of Long Island Sound. Ultimately, Clinton called off his plan to attack Newport for several reasons, including a lack of coordination with the Royal Navy, Washington’s diversionary attack, and French defensive preparations at Newport.

[2]Benjamin Tallmadge to George Washington, November 7, 1780, Papers of George Washington, Library of Congress, Washington, D.C.

[3]George Washington to Benjamin Tallmadge, November 11, 1780, Papers of George Washington, Library of Congress, Washington, D.C.

[4]Woodhull may here refer to General Edward Mathew, who in May 1779 attacked Portsmouth, Suffolk, and Norfolk, Virginia. Rather than going to Virginia, however, as reported here, Mathew returned to England late in 1780. In October 1780, British General Alexander Leslie entered the Chesapeake Bay with 2,500 troops and used Portsmouth as a base. After Patriot militia scored a decisive victory over Loyalist militia at the Battle of Kings Mountain at the North Carolina/South Carolina border on October 7, 1780, Leslie moved to join the forces of Lord Cornwallis in South Carolina. At the very end of December 1780, Benedict Arnold arrived in Virginia with a small raiding force. In January 1781, he marched unopposed to Richmond and sacked the capitol. Two additional raids led to the concentration of British forces in the South in Virginia, setting the stage for the decisive Siege of Yorktown in September and October 1781.

[5]Benjamin Tallmadge to George Washington, November 14, 1780, Papers of George Washington, Library of Congress, Washington, D.C.

[6]George Washington to Benjamin Tallmadge, November 28, 1780, Washington Headquarters Library, Morristown, New Jersey.

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