The Talented Major Tallmadge

Benjamin Tallmadge is currently enjoying a burst of posthumous fame. Most of the attention given him in recent publications and the AMC series Turn centers around his intelligence activities, a logical choice considering his organization of the Culper Ring and pivotal role in exploding the Arnold plot. But the attention paid to the espionage part of his career, however merited, often overshadows his distinguished service in more “conventional” wartime activities which were varied, essential, aggressively executed, and a significant contribution to the survival and triumph of the Revolution.

Tallmadge was born February 25, 1754 in the predominantly Calvinist-Whig community of Setauket, Long Island, New York. Second oldest of five sons, he  graduated from Yale College in 1773, having befriended the doomed Nathan Hale while a student there. Caught up in the rising anti-British agitation, he enlisted as a lieutenant in a six-month Connecticut militia regiment early in 1776.

Benjamin was not the only Tallmadge to join the Revolutionary cause. One brother, Samuel, served as a lieutenant with New York regiments throughout the entire conflict. Tallmadge’s oldest brother, William, (for some reason Turn reverses the two brothers) was captured at the Battle of Long Island, and confined to a British prison hulk from whose fetid hold he did not emerge alive. For Tallmadge the war was both ideological and personal.

Benjamin Tallmadge as a dragoon, by John Trumbull, c. 1783. Source: Memoir of Colonel Benjamin Tallmadge.  Sons of the Revolution, New York, 1904.
Benjamin Tallmadge as a dragoon, by John Trumbull, c. 1783. Source: Memoir of Colonel Benjamin Tallmadge. Sons of the Revolution, New York, 1904.

Tallmadge fought from Long Island to White Plains in the summer and fall of 1776, earning recognition from superiors, and gaining crucial military experience. But the most important phase of his military career began when he accepted command of a troop (company) in the 2nd Dragoons commanded by Colonel Elisha Sheldon in December 1776.[1]   While Washington and the bulk of the army settled into winter quarters at Morristown, New Jersey, the 2nd Dragoons spent the winter near Wethersfield Connecticut, where Tallmadge prepared both horses and men for the resumption of major combat in the spring.

In June, 1777 Washington called for trained troops from New England to join him, and Tallmadge led a detachment of the best prepared dragoons to New Jersey.   Recently promoted to major, Tallmadge saw heavy service in the Philadelphia campaign, and was sent by Washington to stem the Continental rout at Germantown, which proved fruitless. As the Continentals settled into their miserable quarters at Valley Forge, Washington assigned Tallmadge and his dragoons to picket duty between the Delaware and Schuylkill Rivers. His task was to report on British movements and prevent “the disaffected from carrying supplies to Philadelphia” an assignment which involved near continual skirmishing with British light horse units.[2]

In 1778, the center of operations returned to British occupied New York, and for the remainder of the war the Lower Hudson Valley/Connecticut coastal area became the base of operations for Tallmadge and his men. The dragoons were in near constant service. They patrolled the no-man’s land in Westchester County between British controlled areas near Manhattan and the rebel held areas further north. This entailed scouting, suppression of “cowboys”—nominally Tory bandits who often preyed on civilians without regard to political loyalty—parrying British incursions and raids—largely conducted by Tory units—and unleashing raids of his own as the opportunity arose.

Tallmadge was also tapped as the controlling officer for Washington’s most active intelligence network in New York and Long Island. He never spoke directly about his activities in his role as Washington’s spymaster, nor did he reveal the identities of his agents, even after the war. In his memoirs he remarked opaquely that in 1778 “I opened a private correspondence in New York (for Gen. Washington) which lasted throughout the war. How beneficial it was to the Commander-in-Chief is evidenced by his continuing the same to the close of the war.”[3]

Intelligence comprised only a part of Tallmadge’s duties and he was constantly engaged in attacks and reprisal raids in Westchester County’s “Neutral Ground.” Not all of these went his way. On July 1, 1779, a Loyalist force headed by Banastre Tarleton, consisting of light horse and infantry, launched an attack on Sheldon’s dragoons at Pound Ridge. “The onset was violent,” Tallmadge remembered, “and the conflict carried on principally with the broad sword, until the light infantry appeared on our flanks, when Col. Sheldon found it necessary to retreat.”[4] American losses were slight, eight wounded and four missing, though Tallmadge lost his horse and the twenty guineas in his saddlebags which were intended to fund intelligence work.[5]

Despite the whirling action in Westchester, Tallmadge turned his attention to his native island whose inhabitants endured a frequently harsh British occupation. Foremost in his list of targets was Fort Franklin, named in honor of Benjamin Franklin’s Tory son, which stood on a bluff on Lloyd Neck, a peninsula extending northwards from Huntington. Commanding the entry to Oyster Bay and Cold Spring Harbor, the stronghold was perfectly selected to choke off any American attempt to penetrate those waterways. Additionally, the fort and its 500 man garrison gave protection to Tory whaleboat raiders who “continually infested the Sound and our shores.”[6]

On September 5, 1779, Tallmadge launched a 130 man expedition to clear out the nest of Tories who sheltered under the fort’s guns and reduce the Fort itself. The force left Shippan Point near Stamford, and landed on Lloyd’s Neck about ten at night whereupon they quickly invested the Tory camp. The Loyalists were taken totally unawares, and almost all were captured. Unfortunately for Tallmadge’s larger objective, the sound of the musketry alerted the troops inside the fort. Without the element of surprise, all prospects of taking the bastion were lost. Tallmadge burnt the Tories’ boats and camp, and sailed back to Connecticut with his prisoners without losing a single man.[7]

The Lloyd’s Neck raid only whetted his appetite for further action on his home turf. Tallmadge went to Washington and laid out his plans “for beating up the enemy’s quarters and disturbing their repose.”[8] Washington listened carefully and went one step further, giving his pugnacious young subordinate an autonomous command which Tallmadge described as “consisting of the dismounted dragoons of our regiment and a body of horse. Our dismounted dragoons had been formed into two companies of light infantry, and were commanded by excellent officers, who, to a man, rejoiced at the idea of separate and active duty.”[9] Though technically still part of the 2nd Dragoons, he effectively headed his own legion, a body of men perfectly adapted to the circumstances of war in the disputed ground of Westchester, as well as ranger-like operations behind British lines on Long Island.

But Long Island would have to wait, as Tallmadge and his men patrolled what he described as “the most rascally part of the country I was ever in”—the “Neutral Ground” or Middle Patent of Westchester. Changing camps and positions frequently to prevent surprise, laying ambushes and guarding against enemy attacks, Tallmadge’s men were frequently sniped at by Tory guerrillas and members of James DeLancey‘s Loyalist Refugee Corps. The fighting, as in most civil wars, was remorseless. Captured snipers were hanged as spies, and Tallmadge sometimes subjected suspected guerrillas to “half-hanging” to extract information. The eighteenth century equivalent of water-boarding, half-hanging involved hoisting a prisoner by a rope, and strangling him short of death. He was then released and questioned. The process could be repeated until the victim provided information demanded or the captors concluded he had none.

Map of Fort St. George. Current location: Connecticut Historical Society
Map of Fort St. George. Current location: Connecticut Historical Society

Returning to camp from a scout on September 23, 1780, Tallmadge was informed that American militiamen had captured a man calling himself John Anderson who was carrying suspicious papers hidden in his boot. In reality, Anderson was John André, adjutant-general of the British Army, and the conduit between British General Sir Henry Clinton and General Benedict Arnold, who was conspiring to betray West Point to the British. Tallmadge was instrumental in preventing André from proceeding to West Point under the cover of Arnold’s pass, and the nefarious scheme was foiled. Arnold made good his escape to British lines, but André, who was captured in civilian clothes, was convicted of espionage by an American court-martial and hanged as a spy.

After a burst of fighting following André’s execution, combat in Westchester subsided, and Tallmadge returned his attention to Long Island. He directed “my agents” to gather up-to-date information on Fort St. George near Mastic located at a point where the Carman’s River enters the Great South Bay. Tallmadge’s sources reported that the fort was a triangular stockade enclosing several acres. Well-built houses secured two points of the triangle while the third was dominated by a bastion protected by a deep ditch and abattis.

Tallmadge presented Washington with his plan to take the fort. His raiders would have to cross the Sound undetected by British naval patrols and march across Long Island from the Sound to the south shore without being discovered and cut off. Then, after attacking the fort, they would have to retrace their steps, evade the enemy, and recross the Sound to safety. The commanding general decided the undertaking was too risky.

Undeterred, in late October Tallmadge slipped onto Long Island himself and carried out a personal reconnaissance of the British stronghold.   On his way back, he discovered that the British had accumulated a large quantity of hay and forage at Coram in the center of the Suffolk County, presenting an enticing second target for his proposed raid. The opportunity to deliver a double-blow to the British convinced Washington to approve the expedition.

Tallmadge and 100 selected men embarked in whaleboats at Fairfield at 4 PM on November 21, and reached Long Island about five hours later. A heavy rain forced Tallmadge to remain near the shore a day, but the following evening the dragoons set off across Long Island, nearing Ft. St. George about four the following morning.

As the first flickers of light broke over the Great South Bay, Tallmadge’s men, led by their pioneers, primarily axmen, rushed the stockade. A sentry called “Who comes there?” and fired, but was quickly bayoneted by Tallmadge’s sergeant. Shouting “Washington and Glory!” the surging Americans “seemed to vie with each other to enter the fort.”[10] The dragoons took the fort by bayonet, no shots having been fired by the raiders up to this point. The British struck their colors over the bastion, but the defenders of one of the large house fired a volley which set off a burst of answering musketry. The axmen chopped through the house’s doors and the dragoons surged through the entryway. Believing the British had fired on them after surrendering, the attackers showed little mercy, throwing some defenders headlong from second story windows until Tallmadge and his officers were able to stop them.[11] As the fighting faded in the fort, a vessel loaded with forage and stores attempted to escape from the dock. Tallmadge trained the fort’s guns on the ship which quickly surrendered.

As the sun steadily rose, the raiders demolished the fort and destroyed the ship and such stores as they could not carry.[12] About 8 AM the dragoons began their return with prisoners in tow. As they neared the center of the Island, Tallmadge took about twelve men, mounted on horses captured at Fort St. George, and rode to Coram where they destroyed about 100 tons of forage.[13]   The Coram party soon rejoined the main column, and by four o’clock the raiders, their prisoners, and the spoils they had brought off, sailed over Long Island Sound to Fairfield, arriving around midnight.

The operation was an unqualified success. Tallmadge’s audacity had resulted in the destruction of a major British outpost, the loss of one ship and supplies, as well as the torching of forage much needed by the British in Manhattan. Tallmadge’s prisoner returns listed one “half pay” lieutenant colonel, one “half pay” captain, a lieutenant, a surgeon, and fifty enlisted men.[14] In exchange the Americans suffered only one man badly wounded who was brought back to Connecticut. Both Washington and Congress lavished praise on Tallmadge for his expedition which surely raised the spirits of the patriot inhabitants of Long Island, especially Suffolk County.

The British naturally took a different view the raid. On December 2, 1780 the Royal Gazette, James Rivington’s Tory publication in Manhattan, ran an article on the raid which seemingly drew on testimony from loyalists and wounded survivors at Mastic whom Tallmadge left behind. Rivingtoncredited Tallmadge with leading the expedition and named a few other principles including Caleb Brewster, perhaps the Revolution’s most prominent whaleboat warrior who often served with Tallmadge. The Tory writer credited the revolutionaries’ “old friends on the Island” for their ability to carry out the brazen raid so successfully.[15]

As the Franco-American armies prepared to tighten a noose around British general Cornwallis’s neck in September 1781, Tallmadge, whose command remained in New York, revived his plan for “annoying the enemy on the Sound, and on Long Island…”[16] He turned his gaze toward Fort Slongo, a blockhouse situated about eight miles east of Huntington. A usual, his agents in Suffolk had kept him abreast of British actions and dispositions, and provided him with a map of the fort. This time he did not lead the expedition himself, but gave the assignment to Major Lemeul Trescott of the 9th Massachusetts Infantry, providing him with both the map and detailed guidelines for the assault.[17]

On October 2, Tallmadge escorted his legion to the Saugatuck River near Norwalk where Trescott embarked the men at about 9:00PM. The raiders reached Long Island about four the next morning, quietly moved into position, and stormed into Fort Slongo at dawn. Trescott’s men quickly overran the fortification, forced the stunned garrison to surrender, and proceeded to set fire to the blockhouse and any stores they could not carry off. They returned to Connecticut with a stand of colors, twenty prisoners including three officers, seventy muskets and a brass three pound cannon. Two British soldiers were killed, and two mortally wounded were left at the smoldering fort.[18] The only American causality was Elijah Churchill, a veteran of the Mastic raid, who received a slight wound. When Washington later instituted the “Badge of Merit” for conspicuous service, Churchill became one of the first recipients for his distinguished conduct at Fort Slongo. While hardly on the scale of the Yorktown victory, the Fort Slongo raid kept the British off-balance, and added to their roster of miseries during the year.

As Washington’s army returned triumphantly from Virginia, Tallmadge’s men resumed their duel with DeLancey’s Tories in Westchester County. Tallmadge was also increasingly involved in suppressing smuggling between Long Island and Connecticut. But Long Island would seize his attention in a more dramatic manner in November, 1782 when he received reports that 600 British Light Horse and infantry under the Tory commander, Benjamin Thompson, had moved into Huntington village. Thompson forced the local militia to tear down the Presbyterian Church and use the wood to erect a fort on the town’s burial grounds.[19] Though it was past conventional campaigning season, Tallmadge, well informed of the British defenses, determined to attack the Huntington fort, believing that the lateness of the season would have lulled the enemy into complacency.[20]   Assembling 700 men from his own legion and Connecticut militia, he prepared to cross the Sound on December 5, 1782.

As always, Tallmadge had planned well, and the raid would have been his largest operation of the war if he hadn’t been thwarted by one factor beyond his control—the weather. The raiders were ready for embarkation at Shippan Point, when squalls and heavy seas forced Tallmadge to postpone the raid for two nights. As they waited out the weather, Caleb Brewster discovered three Tory whaleboats off Norwalk. Tallmadge quickly approved Brewster’s request to capture them, and Brewster set off after them with his own vessels. Despite being shot through the body, and struck on the head with an iron cannon rammer, Brewster and his men captured two of the Loyalist craft. But one escaped to the safety of Huntington, robbing the dragoons of the element of surprise so crucial to the expedition’s success.[21]

Disgusted, Tallmadge scrubbed the raid, and on December 8, 1782, “more mortified and chagrined than I had ever been in my life,” submitted his report of the failed expedition to Washington.[22] Washington responded with a consoling letter. “Tho’ you have not met with that success you deserved and probably would have obtained had the Enterprise proceeded, yet I cannot but think your whole conduct in the affair was such as ought to entitle you still more to my confidence and esteem….Another time you will have less opposition from the Winds and Weather, and success will amply compensate you for this little disappointment.”[23]

In the last months of the war, Tallmadge acted more as a naval officer than a dragoon. His major task was suppressing the “London Trade,” in which British goods were smuggled to Connecticut in exchange for produce, fodder and foodstuffs which the British sorely needed. Tallmadge’s “navy” took several ships, British and American, selling the vessels and cargoes as prizes of war with the proceeds divided among men and officers, a greatly appreciated dividend for the poorly paid troops.

With the announcement of the ensuing peace and expected British evacuation of New York, Tallmadge asked Washington for permission to enter the City to arrange protection for his “emissaries” who had feigned loyalty during the British occupation and who were now vulnerable to patriot retribution. Washington readily acceded to Tallmadge’s mission and arranged for him to enter the city under a flag of truce. As he rode south into Manhattan, Tallmadge found himself “surrounded by British troops, tories, cowboys, and traitors.”[24] Nevertheless, he was well treated by the British army and navy officers, and the British Commander-in-Chief invited him for a dinner attended by other high ranking British officers. Tallmadge happily remembered that when the Continental army entered New York “not one instance occurred of any abuse, after we took possession of the city, where protection was given, or engaged.”[25]

Tallmadge accompanied Washington into New York on November 25, 1783, and was present when Washington bade an emotional farewell to his officers a few days later.[26] He then returned to Setauket where he was acclaimed as a hero, as indeed he was all across Suffolk County, remaining Loyalists excepted. The same year he married Mary Floyd, daughter of Declaration of Independence signer William Floyd, and the couple moved to Litchfield, Connecticut, where he died in 1835. After the war, Tallmadge flourished as a successful businessman, land speculator, and served several terms as a Federalist Congressman.

Late in life, looking back on his service in the Revolution, Tallmadge marveled at the sheer audacity of the Revolutionaries in challenging the British Empire. “It looks almost like madness to have ventured on the mighty conflict,” he concluded, adding that it was “…a little less than a miracle that we were sustained through such a bloody war, and finally came out of it victorious.”[27] Yet, he was one of the reasons the cause of independence prevailed. Horseman, spymaster, spycatcher, master of combined operations—few of Washington’s junior officers matched him in the successful execution of such a variety of operations. It’s less surprising that he is now receiving belated public attention for his exploits, than a puzzle that it took so long.

[FEATURED IMAGE AT TOP: Guidon of the Second Regiment of Continental Light Dragoons, also known as Tallmadge’s Dragoons. Source: Memoir of Colonel Benjamin Tallmadge.  Sons of the revolution in the State of New York, 1904. Also see Smithsonian.]

 


[1] Captain’s Commission, Benjamin Tallmadge, December 14, 1776. Fraunces Tavern Museum. Sons of the Revolution Collection.

[2] Memoir of Col. Benjamin Tallmadge. Prepared at the Request of His Children, (New York: Thomas Holman, 1853), 26.

[3] Memoir of Col. Benjamin Tallmadge, 29.

[4] Memoir of Col. Benjamin Tallmadge, 32. In his memoirs, Tallmadge identified Lord Rawdon as the leader of the raid. This was erroneous, and he may have been thinking of a fight near Philadelphia when Rawdon’s men drove off the dragoons.

[5] Tarleton also took a stand of colors which, along with three others he captured in the war, which were auctioned by his descendants at Sotheby’s in 2007.

[6] Memoir of Col. Benjamin Tallmadge, 32.

[7] Letter, Tallmadge to General Robert Howe, September 6, 1779. Benjamin Tallmadge Collection, Litchfield Historical Society, T4&5, T4, P14.

[8] Memoir of Col. Benjamin Tallmadge, 33.

[9] Memoir of Col. Benjamin Tallmadge, 34.

[10] Memoir of Col. Benjamin Tallmadge, 41.

[11] Memoir of Col. Benjamin Tallmadge, 41.

[12] Letter, Tallmadge to Washington, November 25, 1780. George Washington Papers. Library of Congress.

[13] New York Loyal Gazette, December 2, 1780 in Henry Onderdonck, Jr. Revolutionary Incidents in Kings and Suffolk County (Reprint, Port Washington, NY: Kennikat Press, 1970) , 99. Tallmadge estimated his party destroyed 300 tons of forage.

[14] Return of Prisoners Taken at Fort St. George on the Morning of November 23rd, 1780. Fraunces Tavern Museum. Sons of the Revolution Collection.

[15] Royal Gazette, December 2, 1780.

[16] Memoir of Col. Benjamin Tallmadge, 46.

[17] Letter, Tallmadge to Lemuel Trescott, Norwalk, Connecticut, September 25, 1781. George Washington Papers.

[18] Lemuel Trescott, Return of Prisoners and Ordinance, October 3, 1781. George Washington Papers.

[19] Order, Capt. Conkling to Huntington Town Militia, November 26, 1782, Huntington Town Archives.

[20] Letter, BT to GW, Nov. 18, 1782George Washington Papers.

[21] Letter, Caleb Brewster to Henry Knox, December 21, 1782. Gilder-Lehrman Collection.

[22] Memoir of Col. Benjamin Tallmadge, 49.

[23] Letter, Washington to Tallmadge, December 10, 1782.Founders Online, http://founders.archives.gov/documents/Washington/99-01-02-10171.

[24] Memoir of Col. Benjamin Tallmadge, 61.

[25] Memoir of Col. Benjamin Tallmadge, 62.

[26] Tallmadge left the only written account of that emotional meeting.

[27] Memoir of Col. Benjamin Tallmadge, 67.

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4 Comments

  • Excellent article! And I have just finished your excellent book, “General Washington’s Commando.” I have several questions about the book, specifically about Austin Roe and Fort Slongo, that I wish to present to you with hope that we can dialogue privately from the email I provided.

    • Thanks for your kind words, Mike. Perhaps the editors will be so kind as to forward your e-mail address to me.

      • Hello Richard: I’ve been traveling the last two weeks and assume the editors did not send my email to you. Please drop me a note at mvirgintino@yahoo.com and then I will come back to you with my questions.

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