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Sunday, May 7, 2017

Dangerous Interlude: Colonel Benjamin Tallmadge’s Rebel Raid on Fort Saint George, November 23, 1780and Culper, or The Spy

By Michael Mauro DeBonis

It is late November, in 1780. The City of New York and its adjacent territory of Long Island have been under total British military control since the autumn of 1776. It was then that British General Lord William Howe chased American General George Washington and his ragtag ranks of bluecoat battalions from the Isle of Manhattan and its neighboring vicinities of Staten Island and Long Island. Despite the rebel army being outgunned and out-manned by their British opponents, Washington skillfully flees from upper Manhattan north to Westchester County (Tallmadge, 13) by crossing the Harlem River, and he miraculously keeps most of his body of Continental troops intact.

Much of New York City mysteriously burned to cinders during the American withdrawal to the mainland (Rose, 35). But, one fact remains plainly glaring and undisputed… the principal portion of the British Army is in command of Manhattan and its suburbs, and Britain enforces its presence in these dominions with martial law (Rose, 47-48).

In spite of this humiliating defeat at the hands of the British, Washington and his Continental Army fight on. Between the end of December of 1776 and early January 1777, Washington defeats the British forces in the New Jersey Battles of Trenton and Princeton (Rose, 42). American morale is no longer depleted. Yet the American goal of independence in 1780 has not been achieved.

New York City is the headquarters of British Military Intelligence. And in order for Washington to defeat the British, he needs to be able to read his enemies’ minds. In the fall of 1778, he decides to create a spy network that will be first-rate and that will put all others to shame. It will be called the Culper Spy Ring (Rose, 75) and it will be operated from three locales: New York City, Connecticut and Setauket, Long Island.

Its purposes are simple. The Culpers must secretly and silently keep track of British troop movements and numbers, British fighting tactics covertly gained from unsuspecting British military officers by Culper spies in NYC and Long Island, and the Culpers must swiftly and subtly courier the dispatches back to General Washington. Then Washington and his aids would be able to successfully respond to their opponents’ aggression and modes of attack.

Washington selects one of his most loyal and choicest officers, a Long Island cavalryman by the name of Benjamin Tallmadge, to manage the Culper Ring (Kilmeade & Yeager, 40). In late 1778, Tallmadge is a Major in the Continental Army. He has been only recently given command of Washington’s Army Intelligence Unit. Tallmadge will quickly prove himself to Washington as a very valuable resource, and by the fall of 1780, Tallmadge has been promoted to the rank of Colonel (Kilmeade & Yeager, 182). Tallmadge is an excellent spymaster and a superb leader of his division of Second Continental Light Dragoons, even though he is only twenty-four years old. The Culpers, under Tallmadge’s direction, will tremendously aid the patriot cause. Washington’s spies, under great scrutiny from their British overseers, doggedly penetrate New York City. The Culpers accurately report to Washington on England’s number of troops and on the numbers of their adversaries’ ships docked in Manhattan’s numerous harbors. Yet in November of 1780, Washington and Tallmadge have devised a strategy that “would truly shock the enemy,” (Rose, 236). Prodded by fellow Culpers Abraham Woodhull and Caleb Brewster, who had both given to Tallmadge and to Washington reliable and sage intelligence reports (Rose, 237)… of a substantial British and Tory stronghold called Fort Saint George being built at Mastic on Long Island and a huge stockpile of King George’s hay and forage being kept at Coram, also on Long Island, Washington and Tallmadge now saw an excellent opportunity to strike the British Army at New York, via Suffolk County.

Their strategy was quite bold and very wise. By making a raid at both Coram and Mastic, the Continentals could badly disturb and upset British military plans in New York City. If the rebels were able to annihilate the redcoat supplies of hay at Coram, they would drastically restrict British General Sir Henry Clinton’s ability to feed the Royal Cavalry’s horses and supply trains. Without ample hay, the British Army would have difficulty marching anywhere in the tri-state area, specifically during the coming winter of 1780-1781. And without Fort St. George on Long Island’s south shore, the British would be significantly deprived of moving troops, arms and other military supplies, by way of the Great South Bay, to NYC from Suffolk County and Brookhaven Town, and vice-versa.

Time had come for Tallmadge to move against his enemies. Tallmadge described Fort Saint George as Britain’s “most easterly point of defense” (Tallmadge, 39) on Long Island and a “most formidable” (Tallmadge, 40) bastion. Built on the prominent (patriot) Smiths’ family estate, Fort St. George was a triangular-designed outpost situated on the Great South Bay, and it thus had full access to the sea. Its outer wall was constructed of logs and stakes, sharpened severely at their ends (to prevent entry of any sort) and the impressive stockade was tightly held together from behind by a strong rail fence, made (too) of lumber. The perimeter of the stockade was bolstered further, at one of its corners, by a “deep ditch” (Rose, 237). At the center of the triangle were three small houses put up to shelter much of the fifty-man British garrison stationed there (Furman and Furman, 9).

Tallmadge, the shrewd operator he was, before embarking on his mission of sabotage and pillaging, visited Long Island himself (incognito of course) in the last week of October or the first week of November 1780, to scout ahead for his mission and he returned safely to Connecticut (Tallmadge, 39). To further insure his success, Tallmadge had secret assistance from Fort St. George’s superintendent, William Booth (a reputed Tory)… who “supplied Colonel Tallmadge with vital information concerning the structural layout of the Fort, and of the British garrison consisting of about fifty men” (Furman and Furman, 10).

After getting approval from General Washington for the raiding expedition, on November 11, 1780, Tallmadge and Brewster promptly went into action (Tallmadge, 40). With a raiding party consisting of about 100 men (mainly dismounted dragoons) Tallmadge and Brewster left Fairfield, Connecticut and they crossed the Long Island Sound on November 21, at 4 PM. And, at 10 PM, their eight whaleboats landed successfully at a harbor on Suffolk County’s north shore called "The Old Man’s "(Rose, 238). This site is present day Mount Sinai (Kilmeade & Yeager, 182)… and six miles east of Tallmadge and Brewster’s native Setauket. Colonel Tallmadge’s intended destination of Mastic is located roughly twenty miles south of Mount Sinai. Brewster and Tallmadge left twenty Continentals behind at the Old Man’s Harbor to guard their whaleboats from any redcoat or Tory patrols (Furman and Furman, 10).

After an initial march of five miles southward to Mastic, a horrible rain storm came over the Americans, and Tallmadge’s group of soldiers were forced to return to their starting point so they could shelter under their overturned whaleboats for the night (Rose, 238). After the storm lifted, some 24 hours later, Tallmadge and his men resumed their southward march (Rose, 238). In the early morning on November 23, they found William Booth, who urged them onto their mission (Furman and Furman, 10). Two miles after their meeting with Booth, Tallmadge’s and Brewster’s company reached the grounds of Fort St. George. It was 4 AM (Rose, 238).

Tallmadge divided his men into three columns for attack (Rose, 238). One column would attack the Fort’s stockade savagely and they would quickly hack through. They were called pioneers and they were trained soldiers to do such work. By then, though, Tallmadge and his two other columns of men had already breached the outpost’s main gate and they all had taken the principally sleeping British completely off-guard. After swiftly bayonetting the gate’s sentry, Tallmadge’s men quickly took the rest of Fort St. George into Yankee custody…their battle cry to signal this result was “Washington and glory” (Rose, 239). Their interjections of victory were premature. The Americans were fired on by British troops who had barricaded themselves in one of the remaining buildings. Tallmadge and his rebels quickly returned fire and they stormed the house where the British were by kicking down its front door (Rose, 239). The Americans subdued their British rivals in a somewhat chaotic fight. Deciding that since the British had fired on them after their fellow British citizens had surrendered to the Americans, Tallmadge and his merry band threw their redcoat prisoners headfirst through the home’s second story windows (Tallmadge, 41).

At this point the British and their Tory allies were shackled together and they were marched north back to Mount Sinai, carrying the small plunder Tallmadge and Brewster had seized from Fort St. George (Rose, 240). The entire British stronghold was set ablaze, as well as two British supply ships docked near the Fort (Tallmadge, 41). The Americans were victorious, but they were not done.

Their main target had always been Coram and its hay and forage (which were both gathered from Long Island’s east end). Tallmadge wasted no time. He took twelve men with horses from Fort Saint George and they broke off from the chief body of American soldiers, heading northwest to King George’s magazine at Coram. Tallmadge “made a vigorous charge upon the guard” (Tallmadge, 42) who had been left there to secure the supplies, and the dozen or so Americans, under Colonel Tallmadge’s direction, set 300 tons of hay and forage afire (Furman and Furman, 10)… an inferno worthy of the devil himself. Then they rejoined their parade and hiked safely back to Old Man’s Harbor.

Tallmadge’s raid on Fort St. George and Coram was entirely successful. His force lost no men and only one soldier was wounded, though horribly (Rose, 241). The British lost seven men and they had numerous wounded, most of them severely (Rose, 241). By 1 AM on November 24, 1780, Tallmadge and all of his men were back across the Sound when they reached home at Fairfield, Connecticut (Tallmadge, 42). Congress gave high regards to all those involved in the operation. Washington himself to Tallmadge declared, “thanks for your judicious and spirited execution of this business” (Rose, 241) and of the loss of the hay, Washington commented it, “must be… severely felt by the enemy at this time,” (Rose, 241).

Yet once we place the Tallmadge raid on Fort Saint George in its proper historical context, it seems to us moderns even more amazing. Yes, Tallmadge and Brewster were both native Long Islanders and they were both very familiar with Long Island’s topography and geography… but when they traveled to Long Island they were entering mainly hostile territory. If caught, they all faced execution at the hands of British authorities. Long Island was from 1776-1783 (when the British finally withdrew from New York City) a place of foreign occupation.

Brookhaven Town Historian Barbara Russell comments that, “Benjamin Tallmadge was a first-rate military man. In a battle that lasted roughly ten minutes (at Fort St. George)…the Colonel was able to bring to fruition a very difficult logistical task. Despite the huge risks of being detected and captured by the enemy…and even being beaten down by horrible weather, Tallmadge and Brewster never gave up. They retained incredible mental focus while carrying out their goals. As a consequence, they and their 100 men of Continentals were very instrumental in stifling the British war efforts, during a conflict which was far from won.”

That the Culpers (mainly Woodhull) helped Tallmadge and Brewster with their enterprise is equally remarkable. Occurring at the middle point of the Culper Ring’s years of operation (1778-1783) Woodhull very well knew, if caught, spies were hung from the gallows and they were very rarely imprisoned. Abraham literally risked his neck to advance the cause of American liberty. Is this not a definitive way to partake in history and to describe the substance of what history is?

About the author: Michael Mauro DeBonis  is native Long Islander of Italian descent who loves and thrives on literature and history. 


1) George H. Furman and Judith Furman. “The Manor of St. George,” compiled by the Trustees of the Estate of Eugenie A. T. Smith at Mastic, NY, in the month of August 1955.

2) Brian Kilmeade and Don Yeager. George Washington’s Secret Six. New York, NY: Sentinel and Penguin Books, 2013-2014.

3) Alexander Rose. Washington’s Spies. New York, NY: Bantam Books, 2006.

4) Barbara Russell. “Brookhaven Town Historian’s Interview with Michael M. DeBonis,” at Brookhaven Town Hall, Farmingville, NY: July 20th, 2016, at 1 PM.

5) Colonel Benjamin Tallmadge. Personal Memoir of Col. Benjamin Tallmadge. London, England: Forgotten Books, 2015.


Culper, or The Spy
by Michael Mauro DeBonis, August 6, 2016.  

Like cats in the shadows, they are not timid…
they all make it a point to stay well-hid.
Some sneak for power, while others skulk for pelf.
The best one will venture to find the truth in himself.
And actors they all are, playing out their roles,
though their voices are said in secrets on scrolls.
A spy has one true accent, but many different lips:
a good one leaves no trace, on the cup from which he sips.

Many think they are jackals, a-hunt in the night,
but spies can be as angels, invisible in daylight.
They will snatch your trust, when you little suspect…
they will grab for every idea your mind can detect.

But eyes keenly trained can see them fully in view.
Be as a hawk when spies come nearest to you.
Once his plunder is taken, he’ll leave off as a ghost.
He’ll take anything he can, ere he comes lost.

This much is his goal. And a woman spy is the same.
She takes from her target, under an assumed name.
For agents of the black arts, derring-do is the game. 

Long Island and New York are their playgrounds of sorts.
While slinking between British and Yankee forts,
they could be friend or foe…
yet with the greatest spies, you may never know.