The greatest patriots of the Revolutionary War are innumerable and nameless. Most were soldiers and some were statesmen and diplomats. But to students of the American War for Independence, one name stands out as an undisputed paladin in the Yankee cause for liberty. His name is Caleb Brewster. Brewster was truly a jack-of-all-trades, as well as the proverbial master of many. A native Long Islander and a highly talented sailor and soldier, Caleb Brewster confronted Death countless times to bring success to the infant nation he was helping to create. Mister Brewster did such on land and sea. And more to the point, this outstanding member of Washington’s Continental Army was part of the most secret component of the American war machine against their British enemies. Caleb Brewster was a spy and he has a tale to be told.
Caleb Brewster was born in the month of September (1747) at Setauket, NY (Rose, 82). On the north shore of Long Island, and positioned on the Sound, Setauket was (and, to a large extent, still is) a small fishing and agricultural community, belonging to the Township of Brookhaven. Brewster was descended from a family who emigrated from England to the Colonies in the 1660’s (Rose, 79). The Brewster clan had been living in the village of Setauket for many generations, prior to the birth of Caleb (Rose, 79).
And it was to the sea that the young Caleb Brewster took to early in his youth (Flockerzi, 1). Dulled by farming life, Brewster enlisted as a sailor on a whaler, bound for Greenland, when he was just nineteen years of age (Rose, 82). Within a few years of becoming a whaleboatman, Caleb Brewster, already accustomed to a harsh life at sea, joined on a merchantman, which was headed for the English capitol (London). He gained further significant maritime expertise in his role aboard this vessel as mate (Rose, 82). Adding to Brewster’s nautical insights, this experience of his on the high seas would become very useful for Caleb later on. This was especially the case when Brewster was steering through the stark black evening skies and waters of the Long Island Sound to ferry (fellow Culper spy) Abraham Woodhull’s intelligence reports (intended for Benjamin Tallmadge and General George Washington) to and fro Setauket and the Connecticut coast.
By Caleb Brewster’s early twenties he was a “bull of man of man…physically huge and imposing,” (Kilmeade and Yaeger, 55) “and was using his…tremendous athletic skill,” (Kilmeade and Yaeger, 55) to “nuisance the British,” (Kilmeade and Yaeger, 55). This meant that Brewster (a staunch American patriot early on) stoically and courageously breached the so-called “Devil’s Belt,” a.k.a. the Long Island Sound, and he smuggled goods across those heavily patrolled British (and coincidentally American) waters…carefully and effectively…avoiding prying redcoat eyes and attention. Brewster did so by utilizing his own unique brand of stealth and skulking (Kilmeade and Yaeger, 55). Brewster’s hidden and mischievous conduct was a genuinely risky business. Likewise, Brewster’s clandestine behavior was spawned from an authentically strong desire to hurt any and all British military operations in the Long Island-Connecticut area, as well as to facilitate his own sincere wishes to assist his Yankee colonial comrades in separating from the English mother country.
Brewster was back in New York Colony in May 1775 (Rose, 83). He had then brazenly signed two official public documents formally backing the Continental Congress (Rose, 80 and 83) the first one being in May, and the other being in June. Brewster’s “quick wit and ribald sense of humor,” (Rose, 67) will embarrass, thwart and frustrate the British Army on more than one occasion. Yet, in spite of Caleb Brewster’s incredible defiance towards the dicey odds stacked against him, and the remainder of the Continental Army, it was his incessant and overwhelming presence of mind that kept Brewster out of British clutches throughout the war. The British Army and its Imperial Navy were better trained, funded and supplied than their American counterparts. It is this pervasive and concrete reality that will dictate Washington’s successful Fabian strategy, which he will use against the Crown. It was also this same fact, which acted as a major catalyst in the creation of Washington’s Culper Spy Ring, that prods Caleb Brewster into the murky and mired world of espionage.
In was in this same year (December) of 1775 that Caleb Brewster enlisted in the Suffolk County Militia “as second lieutenant,” (Rose, 83) but was subsequently advanced to a full lieutenant by Captain Selah Strong, “in the spring of 1776,” (Rose, 83). But after the disastrous Battle of New York (autumn of 1776), Caleb Brewster fled to Connecticut and Rhode Island, to attach himself to the Continentals there and he resumed his fight against the British (Rose, 83).
Brewster’s initial efforts against the British hence escalated from smuggler and soldier, and then (by necessity) to spy. Both aforementioned offences were punishable under British law by imprisonment (no mean experience in the 18th century)…but spying itself was purely and contemptuously regarded (by both the French and the English) as a hanging offense. This meant that one caught practicing the “dark arts,” as they are called, was considered guilty of a capital crime. Espionage was thought by European powers (at this time, specifically) as something worse than treason, as opposed to simply being only treason.
Brewster’s seemingly unlimited courage literally had no bounds. After the fall of New York City in late 1776, Caleb Brewster took part in no less than three significant skirmishes on Long Island against the redcoats, and was each time on the winning side of things (Rose, 83). Brewster “in early 1777…had transferred to the 2nd Continental Artillery, stationed in Connecticut…there…he remained until August 1778, when…[Brewster] wrote his first letter to General Washington,” (Rose, 83). As Washington had totally lost control and possession of Manhattan Island and all of Long Island to General Howe and the British Army the year before (1776), there existed for the great American General a gaping hole in his intelligence availability, precisely concerning NYC and Long Island.
As Manhattan, Staten Island and Long Island were all the British Army’s main centers of operation during the War for Independence against the Continental Army, Washington needed a vital network of scouts and spies to discover how the British were planning to undo him. Finding out these secret facts: troops numbers and positions, docked ships and ship types, fort locations, etc., would allow General Washington to see ahead of time British war strategies and tactics being used against him. These pertinent details would permit the Continentals to avoid defeat at the hands of their British enemies, by allowing the Americans to successfully counter every move made opposing them, in advance. And the spy ring that was to come from Washington and his subordinates (Benjamin Tallmadge and Caleb Brewster amongst them) would become known today as Culper (Rose, 75).
Brewster was a perfect candidate to serve in the Culper Ring from its very inception. Courageous, cagy and supremely reliable Brewster was, thought the more sagacious and capable Major Benjamin Tallmadge (Washington’s new head of Army Intelligence). Caleb was a most splendid choice for utilization. The rugged Long Islander could be trusted in almost any and all circumstances to do his duty…and well Brewster would do it. As it so happened, Brewster was the second party to be included into the Culper Ring, with his childhood friend Abraham Woodhull being the first (Rose, 75). And it was with Tallmadge who was tasked (by Washington himself) to design and to oversee the Ring (Tallmadge, 29).
General George Washington met with Major Tallmadge on August 25th 1778 to discuss the specifics of the Culper Spy Ring’s operation (Kilmeade and Yaeger, 52-53) at White Plains, New York. Subsequently, the Culper Ring would begin functioning for the first time, with farmer Abraham Woodhull and housewife Anna Smith Strong, both of Setauket, Long Island, playing key roles within it. Woodhull would be the chief spy in the field…journeying 55 miles west into Manhattan to probe the British military situations there. Anna Smith Strong (from her seaside home) would act as the Ring’s signal person, carefully and subtly alerting the oceangoing Caleb Brewster, as to which cove to properly park his whaleboat. Anna Strong accomplished this by hanging her laundry from her clotheslines in unique, but nonchalant ways, as to which way to direct Brewster. This allowed Caleb to secretly and safely retrieve Woodhull’s intelligence reports from Culper dead drops…thus evading British patrols along Long Island’s (and Setauket’s) north shore.
And yet, Brewster (like Tallmadge, Woodhull and Strong) would be playing multiple roles within Culper’s overall schemata: messenger, raider, spy and soldier. Brewster’s knowledge and recollection of New York State’s and New England’s coastlines, coves and beaches was truly encyclopedic and photographic. Brewster’s prior history of being an expert seaman made him the optimum selection to carry messages back and forth across the Long Island Sound (The Devil’s Belt). Washington’s flow of information would always be secure (at least on Brewster’s end). Brewster was a sort of aquatic prairie dog, while seemingly dodging into one cove or inlet, he would miraculously reappear in an altogether different seaside spot, to the absolute amazement and anger of his British adversaries (Kilmeade and Yaeger, 55).
Brewster’s slick and quick disposition was matched only by his feistiness and loyalty. Every member of the Culper Ring had a friend in him, from Agent 711 (George Washington) right on down the line to Anna Strong, Abe Woodhull and all the rest. By early 1777, Brewster was once more a lieutenant in the Continental Army, though he was not in a New York unit…but was part of a Connecticut one (Rose, 83). And by 1778 (August) he initiated a correspondence with General Washington (Rose, 83).
Brewster had been communicating with Washington to inform the General “…on the state of the British warships in New York Harbor, as well as troop movements and naval preparations around Long Island,” (Kilmeade and Yaeger, 56). Brewster’s accounts to Washington were of mixed importance to the General, since the time it took to return Brewster’s intelligence dispatches to the American high command was slightly sluggish (Kilmeade and Yaeger, 56). Yet Brewster’s efforts for Washington revealed three major character traits of Caleb’s that were to impress the Commander-in-Chief: fidelity, daring and effectiveness. George Washington hence considered Brewster as a very valuable asset, specifically for purposes of espionage and the Culper Ring, which was subsequently to begin operating (Rose, 87).
Caleb Brewster’s close friend and fellow Setauket native Abraham Woodhull was the one who first prodded Benjamin Tallmadge to include Brewster into the Culper Spy Ring (Kilmeade and Yaeger, 55). The historical record is clear on two main facts concerning Captain Brewster: the first is, that in all of Brewster’s raids and forays from the shores of Connect to those of Long Island, he was never caught a single time…and the second is that Caleb Brewster visited Long Island (at least from 1778-1783) on hundreds of occasions. This was no mean feat of freakish magic or luck, but it was positive proof of Caleb Brewster’s severe skills of stealth, cleverness and undeniable competence.
During the Revolutionary War, the Devil’s Belt was heavily patrolled by the British in the south (Long Island) and the Americans in the north (Connecticut and Rhode Island). Britain took every tactical measure at its disposal to fortify Long Island, by strategically placing a chain of forts along the Island’s north shore from Brooklyn in the west, to Suffolk County in the east (See Map of Long Island in Rose’s Washington’s Spies). Fort Franklin at Suffolk’s Lloyd’s Neck was (by far) one of the most heavily manned, supplied and best designed of these strongholds (Rose, 235, and Tallmadge, 32 and 43). And other British outposts and supply depots existed elsewhere on Long Island. These included those at: Huntington, Northport, Smithtown, Setauket, Coram, Mastic and Southold (to name just a few).
This meant that (for the patriots) penetrating northern Long Island (by sea and land both) was extremely dangerous and almost impossible. But Brewster was an exceptional soldier and sailor. It was he who was successful in his early raid on Setauket (in 1776). Brewster was then (again) victorious in more successful raids (further bolstered personally by Major Tallmadge) at Lloyd’s Neck in 1779, at Fort Saint George (in Mastic) and at King George III’s supply magazine at Coram, both together, in November of 1780. Caleb’s final raid was at Fort Slango (Salonga) in late 1781(Tallmadge, 46).
The Devil’s Belt, being, “…110 miles long...,” (Encyclopedia Americana, vol. 17, 736) and (on average) “…10 to 25 miles wide,” (Encyclopedia Americana, vol. 17, 736) was, thus, a formidable geographic and geological obstacle in this sense: the Continentals, whether by whaleboat or sailboat, could almost never avoid being obvious when traversing it. The Long Island Sound’s relatively small size was the primary cause for this easy detection. The British, too, shared this problem. One could only hope (if a spy, soldier or even a smuggler) that cover of night or of a good fog were either present, should the necessity exist for one’s crossing. Brewster showed very good discrimination whenever confronted with this dilemma.
But, although Captain Caleb Brewster was brave and brilliant in his military pursuits, he was neither invincible nor perfect. “Setauket’s Caleb Brewster was perhaps the most bold and daring of the Revolutionary War spies, a boldness that occasionally put other patriots in danger,” (Tyler, 3). This is so (partially) because Brewster, “…was the only one of the Culper Spy Ring that the British eventually identified as a spy,” (Tyler, 3). As it turned out, during Brewster’s entire tenure with the Culpers, he was the only principal of the Spy Ring never to use his code name of 725 (Rose, 121) in formal Culper documents…because “…Being a bluff and reckless fellow willing to take his chances, he always insisted on scrawling his real name, on all of his correspondence,” (Rose, 75). This was (at least strategically) a real-life blunder. Speaking blatantly and factually, in the world of espionage, an ironclad alias is much more useful to a spy than a loaded weapon is. It shields a secret agent from not only detection by the agent’s enemies, but an effective alias helps to procure insulation from torture and criminal prosecution by the agent’s adversaries on behalf of the agent, additionally.
Brewster was, thus, committing a big no-no here with respect to other members of the Culper Ring. By his indiscretion in this specific capacity, Caleb Brewster jeopardized the entire covert integrity of the Spy Ring. This is so, because while his sly, evasive and ever-cautious personality successfully kept him out of Britain’s grasp for all the expanse of the American Revolution, the British could still strike Brewster by targeting those in Setauket, relatives and friends (e. g.), who were close to Caleb. That the British did not attack Captain Brewster in this way is much more a very good stroke of good luck, as opposed to him practicing sound and secure intelligence procedure.
A particular incident happened at Strong’s Neck (in Setauket) sometime during the war when Judge Selah Strong (husband of Culper spy Anna Smith Strong) and Captain Brewster were “walking one day…[and] they saw a British officer on the shore below. Brewster aimed his gun, but my ancestor stopped him, explaining that while Caleb could flee in his boat, he himself [Judge Strong] still lived here and would have to bear the brunt of the shooting,” (Tyler, 3). This tale (there is no reason to doubt its historic authenticity) was related by Anna and Selah Strong’s direct descendant, Kate W. Strong, in her July 1955 article, “Bits of Long Island History,” (Tyler, 6). This intercession of Judge Selah Strong on behalf of the unnamed British soldier indirectly saved the Culper Spy Ring from undue scrutiny by the occupying British authorities. If Caleb Brewster would have neutralized his British target, retribution could very well have been doled out by English redcoats stationed in Setauket, against the Strong family. This likely would have removed (unintentionally) Anna Smith Strong from the Culper Ring altogether, and hence hurt Washington’s intelligence efforts against those of King George III.
But in most other circumstances, Caleb Brewster was discreet, quick-witted and certainly cunning. Sometime during August of 1780 (Rose, 336…endnote 65), Brewster was at Strong’s Neck (once again) to recover another of Abraham Woodhull’s (and also Robert Townsend’s) intelligence reports to Washington. Hiding in Anna and Selah Strong’s “back garden,” (Rose, 234) Brewster, who was “…waiting for Woodhull,” (Rose, 234) had another unexpected British visitor come near the Strong’s home (Rose, 234). The British man was an officer of His Majesty’s 17th Royal Army Regiment, a lieutenant to be precise (Rose, 234).
The Army lieutenant “was out hunting,” (Rose, 234) very near to Brewster’s hiding spot (a coincidence). Brewster and his company removed the British soldier from off his horse’s saddle (Rose, 234) and they tried to take him [the British lieutenant] to Connecticut (as a prisoner). But Brewster smartly hesitated, knowing that the close proximity to Strong’s residence would prove exceptionally problematic (Rose, 234) to the Ring, and would unnecessarily draw local British and Tory focus to the Culpers, especially to Anna Strong. Brewster and his men released the redcoat officer, who “…would assume his assailants were thieves who chanced upon him rather than whaleboatmen on a more sensitive mission,” (Rose, 234). Caleb Brewster saved the Culper Ring in this instance to continue their fight for American freedom and autonomy.
As the Revolutionary War was winding down in December, 1782, Brewster was pursuing with his fleet of whaleboats some British naval vessels on the Long Island Sound (a.k.a. the Devil’s Belt), when he was wounded seriously in a firefight by enemy guns (Tallmadge, 48). “Capt. Brewster received a [musket] ball in his breast, which passed through his body (Tallmadge, 48), “…yet he recovered, and lived to be nearly 80 years old,” (Tallmadge, 49). Brewster’s physical and mental vigor were indeed superb and they would last him to his very end.
General Washington’s great victory over British General Lord Charles Cornwallis (at Yorktown, Virginia) the previous year (autumn 1781) had virtually brought the Yankee conflict with King George III and the British motherland to a total end. American independence had been finally achieved after eight years of very brutal, bloody and arduous battle. The impossible being brought to fruition, the Culper Spy Ring’s days were coming to an end. When the last of the British military and government departed American soil (from New York City, ironically) on November 25, 1783 (Tallmadge, 62) the need for the Culper Spy Ring no longer existed. All of the Spy Ring’s constituents returned to their peaceful civilian lives, minus Captain Caleb Brewster. It was Brewster who remained “…as an officer in the Revenue Cutter Service…” (Flockerzi, 3), an ancestor to the U. S. Coastguard. After some sixteen years of faithful participation in the Cutter Service and while earning a captain’s commission in 1801, Caleb Brewster left military life shortly following the end of the War of 1812 (Flockerzi, 3). Life at sea was always important to Caleb Brewster, whether it was fighting smugglers from aboard his Revenue Cutter’s vessel Active or making vital and vicious raids against redcoats and their strongholds on Long Island. Brewster was a successful blacksmith, ferryman, farmer, whaler, soldier and patriot throughout his long and prosperous life.
He died at Black Rock, Connecticut (at his farm) in the year 1827, with an esteemed and a very well founded reputation as “a hero,” (Flockerzi, 3). Yet his activity as one America’s and General George Washington’s most effective and valuable spies was not widely known until the 1939 publication of General Washington’s Spies on Long Island and in New York, by noted Americanist and New York historian Morton Pennypacker. The Culper Spy Ring had finally had gotten the respect of their nation (on the eve of WW II) after initially receiving it from an eternally grateful (but singular) Washington. It was Pennypacker (of Easthampton, Long Island) who was the first to skillfully and (historically speaking) to accurately cast the light on Washington’s Culper Spy Ring. This was a badly needed ray of sunshine that Morton Pennypacker blazed in opening up a piece of history to the American public which was not popularly or properly recognized. Caleb Brewster and all the remaining Culper spies had truly garnered a determined and a thorough historical researcher in Pennypacker, who made their obscure and long-forgotten tale breathe life once more. And it was the blood, bravery and brawn of Captain Caleb Brewster that broke the Devil’s Belt and shamed the British enemies that fought against him, time and time again. In this process, the country of the United States of America went from being a sublime political notion to becoming a concrete historical reality.
About the author: Michael Mauro DeBonis is a poet and a historian from Long Island, New York.
Works Cited:
1) “Long Island Sound,” Encyclopedia Americana, vol. 17, New York, NY, USA: The Americana Corporation, copyright 1970.
2) USCG Petty Officer Alissa Flockerzi. “Caleb Brewster: Revolutionary War Hero,” Coast Guard Compass, USA, 9th of July 2014.
3) Brian Kilmeade and Don Yaeger. George Washington’s Secret Six. New York, NY: Sentinel and Penguin Books, 2013-2014.
4) Alexander Rose. Washington’s Spies. New York, NY: Bantam Books, 2006.
5) Benjamin Tallmadge. Memoir of Colonel Benjamin Tallmadge. London, England: Forgotten Books, 2015.
6) Beverly Tyler. “A Case for Anna Smith Strong: Her Relationship with the Setauket-Based Culper Spy Ring,” The Historian, vol. 52, Issue 1, East Setauket, NY, Winter 2015.
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Mariner By Moonlight
“I am a whisper, in wind and word. Shadows are my shrouds.
Ferrying phrases, I’m a midnight bird…
an owl-eyed echo, deep in clouds.
Black-skinned waters, white with fog,
my oars roll through secrets, sea and bog.
Stars are fixed in skies they roam:
I beach my boat from off the foam.
I flitter my form across the breeze
to carry some voices over some seas.
Quick am I to snatch my snare,
I leave not a wrinkle in the air.
I move as a moth through brush and trees,
I flip and dip and I tuck my knees.
Behind some rock, I’ll set down on the ground…
never I’ll make any sort of sound.
My eyes are moving for ghosts and guests,
for a spy in motion is not one who rests.
I am here for notes, to grab and grip…
from my hands, they’ll never slip.
They tell of British soldier and ship.
Words are pellucid, so none can read
invisible thoughts, by specters made.
I’m a squid in some water, in an ink-poured puff.
But I have all my booty. So, I leave off.”
--- Michael Mauro DeBonis, June 9, 2017.
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