Capt. Caleb Brewster, Culper Spy Ring

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Caleb Brewster

Birthdate: (79)
Birthplace: Setauket, Suffolk County, Colony of New York, British Colonial America
Death: February 13, 1827 (79)
Black Rock, Bridgeport, Fairfield County, Connecticut, United States
Place of Burial: Fairfield, Fairfield, Connecticut, United States
Immediate Family:

Son of Benjamin Brewster and Mehitabel Brewster
Husband of Anna Brewster
Father of Sarah Brewster; Jonathan Lewis Brewster; Sturges Brewster; Anna Brewster; Elizabeth Burr Brewster and 3 others
Brother of Benjamin Brewster; Elizabeth Brewster; Ann Brewster and Orpha Hawkins

Occupation: Revolutionary War Spy, Culper Spy Ring, DAR Ancestor #A014156
Managed by: Private User
Last Updated:

About Capt. Caleb Brewster, Culper Spy Ring

Caleb Brewster in the Revolutionary War By Robert Foley

Caleb Brewster left the quiet life on his family farm home in Setauket, Long Island, at 19 years old for the adventure of a position on a Nantucket whaler. He then pursued a life at sea as a mate on a merchant ship. However, as soon as news of the American Revolution and of the shots of the Battle of Lexington and Concord reached his ship, he quickly returned home. It was war against British oppression.

It was May of 1775. He was 28 years old and the timing was perfect. The Continental Congress authorized our country’s first Navy soon after. Brewster’s skills in navigating whaleboats and merchant ships would prove essential in outmaneuvering British ships. His knowledge of the shoreline and his close relationships with other key patriot spies, his courage to enter enemy territory and retrieve spy letters, his whaleboat battles, were all noteworthy contributions to the patriot effort.

In December 1775, Brewster joined the Suffolk Country Minute Men, local self-trained colonists who independently organized militia companies known for being ready in a minute’s notice. They were among the first to fight in the American Revolution. Brewster was one of seventy Minute Men in that company. The patriots opposed the “intolerable acts” imposed upon by the British, which included immunity from prosecution. If British troops harmed local residents, they could avoid prosecution for criminal offence, which some at the time called the “murder act.”

Brewster’s hometown was soon under occupation. In 1776, when the British invaded New York City, Setauket, Long Island became a center for British commanders and would soon be under martial law. Residents could not travel to or from the city or bring any goods without a permit. Moreover, anyone who had signed a patriot document such as that of the Minute Men, stating the necessity of taking up arms against the British, was at great risk. Brewster fled to Black Rock, Connecticut, which was part of the town of Fairfield at the time. Brewster would find Connecticut to be a relatively safe place and home to the Patriot cause. He was not alone in fleeing the British occupied Long Island. One in six Long Islanders departed to Connecticut as refugees in 1776. One of Brewster’s initial actions after moving to Connecticut, was to assist other patriot refugees to escape Long Island by using his boat to crisscross Long Island Sound, ferrying out the patriot sympathizers in clandestine operations. One of his passengers was a signer of the Declaration of Independence, William Floyd.

The Black Rock harbor was the point of attack for the patriot cause. The deep-water, historic shipbuilding seaport was a depository for privateers, British prisoners, and launching ground for schooners, sloops and whaleboats. Black Rock became a focal point for battles and espionage during the entire war period from 1776 to 1783, during which the British occupied New York City, part of Westchester and Long Island.

Brewster carried out a number of different missions during the war. He acted as intelligence gatherer, lieutenant in the artillery, spy letter courier, privateer, and army officer commanding a fleet of whaleboats against the British. By the spring of 1776, Brewster joined the Continental Army as Lieutenant. By 1778 he had fleet of three whaleboats. Brewster was under direct orders from George Washington through Benjamin Tallmadge, organizer and leader of the Revolutionary War’s Culper Spy Ring, which began in 1778 and operated on Long Island, New York City and Black Rock. Codes and aliases concealed the identities of the spy members. Brewster was the only spy to sign letters under his real name instead of his secret agent code 725.

The spy ring provided valuable information to General Washington at the height of the American Revolution. Having reliable intelligence of expected British troop movements was essential. George Washington was unable to setup a spy network prior to the 1776 battle in New York due to his hurried retreat from the British. Outwitting the enemy in surprise attacks would prove more effective against the much more powerful British navy. Therefore George Washington’s most valuable strategic weapon was not his military force, but rather intelligence and Brewster was at the center of the spy ring.

From the moment General Washington lost the battle in New York in 1776, he set Black Rock as one of the front lines of the war and counted on intelligence from Brewster. If you could not defeat the enemy by numbers of troops, you would have to do so with information and strategy.

Today, we know of a total of fourteen letters of correspondence between George Washington and Caleb Brewster, thirteen of which are in the Library of Congress. There are nine letters from Washington to Brewster, and five letters to the General from Brewster. The very first letter from Brewster has not yet been found. In his first letter to Caleb Brewster, writing from White Plains on August 8, 1778, General Washington sets the tone for the espionage needs. Washington requested the Black Rock patriot to “have a strict watch kept upon the Enemy’s Ships of War, and give me the earliest notice of their Sailing from the hook. To obtain speedy and certain intelligence of this matter may be of great Importance to the French Fleet.”

After this first correspondence with Washington, the Black Rock spy gathered intelligence on the British military movements and wrote Washington that “the Ships of war are Left the Harbours in and about Huntington—Genrl Tryon and Delancee have their Quarters at the Fly at the Head of Flushing Bay with about Seven Hundred Troops that Returnd with them from the East End of the Island.”

Caleb Brewster and the Culper Spy Ring achieved major milestones. For example, the spy ring prevented advance British knowledge of the French arrival in America to help the patriot cause. It was also through such intelligence gathering, that the patriots revealed the identity of American’s most famous of traitor, Benedict Arnold. Brewster’s intelligence missions would also successfully warn General Washington of the burning of Fairfield in 1779. Unfortunately, Washington was unable to respond in time because he was away inspecting the troops for several days.

Timing was essential for intelligence to be of any use. Delivery time was reduced to one week when Washington’s cavalry was stationed close by, in the Greenfield Hill section of Fairfield. Having a mounted horseman ready to deliver messages that Brewster picked up from across Long Island shortened the total delivery time of spy letters picked up from New York. The new express delivery service utilized Washington’s cavalry, the 2nd Continental Light Dragoons, Sheldon’s Horse that had been commissioned by the Continental Congress on December 12, 1776 and named after Colonel Elisha Sheldon. The cavalry is still in existence today. The espionage ring provided messages and spy letters originating in New York, then carried 55 miles from Manhattan to Setauket by horse. Brewster would pick the letters up after crossing Long Island Sound by whaleboat. Upon returning to Connecticut, Brewster would pass the letter to a Sheldon’s horse courier in Black Rock, who would ride quickly to George Washington’s headquarters.

Apart from providing intelligence, Brewster was also involved with battles against the British. When Brewster arrived in Black Rock, where the first privateers were commissioned in Connecticut, it had been just months before in November, 1775, that the Continental Congress created the Letter of Marque and a list of “Resolutions” defining parameters for prize money. Privateers were authorized to capture enemy ships and its cargo. This was called a prize of war since they could keep a percentage of the cargo. Brewster became a privateer in November of 1776, and was engaged in many boat fights. On November 13, 1780, he proudly wrote George Washington on capturing an enemy ship. “I took a prize coming home today. A fine large boat from New Haven.”

Brewster was also involved in many whaleboat wars. He was known as the “terror of the Tories”, especially for his successful nocturnal raids on Long Island, which would help protect Connecticut from British attacks. Brewster’s efforts were successful in lowering the frequency of British kidnapping and plundering expeditions carried out against the patriots in Connecticut. Many of the British attacks against Connecticut were directed from forts built up by the British on Long Island. Therefore it was a strategy of General Washington, to target these enemy strongholds.

Of Brewster’s many expeditions the most documented ones occurred from 1779 to 1781. The attacks also involved much planning by Benjamin Tallmadge and sometimes George Washington, to execute a successful surprise attack. An important first important step was to avoid getting noticed by the vigilant Loyalist scouts while crossing the Long Island Sound. Brewster would keep his sail down and even coordinated his expeditions with the moon cycles to keep from being noticed.

The first attack organized by Caleb Brewster was against a headquarters of pro-British Loyalists on Lloyd’s Neck at Huntington harbor. The target, the firmly entrenched barracks called Fort Franklin, from which the enemy directed many attacks against the patriots in Connecticut. It was one of eight Long Island fortifications established by the British on Long Island. On a Sunday, September 5th, 1779, commanding a collection of sloops and whaleboats and one hundred and thirty of Tallmadge’s dismounted dragoons, Brewster reached Long Island at ten o’clock and attacked Fort Franklin so quickly that the patriots were able to capture five hundred Tories behind their barricades with little resistance and no loss of a patriot.

In a second attack, at Smith’s Point on the southern coast of Long Island near Mastic Beach, the target was Fort St. George, a fortification built by Rhode Island Loyalists. The mission also entailed destroying a stockpile of three hundred tons of hay, which was in reserves for the British army. Leaving on Saturday, November 18th, from Black Rock Harbor with a total of eighty men, Brewster crossed Long Island Sound. He left the whaleboats on the coast with someone to keep watch, then led the troops in a march over twenty miles across land and then successfully attacked the fort. Brewster burned the hay stockpiles without a man killed in the expedition. Washington congratulated Brewster and Tallmadge, saying of the hay, that it must be “severly felt by the enemy at this time,” as winter was approaching.

A third attack on Tuesday, October 9, 1781, was against a group of Tory woodcutters. The target was Fort Slongo in north, central Long Island, and involved one hundred and fifty dismounted dragoons. The attack was successful with no patriot troops lost in battle.

Caleb Brewster’s role in winning the War of Independence has not been fully assessed by historians. This is due to the fact that the existence of the Culper Spy Ring itself was hidden for approximately 150 years. The heroic story of Brewster and the other members of our nation’s first espionage ring has therefore not become part of the legends of the American Revolution. Their achievements and contribution in the War of Independence were at least equal if not exceeding those of the legendary patriotism of Paul Revere. In fact, the intelligence used in defeating the British and the very horse ride (55 miles from Manhattan to Setauket, Long Island) was more extensive than the famous horseback rides of Revere. Today, the degree of importance of the ring and its spy members is still being studied, thus there are sometimes references to the spy ring is as a “tale untold.”

The existence of the spy ring was not known until the 1930s. After the Revolution ended, no one revealed the double life that the spies led, nor their secret agent numbers or aliases. It was not until September 1930, that a Long Island historian matched signatures of the spies to their actual names. The researcher, Morton Pennybacker, was studying a merchant from Long Island and realized that George Washington’s spy correspondence matched the writing style of what was once considered to be this obscure, local merchant.

Caleb Brewster’s achievements were as noteworthy as his distinguished ancestors. He was born in Setauket, Long Island on September 12, 1747. His grandmother, Sarah Ludlow, was the wife of Roger Ludlow, the English lawyer, magistrate, military officer, and colonist who helped found the Colony of Connecticut as well as the town of Fairfield. Caleb is related to the celebrated William Brewster, the Elder, and highly esteemed member of the Plymouth Colony, who arrived on the Mayflower passenger and was the only such passenger with a university education.

Caleb Brewster married in 1783 to Anne Lewis, daughter of Jonathan Lewis, a shareholder in the Middle Wharf in Black Rock. He became a blacksmith, often trading with the Black Rock merchant Thomas Bartram, and became Captain of the first United States Coast Guard revenue cutter ship for the district of New York from 1793 to 1816. Main Street in the historic Black Rock Harbor village was renamed after Caleb Brewster in 1901 and is now called Brewster Street.


Danenberg, Elsie Nicholas, Naval History of Fairfield Country Men in The Revolution, A Tale Untold, Fairfield Historical Society, 1977

Rose, Alexander, Washington’s Spies, The Story of America’s First Spy Ring, Bantam Dell, 2006

Radune, Richard, Sound Rising, Long Island Sound at the Forefront of America’s Struggle for Independence,

Mather, Frederick Gregory, The refugees of 1776 from Long Island to Connecticut, B. Lyon Company, printers, 1913.

Various articles by Historian Beverly Tyler, Education Chair of the Three Village Historical Society. Setauket, New York, Long Island.

Web site on Black Rock history:


Caleb Brewster

Allegiance: United States

Service: Continental Army

Born: September 12, 1747, Setauket, New York

Died: February 13, 1827 (aged 79), Black Rock, Connecticut

Caleb Brewster (September 12, 1747 - February 13, 1827) was a member of the Culper spy ring during the American Revolutionary War, reporting to General George Washington in the nation’s first intelligence-gathering organization.

Brewster was born in Setauket, New York, a hamlet now part of the town of Brookhaven. He was the son of Benjamin Brewster, grandson of Daniel Brewster, and great-grandson of the Rev. Nathaniel Brewster (the first minister of the old town church in Setauket).


DAR Ancestor #: A014156

Caleb Brewster of Setauket

Caleb Brewster of Setauket was an important member of the American spy ring that operated out of Setauket during the Revolutionary War under the direction of Major Benjamin Tallmadge.

Austin Roe of Setauket, brought the secret messages from the chief spy in New York, Robert Townsend (alias Culper, Jr.). These were turned over to Abraham Woodhull, who in turn gave them to Caleb Brewster, who carried them across the sound in one of his boats and delivered them to Major Benjamin Tallmadge, who delivered them to General washington, wherever he might be located.


Caleb Brewster was born in Setauket in 1747. He was the son of Benjamin Brewster, grandson of Daniel Brewster, great-grandson of the Rev. Nathaniel Brewster (the first minister of the old town church in Setauket). His father was a farmer and, as was too often the case in that day, gave his son only a limited education. Caleb was an active boy and was anxious to explore the world beyond his native village, so at the age of 19 went on a whaling ship bound for the coast of Greenland under command of Capt. Jonathan Worth.


His next voyage was to London in a merchant ship, and upon his return found his country engaged in the Revolutionary War. He immediately volunteered his service and within a short time was made a lieutenant of artillery. he was help in such high esteem by his officers and the commander in chief for his integrity, courage and patriotism, that in 1778 he was employed as a secret agent by Congress. Through the rest of the war he devoted himself in procuring and transmitting important information relative to the movements of the British Army in New York and on Long Island.


Brewster was among those who under Col. parsons crossed the sound in 1777 for the purpose of capturing a company of British soldiers who had taken possession and made a fort of the Presbyterian Church at Setauket. This expedition was not successful, as, while they were making their attack on the British in the old church word came that reinforcements were coming down the sound to the aid of the British, so the attack was abandoned.


For several years, Brewster was the trusted messenger of the secret messages from Setauket to the headquarters of major Tallmadge, across the sound, and in his lightly armed whaleboats, with good men, traveled this route as often as was necessary. he sailed under his own name and made no attempt to keep secret which side he served on. In addition to this he captured several supply ships headed for the British Army in New York, and also led his men on raids across Long Island, burning and wrecking whatever they could find belonging to the British. He had many encounters with the enemy and was sometimes wounded, but always came off victorious and was never caught.


He was with Major Tallmadge in November 1780 in the expedition that came across the sound from Fairfield, Conn., and landed at Mt. Sinai; then marched across the Island and made a successful attack on the British Fort St. George at Mastic. They returned the same way with their prisoners and part of the force went back by the way of Coram, where they burned a hay stack of 300 tons collected by the British.


On December 7, 1782, Capt. Brewster, with the whaleboats under his command, gave chase to several armed boats of the enemy in the sound, and after a desperate fight succeeded in capturing two of them. During this encounter his shoulder was pierced with a rifle ball and he was hospitalized for some time, after which he was placed on the pension roll of the army for the rest of his life. He was engaged in several other important encounters with the enemy on the water after this, and in 1783 captured the Fox, an armed British vessel in the sound during a short but fierce encounter.


In 1784 he married Anne. daughter of Jonathan Lewis of Fairfield, Conn., where he continued to live when not in public service. he was long remembered for his great size, his fine proportions, vigorous constitution, unrivaled wit and his devil-may-care bearing. He died on his farm at Black Rock, Conn., at the age of 79.


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Last Will of Caleb Brewster

Caleb Brewster made his will on February 25, 1825. This will can be found in the Probate Records of Fairfield, Fairfield County, Connecticutt, Vol. 30 (1807-1827), pages 497-502 (Mormon Microfilm #0004284, and is as follows:

 Know all persons to whom these presents may come I Caleb Brewster of the Town and County of Fairfield in the State of Connecticutt do make this my last Will and Testament viz - Sect 1st I order my Executor hereafter named to pay all my Bills that may be legally due at the time of my decease out of such of my Estate as he may think to be most beneficial for my Estate- 
 Sec.2d. next, I give and bequeath to my beloved wife Ann Brewster one horse and Carriage & harness for the same & one Cow which  horse carriage harness and Cow shall be Just as she may choose among them which I may own at my decease. And so ["must" crossed out] much of the provissions on hand at my death as she may Judge needful for herself and such Family as she may think proper to have the property thus given to my said Wife to be her own forever and exempt from the payment of Debts expenses and Legacies and in lieu of all dower in my Estate in this state - the state of New York and Elsewhere and of all other claim in my Estate whatsoever_ 
 Sec.III. Next I give and bequeath to my Daughter Sally hereafter named the sum of one hundred dollars over and above what I shall hereafter give her to be paid out of my Estate before a divission thereof be made as her own forever - and to be paid to her  within one year after my decease with the Interest Thereon as long as the same may remain unpaid to be computed after the expiration of said year until paid -- 
 Sec. 4th. Next, I give and bequeath to my grandson Caleb B. Brewster the sum of Fifteen hundred dollars to be paid with the interest that may arise thereon when he arrives to the Age of Twenty one years - unless such Interest be applied from time to time for his education but in case my said Grandson shall die before he arrive to the age of twenty one years, leaving no issue of his Body this legacy and such part of the Interest as may then be unexpended for education is to be and belong equally to my surviving children & grand children and their representatives - and to be divided between them in such manner and portions as I hereafter give and provide for them in this Will; but in case of his leaving Issue on his death before he arrives at the age of twenty one this legacy is to be considered as having vested in my said Grandson, and if he attains to the age of twenty one the same to be his forever whether he leaves issue or not - 
 Sec. 5th, Next if any devise or legacy in this Will shall not take effect by reason of any event hapening before my death the same shall be considered as part of the rest and residue of my Estate 
 Sec 6., Next after my debts, funeral expenses, the said legacies or Charges of settling my Estate are paid (the legacies be the same I hereby my sd Wife & daughter) my Will is that all my Estate both Real and personal in what state or place where the same may be (although I know of no Real Estate belonging to me except in the State of New York) shall be divided into four parts equal in value. And I give devise and bequeath to my son Sturges Brewster the one of said parts which he shall choose to be his own farm, to be set off and aparted to him by metes and bounds so far as regards my real Estate by persons hereafter named in this Will - This fourth part however I make Subject to and chargable with the payment of the one fourth part of the legacy hereafter given hereafter given to my Grandson Caleb B Hackley, and in case his legacy not vesting in the said Caleb B Hackley by reason of the happening of any event before mentioned, then the said fourth part of that legacy with the unexpended Interest thereon shall be and belong to my said ["for" crossed-out] son Sturgis forever -- 
 Sec 7th next I give devise and bequeath to my Daughter Sally forever one other of one said fourth part; and the real Estate contained in sd part shall be set off to her by wetes and bounds by the same persons before refered To this fourth part given to my daughter Sally I make also subject to and chargeable with the payment of one fourth part of the legacy heretofor given to my Grandson Caleb B Hackley and in case his legacy not vesting in the said Caleb B Hackley by reason of the hapening of any Event before mentioned then the said fourth part of that legacy with the unexpended Interest thereon shall be and belong to my said Daughter Sally -- 
 Sec 8th Next I give devise and bequeath to my said son Sturgis subject to and chargeable with one fourth of said legacy to said Caleb B Hackley one other fourth part of the said [another "of the said" crossed out] fourth part of my Estate and the Real Estate contained in said fourth part shall be designated and set off by metes and bounds by the same persons before referd to and the said fourth part thus given to my said son Sturgis he is To hold in trust for the following Uses, Intents and 

purposes (viz) the said Sturgis Brewster shall use occupy and improve the same both real and personal in such manner as shall be most in the benefit and Value thereof, and the clear profits and products of the same after deducting all necessary charges and expences incident to the management thereof - he shall account for and pay over to my son Jonathan L Brewster for so long a time as the said Jonathan shall live and be personally entitled to the same and no longer - but if he shall die or in any way to cease to be personally entittled to the same, my will is that two third parts of said clear profits and products thereof which shall thereafter accrue shall be paid to the Children of said Jonathan & their issue or to their legal Guardians respectively in equal parts respectively -- the issue of any child to be entitled to such part as such Child would have been entitled to if living - And the other third thereof to the present Wife of said Jonathan to her sole and separate Use so long as she shall live and be personally entitled to the same and no longer, and whenever neither the said Jonathan nor his said Wife shall be living or whenever they both in any way cease to be entitled to my part thereof of the said fourth part shall go over to and vest equally in the Children of the said Jonathan and the issue of such as shall then be dead - the issue to have such part as the parent would have been entitled to if living - and thereupon the trust hereby vested in the said Sturgis shall thereafter cease and determine and if there be no issue of said Jonathan then living the said Fourth part shall enure to and follow such of the bequests, devises and trusts herein made and declared of the other three fourths of the said residue of my Estate as relate to any of my issue then living -

 Sec 9th Next, I give, devise and bequeathto my sd son Sturgis Brewster subject to and chargeable with the one quarter part of the said Caleb B Hackley, one other fourth partof said Residue of my Estate, and the Real Estate contained in such fourth part shall be set off by metes and bounds by the same personsbefore alluded to them the said Fourth part thus given to my said son Sturgis he is to hold in trust for the following uses - Intents and purposes viz, the said Sturges Brewster shall use occupy and improve the same both real and personal in such manner as shall be most for the benefit and Value thereof -- and the clear products and profits of the same after deducting all necessary charges and expences incident to the management thereof - he shall account for and pay over to my daughter Ann, the wife of Robert Anderson to her sole and Separate use for so long a time as she shall live and be perssonaly entitled thereto and no longer, And if she shall die and the said Robert shall survive her, the clear profits and products which shall thereafter accrue shall be paid to my son in law, the said Robert Anderson, for so long as he 

shall live and be personally entitled to the same and whenever the said Robert and Ann shall die, or both shall cease in any way to be entitled to said profit and products, the said Fourth shall go over and vest equally to the Children of the said Ann and other issue of any of such as are then dead - the issue to take such part as the parent of such Issue if living would be entitledto, and thereupon the trusts hereby vested in said Sturgis in regard to this fourth part shall cease and determine, but if there be no issue of the said Ann then living this fourth partshall enure to and follow the bequests, devises and trusts herein made and declared as to such of the other three fourths of said Residue as relates to any of my Issue then living -- Sec 10th next, I order and direct that in case of the said legacy hereafter given to my Grandson Caleb B Hackley shall not vest in him by reason of the happening of any Event before mentioned then the two fourths of said legacy chargeable in the two devises under the Eighth and ninth paragraphs of this Will shall with the unexpended Interest thereon, he and tiling(?) to such devises respectively, and be considered as parts thereof, subject to the same trusts and be treated in the same manner as is directed respecting under the said two devises --

 Sec 11th I order and direct that if any of my Children shall exhibit for payment for any account or demand against my Estate that such Child shall be deprived of the Gift therein and hereafter given them and the Property within the devises or devise to such Child or children shall go to and be considered as belonging equally to be under the same conditions and trusts as heretofore mentioned as regards each devisee respectively - 
 Sec 12th next, in order to make a just divission of said residue of my said real Estate in the State of New York agreeable to the directions and provissions of this Will I do hereby nominate and appoint and enpower Thomas Paines Esqr and Mr. Robert Shoemaker of the Town of German Flatts - Jonas Bleeland(?) Esquire - Dut(?) Rufus Craine and Nicolas Shoemaker of the Town of Warren all in the County of Herkimer in said State of New York, any three or more of whom to have the Power of the whole, to make the aforesaid divission (and after the choice of said Sturges as to his part) to set off and apart the other three parts and designate to whom each separate three parts shall belong to severally - having reference to the equal Value of each part, to make the divission equal and Just betwean my said Children, and such designation to be meted and bounded by plain monumental marks &c and in case any one or more of the above nominated and appointed Gentleman die before or refuse at the time when their services may be wanted to perform the duties of this appointment by me desired - I then do request authorise and enpower the surrogate or Judge of Probate to return(?) office(?) in the probation of this Will in the State of New York, shall might or may appurtain, to fill up such ["the" crossed out] vacancy whether by death or refusal as aforesaid, with such Person or Persoons as such Surrogate or Judge for the time being may Judge proper for the purposes intended --Sec 13th Next, if by the death of my son Sturges Brewster or any other cause it should so happen that their should be no constituted Trustee to perform the trusts herein before declared at any time before the same are fully executed and accomplished, then I do devise and bequeath the 

premisses mentioned in the Eighth and ninth paragraphs or sections of the Will to such Person or Persons in succession as the said Judge or Surrogate shall from time to time appoint administrator with the Will annexed or Trustee for the purposes therein named, and do hereby devise and bequeath to such person for the time being all the trusts and duties and confer on him all the powers which are in said sections or paragraphs theresaid --

 Sec 14th next, I order and direct that there be charged as part payment of the legacy hereafter given my said Grand son Caleb B Hackley the sum of two hundred fifty dollars having advanced his dead Mother that sum before her death - Also I order and direct that there be charged as part payment of the legacy, bequest and devise made under the ninth Section of this Will to my sd son Sturges in trust for Mrs Anderson the sum of five hundred dollars having advanced her that sum before my decease. And I hereby discharge all my Children & Grandchild from any demand I may have or ought to have against them or either of them in book -- 
 Sec 15th Next I hereby order and direct that if the said Sturges Brewster which trustee as aforesaid, be disposed to sell said two fourth parts to him given in trust as aforesaid, or any part or parts thereof and convey the same in fee simple or any less Estate and to invest the avails in Bank stock, Canal stock or any other safe stock he is hereby fully authorized to do the same and the stock in which he shall invest the avails of such sale or sales shall be and remain for the same uses, trusts, bequests, devises Limitations and Import as the property so sold was subject to - Finally I hereby nominate appoint and empower my said son Sturges Brewster to be the Executor of this my Last Will and Testament annuling and revoking all former Wills by me made - in Testimony whereof I have hereby set my hand and seal this twenty fifth day of Februy Anno Domini 1825 Signed sealed declared and pronounced as the last Will and Testament of the Testator in presence of - 

Joseph O Nichols Caleb Brewster (Seal)

Samuel Inslie (?) Ransom Tryon

                          State of Connecticutt Fairfield County ss Fairfield February the 25th 1825 -- personally appeared before me the subscribing Authority Joseph C Nichols Samuel Inslie(?) and Ransom Tryon the three Subscribed Witnesses together, and made solemn? oath that they saw Caleb Brewster the signer and maker of the same sign and seal and heard him declare the same to be his Last Will and Testament, that they set to their hands as witnesses in presence of the Testator and of each other and that they Judged him to be of a sound and disposing mind and memory - The Court of Probate held at Fairfield February 17th 1827 Samuel Newton(?) Jus Peace the original Will of which the foregoing is a true copy being proved was approved and ordered to be recorded -

David Hill Ju Clerk(?) The Court of Probate held at Fairfield February the 17th 1827 Sturges Brewster of said Fairfield appeared accepted of the appointment of Executor of the last Will of Caleb Brewster dec -- and gave Bonds of twenty thousand dollars with Robert Andissin(?) of Hartford in Connecticutt as surety for a faithful performance of the duties of the trustee -- Six months was limited for the exhibition of claims, and Seth Perry and Agur Judsen of said Fairfield were appointed appraisers of the said Estate -- David Will Judge

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Capt. Caleb Brewster, Culper Spy Ring's Timeline

September 12, 1747
Setauket, Suffolk County, Colony of New York, British Colonial America
March 5, 1785
Age 37
Fairfield, Fairfield, CT, United States
November 5, 1786
Age 39
Fairfield, Fairfield, CT, United States
January 20, 1789
Age 41
Fairfield, Fairfield, CT, United States
July 22, 1790
Age 42
Fairfield, Fairfield, CT, United States
July 11, 1792
Age 44
Fairfield, Fairfield County, Connecticut, United States
April 17, 1794
Age 46
Fairfield, Fairfield, CT, United States
August 17, 1796
Age 48
Fairfield, Fairfield, CT, United States
April 14, 1802
Age 54
Fairfield, Fairfield, CT, United States