General Washington's spies on Long Island and in New York

by Morton Pennypacker

CALEB BREWSTER

Caleb Brewster at the time of his birth had for near neighbor Samuel Thompson of Setauket, whose son the historian, Benjamin F. Thompson, left a carefully prepared sketch of his life in 1843. In full Thompson says:

“Among those who engaged in defence of their country, against the oppression of a foreign power, few have had as good fortune to be remembered by posterity, or to receive their due share of respect and gratitude. It therefore devolves upon the historian, when opportunity offers, to rescue from oblivion the memory of the virtue and services of those, to whose exertions and sufferings we are indebted for the many privileges we enjoy. Great were the sacrifices of those who aided in the achievement of independence, and the establishment of the happy form of government under which we live. In this array of zeal and suffering, the subject of this notice stands pre-eminent.

“Mr. Brewster was the son of Benjamin, grandson of Daniel, and great grandson of the Rev. Nathaniel Brewster of Setauket, who was the son of Jonathan, and grandson of elder William Brewster of Plymouth, one of those worthies who arrived in the May Flower in December 1620.

“The father of Mr. Brewster was a farmer, and, as was too often the custom of the day, gave his only son a limited education. He was born at Setauket, in 1747, and learned such branches as were taught in the country schools of that period, comprehending little else than reading, writing, and arithmetic. Being naturally of an ardent and enterprising disposition, and anxious to explore beyond the confines of his native town, he chose the life of a sailor; and at the age of nineteen, engaged himself on board a whaling vessel, commanded by Captain Jonathan Worth, bound to the coast of Greenland. His next voyage was to London in a merchant ship, and upon his return, he found his country involved in the Revolutionary contest. His enthusiasm in the cause of liberty did not allow him to hesitate, for a moment, the course which his duty called him to pursue, and he immediately volunteered his services in securing American Independence. He was honored, in a short time, with the commission of lieutenant of artillery, and from that time forward was eminently distinguished for zeal and intrepidity, possessing to the fullest extent the confidence of the officers of the army and that of the commander-in-chief. In short, such was the exalted opinion entertained of his integrity, courage, patriotism, and prudence, that in 1778 he was employed as a confidential and secret agent of Congress; and he devoted himself, through the remainder of the struggle, in procuring and transmitting the most minute, accurate, and important intelligence relative to the movements and intentions of the enemy at different points, and particularly in New York and on Long Island; for which he was uncommonly well qualified, as well by his intimate topographical knowledge of the country, as his acquaintance with the people on both sides the political question, and therefore knew in whom, of either party, he could venture to confide. He was among those who, under Col. Parsons, crossed the Sound to Long Island in 1777, for the purpose of capturing a body of British and tories, which, under Col. Hewlett, had taken possession and garrisoned the Presbyterian church at Setauket. On the 23d of June, 1780, he was appointed captain of artillery, and was frequently engaged with separate gangs of marauders, who sometimes extended their predatory excursions upon the main.

“In November 1780, he was a volunteer with Benajah Strong and Heathcote Muirson, in the expedition under Maj. Tallmadge, to the South side of Long Island, where they surprised and took prisoners a party of British troops encamped upon Smith’s Point at Mastic, and on their return destroyed a large quantity of hay and military stores at Corum. In 1781 he engaged with, and captured an armed boat with her whole crew, in the Sound, which he carried safely into Black Rock Harbor.

“On the 7th of December, 1782, Captain Brewster, with the whaleboats under his command, gave chase to several armed boats of the enemy in the Sound, and after a desperate encounter, in which most of the men on both sides were either killed or wounded, he succeeded in capturing two of the enemy’s boats. This action has generally been denominated, by way of distinction, the boat fight; and at the time was justly considered, in connection with its attendant circumstances, one of the most valorous and extraordinary engagements of that portentious period. It was indeed a truly perilous adventure; yet the contest lasted only twenty minutes, and some of his boats refusing to come up, he was compelled, from his peculiar situation, to engage with the enemy almost single handed. During the short but terriable conflict his shoulder was pierced by a rifle ball, which passed out at his back. His prudence and resolution enabled him to keep this occurrence a profound secret till the enemy surrendered, when he found himself exhausted from the effusion of blood. After reaching the shore, he was confined, under the hands of a surgeon, for some time; for the injury thus received, he was placed upon the pension roll of the army, and continued to receive a gratuity from his country for the remainder of his life. He participated in several other important and hazardous engagements, while attached to the line of the army, the interesting particulars of which it is impossible to ascertain, as none of his compatriots on those occasions are now living. On the 9th of March, 1783, he took command of a sloop at Fairfield, for the purpose of attacking the Fox, a British armed vessel in the Sound; and as soon as he came near, he ordered his men to board her with fixed bayonets, himself leading the way. In less than two minutes, she became their prize. Captain Johnson, of the Fox, and two men, were killed, and several others wounded; while Captain Brewster had not a person injured. This extraordinary exertion on his part was more than his then state of health could endure, and in consequence of which he was confined to his bed for several months. When he recovered, the preliminaries of peace had been exchanged, and his beloved country had assumed her appropriate station among the free nations of the earth. In 1784 he married Anne, daughter of Jonathan Lewis of Fairfield, Connecticut; where he continued afterwards to reside, when not in public service, to the close of life. In 1793 he was commissioned a lieutenant of the revenue cutter for the district of New York; and such was his well known skill and prudence, that on the death of Captain Dennis, soon after, he was appointed her commander, which he retained till 1816, with the exception of three years of Mr. Adam’s administration, to which he was opposed. In that year he retired to his farm at Black Rock, where he departed this life at the age of seventy-nine years, February 13th, 1827. In stature, Captain Brewster was above common size, of fine proportions, a commanding countenance, a constitution athletic and vigorous, and of extraordinary activity. His talent for wit and humor was almost unrivalled, and for relating anecdotes few men could be found more entertaining.

“His excellency Governor Tompkins, Dr. Mitchill, James Fairlie, Esq., and several other gentlemen, accompanied Captain Brewster in a voyage around Long Island, in September, 1809; and so highly gratified were they all with his polite attention to their comfort, that it was resolved to present him a silver cup as a token of their obligation and regard. The fort at Staten Island, where most of the gentlemen were present, was the spot chosen for delivering the cup, on which occasion Dr. Mitchill made an address in his usual able manner, and was happily responded to by Captain Brewster. On the subject of his military services, Mr. Knox, former secretary of war, on the petition of Captain Brewster, reported to the House of Representatives, the 21st of June, 1790, that ‘he was a lieutenant of artillery during the war, and was confidentially employed in an armed boat by the commander-in-chief, to keep open the communication between Connecticut and Long Island, for the purpose of obtaining intelligence. That he performed this ardous and hazardous service with fidelity, judgment and bravery, and to the entire approbation of General Washington, appears by his letters written to Captain Brewster, as well as his certificate, bearing date June 10, 1784.’

“By the zeal and activity which he manifested in this employment, he became, as a matter of course, a peculiar object of the enemy’s hate, who made many attempts, and in various ways, to take or destroy him. He, and those under his command, in the month of Dec., 1782, behaved with the highest gallantry, in an engagement with the enemy’s armed boats, the largest of which he captured, after an obstinate resistance, in which perilous action he was dangerously wounded, and was carried to Connecticut, at a distance from any hospital, where he languished for a long time under the pain of his wounds, from which he finally recovered.

“His widow survived her husband several years, and died in 1835, leaving a number of children, one of whom, Sturges Brewster, Esq., has been for many years attached to the New York Custom House.”