e 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