By all measures, the American Revolution should have turned out differently. On paper, the Colonists did not have a prayer against the might of the British Empire, which, at that time, was the strongest military power on Earth. The only advantage they had was local knowledge of the terrain and their incredible resourcefulness.
George Washington learned quickly that the Continental Army and the local militias needed as much help as possible from the general populace in order to survive and fight. One crucial item he had to have was intelligence. It was imperative for Washington to have behind the lines information on British troops’ strength and plans. His first choice did not turn out well. Nathan Hale, who uttered the famous words, “I regret I have but only one life to lose for my country,” was captured and hanged on Manhattan Island in 1776.
A year later, Washington chose Maj. Benjamin Tallmadge of the Second Continental Light Dragoons to lead a spy ring in Manhattan to provide information on British troops and movements. Unlike Hale, Tallmadge had grown up on Long Island and was thoroughly familiar with the area and the people, making him an excellent choice. Tallmadge had also spent much time with Washington and endured the winter of 1777-78 at Valley Forge with him. Washington knew he was capable and loyal to the patriot cause.
Tallmadge connected with an old neighbor from Long Island, Abraham Woodhull, to recruit more spies living in Manhattan. Woodhull took on the pseudonym of Samuel Culper, and the six members that became spies were known as the Culper Spy Ring. Incredibly, no one knew of these spies until the 1920s when a man by the name of Morton Pennypacker painstakingly researched letters and other primary sources, unveiling the ring and the identity of all but one of the members.
The Culper Ring was comprised of people from different walks of life: a longshoreman, tavern keeper, shopkeeper, newspaper editor, and socialite woman. The woman, only known by her code name “355,” has not been identified, but the rest have and a great deal of information about them is brought out in George Washington's Secret Six by Brian Kilmeade. Robert Townsend, the shopkeeper, provided the bulk of the reports on the British. He would hand them off to Austin Roe, who would take them to Caleb Brewster in Long Island, who would then row across the sound to Connecticut and pass the report to Tallmadge, who would then ride down to Washington in New Jersey. This whole process took approximately two weeks. Due to several close calls, the ring devised a code and used an invisible ink that was only made visible by a special compound to avoid detection. If they had been caught, they would have suffered the same fate as Nathan Hale.
The Culper Ring was responsible for uncovering a British counterfeiting operation, preventing French troops from being ambushed, providing the British naval codebook to the French before the Battle of Yorktown, and stopping Benedict Arnold from handing over West Point to the enemy. These incredibly brave patriots who risked their lives daily received no medals or recognition for their service, were unpaid, and at times did not even receive reimbursement for their expenses.
After the war, they even risked and underwent persecution for the false belief that they were loyalists, a necessary part of their spy disguise during the war. If not for Morton Pennypacker, we may not even know about them today.