The American Continental Army had, in fact, lost New York in part because of a lack of information. George Washington underestimated British troop strength and the Americans were quite handily driven out of the city leaving it to the British.
With Benjamin Tallmadge in charge, the Americans launched a spy ring to infiltrate New York and bring information back to Washington.
Benjamin Tallmadge was a Long Islander who Washington placed in charge of the army’s intelligence gathering operation in 1778 – after previous efforts had struggled. Based in Connecticut, Tallmadge moved away from a system relying on single spies on specific missions to a network system that passed on what information it gathered through a single source – Tallmadge.
But Tallmadge had to get the information out of New York to his location in Connecticut. And that’s where Caleb Brewster, Anna Strong and her bloomers come into the picture.
Anna’s husband Selah had been imprisoned for spying for the Americans. Upon his release from custody, which Anna negotiated through her Tory relatives, he moved from the family’s Setauket, N.Y., home to Connecticut – leaving Anna behind.
Caleb Brewster was an expert seaman. He had worked on whaleboats since his childhood and was knowledgeable about the Long Island Sound – known in Colonial times as the Devil’s Belt. Caleb Brewster knew both the Long Island side where he grew up as a child and the Connecticut coast around Fairfield and Bridgeport.
Anna’s clothesline was conveniently visible both to Brewster and the coordinator of the New York spies. Her role was to hang her washing as a signal to the spies who visited New York for information. The black petticoat meant Brewster was ready to make a trip from New York to Connecticut. She would hang white handkerchiefs to let the spies know which cove he would be waiting in with his boat.
The work was dangerous. At one point Brewster encountered a British army lieutenant. He attacked the soldier. Rather than take him prisoner, however, Brewster robbed the man to make him think it was only a robber he had happened on, not a rebel operative. Secrecy was so important not even Washington knew the identities of all the men in the Culper Ring – which was named for Samuel Culper, a phony name given to one of the key spies who slipped in and out of New York City with information.
The Culper Ring provided needed information to Washington, including specific counts of troops and weapons, details of boats being built, information about British plans to use privateers to augment its Navy and names of loyalists covertly supporting Britain.
As the focus of the war shifted south, the Culper Ring wound down its operation. Brewster would eventually make Connecticut his home, becoming a blacksmith after the war and joining the forerunner of today’s Coast Guard.