Anna Smith Strong was born on April 14, 1740, and married Selah Strong III in 1760. Selah served as a delegate to the first three provincial congresses in colonial New York and became a captain in the New York militia in 1776. During the Revolutionary War in 1778, Selah was imprisoned in the sugar house of New York City and later on the HMS Jersey for “surreptitious correspondence with the enemy,” as the British suspected him of being a spy.

Unbeknownst to the British, it was Anna who would become the family's spy.

Leveraging her wealthy Tory (British loyalist) family connections, Anna bribed British officials to parole Selah to Connecticut, where he remained with their children for the rest of the war.

Anna stayed behind on Strong’s Neck, a hamlet on Long Island, to maintain the family home and avoid its potential destruction by British forces. She had another crucial role to play. Major Benjamin Tallmadge from Setauket, Long Island, was tasked by General George Washington to recruit trusted spies for gathering intelligence from New York City. This group became known as the "Culper Spy Ring," which operated mainly in New York City, Long Island, and Connecticut. Tallmadge, a childhood friend from Setauket, enlisted Anna, making her the only female spy in the ring.

Anna's mission was perilous. She was to relay information to Abraham Woodhull, another Culper spy in Setauket, regarding the whereabouts of Caleb Brewster, a fellow spy known to the British. Brewster crossed the Long Island Sound in his whaleboat to deliver information from Woodhull to Tallmadge, who then passed critical details to General Washington’s headquarters in Westchester County, New York.

Anna's role involved signaling Woodhull of Brewster's arrival. She would hang a black petticoat on her clothesline, visible to both Brewster and Woodhull. Since Brewster used six different coves to hide his boat, Anna needed to specify the exact location. She devised a system using white handkerchiefs: the number of handkerchiefs indicated the cove Brewster was hiding in—one handkerchief for the first cove, two for the second, and so on. This simple yet effective system allowed Woodhull to quickly locate Brewster.

Thanks to Anna's discreet signaling, the Culper Spy Ring played a crucial role in uncovering Benedict Arnold's infamous plot to surrender West Point to the British in exchange for 20,000 pounds and a position in the British command. This intelligence was relayed to General Washington, though Arnold escaped before he could be captured.

Despite intense British scrutiny and arrests of some members during the war, not a single member of the Culper Spy Ring was ever exposed. The secrecy was so well-maintained that even General Washington did not know all the identities of his spies. The existence of the ring remained largely unknown until the discovery of correspondence in 1929.

After the war, Anna reunited with Selah, and they had their tenth child, George Washington Strong. Anna's bravery and ingenuity left a lasting legacy in the history of American espionage.

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