Anna Strong (spy)

Family

Anna's father was Colonel William Smith, son of Henry Smith and grandson of Colonel William Smith, a justice of the supreme court established in New York in 1691. He was clerk of Suffolk County, New York and judge of the Common Pleas court for the county for several years before the American Revolution. Anna's mother was Margaret Lloyd Smith, daughter of Henry Lloyd of Lloyd's Neck. Anna was described in an 1839 book by Benjamin Franklin Thompson on the history of Long Island as "a lady of much amiability and worth."

Anna's husband Selah Strong (December 25, 1737 – July 4, 1815) was related through his mother Hannah to General Nathaniel Woodhull and Abraham Woodhull, the "Samuel Culper " of the Culper Ring of American spies during the revolutionary war. He was a delegate to the first three provincial congresses in New York, which convened on May 22 and December 6 in 1775 and in May 1776. He also was a captain in the New York militia in 1776. According to Rivington's Gazette of January 3, 1778, Selah Strong was imprisoned in the sugar house at New York City as a presumed spy. Family tradition has him later imprisoned on the prison ship HMS Jersey. Later works mention only his imprisonment on the prison ship. Tradition says that Anna brought him food. Author Ryan Ann Hunter states that Anna eventually got Selah paroled through the influence of Tory relatives. Upon his release, he spent the rest of the war in Connecticut with the family's younger children while Anna stayed on Long Island. Anna Smith's step-mother, Ruth Smith, was Tabitha Smith's sister. Tabitha was mother to Ruth Floyd, wife of Brig. Gen. Nathaniel Woodhull.

The Strongs' children were Keturah S. (a daughter who married James W. Woodhull), Thomas Shepherd, Margaret, Benjamin, Mary, William Smith, Joseph, George Washington, and another Joseph. Mary and the first Joseph both died young, while Thomas later became a judge.

Formation of the Culper Ring

On August 25, 1778, Continental Army Major Benjamin Tallmadge convinced General George Washington that Abraham Woodhull of Setauket on Long Island would make a good agent to gather intelligence in New York City, the British Army's headquarters and base of operations during the American Revolutionary War. For a short time, Washington continued to support Tallmadge's superior Brigadier General Charles Scott as chief of intelligence. Contrary to Tallmadge, Scott favored single missions by agents, usually officers, across enemy lines.

One of Scott's intelligence missions to New York City failed when three Continental Army officers were discovered and executed in September 1778. After this, Washington gave Tallmadge the assignment to set up a network of spies and couriers in New York City. Scott soon went on furlough and was replaced by Tallmadge as chief of intelligence. In October 1778, Tallmadge started the New York City operation; Woodhull began to make trips into New York under the pretext of visits to his sister Mary Underhill, who operated a boarding house with her husband Amos Underhill. Woodhull's reports were written under the alias "Samuel Culper" (later "Samuel Culper Sr."); Tallmadge was called "John Bolton". On October 31, 1778, Woodhull was questioned threateningly at a British checkpoint. He hoped to pass on the work in New York to Amos Underhill but Underhill was unable to make clear or useful reports. Woodhull was obliged to continue his visits, although he became increasingly anxious that he might be discovered as time passed.

In June 1779, Woodhull engaged Robert Townsend ("Samuel Culper, Jr.") to gather intelligence in New York City. Townsend was engaged in business there and his presence was expected to arouse less suspicion than Woodhull had. He also had access to British officers through the authorship of a society column in a Loyalist newspaper and his tailoring business, as well as his interest in a coffeehouse with Tory newspaper owner James Rivington, also a secret member of the ring.

A network was then established in which Townsend would pass intelligence to a courier, Jonas Hawkins or Austin Roe, who would take it 55 miles (89 km) to Setauket and pass it on to Woodhull, usually via dead drop. Woodhull would evaluate and comment on it and pass it to Caleb Brewster, who took it across Long Island Sound to Tallmadge, who would then usually add a cover letter with comments. Tallmadge found that personally taking the message to Washington was too time consuming, so he eventually began to send these reports to Washington via dragoons and then by relays of dragoons.

According to widely accepted local and family tradition, Anna Strong's role in the ring was to signal Brewster that a message was ready, as he ran regular trips with whaleboats across the Sound on a variety of smuggling and military missions. She did this by hanging a black petticoat on her clothesline at Strong Point in Setauket, which was easily visible by Brewster from a boat in the Sound and by Woodhull from his nearby farm after he began to operate almost exclusively from home. She would add a number of handkerchiefs for one of six coves where Brewster would bring his boat and Woodhull would meet him. Historian Richard Welch writes that the tradition of the clothesline signal is unverifiable, but it is known that the British suspected a woman of disloyal activities at Setauket who fit Anna's profile.

In a less scholarly treatment, authors Brian Kilmeade and Don Yaeger speculate that she had motive to work against the crown but she also had reason not to. British law said that lands could be confiscated if left abandoned, which forced Anna to remain behind when her husband left for Connecticut. For this reason, they suggest, it is possible Anna would not have wanted to risk losing their home. Her children were also with her, so her arrest would have left those children parentless. Additionally, her family was already under close scrutiny since her husband was a known dissident. They offer no facts about Strong and her activities in support of these opinions or anything to contradict other sources noted here.

Missions to New York

Woodhull had to continue to visit New York for meetings with Townsend, who occasionally needed to be encouraged to continue his work or to discuss instructions or information. In October 1779, Woodhull was attacked by four armed men who searched his clothes, shoes and saddle but did not find the letter from Townsend that he was carrying. Woodhull told Tallmadge that this occurred and asked him to keep it secret so that others in the ring would not be intimidated. He also wrote to Tallmadge that he would soon be visiting New York again and "...by the assistance of a 355 [lady] of my acquaintance, shall be able to outwit them all."

Historians Alexander Rose, Mark Anthony Phelps and Kenneth Daigler write that the lady identified only as "a 355", 355 being Tallmadge's substitution code for "lady", was Anna Strong. Men traveling alone might come under suspicion as spies and be stopped and searched but a man traveling with a wife drew less suspicion and might not even be stopped, much less searched. Anna had her own reason to visit New York to visit her husband aboard the prison ship where he was confined and to bring him food if possible. Her main service on their trips would have been to divert attention from Woodhull.

Work with Brewster

On one of his trips to Setauket, Brewster was waiting for Woodhull in Strong's back garden. While waiting, he surprised a passing British lieutenant, pulled him off his horse and had the opportunity to capture or kill him. He refrained from doing so in order to avoid drawing suspicion on Anna by leaving the impression that Brewster and his men were thieves.

On February 4, 1781, the double agent, or simple self-dealing mercenary, William Heron told British intelligence chief Major Oliver De Lancey of the Seventeenth Light Dragoons that private dispatches were being sent from New York City by some traitors to Seutaket "where a certain Brewster received them near a certain woman's." Since the British were never able to catch Brewster and get him to disclose the woman's name, Anna's identity remained secret.

Aftermath

Selah Strong was on Washington's list of persons to be reimbursed for expenses that they incurred in connection with their activities for the Culper Ring. Rose and Phelps state that the reimbursement must have been for expenses incurred by Anna since Selah was imprisoned for much of the relevant time period.

After the war, Selah Strong was a state senator in New York between 1792 and 1800 and a member of Council of Appointment in 1794. He was the first judge of Suffolk County between 1783 and 1793 and county treasurer between 1786 and 1802. He was a supervisor between 1784 and 1794 and President of Board of Trustees of Brookhaven, 1780–1797 (1780 is almost certainly a typo for a later date).

No information has been found concerning Anna's activities after the end of the war other than that she and Selah lived quietly in Setauket for the rest of their lives. She died on August 12, 1812.

In popular culture

In AMC's Revolutionary War spy thriller period drama series, TURN: Washington's Spies, based on Alexander Rose's historical book Washington's Spies: The Story of America's First Spy Ring (2007), Heather Lind plays Anna Strong.