In August 1776, George Washington and the Americans had to beat a hasty retreat leaving the British in control of New York City. This was thought by many as the death blow to the Revolution. Washington tried to regroup and desperately needed intelligence from the occupied city of New York. Out of this need, the Culper spy ring was born.
It was organized by Major Benjamin Tallmadge and two main members of the ring were Abraham Woodhull, under the pseudonym of Samuel Culper Sr., and Robert Townsend, who used the pseudonym of Samuel Culper Jr. The covert activities began in 1778 and they were charged with reporting on the troop movements through New York. They were so good at secrecy, that even today we are unsure of some of their agents. Agent 355 is one of these.
We only know her as “355”, which was the code designation for “a lady”. However, this lady was responsible for passing along important intelligence to the revolutionaries. Information gathered by her lead to the arrest of Major John André, who was the head of England’s intelligence operations in New York. André was a dashing and handsome officer, and as such attracted the attention of several members of the opposite sex. 355 took advantage and found herself at the same parties as André and made sure to take heed of what he was saying, especially after a few drinks. It was at one of these parties that she got wind of the British plan to gain West Point by subversion.
West Point was an important strategic fortification on the Hudson River. Whoever held West Point, held the Hudson River Valley. André was actively searching for a way to help his British bosses, and he struck gold in the person of Peggy Shippen. Peggy was a debutante whom he had courted in Philadelphia a few years earlier. Peggy was, to put it frankly, a gold digger. She loved the high life and felt that her husband should keep her in the manner to which she had become accustomed. Who was her husband? Just a guy called Benedict Arnold (Read about him in this post: http://www.historynaked.com/benedict-arnold/ ) Arnold was getting disillusioned with the lack of cash and fame he was getting from the revolution. It probably just took a tiny nudge from his loyalist wife to put him in touch with the dashing André to see if he could do any better if he turned his coat. André offered him 20,000 pounds to hand over West Point without a shot. That’s 3.5 million dollars in today’s money. That would keep dear old Peggy in lots of diamonds. Arnold took the deal. Unfortunately for them, 355 was on the job and got wind of the plot. André was caught with passes signed by Arnold and the plans for West Point at Tarrytown, New York. He was hung for a spy on Washington’s orders. Arnold got away, but West Point was kept out of British hands. In 1780, a female spy was captured and died on the prison ship Jersey. This was thought to be the end of 355.
But who was she? Multiple theories abound. It is thought she was the member of a prominent loyalist family as she had access to so many upper class British officers. Also the designation of “lady” in code was thought to be significant. A lady meant upper class. Candidates include Anna Strong, a known member of the Culper Spy ring and Abraham Woodhull’s neighbor. She transmitted messages via laundry hanging on her clothes line. Other candidates include Sarah Horton Townsend , Robert Townsend’s cousin, or Elizabeth Brugin, who helped American prisoners on British prison ships. The popular television series Turn: Washington’s Spies, theorizes 355 was a former slave of Anna Strong.
One of the most popular theories is that 355 was Robert Townsend’s common law wife. There are stories that Townsend was in love with 355 and when she became pregnant with his child, he insisted she give her dangerous espionage job. However, Arnold found out her identity and turned her over to the British who imprisoned her on the Jersey. There she supposedly gave birth to her son, whom she named Robert Townsend Jr. Then she died. However, most academics do not believe this story. There is one tantalizing piece of information though. Robert Townsend Jr. did exist, and was supposed to be the son of James Townsend, Robert Townsend Sr.’s brother. He became a lawyer and a politician, and was very active in creating a monument to those who lost their lives in the British prison ships. This monument, nearly 150 feet tall commemorates the men and women who lost their lives aboard these ships.
We may never know. Abraham Woodhull wrote she could “outwit them all”, and she still is outwitting us to this day. Hail and Farewell, 355.