The popular TV series Turn delves into the lives and missions of American spies during the Revolutionary War. Based on Alexander Rose's book Washington's Spies: The Story of America's First Spy Ring, the series shows just how hard it is to be in the espionage game. The main characters in the show form the heart of what became known as the Culper Spy Ring. Led by Revolutionary officer Benjamin Tallmadge, this group helped the Americans win the war against the British.
Uncovering Benedict Arnold's plans to betray the American side was one of this spy ring's most important accomplishments. But who were these daring individuals that made up the Culper Spy Ring? Most of them knew each other from their hometown of Setauket, Long Island. Despite their strong bonds, the group members took on code names and numbers to protect themselves. To be a spy in these times meant to risk facing the ultimate punishment—execution for treason. Let's take a look at the four friends involved in this dangerous covert operation.
Considered the mastermind behind the spy ring, Benjamin Tallmadge was born on February 25, 1754, in Long Island. His father, also named Benjamin, was a minister. In 1769, Tallmadge began his studies at Yale College (now Yale University). He completed his degree in 1773 and intended to pursue a career in education. After graduating Yale, Tallmadge took a post as superintendent at Wethersfield High School.
History had other plans for Tallmadge, though. As the battle for independence heated up, he enlisted in the Continental Army in 1776. He served in the 2nd Continental Light Dragoons, and quickly rose up the ranks to become a captain and then a major. (Tallmadge was promoted to colonel in 1779.) In 1778, Tallmadge took on a new challenge. He began developing a secret spy network for General George Washington, which became known as the Culper Spy Ring. He took many measures to protect his operatives, many of whom were his childhood friends. A special code dictionary was created for messages, which replaced words and names with series of numbers. For instance, George Washington was known as "711."
Soon after the war ended, Tallmadge married Mary Floyd, the daughter of General William Floyd, in 1784. The couple settled in Connecticut and had several children together. Tallmadge was appointed the postmaster of Litchfield, Connecticut in 1792. He later enjoyed a career in politics, serving in Congress as a member of the Federalist Party from 1801 to 1817. Tallmadge died on March 7, 1835, in Litchfield, Connecticut.
Born in 1750, farmer Abraham Woodhull was the leading spy in the Culper Spy Ring. He was recruited by longtime friend Benjamin Tallmadge to help the Revolutionary forces against the British by gathering intelligence. Woodhull had good reason to visit New York, a hotbed of British military activities, as his sister and her husband ran a boarding house there. To protect his identity, he took on a code name: Samuel Culper Sr. Woodhull was also identified as "722" in the group's code dictionary.
Woodhull also used other forms of spycraft, including invisible ink and numeric codes, to disguise the content of his messages to Tallmadge. These missives handed off to another of another friend from Setauket, Caleb Brewster, to deliver to Tallmadge. After almost being arrested by the British for spying in 1779, Woodhull then recruited a Manhattan merchant, Robert Townsend, to help the cause. Townsend sent him reports on British military activity in New York under the name "Samuel Culper Jr." Austin Roe, another Setauket resident, helped get Townsend's messages to Woodhull.
After 1780, Woodhull seemed to shift focus from spying to family life. He married Mary Smith in 1781 and they had three children together. Woodhull went on to have several important posts after the war, including serving as the first judge of Suffolk County from 1799 to 1810, according to Rose's book. Two of his children married into the Brewster family. Woodhull, long after the death of his first wife in 1806, married Lydia Terry in 1824. He died two years later on January 23, 1826.
An adventurer and a risk-taker, Caleb Brewster was the only one in the spy ring not to use a pseudonym. He may have signed his name to his letters, but he was still known to the other members as "725" in their code system. Brewster was born in 1747 and was a close friend of Samuel Tallmadge, Benjamin's younger brother. Brewster took to the sea at the age of 19 to work on whaling boats. Returning home in 1775, he soon became involved in the fight for independence. Brewster first served in a local militia before joining the Continental Army.
In the spy ring, Brewster became an important conduit for information from Abraham Woodhull and Benjamin Tallmadge. He would put his strong boating skills to good use, traveling across a part of Long Island Sound known as the Devil's Belt to get Woodhull's reports. In addition to his work with the ring, Brewster was a skilled soldier. He fought under Tallmadge at the Battle of Fort St. George in 1780.
After the war, Brewster settled down in Connecticut with his wife Anne. The couple owned a farm in the Black Rock area, and he worked as a blacksmith for a time. In the 1790s, Brewster returned to the sea, taking command of a government ship, known as a revenue cutter, whose mission it was to stop smuggling. In 1816, Brewster retired to his farm. He died on February 13, 1827.
Anna Smith Strong
Anna Strong may play a substantial role in the series Turn, but her real-life counterpart's position in the Culper Spy Ring is much less clear. Known as "Nancy," she was born Anna Smith in 1740. Her father was Colonel William Smith who had served as the clerk of Suffolk County. She married Selah Strong in 1760, the couple had several children together. Active in the revolutionary cause, Selah had served as a delegate to the Provisional Congress in 1775. He was captured by the British and was held abroad the prison ship Jersey in New York Harbor for much of the Revolutionary War.
With her husband gone, Anna Strong was left to look after her family and farming estate in Setauket, Long Island alone. Many sources say that she helped her neighbor Abraham Woodhull and his revolutionary counterpart Caleb Brewster signal each other through an inventive use of her laundry. A black petticoat on the line meant there was some information to share. The number of white handkerchiefs indicated where to meet up or find messages.
In the Culper papers, there is only one reference to a female spy. The code number "355" indicated a lady was involved, but it didn't indicate which woman. Author Alexander Rose believes that Anna Strong was this secret agent, but others disagree. The truth, unfortunately, has been lost to history. There's also no evidence that she had a torrid relationship with Woodhull as depicted in the television series. The pair, in fact, were later connected through marriage when Woodhull wed her relative Mary Smith in 1781.
Little is also known about Anna's life after the war. Her husband became a state legislator and served as a judge. The Strongs named their last child, George Washington, after the revolutionary general. They lived in Setauket for the rest of their days. Anna passed away in 1812.