General George Washington Sets Up Espionage Ring on Long Island

In February 1777, with the Revolutionary War not going well, George Washington was intent on finding out more information about the British disposition in New York. Washington’s military scouts were unable to gather enough information for him to make any appreciable decisions. So Washington decided to take the drastic step of creating his own ring of spies.

It was one of the first espionage operations and organizations in the history of the United States. Washington himself dabbled in intelligence collection as a young man when he would befriend unwitting French officers in taverns and pump them for information during his travels to Ohio.

During this time of history, spies and spying were deemed “ungentlemanly” and were universally loathed. Untrained operatives were not going to be successful as the first man to volunteer, Nathan Hale was caught only a week after being sent and was hanged.

Washington needed well-trained professionals to do the job but they didn’t exist in 1777. However, John Jay, who later became the first Chief Justice of the Supreme Court, had been running a counter-intelligence operation in New York and recommended Nathaniel Sackett to Washington.

On February 4, 1777, Washington wrote a letter to Sackett where he offered him $50 a month—out of his own pocket—to establish the first formal espionage group for the “advantage of obtaining the earliest and best Intelligence of the designs of the Enemy.”

Sackett is the real founding father of American intelligence although history has largely ignored his contributions, perhaps due to his very short time as the head of intelligence. However, the CIA credits him with the idea of embedding his operatives with the British and Hessian forces.

Sackett much like his successor many years later in WWII General William Donovan, with the OSS would have to start from scratch. Many of the first agents would fail, including Sackett himself only months into the job. Washington would not receive enough timely reports from his operative to properly assess the situation and he would let Sackett go after paying him for his time and effort.

Sackett’s replacement, was a young man, Benjamin Tallmadge who was just 26 years old and developed the very successful intelligence gathering operation known as the Culper Spy Ring. Tallmadge was a Major, and later was promoted to Colonel and went by the alias, John Bolton. Culper was the name proposed by Washington from Culpeper County, Virginia.

Tallmadge’s group included Abraham Woodhull and Robert Townsend. Woodhull used the alias Samuel Culper Senior and Townsend used the alias Samuel Culper Junior. Other operatives consisted of Caleb Brewster, Austin Roe, Anna Strong, James Rivington, Amos Underhill, Jonas Hawkins, Sally Townsend, and Mary Underhill.

Many of the operatives were friends of Tallmadge’s from New York, so their trust factor and bona fides were solid. They used a series of “dead drops” and other clandestine means of communication to prevent exposure to the British.

Many of the methods used would become tried and true espionage methods such as coded newspaper items, invisible ink and a clever numbering system a “numerical dictionary” code that matched 763 cities, names, and words to numbers.

Some of the other means of communication involved the signals that are still used in tradecraft today such as when there was a message to be picked up. Anna Strong, a resident of Setauket, helped pass along messages from the spy ring by posting prearranged signals to indicate when one of the spies was ready to submit intelligence.

If Strong hung a black petticoat on her clothesline, it meant that one of their contacts had arrived in town. Next to that, she would hang a number of white handkerchiefs. The specific number of handkerchiefs indicated one of six hiding places where their contact will be located. The operatives used Strong’s signals to meet one another or to drop messages at one of the meeting places.

The British had caught wind of a woman who supposedly was passing signals to the Revolution and Strong fit the profile of whom they were looking for, but she was never caught.

Their secrecy was such that not even Washington himself knew the identities of all of the operatives. Not one of them were ever compromised or captured by the British.

The Culper Spy ring operated in New York City, Long Island, and Connecticut from 1778 until 1783. However, the majority of their operations ended around 1781. Some of their intelligence coups were extremely important to the cause of the Revolution. Among them were :

• A planned sneak attack on the French forces that were landing to help the cause at Newport, Rhode Island. The French were still organizing after their voyage from France and an attack before they were ready could have thrown them back into the sea.
• A British ploy to counterfeit the paper money that the Revolution was using, “Continental Dollars”, the timely intelligence helped the Continental Congress to act quickly and retire the bills.
• The cell learned that a high-ranking American officer was going to turn over the fort at West Point, NY to the British. The future home of the US Military Academy on the Hudson River was of vital importance. The traitorous officer later turned out to be Benedict Arnold.
• Culper also learned of a planned raid by Lieutenant General William Tryon in Connecticut in 1779 was a ruse to force Washington to split his forces, thus allowing LTG Henry Clinton to attack his forces piecemeal.

At the conclusion of the fighting, the British paid a big compliment to the Culper Spy Ring by stating,. “Washington didn’t really out-fight the British. He simply out-spied us,” a British intelligence officer reportedly said.

After the war, Washington asked for Congress to reimburse him for paying his spy network. His sum? $17,000, which just under $450,000 today. Congress paid him back and it was money well spent.

In 2014, a series aired on AMC based on the Culper Spy Ring “Turn: Washington’s Spies” and also drew on the book “Washington’s Spies: The Story of America’s First Spy Ring”, by Alexander Rose.

The series aired from 2014 – 2017 and starred Jamie Bell (6 Days), as Abraham Woodhull and Seth Numrich as Major Benjamin Tallmadge.

Illustrations/Photo: US Archives