Interesting History: The Beginning of American Espionage

By Clayton Huckaby

The American Revolution is one of the most successful revolutions in modern history. Many of the revolutions that followed the American Revolution had varying degrees of success. The French Revolution, for example, resulted in destabilization that gave rise to Napoleon Bonaparte and his wars. Other revolutions simply ended in poverty for many of the revolutionaries in one way or another.

One of the reasons the American Revolution was so successful was because, in spite of the plethora of riots and brutish killings, the American Revolution began as an intellectual movement. It was not a revolution sparked by the incensed poor against the bourgeois wealthy, but it was a revolution whose very foundation began with the intellectuals at the time.

Men like George Washington, a rich plantation owner from Virginia and war veteran; Alexander Hamilton, a young intellectual who eventually became an attorney and the first Secretary of the Treasury; and Benjamin Franklin, an astute businessman, led the revolution from the beginning. Despite the aforementioned men’s achievements, one of the most brilliant yet lesser known organizations of the war is the Culper Spy Ring.

The Culper Spy Ring remains on the sidelines of history to this day. Their work was instrumental in winning the Revolutionary War, yet they are hardly mentioned in the main narrative of the war’s history. Maybe this is because, while their deeds were heroic in their own way, they were spies, and spies oftentimes do not get the credit they deserve. Possibly, leaving them out of the primary narrative highlights how quickly a widespread narrative can take root and how much staying power it has.

Visions of heroic battles where men stand face to face and fire a volley of bullets until no man remained only highlights a part of the war. The truth is though, unlike the European Wars prior to the American Revolution, this was not a “gentleman’s war.” This was a war where Americans introduced guerilla tactics which the British simply were not equipped to handle. Instrumental in this new type of war was the spy and the Culper Spy Ring was the best of the best at the time.

Benjamin Tallmadge, Robert Townsend, Abraham Woodhull, Austin Roe, Anna Strong and Caleb Brewster were the masterminds behind the Culper Spy Ring. Woodhull took the mantle of Samuel Culper Sr. to protect his identity while Townsend was codenamed Culper Jr. Townsend was instrumental to the success of the spy ring. His job as a reporter for an American newspaper gave him access to British soldiers, whom he could ask questions without raising suspicion. Any information he gathered would then be funneled back to Woodhull and Tallmadge through an elaborate scheme that eventually made its way back to General Washington.

Townsend also worked to feed misinformation to the British Army. When the French decided to join the war effort on the side of the American rebels, the British were preparing to intercept their vessel before they could make landfall. Townsend, through his contacts, was able to convince the British Army that the Americans were planning on attacking New York diverting their attention away from the British. Townsend was also instrumental in finding out who spies were that were working for the British on the side of the Americans.

Woodhull, the original Samuel Culper, was from the town of Setauket, New York. Initially he went to New York City saying that he was visiting his sister, but when the visits became too frequent, the British became suspicious. As a result, he enlisted the help of Townsend to send him information from New York City. Roe was Townsend’s courier to Setauket. Once the letter was handed to Woodhull, Woodhull would add information of his own and Strong would hang out her petticoat to indicate that Brewster had arrived. Furthermore, Strong would hang handkerchiefs to signal where Brewster was hiding. Brewster would take the note across the bay on his whaleboat to Tallmadge who would then put it on a line of riders back to General Washington. This intricate system was put in place to ensure the anonymity of the spies and prevent the British from ending it.

The Culper Spy Ring’s contribution to the war were priceless for the American war effort. Woodhull, Tallmadge, Strong, Brewster, Townsend and Roe were as instrumental to winning the war as any American soldier or intellectual that offered their services to the revolutionary cause.