Espionage has always been a dirty but necessary game in war. Each side plays a game of chess for information and does their best to outwit their opponent. In order to do this each side recruits spies.
These spies never get the honor they deserve.
They live in secret and they die without dignity. To be caught as a spy is certain death and possibly torture.
Each of them risks scorn on themselves, their family, and their friends. If caught they are branded, traitors. The Culper Spy Ring was no different.
Each of these men, women, and slaves risked their lives to deliver information to their side to gain an edge.
Culper Spy Ring Facts: Nathan Hale
Hale was given orders to pose as a school teacher and go behind enemy lines. Once behind enemy lines he would learn the positions of the British army and deliver any information of use back to the Continental Army and George Washington. His attempt was doomed from the start.
Hale was not a trained spy, did not have a good cover, and was much too trusting. While in New York gaining intelligence he came into contact with a man named Robert Rogers. Rogers was a skilled tracker, a veteran of the French and Indian War, leader of the Queen’s Rangers, and had a special knack for exposing secret plots.
Rogers was able to gain Hale’s trust and at the perfect moment capture him just before he crossed back into patriot territory. When Hale was caught he was carrying incriminating documents and sentenced to hang.
Culper Spy Ring Facts: Establishment
Nathan Hale’s death left a bad taste in many provincial’s mouths, including his old friend from Yale, Benjamin Tallmadge. Tallmadge served under General Washington and was promoted to head of intelligence. It was under his guidance that the Culper Spy Ring was put together and would send information back to Washington about the whereabouts of British forces and future plans.
Under the guidance of Tallmadge, the Culper Spy Ring became a thorn in the side of the British. It seemed as though they were always chasing a ghost and could never understand where the intelligence was coming from. There are probably some names that we will never know that was involved in this secret ring, but we do know the names of most of the key players:
- Benjamin Tallmadge – Codename was John Bolton and was the leader of the Culper Spies. He was childhood friends with Abraham and Caleb.
- Caleb Brewster – Brewster sent a letter to Washington asking if he could gather information on the enemy. Washington reluctantly agreed and Brewster became the first spy of the eventual Culper Spy Ring.
- Abraham Woodhull – Codename was Samuel Culper Sr and was from a long line of Woodhull’s in Setauket, New York.
- Robert Townshend – Recruited by Abraham Woodhull and took the codename Samuel Culper Jr. Townshend’s location in New York made him much more accessible to accurate information than Woodhull.
- Anna Strong – The women used to signal Abraham Woodhull when Caleb Brewster was available to retrieve information.
- Jonas Hawkins – Courier used to deliver messages from Abraham to Benjamin Tallmadge
- Austin Roe – Another courier used to deliver messages from the Culpers to Tallmadge. Nicknamed the “Paul Revere of Long Island”
- Hercules Mulligan – Recruited as a spy by Alexander Hamilton. He was a member of the Sons of Liberty and knew Townsend’s father.
- Cato – Mulligan’s slave and best friend. Cato was Mulligan’s most trusted ally.
Initially, Washington assigned General Charles Scott to manage the spies, but soon his lack of interest and innovation caused him to lose that assignment to Tallmedge. Tallmedge favored a different approach to Scott.
Scott favored the single-person mission (similar to Nathan Hale’s mission) in which he would send one man back behind enemy lines to gather information and then return. Tallmadge favored an embedded approach that would require a network of spies embedded in the enemy lines and they would communicate through a line of communication.
After Scott lost 3 of the 5 men he sent, Washington preferred Tallmadge’s methods
Culper Spy Ring Facts: First Operations
Abraham Woodhull lived in Setauket but had a sister that lived in New York City. This gave him a natural cover to journey into New York City. He would make the trek every couple of weeks and during his stay make notes of the British navy, various fortifications, and troop movements. When he arrived back in Setauket, tradition believes, that Anna Strong would put a black petticoat on her clothesline and this would signal Caleb Brewster.
Each time Woodhull learned of new information he would have to follow this procedure which would take a considerable amount of time. In order to speed up the process, Tallmedge implemented express couriers to get the message to him and Washington quicker. The first of these express couriers was Jonas Hawkins and the second would be Austin Roe. The two express couriers sped up the communication while avoiding contact with the enemy.
During the Spring of 1779, Abraham Woodhull became worried about detection and laid low. (Colonel John Graves Simcoe led a mission to capture Woodhull in Setauket that resulted in his father getting beaten. Woodhull was in New York) This brought some concern to Tallmadge and Washington and they began work on the recruitment of another spy for the ring.
On June 13, a letter from Washington was written naming the Culpers, “a liquid”, Tallmadge, and the possible recruitment of George Higday. On July 2, Colonel Banastre Tarleton raided the camp of Benjamin Tallmadge. He managed to capture Tallmadge’s horse and some papers. Within those papers was the mention of Higday.
After Higday was exposed he was useless to either side of the war.
Culper Spy Ring Facts: Recruitment of Robert Townshend
In June 1779, Woodhull engaged Robert Townsend to gather intelligence in New York City, using the alias “Samuel Culper, Jr.” Townsend was engaged in business there, and his presence was expected to arouse less suspicion than Woodhull’s visits would.
He also had access to British officers through several channels, including his own tailoring business. He wrote a society column in a Loyalist newspaper, and he owned an interest in a coffeehouse with Loyalist newspaper owner James Rivington, who also was a secret member of the Culper Spy Ring.
One of the factors that led to Townsend joining the fight against British rule was the treatment of his family by British soldiers in Oyster Bay.
A number of British officers thought that anti-British sentiment had been ingrained into the colonists’ spirit, and they believed that “it should be thrash’d out of them [because] New England has poyson’d the whole.” This led to numerous incidents of violence and pillage directed at colonists.
On November 19, 1778, one such instance drove Townsend to the Patriot cause.
Colonel John Graves Simcoe of the Queen’s Rangers and roughly 300 of his men were stationed in Oyster Bay during the winter months. Simcoe took the Townsend home as his headquarters, and he and his men used the home when and however they wanted. Townsend’s father Samuel was distraught after his prized apple orchard was torn down by Simcoe’s men.
After Townsend began his intelligence activities in New York City, Woodhull operated almost exclusively from Setauket. A revised communications network was then established, in which Townsend would pass intelligence to a courier—at first Hawkins, then Hawkins and Roe, and exclusively Roe after September 1779.
The courier would take it to Setauket and pass it to Woodhull, usually via dead drop in a box hidden in a field that Roe rented from Woodhull. Woodhull would evaluate and comment on it and pass it to Brewster, who would take it across Long Island Sound, occasionally adding an intelligence note of his own, and pass it to Tallmadge. Tallmadge would usually add a cover letter with comments.
As noted before, tradition holds and many sources state that Anna Strong signaled Brewster that a message was ready with a black petticoat on her clothesline in Setauket, which was easily visible by Brewster from a boat in the Sound and by Woodhull from his nearby farm. Tallmadge sent the messages or received messages from Washington by a relay of dragoons acting as couriers.
Woodhull wrote in a coded message on August 15 that Hawkins had to destroy a letter from Culper, Jr. or be captured. In his August 15 message, Woodhull wrote that Hawkins insisted that his next meeting with Townsend be in an out-of-the-way location.
Townsend did not like taking the additional risk and was beginning to doubt Hawkins’s reliability. Finally, in September 1779, Hawkins stopped his courier services for the Ring, as Townsend refused to deal with him any longer. Woodhull acted as a courier on September 11 so that he could explain to Townsend the loss of the earlier letters.
Austin Roe then became the sole permanent courier for the Ring
Culper Spy Ring Facts: Secret Identities and Mulligan
The identities of the members in the ring were so secret that even Washington did not know the name of the spies involved. They each were referred to by their aliases and there was a code used during communications. Also, the communications utilized invisible ink as to not raise suspicions. This allowed the spies to use a variety of methods to slip information past the British.
The identities of these spies were so secret that it would take over a century to learn of the identities of these men and many in the ring will never be identified.
This included the recruitment of Hercules Mulligan and his slave Cato. These two were recruited by a young Alexander Hamilton. Mulligan operated independently of the ring but was aware of the ring. He operated more as a lone spy and would pass on information to Robert Townshend which Townshend may or may not add to his reports.
Cato was a reliable companion to Mulligan and passed on vital information that exposed a British plot to capture/assassinate rebel leaders, specifically George Washington and New Jersey Governor William Livingston.
Mulligan was caught by the British with a charge of espionage, but their inability to prove anything led to his release. After Mulligan’s release, he continued his spy activities but was unable to communicate with Washington directly.
Mulligan learned of a plot to capture Washington on his way to visit Rochambeau. He passed the message on to Robert Townshend who sent it via the Culper Spy Ring.
Washington was alerted and went a different route for his visit.
Culper Spy Ring Facts: Accomplishments
This was one of the first successful spy rings in the American Revolutionary War. Their intelligence successfully did the following:
- Kept eyes on the British in New York and accurately provided intelligence of British ships, cargo, movements, fortifications, and troop strength.
- Exposed a plan for the British Army to ambush the newly arrived French in Rhode Island.
- Exposed Benedict Arnold’s Treason which led to the capture of Major John Andre.
- Provided intelligence of the British Navy’s attempt to rescue Cornwallis from Yorktown. This intelligence tipped off the French who were waiting for the British.
- Exposed plot to ambush George Washington.
What makes a successful spy?
Because these guys were so successful in their espionage we will probably never know the extent of what they did and how much they exposed. That is the way it works when you are a spy. We only know of the major accomplishments of this ring and even some of those accomplishments are questioned as to whether or not they were involved.
Culper Spy Rings Facts: Online Resources
- Wikipedia – Culper Spy Ring
- Mount Vernon – The Culpers
- Spy Museum
- CIA.Gov – The Founding Fathers of Intelligence
- Woodhull Genealogy
- The History Junkie’s Complete Guide to the American Revolutionary War
- The History Junkie’s Guide to the American Revolutionary War Timeline
- The History Junkie’s Guide to George Washington
- The History Junkie’s Guide to Colonial America