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Benjamin Tallmadge

A New Yorker, Tallmadge (1754-1835) graduated from Yale in 1773, and went to work for the Connecticut school system. When the Revolution broke out in 1775, he immediately volunteered as a member of that state's militia and was commissioned with the rank of lieutenant. He was promoted to the rank of captain in 1776 and a major the following year, distinguishing himself in the battles of White Plains, Long Island, Brandywine, Germantown, and Monmouth.

By 1778, Washington resolved to have an effective spy network. All of his secret agents before that time had proved brave but ineffectual like the unfortunate Nathan Hale, who had been hanged for his espionage by the British in 1776. He had had bad luck with those spies he had developed on his own, such as George Higday, who lived in British-occupied territory and who had offered to take messages from spies to Washington and even serve as a spy himself. Washington wrote to Tallmadge about this spy, but the letter was intercepted by the British, who were thus able to identify and arrest Higday on July 13, 1778.

The hapless Higday, a well-intentioned amateur, was typical of the agents working for Washington until he ordered Major Tallmadge to establish a reliable spy ring in New York City, which was then occupied by British forces under the command of General Clinton. Washington wanted intelligent, well-placed agents who .knew what information would be of value to him.

Tallmadge knew just the right people to contact, his good friends Robert Townsend and Enoch Hale (Nathan Hale's brother), who had graduated from Yale with him in 1773, along with Austin Roe, Abraham Woodhull, and Caleb Brewster. This network of New York spies was known as the Culper Ring and Tallmadge directed it under the alias of John Bolton.

Almost at the same time, his opposite number in Clinton's army, John Andre (using the alias of John Anderson), was attempting to establish a network of spies inside the territory occupied by Washington's army at White Plains. It was really no match for the Culper Ring, which quickly established the polished methods of professional spies. All of its members in New York operated with tight secrecy, each agent using an alias which was only known to Tallmadge. Woodhull used the alias Samuel Culper Sr., Townsend employed the name Samuel Culper Jr.

Townsend was the real leader of the Culper Ring, a successful businessman in New York who was thought by the British to be a loyalist. His mercantile business was ideally suited to conveying messages to Washington. His employees brought foodstuffs from Long Island farms into New York, pack trains operated by Austin Roe, who served as a courier for the network. Roe took Townsend's coded reports to Woodhull, who lived in Setauket, Long Island, on the shores of Long Island Sound.

After receiving Townsend's messages, Woodhull would hang a black petticoat on a clothesline. Brewster, a boatman, knew this signal meant Woodhull was safe to approach and had information to be picked up. The boatman would retrieve the message and take it to Enoch Hale or Tallmadge, who, in turn, presented the information to Washington. The group invented its own code, which became so complicated that they had to provide members with a "pocket dictionary" defining the espionage terms they employed.

Through the enterprising Townsend, Tallmadge was able to present Washington with an accurate, almost day-to-day report on British military operations and positions in New York, as well as Clinton's stores and military supplies, including information on all British shipping and the arrival of reinforcements.

In the fall of 1780, Tallmadge inadvertently became involved with Benedict Arnold's traitorous scheme to deliver West Point to the British. Arnold had been in communication with British intelligence chief Major John Andre and he had arranged to meet Andre behind American lines to prepare for the seizure of the American bastion. Knowing Tallmadge might intercept Andre, he boldly wrote to Washington's spymaster: "If Mr. John Anderson, a person I expect from New York, should come to your quarters, I have to request that you will give him an escort of two horsemen to bring him on his way to this place, and send an express to me, that I may meet him If your business will permit, I wish you to come with him "

John Anderson was the alias used by Andre as he made his way through the American lines. Andre went up the Hudson in an armed British sloop, met with Arnold, and then, when attempting to return to the British lines, foolishly changed from his military uniform into civilian clothes. He was stopped while riding alone by three American soldiers, who took him to their commanding officer. He was turned over to Tallmadge on September 26, 1780. Instead of sending Anderson on to Arnold, Tallmadge had the prisoner searched and the plans for West Point were found in Andre's boots. Almost at the same time, Tallmadge received a coded message from Townsend through the Cupler Ring courier system that he should be on the lookout for a "John Anderson," who was none other than the British spymaster John Andre.

Concluding that Arnold had turned traitor, Tallmadge escorted Andre to Washington, who refused to see the British officer. Andre was imprisoned, charged with being a spy. A military tribunal sentenced him to death and he was hanged on October 2, 1780. Tallmadge accompanied Andre to the gallows, full of admiration for the brave British soldier who fearlessly accepted his fate. Tallmadge attempted to overtake Arnold, but Arnold had learned of Andre's capture and had successfully escaped to the British lines to live out his life in misery.

When Tallmadge's master spy Townsend heard of Andre's death, he closed his store for several weeks, telling his agents to cease their operations. He feared that the British might somehow, through Arnold, expose the Culper Ring. His fears were groundless and he was soon back in operation, sending Tallmadge vital information.

Arnold, however, was not finished with his deviltry. As part of his bargain with General Clinton, he was made a brigadier in the British army with specific instructions to convince revolutionary leaders and their men to desert Washington and come over to the British side. He did manage to persuade some turncoats to join him but these were ragtag opportunists and mercenaries. Cleverly, Arnold then wrote a letter to Tallmadge, a man he did not know well, asking him to abandon the American cause and join him and the British.

On October 25, 1780, Arnold wrote to Tallmadge: "As I know you to be a man of sense, I am convinced you are by this time fully of the opinion that the real interest and happiness of America consists of a reunion with Great Britain. To effect which happy purpose I have taken a commision in the British army and invite you to join me with as many men as you can bring over with you. If you think proper to embrace my offer, you shall have the same rank you now hold, in the cavalry I am about to raise. I shall make use of no arguments to convince you or to induce you to take a step which I think right. Your own good sense will suggest everything I can say on the subject."

This letter was sent by a secret agent to the American lines but the agent did not deliver it at that time since Tallmadge had just succeeded in leading a victorious raid against a British position in Oyster Bay. The agent thought it imprudent to deliver such a message to a man who was then tasting the fruits of triumph, believing that Tallmadge would be more susceptible to Arnold's offer after Washington suffered some military setbacks. The letter was not delivered for several months and when Tallmadge finally read it, he was shocked. He also immediately realized that Arnold had somehow learned that he was Washington's spymaster and suspected that the letter was nothing more than a device to compromise his image and reputation as a fierce and loyal patriot.

Arnold was not the only former patriot to entreat Tallmadge to return to the British fold. He, along with many other revolutionary leaders, received an undated missive from Silas Deane, the one-time American representative in Paris who had helped Benjamin Franklin to persuade the French to enter the war on the American side. Deane had reportedly become disillusioned with the American cause and had gone over to the British. He wrote to Tallmadge, asking him to help effect a reunion with Great Britain. This was another letter Tallmadge did not answer. The enigmatic Deane finally went to live in England, aided by the British spy Paul Wentworth, but his one-time services to America were posthumously recognized by the U.S. Congress.

Tallmadge increasingly doubled his duties as spy- master with those of a military commander, leading raids against British strongholds such as Fort George, where he destroyed great quantities of British supplies. He continued to serve Washington faithfully until the end of the war. In 1783 he was promoted to the rank of breveted lieutenant general, a strictly titular position.

Following the war, Tallmadge became a successful merchant in Litchfield, Connecticut. In 1801 he was elected to Congress and served there until 1817 as a staunch Federalist and supporter of the policies advocated by his old commander, George Washington. He and Washington remained close friends until the commander-in-chief's death. Until that time, Washington, whose ledgers revealed that he had spent $17,617 to support his spy networks throughout the Revolutionary War, remained in contact with all of the Culper Ring spies, visiting Tallmadge, Townsend, Woodhull, and others regularly.

Washington frequently expressed his gratitude to them for the risks they had run. He was also determined that no retaliatory harm would ever come to them for their services and, to that end, ordered that the records involving the Culper Ring be sealed. For more than a century, no one knew, except Tallmadge and Washington, the actual identities of the New York spies.

Jay Robert Nash. Spies: A Narrative Encyclopedia of Dirty Tricks and Double Dealing from Biblical Times to Today.. M. Evans and Company, Inc., New York. 1997.

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