Founding Father Spies
George Washington was the obvious choice for acquisition of foreign intelligence. The Father of our Country was an adroit spymaster. Over the course of his long military career, he directed numerous agent networks, provided comprehensive guidance in intelligence tradecraft to his agents, and used their intelligence effectively when planning and conducting military operations.
John Jay–who later became Chief Justice of the United States–is considered the Founding Father of American counterintelligence. Jay is seldom cited for his achievements in this arena; his historical reputation stems largely from his political and judicial accomplishments. But he clearly deserved to be considered the first national-level American counterintelligence chief.
Benjamin Franklin was the American icon after whom the remaining room was named. His efforts in what is known today as covert action were wide-ranging and usually successful. During the Revolutionary War period, Franklin engaged in propaganda operations and agent-of-influence activities and directed paramilitary operations against British property.
George Washington: The First American Intelligence Chief
“There is nothing more necessary than good intelligence to frustrate a designing enemy, & nothing requires greater pains to obtain.”
George Washington’s role as the first American intelligence chief has received far less attention than his numerous exploits as a military and political leader. Yet, without his skillful management of American intelligence activities, the course of the Revolutionary War could have been quite different.
Washington’s first experience in intelligence collection came in 1753, when he was 21 years old. The British colonial government sent him to the Ohio Territory to gather information about French military capabilities. He was instructed to observe French forts, determine troop strengths, and try to ascertain French intentions and plans for responding to the expansion of British colonization into the region. During this mission, Washington showed himself to be a skillful elicitor. One of the things he did particularly well was to exploit the social environment of drinking sessions and meals with French officers to acquire useful intelligence.
In 1755, at the battle of Fort Duquesne during the French and Indian War (1754-1763), Washington learned a harsh lesson. His British commander, General Edward Braddock, did not bother to have his men collect intelligence on the enemy. As a result, Braddock’s forces stumbled into a French ambush along the Monongahela River. They fought for more than three hours trying to extricate themselves from the trap, suffering a major military defeat. No doubt with this experience in mind, Washington wrote, “There is nothing more necessary than good intelligence to frustrate a designing enemy, & nothing that requires greater pains to obtain.”1
During the Revolutionary War, Washington spent more than 10 percent of his military funds on intelligence activities. Two weeks after taking command of the Continental Army on 2 July 1775, he recorded his first expenditure for intelligence collection–$333 to an unidentified officer to travel to Boston and establish a network of agents to gather intelligence on enemy movements and intentions.
A year later, Washington established a unit known as Knowlton’s Rangers, under the command of Lt. Col. Thomas Knowlton, to carry out reconnaissance and raids against British facilities. This unit was the first American military intelligence organization; the US Army has characterized it as a historical parent of the modern-day Army Rangers, Special Forces, and Delta Force. The ill-fated American spy Nathan Hale was recruited from this early Ranger force.
But it was Washington’s adroitness as a manager of agents and his skillful use of their reporting that best commend him as the Founding Father of American collection of foreign intelligence. In addition to managing countless spies around British forces’ locations, he ran numerous agent networks inside British-controlled New York City and Philadelphia. His operatives provided daily reporting on British troop movements and often were able to report on the plans and intentions of enemy commanders.
After the British seized control of New York City in autumn 1776, Washington directed the activities of numerous spies there. Of particular note was the Culper spy ring, which comprised about 20 people. This network, established in the summer of 1778, was managed by Major Benjamin Tallmadge of the 2nd Connecticut Light Dragoons, who operated from an outpost on the Hudson River above the city. The Culper ring was the most professional of Washington’s agent networks. It used code names, secret writing, enciphered communications, couriers, dead drops, signal sites, and specific collection requirements.
The most important piece of intelligence obtained through the Culper ring came in July 1780. A network member known to this day only as “Lady” reported that British General Sir Henry Clinton had decided to send British troops by sea from New York City to Newport, Rhode Island, to attack newly arrived French forces under General Rochambeau. The French troops had been at sea for two months, and Clinton wanted to attack them before they recovered from the trip.
Washington received this intelligence on the afternoon of 21 July and immediately drew up plans for a fictitious attack on New York City. He then had the “plans” delivered to a British outpost by a local farmer, who claimed to have found them on a nearby road. In the meantime, Washington also marched his army toward New York City to provide further “evidence” that he was preparing to launch an attack there. Faced with what he thought were Washington’s attack plans–which were even signed by the American leader–and the readily discernible American Army movement, Clinton concluded that an attack was imminent and recalled troops then at sea to strengthen the city’s defenses. “Lady’s” intelligence and Washington’s deception scheme thus saved the ailing French troops from probable defeat and enabled them subsequently to join with the understrength American Army.
In addition to the Culper ring, Washington had numerous other agents reporting on enemy activities in New York City. Among them were James Rivington, a prominent Tory newspaper publisher; Joshua Mersereau, his son John, and another relative; Hercules Mulligan and his brother Hugh; Army Captains (and brothers) John and Baker Hendricks; and two former counterintelligence agents–Nathaniel Sackett and retired Army Capt. Elijah Hunter. The latter became close to both General Clinton and Royal Governor William Tryon.
Another American spy, 1st Lt. Lewis J. Castigin, operated in a manner that was similar in some ways to the modus operandi of modern-day defense attaches. The British captured Castigan in January 1777 and subsequently paroled him. He then went to New York City, where he was permitted to move around freely. Castigan reported to Washington and other American military leaders on what he observed concerning British military strength and positions. Through social activities with British officers, he was able to glean advance information on their campaign plans. Washington spoke highly of Castigin’s reporting.
Washington also ran several agent networks in British-occupied Philadelphia. Major John Clark managed these networks, which used such names such as “old lady” and “farmer” to describe individual agents. Lydia Darragh, acting as a lone agent, had members of her family carry information to Washington. Her social position gave her access to senior British officers, and her elicitation skills resulted in reliable advance notice of British troop movements. An entry in Washington’s official expense account, dated 18 June 1778, listed $6,170 spent for secret services in Philadelphia.
In addition, Washington utilized individuals as spies for single, specific missions. One such agent, John Honeyman, was personally recruited by Washington to report on enemy capabilities at Trenton, New Jersey. Honeyman, an Irish immigrant and a weaver by trade, had previously informed the American leader that he was willing to assist the Revolutionary cause. In autumn 1776, Washington asked Honeyman to move to New Brunswick, New Jersey. Honeyman did so, entered the cattle business there, and supplied meat to British forces in the area. Washington arranged for him to be publicly denounced as a British sympathizer.
In mid-November, Washington tasked Honeyman to report on British activities around Trenton. Through his business dealings with the British and the Hessians (British-employed mercenary soldiers from the Hesse region in what is now Germany), and by underscoring his service on the British side in the French and Indian War, Honeyman was able to develop close relationships with–and elicit intelligence information from–British officers in Trenton, including their commander.
In mid-December 1776, Washington directed American forces to seize Honeyman; the order was implemented on 22 December. The “arrest” enabled Washington to debrief Honeyman on enemy activities and intentions in the Trenton area without compromising the fact that he was an American agent. He was also given false information to pass to the British after his “escape” from the Americans.
Honeyman reported that British troops had been sent to New York City for the winter, leaving only Hessian forces in Trenton. He also noted that the Hessian commander, Col. Rall, was an arrogant individual, contemptuous of American forces. The commander was lax about defensive preparations, had not ordered his men to build fortifications, and had a serious drinking problem. Honeyman also provided a map showing all enemy locations around Trenton.
After his “escape”, Honeyman told the Hessians that he had seen the American winter quarters and found no signs of any troop movements. Washington, acting on Honeyman’s intelligence and having sown the seeds of deception through Honeyman’s remarks to the Hessians about American inaction, moved his forces across the Delaware River on Christmas night and launched a surprise attack the next morning. The Hessians were hung over from their Christmas partying, had no time to organize, and were quickly forced to surrender. While a minor triumph in military terms, the victory at Trenton came at a critical time for the American side and was a strategic victory in political and morale terms–thanks in large part to excellent intelligence work.
John Jay: America’s First Counterintelligence Chief
In addition to his work as America’s first national-level counterintelligence chief, Jay played a critical role in establishing the right of the Executive Branch to conduct intelligence activities in secrecy.
At the start of the Revolutionary War, American counterintelligence efforts focused on detecting and arresting Tories and Tory sympathizers–especially those viewed as conspirators, spies, or potential spies. Personal rivalries and business feuds among the colonists often were the real causes of such counterintelligence actions and accusations. Even so, genuine supporters of the Crown were numerous in the American colonies. Less than a third of the populace appears to have actively supported the drive for independence. In fact, the colonials serving in the British Army far outnumbered those in the American Army.
Future Chief Justice John Jay’s first venture into the counterintelligence arena occurred in the summer of 1776. Jay, a member of the New York legislature, chaired a legislative committee that was investigating a Tory plot to recruit people to sabotage defense and infrastructure targets in New York City and its environs. The Tory goal was to pave the way for British occupation. The conspiracy was well organized and amply financed. It was directed by the British Royal Governor of New York, William Tryon, and New York City’s Mayor, David Matthews.
The British recruitment effort even extended to the personal bodyguard of George Washington; the goal was to capture or kill the American leader. An investigation led by Jay in June 1776 exposed the entire scheme. One of the bodyguards, Thomas Hickey, was executed for his involvement. Numerous other plotters were arrested, and Mayor Matthews was jailed. Governor Tryon avoided arrest by taking up residence on the British warship “Duchess of Gordon” in New York harbor.
Discovery of this conspiracy prompted the Americans to intensify their efforts to develop a larger, better organized counterintelligence program, focusing primarily on the strategic Hudson Valley area north of New York City. This came at a time when the British were on the offensive in the region. General Sir Henry Clinton’s forces seized New York City in autumn 1776, after which Clinton launched an aggressive campaign to enlist Tory sympathizers in the area surrounding the city. He offered land and money to those colonials willing either to join the British forces or to work as spies in a contested area along the Hudson River, providing information on American activities.
American counterintelligence efforts against these Tory operations were conducted under the auspices of the “New York State Committee and Commission for Detecting and Defeating Conspiracies,” which Jay headed until mid-February 1777. While in this post, he conducted hundreds of counterintelligence investigations, arrests, and trials. Most of the suspects were influential businessmen and political figures with longstanding ties to the Crown.
Jay also stationed prison ships on the Hudson River to house the more dangerous of the loyalists arrested by American forces. The “Committee and Commission” investigated, tried, and sentenced suspects outside the established legal system. In May 1777 Jay proposed that civilian courts be established to handle cases of treason, insurrection, and violation of oaths of allegiance. He maintained that such courts would conduct more objective investigations and trials than those that had prevailed under the “Committee and Commission.” Subsequently, however, American military courts gradually took over the judicial process for such cases.
Jay employed at least ten counterintelligence agents in conducting his investigations. Among the better known of these operatives were Nathaniel Sackett, Elijah Hunter, and Enoch Crosby. Elijah Hunter was Jay’s favorite agent. Hunter supervised a network of counterintelligence agents operating in the Fishkill area. He later worked for the American side as a spy and double agent in New York City.
Enoch Crosby was perhaps the best known–and the most successful–of Jay’s agents. His reputation stemmed to a considerable degree from a widely held belief that he was the model for “Harvey Birch,” the protagonist in James Fenimore Cooper’s novel, The Spy. After the war, Jay and Cooper did discuss the exploits of Jay’s counterintelligence agents in the Fishkill area, but Cooper seems to have modeled Birch after a composite of several agents, not Crosby alone.
Crosby, a shoemaker, worked for Jay from August 1776 until spring 1777 in the Fishkill area. During this time he joined various Tory groups, gathered evidence on their pro-British activities, and then passed to Jay the specifics that were necessary to have these people arrested and convicted. While penetrating the groups, Crosby used aliases such as John Brown, John Smith, Levi Foster, and Jacob Brown. He invariably managed to “escape” just as a group was captured. Crosby also was sent on missions to identify pro-Tory groups and individuals in New York City and Vermont.
Crosby’s missions were highly dangerous. He was in constant danger of being killed by the Tories if unmasked as an American agent, or harmed by unwitting Americans when captured along with Tories. The geographical area in which he operated along the Hudson River, north of New York City, was a small region, with residents clustered in several villages. The physical and social proximity among the populace meant that Crosby became widely known in the region rather quickly. As a result, his value as a counter-intelligence agent diminished with each mission.
In October 1777, Jay dispatched Crosby on a mission to the town of Marlboro, located on the western bank of the Hudson River. This mission typified Crosby’s operational approach and the dangers he constantly faced. He posed as John Smith, a shoemaker and pro-British loyalist. Upon arriving in Marlboro, he sought out a tavern known for its loyalist patrons and began getting acquainted with the local Tories.
Crosby’s skillful performance as a British sympathizer impressed some influential local people. As “Smith”, he was welcomed as a recruit in a military unit being formed among local Tories under the direction of a British officer from New York City. The company was formed in a week’s time. Crosby soon sent the following message to Jay:
“I hasten this express to request you to order Captain Townsend’s company of Rangers to repair immediately to the barn, situated on the west side of Butter-Hill, and there to secrete themselves until we arrive, which will be tomorrow evening, probably about eleven o’clock; where, with about thirty Tories, they may find.”
Your obedient servant,
John Smith 2
The trap was sprung by Townsend’s Rangers as Crosby had suggested. Crosby attempted to hide in a nearby haystack to avoid capture and to be able to explain his future freedom. But the American Rangers probed the haystack with their bayonets, and he hastily gave himself up. Townsend, who was unaware of Crosby’s true loyalty, took him along with the other Tories and decided to lock him in a secure room in Jay’s residence. Jay was not home, but his maid recognized Crosby and managed to give the guards at the residence some drugged brandy so that he could flee. The next day, his “escape” was made known to the other prisoners, and Crosby was off to join yet another Tory group.
In addition to his counterintelligence work, Jay played a critical role in establishing the right of the Executive Branch to conduct intelligence activities in secrecy. During the debates surrounding the creation of the United States Constitution, Jay wrote in Federalist Paper No. 64:
There are cases where the most useful intelligence may be obtained, if the persons possessing it can be relieved from apprehensions of discovery. Those apprehensions will operate on those persons whether they are actuated by mercenary or friendly motives, and there doubtless are many of both descriptions, who would rely on the secrecy of the President, but who would not confide in that of the Senate, and still less in that of a large popular assembly. The convention has done well therefore in so disposing of the power of making treaties, that although the president must in forming them act by the advice and consent of the Senate, yet he will be able to manage the business of intelligence in such a manner as prudence may suggest.
Benjamin Franklin: Master of Covert Action
Franklin used his intellect and humor to win friendships and build French support for the American independence struggle.
Benjamin Franklin was perhaps the most intellectual and worldly member of America’s Revolutionary War leadership. Long before the war started, he was recognized in the colonies and Europe as a scientist of distinction, a seasoned diplomat, a world-class thinker, and a talented public servant. He subsequently used all these skills as an agent of influence, propagandist, manager of covert French aid to the American Revolutionaries, and director of American paramilitary activities against the British.
When Franklin became the head of the quasi-diplomatic American Commission in Paris in December 1776, he began a relationship with the French Government that involved much more than diplomatic work. His real mission was to obtain French agreement to a military alliance against Britain. In pursuing this objective, he burnished his public image as an American with virtues that were appreciated and respected by the French populace, while simultaneously mounting a carefully planned, low-profile campaign to gain the support of key French political and business leaders.
In his public role as America’s envoy, Franklin took pains to display the traits of honesty, altruism, and common sense that were reflected in his “Poor Richard’s Almanac” and for which he was widely admired. His clothes and mannerisms reinforced his image as a friendly, humble, and industrious American–a stark contrast to the image of the British in the eyes of many if not most French people at that time.
In his private dealings with influential French individuals, Franklin was charming and subtle in his lobbying for the American cause. He used his intellect and humor to win friendships and build support within the French Government for the American independence struggle. Franklin was skilled at manipulating official French perceptions of America. On numerous occasions he was able to convince the French authories not to reduce secret aid or block American privateer ships from using French ports in the face of British protests and threats conveyed by London’s Minister in Paris.
A major example of Franklin’s ability to convince the French Government that its own interests coincided with American objectives occurred during the winter of 1777-78. America had won a strategic victory in the Battle of Saratoga, and Britain was expressing interest in some form of peace settlement with its colonies. French leaders, while impressed by the defeat of a sizable British force, remained hesitant to enter a formal military alliance with America. Spain, for its part, was willing to provide secret assistance to the Americans through France, but it was not prepared to join the French in an anti-British alliance.
At this critical time, Franklin orchestrated meetings between the American Commissioners and British envoys, fueling French fears that an Anglo-American reconciliation might occur. Franklin skillfully flirted with the British, meeting privately with one of their representatives and speaking encouragingly with others about reconciliation. He informed the French authorities about these meetings, but he gave them only carefully selected portions of the Anglo-American discussions. Based on Franklin’s “perception management”, which was aimed at convincing the French leadership that he was seriously considering the British peace proposals, the French Royal Council decided on 7 January 1778 to negotiate an offensive and defensive alliance, as well as a treaty of commerce and amity, with America.
Franklin’s best-known efforts as a propagandist focused on generating dissatisfaction among mercenaries from what is now Germany who were serving with the British forces in America, and on exposing British human rights violations committed against Americans. In 1777, he concocted a letter, supposedly written by a Prussian Prince to the commander of the Prince’s mercenary troops serving with the British forces in America. The letter questioned casualty figures provided by the British Government to the Prince. According to the letter, the Prince believed that the actual figures were higher and that he was being cheated of payments due him for dead and wounded soldiers.
The contrived letter also advised the commander to let his wounded soldiers die because the British would pay more for a death than for a wounded soldier. Wounded soldiers, the letter concluded, were of no use to the Prince; they were merely “cripples”, unable to serve. The letter was widely circulated in Europe and among Prussian troops in the colonies, and was credited with causing numerous desertions. It also prompted protests within Britain against the payment of “blood money” to foreigners who “sold” their subjects to the British Government.
Another example of Franklin’s handiwork was a forged copy of a 1782 edition of a Boston newspaper, complete with actual advertisements and local news. The paper contained an article that said the British Royal Governor of Canada was paying his Indian allies for each American scalp provided to him. The article also noted that many of the scalps “sold” to the Governor were from women and children. This story touched off a public uproar in Britain and was used by opposition Whig politicians there to attack the conduct of the war.
In the field of paramilitary operations, Franklin coordinated the efforts of dozens of privateers operating out of French and other European ports against British shipping. He convinced the French Government to ignore its neutrality obligations regarding these activities, and he negotiated a secret arrangement permitting the privateers to sell their captured British ships and cargo to French merchants.
Franklin also established a system of American port agents to handle re-supply, refitting, crew recruitment, and disposal of captured goods and ships. This network–referred to by some as “Franklin’s Navy”–produced military, economic, and psychological benefits for the American cause. Money generated by these activities was utilized by the Americans to purchase military supplies and European ships for colonial naval use and for refitting captured ships. In the economic/financial realm, frequent attacks on British shipping were driving up maritime insurance rates, making business less profitable for the politically influential British merchant class. These attacks also made the consequences of the war in North America more real for the British public.
Franklin, moreover, played a role in the only American military attack on the British Isles during the Revolutionary War period. In April 1778, Captain John Paul Jones, who later became one of America’s most famous naval heroes, raided the British port of Whitehaven. Franklin and Jones had planned to burn the hundreds of ships crowded in the port’s anchorage. But once the attackers were ashore, the element of surprise was lost and they had to make a hasty retreat after partially burning only one ship and spiking a few cannon. The British later estimated the cost of the damage at no more than 250-300 pounds. The raid nonetheless was an important achievement for America in terms of propaganda and morale. A British town had been invaded for the first time since the late 1600s. The attack aggravated concerns about insecurity in ports all along he British coast. It also triggered a new hike in shipping insurance rates and sparked considerable anxiety in the British shipping industry.
Thus the practice of American intelligence in its various forms is readily traceable to the earliest days of the nation’s existence. The Founding Fathers–particularly the three who form the central focus of this booklet–fully recognized that intelligence is as vital an element of national defense as a strong military. Their intelligence operations typically were disciplined and well-focused and were designed to support specific national objectives. And, for the most part, these activities were hidden from public view; the Founding Fathers understood the importance of secrecy for conducting effective intelligence operations.
Then, as now, it was clear to American decision makers that skilled and motivated intelligence officers, led by people of vision and courage, are essential to the security and well-being of the United States.