A New Nation’s First Spies

While one Founding Father was rooting out British spies from American government and the Continental Army, another was cultivating networks of skilled espionage agents throughout New York, Philadelphia, and other cities and territories under British control. In addition to collecting intelligence, the American spies proved masterful in spreading disinformation among their adversaries, influencing strategies, and even tilting outcomes throughout the war.

Execution of Nathan Hale, 1776
Washington did not really outfight the British, he simply outspied us.
—Senior British Army officer

Washington’s Spymasters

George Washington had long prized the value of intelligence. In 1753, Washington was a 21-year-old major in the Virginia militia, sent off on a diplomatic mission to inform French officials that forts in the Ohio Valley (now western Pennsylvania) had been built within British territory and must be relinquished. Beyond delivering that demand, Washington was also to play the part of a spy, and gather intelligence on the French defenses as well as their intentions in the region. The French ultimately refused to budge, but Washington returned far from empty handed, providing considerable details to his superiors about the fortifications and likely French objectives.

That mission, as well as his front-line experience in the French and Indian War, shaped Washington for later command of the Continental Army, and his appreciation for wartime espionage operations.

The early war experiences of the Continental Army’s first reconnaissance unit – Knowlton’s Rangers – and the capture and execution of one of its wayward spies, convinced Washington he needed to create a formal and lasting intelligence operation to support his forces. In early 1777, Washington selected Nathaniel Sackett, a member of John Jay’s Committee for Detecting and Defeating Conspiracies, as his first chief of intelligence. Major Benjamin Tallmadge of the 2nd Continental Light Dragoons was then appointed as Sackett’s liaison with the Continental Army.

Sackett’s tenure was brief as Washington was underwhelmed with his performance. He was replaced by Major John Clark, a practiced spy who was experienced in infiltrating enemy lines and had managed espionage networks in the Philadelphia area during the British occupation. Washington used Clark and his networks not only to collect intelligence, but also to leak false information to the British about American strategy and planning. Clark proved an effective spy chief, but his command was also cut short when he was unable to sufficiently recover from a severe shoulder wound.

Washington chose as Clark’s successor Brigadier General Charles Scott, a veteran of the French and Indian War and several Revolutionary War campaigns. Benjamin Tallmadge was called on again to assist the new spy chief as his deputy. One of Scott’s first taskings from Washington was to develop intelligence networks in British-occupied Long Island and New York City – networks that eventually evolved into the renowned Culper Spy Ring. In October 1778, Washington replaced Scott, elevating Tallmadge to be the Continental Army’s new spy chief. He was just twenty-four years old.

George Washington often learned of British troop movements from his spies. camera icon - click to for more details about the image Letter to General Washington from his intelligence chief, Major John Clark, 1777
George Washington often learned of British troop movements from his spies. camera icon - click to for more details about the image
Letter to General Washington from his intelligence chief, Major John Clark, 1777

American Spies from New York To Yorktown

Knowlton’s Rangers: An Army Legacy Begins

In the summer of 1776, with the ink barely dry on the new Declaration of Independence, Washington established a unit of rangers under the command of Lieutenant Colonel Thomas Knowlton, a former ranger in the French and Indian War and veteran of the Battle of Bunker Hill. Knowlton’s Rangers became the Army’s first military intelligence organization, using information collected from reconnaissance missions to carry out raids on British encampments. The Rangers had a short existence: Knowlton was killed in action at the Battle of Harlem Heights just a month after its formation, but the “1776” incorporated in the emblem of U.S. Army Intelligence today is a tribute to Knowlton and his trailblazing path.

Execution of Nathan Hale Execution of Nathan Hale
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Nathan Hale: An Ill-Fated Spy

21-year-old Nathan Hale, perhaps America’s best-known early spy, served with Knowlton’s Rangers. In September 1776, Washington ordered Knowlton to send some of his men behind British lines in Long Island to reconnoiter enemy forces gathering to attack the Continental Army in Manhattan. Hale eagerly volunteered for the mission. His cover was a schoolmaster looking for work, a logical guise as that was his former profession.

It made little difference. The Connecticut-reared Hale was unfamiliar with Long Island and lacked espionage experience. Soon after landing in Long Island, he was arrested by British Lieutenant Colonel Robert Rogers and his Queen’s American Rangers, who were in the area searching for suspected Continental spies. After a search turned up incriminating notes found in his shoes, Hale was denied a court-martial because of his civilian attire and ordered to be executed as a spy.

A scene from an 18th century tailor shop camera icon - click to for more details about the image A scene from an 18th century tailor shop

Hercules Mulligan: A Tailor-Made Spy

Hercules Mulligan was an Irish-born tailor in New York City and married to the niece of a British admiral. Mulligan was also a longtime friend of Washington’s aide, Alexander Hamilton, strengthening his credibility as an asset.

Mulligan, who was loosely associated with the Culper Spy Ring – a network of American spies operating in New York City and Long Island – elicited numerous details about British operations from his clients and social connections. In one case, while fitting a British officer for a coat, Mulligan learned of a planned attempt to capture Washington. The warning he passed likely saved the Commander in Chief’s life. In another twist of fate, the tailor was arrested by Benedict Arnold not long after the former American general’s defection to the British. Mulligan was eventually released for lack of evidence.

Mulligan often used a slave he owned named Cato as a conduit with the Culper Ring. Suspected of espionage, Cato was once detained by the British and subjected to considerable interrogation. He remained faithful, however, never divulging a word about Mulligan or the Culper Ring, and Mulligan later used his influential network of British social contacts to secure Cato’s eventual release.

After the war, Mulligan received a visit from Washington, both to convey the general’s gratitude for Mulligan’s wartime spying, and to dispel concerns among neighbors and associates that the tailor may have been a British sympathizer. Washington even permitted Mulligan to display a sign that read “Clothier to Genl. Washington.”

American spy Lewis Costigin camera icon - click to for more details about the image

Lewis Costigin: Z Is For Espionage

In 1776, Lewis Costigin, a former merchant from New Brunswick, New Jersey, was serving as a lieutenant in the Continental Army. Following the American victory at the Battle of Trenton, General Washington learned the British were advancing on New Brunswick and ordered a mission to reconnoiter enemy troop strength. Costigin was chosen, likely owing to his familiarity with the area, but he was soon captured by British cavalry. Because he was in uniform, Costigin was treated as a prisoner of war instead of a spy, saving the officer from certain execution. Escorted to British-occupied New York, Costigin was paroled and entrusted to roam freely through the city, in uniform, on the promise he would not communicate with the Continental Army.

Letter from General Washington ordering a prisoner exchange to return Lewis Costigin to the American lines. camera icon - click to for more details about the image
Letter from General Washington ordering a prisoner exchange to return Lewis Costigin to the American lines. camera icon - click to for more details about the image
Letter from General Washington regarding spy Lewis Costigin
American spy Lewis Costigin camera icon - click to for more details about the image American spy Lewis Costigin
Letters from General Washington regarding spy Lewis Costigin

Costigin remained in New York for nearly two years, befriending enemy officers and collecting information about British troop deployments, fortifications, and supplies. In late 1778, Washington ordered his exchange for a captured British officer. Instead of returning to the Continental Army, Costigin chose to remain in New York – likely feigning Loyalist sympathies – to continue his espionage. He kept up the ruse for four more months, gathering more intelligence while still in uniform and passing it through the lines to Washington, each note signed simply with the letter Z.

Costigin eventually returned to the Continental Army, and the value of his intelligence is evident from both the praise he later received from Washington, and the considerable alarm Washington expressed when reports from his “Z” spy ceased, unaware Costigin had returned. Costigin survived the war and died in 1822.

Battle of Whitemarsh, 1777 camera icon - click to for more details about the image Battle of Whitemarsh, 1777
Lydia Darragh’s former house in Philadelphia camera icon - click to for more details about the image Lydia Darragh’s former house in Philadelphia
red horse with rider silhouette

Lydia Darragh: Neighbor & Spy

Following the British seizure of Philadelphia in 1777, the ranking British commander established his residence in the vacated house of one of Washington’s generals. Across the street lived the Darragh family, who, like most Quakers, appeared to be neutral toward the war.

Once British senior officers – including John André, then serving on the staff of the British Commanding General – began using the conveniently located Darragh home as a meeting site, the family of Quakers became a family of spies. Lydia, the family matriarch, secretly collected intelligence she overheard. Her husband then encoded messages in a unique shorthand, which were sewn into the clothing of their 14-year-old son. He carried the messages to Washington’s headquarters several miles away at Whitemarsh, where they were decoded by his brother, serving in the 2nd Pennsylvania Regiment.

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A notable exception to this routine occurred in December 1777, when Lydia learned the British were planning a surprise offensive against Washington’s army at Whitemarsh. On the pretense of needing flour from a nearby mill, Lydia travelled across the British lines the next day to deliver a coded message herself to the Continentals. Her warning confirmed other intelligence Washington had received, and he surprised the British with a stout defense, repelling the British advance at the Battle of Whitemarsh. It wasn’t until 1827, when Lydia’s daughter published a book about the family’s wartime spying activities, that Lydia’s role in the skirmish became known.

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Daniel Bissell: A Meritorious Spy

In 1775, 20-year-old Daniel Bissell enlisted in the Continental Army, becoming a sergeant in his Connecticut regiment and serving with distinction in multiple battles.

Perhaps encouraged by the success of Lewis Costigin and others, Bissell was handpicked by General Washington in 1781 to pose as a deserter and penetrate British-occupied New York City. To add to the ruse, Washington had him officially declared a deserter. Upon his arrival in New York, Bissell discovered that defectors from the Patriot side were being pressed into the British Navy. To avoid this, he joined Benedict Arnold’s American Legion, a Loyalist unit, where he served for thirteen months as a supply sergeant – a position that provided him with access to information about British troop strength and fortifications in New York. Bissell eventually returned to the Continental Army, providing a detailed report of what he learned, but by that time, peace negotiations were well underway. Had those negotiations faltered, continuing the war, Bissell’s intelligence would have been vital.

Daniel Bissell provided substantial intelligence to General Washington, including this sketch of a British fort on Staten Island. camera icon - click to for more details about the image General Washington’s order awarding the Badge of Military Merit

Near the end of the war, Bissell became one of just three recipients of the Badge of Military Merit, a heart-shaped award made of purple cloth or silk that was created by Washington for gallantry and other extraordinary service. With the Medal of Honor introduced in the Civil War for acts of high valor, the Badge of Military Merit wasn’t used again until the 20th century. During World War II, it became known as the Purple Heart and was awarded only to those wounded in combat.

In the years following the war, Bissell was long believed to be a deserter. When the truth of his loyal service emerged, a monument was established in his hometown of Windsor, Connecticut, describing Bissell as a “Patriot Spy of the American Revolution.” He died in 1824, and a headstone was later added to his gravesite noting “He Had the Confidence of Washington, From Whom He Received a Badge of Merit.”

An image of the Badge of Military Merit, created by General Washington near the end of the Revolutionary War camera icon - click to for more details about the image
He Had the Confidence of Washington, From Whom He Received a Badge of Merit.
—Engraving on Bissell’s headstone

The Art
of Deception

Penned by the Marquis de Lafayette on November 12, 1784, this handbill endorsed James Armistead's petition to the Virginia state government camera icon - click to for more details about the image James Armistead’s petition for freedom

The Art of Deception

James Armistead: Double Agent

James Armistead was one of several African American spies during the Revolutionary War and perhaps the most consequential, serving at the 1781 Battle of Yorktown under the Marquis de Lafayette, a French aristocrat and officer commanding American troops. Armistead was also a double agent.

 James Armistead’s petition for freedom camera icon - click to for more details about the image James Armistead’s petition for freedom

A slave, Armistead’s owner allowed him to join the Continental Army earlier that year. He was assigned to Lafayette, who became aware of Armistead’s extensive local knowledge and, as a regular visitor to the city, his familiarity among the British garrison in Yorktown. Posing as a runaway slave, Armistead crossed British lines into Yorktown and began collecting intelligence for Lafayette. To discourage local British troops from being diverted to Yorktown, he also passed disinformation about non-existent Continental forces – cleverly prepared in Lafayette’s own handwriting for the British to recognize. That ploy, along with Washington’s own efforts to deceive British forces in New York City and tie down the main army, effectively deterred the British from relieving or reinforcing the besieged garrison at Yorktown.

After the war, Lafayette attached a convincing endorsement to Armistead’s petition for freedom. The petition was approved by the Virginia government in 1787 and Armistead became a farmer, even earning a modest pension from the Virginia legislature for his wartime service.

The siege of Yorktown map camera icon - click to for more details about the image The siege of Yorktown, 1781
Marquis de Lafayette portrait camera icon - click to for more details about the image catwalker / Shutterstock.com Marquis de Lafayette