The 10 pivotal missions that defined George Washington’s clandestine war effort are as thrilling as any battlefield drama. From crafty deceptions to daring rescues, each operation showcases the ingenuity and bravery of America’s earliest intelligence operatives.
10 The Man Who ‘Could Not Tell A Lie’ Lied
George Washington first cut his teeth in the art of espionage while serving in the British forces during the French and Indian War (1754–1763). As an American officer, he was tasked with recruiting both white and Native American spies, managing their operations, and even targeting French agents with false intelligence. His commanding officer, General Edward Braddock, employed codes and ciphers, which Washington likely learned and later used himself. The necessity for solid intelligence became starkly evident when Braddock launched an attack on Fort Duquesne on September 14, 1758, without any knowledge of nearby enemy forces. The battle nearly turned disastrous, and Braddock’s command would have been annihilated if not for Washington’s intervention.
When Washington took command of the colonial forces in July 1775, they were laying siege to the British in Boston. During an inventory, he discovered a dire shortage: only 36 barrels of gunpowder—enough for each soldier to fire just nine shots. He realized that a British breakout could spell catastrophe, and that letting his own troops know of the shortage would shatter morale. So, as he often did, Washington fed the British a healthy dose of misinformation. He dispatched men into his own ranks and onto Boston’s streets, loudly proclaiming that he possessed 1,800 barrels of powder. The British stayed holed up in Boston, and Washington’s troops retained their confidence. The legendary cherry‑tree‑cutting boy, famed for never lying to his father, proved he could spin a convincing falsehood when the cause demanded it.
9 The Mercereau Family And The Staten Island Raid
In March 1776, after forcing the British out of Boston, Washington learned that the enemy had landed on Staten Island in June, preparing to seize New York City. On July 12, he convened a council of war to debate attacking the British commander, General William Howe, on the island. The generals unanimously voted against a full‑scale assault, prompting Washington to ask whether a smaller raid could be executed to “alarm the enemy.” The plan received tentative approval, with General Hugh Mercer assigned command after scouting Howe’s dispositions.
Mercer’s captain, John Mercereau, had recently lived on Staten Island, and his brother Joshua still resided there. Captain Mercereau slipped onto the island and, aided by Joshua, discovered that the British were not concentrated in a single encampment but were dispersed across civilian homes, with 600–700 redcoats stationed along the northwestern shoreline. Mercer proposed ferrying 1,400 men across the Arthur Kill to strike the British along the shore on the night of July 17, then retreat before Howe could counterattack. However, inclement weather and unfavorable tides forced a cancellation.
Despite the raid’s cancellation, the intelligence the Mercereau family supplied was so valuable that Washington enlisted them as a permanent spy network on Staten Island for at least three years, making it America’s first true spy ring. The ring was led by Joshua’s son, young John, who disguised himself as a cripple using his withered arm. When his courier was captured, John took over delivery duties, crossing the Arthur Kill on a raft with secret communiques concealed in a weighted bottle, tethered by a string. If intercepted, he could simply release the string, allowing the messages to sink safely. By 1777, the Mercereau Ring had grown so large that Washington assigned a dedicated case officer, trusting the members enough to involve them in prisoner exchanges.
8 Knowlton’s Rangers At Harlem Heights
While still stationed in Boston, Washington met Thomas Knowlton, a Connecticut captain who, like Washington, had fought in the French and Indian War. Knowlton was already a Revolutionary War hero, having repulsed several British attempts to breach the American left flank at Bunker Hill (he appears in the painting on the left, wearing a white shirt and clutching a musket). On January 1, 1776, Washington promoted Knowlton to major, assigning him command of the 20th Connecticut Continental Infantry for “special” missions. Their first task was a raid on Charlestown, Massachusetts, where General Howe was bivouacked on the night of January 8.
That evening, Howe attended a satirical play titled The Siege of Boston, which mocked Washington as a comic rube. Knowlton’s men slipped into town, burned eight buildings, and captured several British officers without a single casualty. When a soldier burst into Howe’s theater with news of the raid, the audience assumed it was part of the performance and roared with laughter.
In late August 1776, Howe prepared to attack New York City from Staten Island. Washington assumed the British would strike Manhattan, so he split his forces between Manhattan and Long Island. Howe, however, focused on Long Island, engaging Washington’s troops at Brooklyn Heights while sending the rest of his army behind the defenders. By the time Washington realized the maneuver and sent for reinforcements, it was too late; the battle resulted in a loss of approximately 1,400 men. Washington’s quick thinking saved the remaining forces, ferrying 9,000 soldiers across the East River to Manhattan in a single night.
That same month, Major John Knowlton was promoted to colonel and given command of an elite light‑infantry unit known as Knowlton’s Rangers. Their mission: reconnoiter British movements to prevent another Brooklyn Heights disaster. Although short‑lived, Knowlton’s Rangers are credited as America’s first military intelligence organization. In September, while Washington’s army recovered on northern Manhattan, Howe crossed to Manhattan and charged Washington’s camp at Harlem Heights. On the morning of September 16, Washington received news that Howe was nearby and dispatched Knowlton’s Rangers to probe the British vanguard. The two forces collided, and, contrary to orders to retreat and report, the Rangers engaged the enemy.
Howe sent the rest of his army in pursuit, prompting Washington to commit his troops as well. The clash ended in a stalemate, with both sides eventually withdrawing. The engagement lifted American morale after a series of defeats, proving they could stand toe‑to‑toe with the world’s most powerful army. However, the victory was bittersweet: Knowlton was shot and killed during the fight. His unit was captured a month later at Fort Washington, and many Rangers perished in British prisons. Despite their tragic end, Knowlton’s Rangers are considered the forerunners of the U.S. Army Rangers, Special Forces, and Delta Force.
7 Nathan Hale’s Mission To New York City
Following the Long Island debacle, Washington was desperate for intelligence on Howe’s next move. Two days after ferrying his men across the East River to Manhattan, he implored his generals to establish a “channel of information… to gain intelligence of the enemy’s designs, and intended operations.” When reliable intel failed to materialize, Washington turned to Knowlton’s Rangers. Lieutenant James Sprague was tasked with crossing back over the East River to reconnoiter Howe’s troops and determine their plans, but he refused to infiltrate enemy lines, saying, “I am willing to go and fight them, but as far as going among them and being taken and hung like a dog, I will not do it.”
Only one Ranger volunteered: Nathan Hale, a Connecticut teacher and neighbor of Knowlton who had just joined the Rangers as an officer. This would be Hale’s first and only mission. Despite his lack of espionage training, Washington sent Hale to Long Island disguised as a Dutch teacher. Hale’s plan faltered when he attempted to use his Yale diploma as proof of his teaching credentials, which displayed his real name rather than an alias. Moreover, his scarred face from a gunpowder accident made him memorable, and he received no money, civilian contacts, or cipher training. He also failed to keep his mission secret, spilling details to a fellow Yale classmate before departure.
Shortly after his mission began, the British crossed to Manhattan, rendering Hale’s original objective moot. Yet Hale chose to stay and gather intelligence anyway. He was apprehended on September 21 with incriminating papers, sentenced to execution without trial, and hanged the following morning after allegedly uttering his famous words, “I regret I have but one life to lose for my country.” Though his mission failed, Hale became a martyr and hero for the intelligence community. His death forced Washington to recognize the value of civilian spies familiar with local terrain—like the Mercereau family—over military operatives who lacked regional knowledge. While some historians debate the authenticity of Hale’s final words, eyewitnesses support their veracity, noting his possible inspiration from Joseph Addison’s tragedy Cato (“What a pity it is that we can die but once to serve our country”).
6 Washington’s Double Agent
After the Long Island loss, the British forced the colonials out of Manhattan, then New York, and finally New Jersey. By early December 1776, Washington’s army had crossed the Delaware River into Pennsylvania, suffering from hunger, disease, desertions, and dwindling enlistments. Morale was at a low point, and with Christmas approaching, a victory was desperately needed.
Enter John Honeyman, a butcher reputed to be a loyalist to the Crown. Born in Ireland, Honeyman served in the British army in Canada, fighting at the Battle of the Plains of Abraham (1759). He was honorably discharged and moved to Philadelphia in 1775, where he may have first encountered Washington. According to his grandson, Honeyman met Washington at Fort Lee, New Jersey, in November 1776 and offered his services. The reasons for a known Tory switching sides remain murky.
Washington accepted Honeyman’s assistance, instructing him to maintain his loyalist façade. As Washington’s army marched toward the Delaware, Honeyman was to pose as a butcher for the pursuing British, caring for their cattle and occasionally slaughtering them. This role allowed him to observe British dispositions, fortifications, and movements. Honeyman operated solo—no supporting agents or couriers—so if he gathered valuable intel, he was to feign capture by Washington’s sentries and be brought to the commander’s tent.
In late December, Honeyman claimed he was hunting cattle along the Delaware when colonial sentries captured him and escorted him to Washington’s tent. There, he reported that Hessian soldiers bivouacked across the river at Trenton were lax and disorganized. Washington staged a diversion, allowing Honeyman to escape. Returning to Trenton, Honeyman informed the Hessians that the colonials were “too disorganized and dispirited to pose a threat.” On Christmas Day, Washington’s forces crossed the Delaware and attacked the Hessians the next morning. The Hessians, either drunk or hung over from holiday celebrations, were quickly overwhelmed, resulting in 900 captured with only two American casualties—precisely the morale boost the Continental Army needed.
Modern historians debate Honeyman’s authenticity as a spy. Some argue he remained a staunch loyalist, offering information reluctantly. He and his family continued to face harassment as Tories after the Trenton battle, even being arrested twice for treason by New Jersey authorities, though both indictments were dismissed—leading some to speculate Washington intervened. Evidence supporting either side remains scant.
5 Lydia Darragh Warns Washington
Following Nathan Hale’s execution, Washington turned to civilians experienced in espionage. He commissioned New York merchant Nathaniel Sackett—formerly of the Committee for Detecting and Defeating Conspiracies—to establish a spy ring in his hometown, offering $500 initially and $50 monthly thereafter. While Sackett’s operation lasted only a few months, it achieved a crucial intelligence coup. By spring, it was clear General Howe would soon go on the offensive, and Washington needed to know his target.
In March, one of Sackett’s agents—an unnamed woman married to a Tory—observed the British constructing flat‑bottomed boats, likely intended to attack Philadelphia. Her report proved accurate: the British used the boats to approach the city, and on September 11, the redcoats defeated Washington at Brandywine Creek, entering Philadelphia two weeks later. Washington promptly established a spy network in the City of Brotherly Love, appointing Major John Clark—familiar with the area—to run it.
Clark swiftly organized a network of spies, assigning simple aliases like “Old Lady” and “Farmer.” Many agents were Quakers, whose pacifist stance made them ideal covert operatives, as they were expected to remain neutral and thus less suspicious. One Quaker, Lydia Darragh, independently spied on the British. Born in Ireland 48 years earlier, Darragh was a midwife, wife of a teacher, and mother of five. Her son Charles had broken with the Quakers to join Washington’s army, camping near Whitemarsh.
When the British occupied Philadelphia, General Howe set up headquarters in the house directly across from the Darragh residence. Redcoat officers became a common sight on the street, prompting Lydia to gather intelligence through observation and eavesdropping. Whenever she acquired valuable information, her husband William would write a coded note on a tiny piece of paper, which Lydia sewed beneath the top of a button. She then attached the button to her 14‑year‑old son John’s coat. John would travel to Whitemarsh, deliver the button and message to Charles, who forwarded it to Washington.
The Darragh home featured a spacious back room. In the fall, Howe demanded the family vacate so he could hold staff meetings there. Lydia convinced the general that they were harmless Quakers, and he permitted William and Lydia to remain while the children were sent elsewhere. On December 2, Howe held a crucial meeting in the Darraghs’ back room, insisting the couple retire to their rooms. Defying this, Lydia slipped into an adjoining room, hid in a closet, and overheard plans for a surprise attack on the Continentals at Whitemarsh on December 5.
The next morning, Lydia obtained a pass to cross British lines, intending to visit her children and collect flour from the Frankford Mill. En route, she encountered an American officer and relayed the imminent British offensive. The officer passed the warning to Washington as Lydia returned home. Washington already suspected Howe of planning an attack—Clark’s agents had reported British preparations—but lacked specifics on timing and location. Lydia’s detailed warning filled that gap.
When the redcoats arrived at Whitemarsh on December 5, Washington was prepared. Surprised, Howe withdrew his forces back to Philadelphia. Lydia and William faced suspicion of tipping off Washington, but Lydia persuaded a British officer of their innocence. Clark’s spy ring continued feeding Washington valuable intelligence throughout the winter of 1777‑78. When Clark’s agents reported that Howe would winter in Philadelphia, Washington decided to camp at nearby Valley Forge.
4 The Culper Ring Saves The French
In February 1778, while Washington’s troops endured hunger and hardship at Valley Forge, France signed a treaty to fight alongside America against England. That same month, General William Howe, frustrated by his failure to end the war, was replaced by General Henry Clinton as the British commander‑in‑chief. Concerned the French might attack New York City, London ordered Clinton to evacuate Philadelphia and reinforce the New York garrison.
The French fleet was en route, bound for British‑occupied Newport, Rhode Island, and requested Washington’s intelligence on British naval activity in New York harbor. Serendipity struck in August when artillery lieutenant Caleb Brewster offered his services. Brewster, an ex‑seaman raised near Long Island Sound, employed a whale boat to scout New York waters. On August 27, Brewster reported that the British were aware of the French fleet’s destination and were dispatching their own fleet to Newport. A severe storm forced the French to abandon their plans to seize Newport.
Washington retained Brewster and built a spy ring around him, appointing Major Benjamin Tallmadge—who had known Brewster since childhood—to oversee operations. Tallmadge, familiar with Brewster’s maritime expertise and the Long Island Sound, had learned espionage under Nathaniel Sackett and was motivated by his friendship with Nathan Hale from Yale.
Washington ordered Tallmadge’s dragoon troop to operate in the lower Hudson Valley and Connecticut coastal region, hunting Tories and countering British raids. Brewster acted as courier, ferrying messages from Long Island to the Continental‑controlled Connecticut shore in his whale boat, then meeting Tallmadge to deliver intelligence.
Tallmadge also recruited another Setauket acquaintance, Abraham Woodhull, and a distant relative, Anna Strong. Neither Woodhull nor Brewster had direct access to British military circles in New York, so they enlisted merchant Robert Townsend, who lived in Woodhull’s sister’s boardinghouse in Manhattan. Townsend and other Setauket residents collected snippets of information to send directly to Washington.
For correspondence, Woodhull adopted the alias Samuel Culper—a nod to Culpeper County, Virginia—while Townsend became Samuel Culper Jr., giving rise to the famed Culper Ring.
Two years later, in July 1780, the French again attempted to land at Newport. With the British having abandoned the port in 1779, the French arrived unopposed. Washington again turned to his spies for insight into British reactions. Townsend, part‑owner of a coffeehouse frequented by Clinton’s officers, learned that Clinton was massing his army on Long Island’s northern tip for an offensive against Newport.
Townsend smuggled his intelligence to Washington using invisible ink—known as “stain” or “white ink”—between the lines of a letter addressed to a Tory. Ten days after his request, Washington received a Culper Ring report: Clinton was marching 8,000 redcoats toward Newport, accompanied by nine British warships. Clearly, Clinton intended to strike the French before they could fortify their position.
While the French rushed to prepare defenses, Washington fabricated a fictitious diversionary offensive against Manhattan. He had a local farmer “discover” plans for the offensive and deliver them to a British outpost. Washington then began marching his army toward New York City. Clinton, fearing an imminent attack, recalled his troops to protect the city, thereby sparing the French forces at Newport from a British assault.
3 The Culper Ring Uncovers Benedict Arnold’s Betrayal
Tallmadge’s Culper Ring employed sophisticated espionage techniques—codes, aliases, and invisible ink—making it Washington’s most successful spy network. The group used “stain” or “white ink” and a codebook based on John Entick’s 1771 New Latin and English Dictionary. Spies could write words using a transposed alphabet, easily decoded with the key.
Meanwhile, Washington remained unaware that a serious problem simmered within his own ranks. General Benedict Arnold, once a celebrated patriot, had morphed into a traitor over just four years. At the war’s outset, Arnold passionately championed the Revolution, even financing his own men. However, the fledgling government could not reimburse him, fostering resentment.
Arnold earned fame at Fort Ticonderoga and Saratoga, rescuing the revolutionary cause twice, but his injuries prevented further battlefield glory. He was repeatedly passed over for promotion, and his stubborn thigh wound barred him from leading troops. Assigned to administrative duties in Philadelphia, Arnold’s frustrations grew, and he turned to a wealthy, charismatic Philadelphian, Margaret “Peggy” Shippen, a known loyalist still in contact with Major John André, a British officer she met during the British occupation.
Arnold married Peggy in April 1779, deepening his financial woes. By summer 1778, Arnold, aided by his wife, approached André with an offer to betray his country for money and a British commission. Over the next year, they negotiated terms. By summer 1780, Arnold began supplying high‑value intelligence, including the French fleet’s planned landing at Newport, Rhode Island. When offered command of West Point, Arnold proposed surrendering it to the British.
The exact moment the Culper Ring intercepted Arnold’s correspondence is unclear, but it appears to have occurred in July or August 1780. On July 30, Arnold was officially appointed commander of West Point; on August 15, the British agreed to pay him 20,000 pounds sterling (roughly £3.2 million today, or about $5 million).
On September 3, Arnold sent a letter to the British to finalize a meeting with André, but someone—likely a Culper Ring operative—rendered the letter unintelligible. When Arnold attempted to cross British lines on September 11, they fired upon his boat, forcing him to abort the meeting. A second attempt on September 23 saw André captured, though Arnold and Peggy escaped to join the British.
When Tallmadge met André, the latter asked about his fate. Tallmadge recounted the story of his good friend Nathan Hale, executed by André’s friend General Howe, concluding with, “Similar will be your fate.” André was hanged on October 2. Arnold received a British general’s commission but was paid only £5,000 because his plot failed.
2 Hercules Mulligan And Cato Save Washington’s Life Twice
Perhaps the least celebrated yet most vital of America’s early spies, Hercules Mulligan was a New York City tailor who immigrated from Ireland at age six. He joined the New York chapter of the Sons of Liberty, a militant anti‑British group. In July 1776, Mulligan led a mob to New York’s Bowling Green and toppled the equestrian statue of King George III. The rebels melted the lead statue into bullets for the Patriot cause.
Three years earlier, Mulligan opened his home to a teenager from St. Croix Island, Alexander Hamilton. The young Hamilton, studying at King’s College (now Columbia University), received his most important education at Mulligan’s dinner table, debating America’s grievances against the British Empire. Though initially a loyalist, Hamilton joined the Patriot cause after hearing Mulligan’s arguments.
When General Howe captured New York City in September 1776, Mulligan was arrested and imprisoned at the Provost Prison. He persuaded the British to release him by claiming he was no longer a patriot. In March 1777, Hamilton, now Washington’s aide, recommended Mulligan as a new New York spy.
As a premier tailor, Mulligan’s shop on Queen Street attracted British officers seeking uniform repairs or alterations. During fittings, Mulligan extracted intelligence from the officers. Once he gathered sufficient information, his enslaved servant Cato would ferry the parcel across the Hudson River ferry to New Jersey, delivering it to a safe house. An express rider would then rewrap the parcel and deliver it directly to Washington.
Although Mulligan occasionally cooperated with the Culper Ring, he usually operated with Cato and a translator named Hyam Salomon. Late one winter night in 1779, a British officer entered Mulligan’s shop demanding a watch coat immediately. When Mulligan asked why the urgency, the officer boasted that that night they would capture Washington, saying, “Before another day, we’ll have the rebel general in our hands.” Washington that night was meeting subordinates, and the British had discovered the meeting’s location, planning a trap. Cato was swiftly dispatched to New Jersey to warn Washington, who, on Mulligan’s tip, avoided capture.
The incident repeated in February 1781, when Washington was traveling to Newport, Rhode Island, to meet French General Rochambeau. Mulligan’s brother Hugh owned an import‑export firm that the British ordered supplies from. When a rush order arrived, an officer told Hugh that 300 cavalrymen were headed to New London, Connecticut, to intercept Washington. After receiving Mulligan’s warning, Washington’s men ambushed the cavalrymen upon their arrival at New London, thwarting the British plan.
1 Armistead’s Intelligence Coup
When France entered the war in 1778, the British attempted to sway the southern colonies against the northern ones. While General Charles Cornwallis could capture coastal cities like Savannah and Charleston, he struggled to hold interior areas of the Carolinas.
In the fall of 1780, Cornwallis marched into North Carolina, aiming to attack Washington from the south while Clinton pressed from the north. Colonial victories forced Cornwallis to retreat to South Carolina. To relieve pressure on Cornwallis, Clinton dispatched Benedict Arnold to Virginia to seize Richmond just before New Year’s Day. Arnold’s men plundered and burned the state capitol.
Just east of Richmond lay the plantation of William Armistead. In March 1781, General Marquis de Lafayette and 1,200 colonial troops arrived near Yorktown, Virginia, to harass Arnold’s army. One of Armistead’s enslaved men, James, asked his master if he could join Lafayette’s forces to drive the British invaders from Virginia. Though the British had promised emancipation to any American slave who aided them, James chose to fight for the Patriot cause. William consented.
When James appeared in Lafayette’s camp, the French commander recognized the value of a man familiar with the region. Lafayette tasked him with infiltrating Arnold’s camp, pretending to be a runaway slave offering scouting services. Arnold accepted James’s story and granted him freedom to roam the British camp, listening to conversations around campfires.
James earned such trust that when Arnold’s army merged with Cornwallis’s forces in May, he was allowed to remain as a scout for Cornwallis. In July, James sent word to Lafayette that Cornwallis planned to move down the Virginia Peninsula to Yorktown to await supplies.
At that time, Washington was planning a joint offensive with the French against Clinton in New York. When Lafayette forwarded James’s intelligence, Washington realized Cornwallis could be cornered at Yorktown. He rushed his army south to surround Cornwallis while the French fleet blockaded the coast. In October, Cornwallis was forced to surrender, effectively ending the war.
Despite his invaluable service, James returned to William Armistead’s plantation as a slave after the war. Although the new republic freed slaves who fought for the cause, James never wore a uniform, so he was not automatically emancipated. It was only through Lafayette’s advocacy that James Armistead was finally freed in 1787.
Steve is the author of 366 Days in Abraham Lincoln’s Presidency: The Private, Political, and Military Decisions of America’s Greatest President and has written for KnowledgeNuts.