The Tailor Spy

Irish Sympathy

The Irish in the American Revolution had their heroes and villains on both sides of the conflict. Although they were celebrated for decades of resisting and fighting their British oppressors, there was little Irish support for the colonials fighting the distant war. The average Irishman was just trying to survive, and many were recruited into British regiments in Ireland. In America itself, Irish immigrants, like the rest of the population, were divided in their loyalties. However, one transplanted son of Erin would play a secret role in helping to free his adopted nation – and perhaps seek some revenge on the British.

Hercules Mulligan at work 

Until recently, only historians and a few enthusiasts of Revolutionary War history knew the name Hercules Mulligan, but it gained worldwide fame through the hit Broadway musical, “Hamilton.” Indeed, Mulligan’s story was connected to that controversial Revolutionary War officer, political operative, and Founding Father. For Hercules Mulligan and his family, in many ways, they provided Alexander Hamilton with the support every new immigrant needs to reach the next level.

Early Days

Hercules Mulligan moved from Coleraine, County Antrim, Ireland, to New York City with his parents, Hugh and Sarah Mulligan, when he was six years old. The year was 1746—long before the French and Indian War and all the political and economic events that would lead to the fight for America. Hercules's father quickly became a successful accountant in New York, and the family prospered in the colonies. Along with Hercules, two brothers also came; notably, his oldest brother Hugh, who became the owner of an import-export business that employed a young man from Nevis named Alexander Hamilton.

King's College

Hercules attended King’s College (now Columbia) and initially became an accountant before switching to the haberdashery business. His first shop was on Water Street, but he later moved to the more fashionable Queen Street in 1773 to attract a wealthier and more influential clientele. That same year, his brother Hugh introduced him to the young prodigy Alexander Hamilton. Hercules took Hamilton under his wing, and Hamilton boarded with Mulligan and his family while attending King’s College.

Secret Politics

While Hamilton’s politics were formed at King’s College, it remains uncertain when and how Mulligan started sympathizing with the rebel cause. Maybe hidden Irish sympathies and resentment toward the harsh Penal Laws in his homeland influenced him. Or was it the events after the French and Indian War—the same events that led more than a third of the king’s loyal subjects toward a different political system? Still, the connection and bond clearly formed during those early days of growing revolutionary fervor.

Stamp Act Protest

At some point along the way, possibly as early as 1765, Hercules helped write an underground tabloid called The Constitutional Courant that opposed the Stamp Act. Mulligan later became a founding member of a radical faction within New York’s Sons of Liberty, organized to defend the colonists’ rights and oppose British taxation. He was also involved, if not a leader, in the mob inspired by the Sons of Liberty that attacked British soldiers in 1770 during what became known as the Battle of Golden Hill. 

Battle of Golden Hill

A Model Citizen

Although he led a secret political life, Hercules publicly remained a member of the establishment. The young Irishman married well—his wife was Elizabeth Sanders, the niece of a Royal Navy admiral and a well-connected member of New York's social elite. The outgoing Irishman leveraged his wife's family connections to grow his business and build relationships with New York’s upper class—most of whom were strong Loyalists. Later, as more British regulars garrisoned New York, he gained a circle of officers as both clients and contacts. 

British-occupied New York

The outgoing haberdasher placed detailed ads in Rivington's Gazette and other leading Tory newspapers—ads aimed at drawing top-tier customers and officers with descriptions of “superfine cloths, gold and silver lace, fancy buttons, and epaulets replete with heavy bouillon.” If you build it, they will come. And come they did. Choosing cloth, accessories, measuring, and fitting all took time—time that could lead to slips of the tongue, nuggets, and the knowing winks of a proud and haughty clientele trying to impress the popular haberdasher. 

Secret Rebel

Mulligan was involved in an incident on August 24, 1775, an attempt against the HMS Asia, which was anchored in New York Harbor. Under the cover of night, a group of New York militiamen, including Mulligan's company known as the "Corsicans," took control of the artillery battery at the southern tip of New York Island (Manhattan). Hercules and his young boarder, Alexander Hamilton, were among them. However, someone had alerted the crew of the HMS Asia, and it fired its own guns on the rebels.  

HMS Asia in New York harbor

Mulligan threw a rope around one of the guns to pull it to safety. As he struggled, Hamilton approached and, despite his small size, dragged the gun away. Hamilton then calmly rejoined the front lines to help move more guns – 20 were taken. Interestingly, one of the shots from the HMS Asia struck the roof of Fraunces Tavern, which later hosted General Washington’s farewell in 1783. With Hercules's support, young Hamilton was promoted to captain and commander of an artillery battery in July the following year – just in time for the British attack on New York.

Artillery would team Hercules with Alexander Hamilton

In 1776, Mulligan was among the Sons of Liberty who tore down a large statue of King George III in Bowling Green. They then melted its lead into musket balls for the rebels. He also joined the New York Committee of Correspondence, a crucial tool for rallying support among the people and keeping the colonies coordinated. An attempt to escape the city failed, and Mulligan stayed in New York after Washington's army was expelled during the summer 1776 New York campaign. By September, New York was occupied by the British, and the situation demanded more than political protests—it required espionage. But to do that effectively, Hercules would need to pretend to be a Loyalist. Since many changed their allegiances during this time, it didn’t attract much suspicion.

King George III statue tumbling down

Tailor Spy

Exactly when our “model citizen” became a spy remains unclear. Fittingly, such matters were not recorded, and secret agents often operated under cover names, code names, or numbers. It is believed Alexander Hamilton suggested him to Washington while serving as aide-de-camp in 1777. However, some sources indicate that the haberdasher did not actually report to Washington until 1779. In any case, the transition was smooth, if not inevitable.

Alexander Hamilton as aide-de-camp to General Washington

At his clothing shop, Mulligan often measured his clients, talking with them and gathering insights through conversation. He was also very attentive to military and political events in the city. Years of secretly waging a political war had sharpened Mulligan's skills, making him an excellent intelligence operative in the occupied city.

The perfect venue for eliciting 

nuggets from powerful customers

As housing for wealthy men became scarce in occupied (and fire-damaged) New York, Hercules opened a few rooms in his home to British officers—an excellent way to avoid suspicion, gather intelligence, build relationships, and develop leads. Some believe Mulligan reported through the Culper Ring—the Long Island-based spy network made famous by the fictional TV show TURN. He might have done so. The main contact for the ring, Robert Townsend, operated his business just down the street from Mulligan’s haberdashery. However, Hercules used other methods too. In fact, Washington’s top intelligence officer and spymaster of the Culper Ring, Major Benjamin Tallmadge, once asked the commander in chief about Mulligan’s status and activities. He was worried that Mulligan's activities might pose a threat to his ring. He would not have made the inquiry if Mulligan was one of his assets.

Major Benjamin Tallmadge

Courier

So how did Mulligan smuggle his intelligence out of the city? One method was through his African American servant, Cato. Cato’s status allowed him to pass through British lines without attracting much attention, as Africans were believed to be loyal to the British (and most were). Some think Samuel Culper used Mulligan’s servant as an alternate reporting channel at least once. Cato made many trips across the lines, but on his last one, he drew enough suspicion to lead his captors, likely local Loyalist militia, to beat him badly. Despite the harsh treatment, Cato did not give up his mission or his boss. In the end, Mulligan used his high contacts to secure Cato's release, although his courier days were over.

Fraternal Affair

Hercules’s older brother, Hugh, was also involved in espionage. His import-export company, Kortwright & Company, conducted business with the British military and many influential Tory merchants in New York. As a shipper, he could visit ships in port, inspect facilities, and track the movement of supplies—offering valuable intelligence on upcoming British operations.

Hugh Mulligan had access to British shipping plans

Saving the Indispensable Man

Little is known about the details of Hercules Mulligan’s reports, but he is credited with providing intelligence that saved General George Washington’s life on at least two occasions. That alone could make him one of the most important figures of the war. 

Cato's message from Hercules saved Washington

Once, a British officer came to Mulligan late at night looking for a coat. Hercules started showing him different coats while joking and questioning his customer, who carelessly revealed he was planning to capture George Washington. Mulligan sent Cato away as soon as the officer left, allowing Washington to escape to safety. Another time, the British found out about Washington’s plan to ride to Rhode Island along the Connecticut shoreline. Luckily, Hugh Mulligan was contracted to supply the British vessels, and he quickly told his brother. Once again, Cato slipped out of the city to warn Washington.

Under Suspicion

The friendly and well-connected Mulligan did come under suspicion at least once during the war. Ironically, this suspicion came from the infamous traitor himself, Benedict Arnold. Arnold was now in New York, holding the rank of Brigadier General in the British Army. One of Arnold’s tasks as commander of the West Point garrison was to help organize resistance against the British in and around New York City. In that role, he suspected that the tailor might be one of General Washington's sources.

Benedict Arnold - British Brigadier General

Washington excelled at “compartmentalizing” operations. Very few of his closest confidants knew who his spies were, and those who did had only the knowledge absolutely necessary.

Hercules under questioning

Arnold had Hercules arrested. Having been interrogated twice before by the British, Mulligan managed to deflect questions and keep his cool. These skills—along with his reputation as a loyal subject and friend to the British—helped him through. Since Arnold lacked any real evidence to back his accusations, our tailor-spy was quickly released.

Under Suspicion (Again)

Hercules was a victim of his own success. By serving as the loyal haberdasher to the British and Tories for nearly eight years, he strengthened his reputation as a collaborator among his fellow New Yorkers—a group known for its cynicism. Patriots and Whigs accused him of being an active Loyalist and a traitor to the cause. After the British departed at the end of 1783, his thriving business and standing in New York society were in serious danger. Many Tories were driven out of town, and their properties were seized. There was no reason to believe that this would not also be Hercules’s fate.

British evacuation of NYC

But the hand of His Excellency, General George Washington, stepped in. After the war, Washington is known to have quietly reached out to many previously unknown individuals and made it clear they were under his special approval. Many of these are believed to have been covert intelligence operatives: secret agents, spies, and couriers. 

True Friend of Liberty

While in New York City, a grateful George Washington visited Mulligan’s haberdashery, had breakfast with the man to whom his life was owed, and was fitted for a new set of clothes, dubbing the secret patriot “a true friend of liberty.” This act protected Mulligan from being labeled a British sympathizer and collaborator. Beaming with pride, Mulligan commissioned a sign that he proudly displayed outside his 23 Queen Street (now 218 Pearl Street) store: “Clothier to Genl. Washington.”

Queen Street post-war

Although Cato’s fate remains unknown, Mulligan fought for democratic ideals in post-war America and co-founded the New York Manumission Society with his longtime friend, Alexander Hamilton. Our tailor-spy died in 1825 at age 80 and is buried next to Alexander Hamilton in Trinity Church.

Trinity Church 1776 pre-NYC fire

The Surgeon Spy

Perhaps the most intriguing case in the world of Revolutionary War espionage is that of Doctor Benjamin Church. An enigma wrapped in American history, Church embodies all the traits of an ideal patriot – and the ultimate traitor.

Doctor Benjamin Church

Yankee Pedigree

Church was a blue-blooded descendant of Yankee ancestors and the envy of the Colonial Dames. Born on August 24, 1734, in Newport, Rhode Island, he was the son of Benjamin Church, a Boston merchant and deacon of the Hollis Street Church. Church hailed from a family of New England military, civil, and religious leaders that traces back to the Mayflower through his great-great-grandmother Elizabeth Warren Church, daughter of Richard Warren, who arrived on the Mayflower.

Benjamin Church was born in Rhode Island

Raised for Prominence

Young Benjamin studied at the Boston Latin School, the typical springboard to Harvard College, from which he graduated in 1754. He then studied medicine under Dr. Joseph Pynchon. Afterward, like many American surgeons, he completed his studies in London, where he married Hannah Hill. Upon returning home, he quickly built a reputation as one of the city’s best young physicians and surgeons, even treating the eye problems of the lawyer and future founder John Adams.

Future  president John Adams was Church's patient

Political Turmoil

In the decade leading up to the break with Britain, Massachusetts, especially Boston, was at the center of increasing discontent and unrest. Benjamin Church appeared to be actively involved in these events. After the Boston Massacre on March 5, 1770, he was the one who examined Crispus Attucks’s body and treated some of the wounded. This involvement positioned him as a staunch Whig, and in 1773, he was chosen to deliver the annual “Massacre Day” oration, a yearly event designed to ignite anti-British feelings. He demonstrated a talent for oratory. 

The Boston Massacre

Dr. Church became a leader of Boston’s Sons of Liberty, working with key figures like Joseph Warren, Sam Adams, John Adams, and Paul Revere. By 1774, the well-known surgeon was a delegate to the Massachusetts Provincial Congress and later joined its Committee of Safety, the colonial group responsible for preparing for armed defense.

Our Surgeon Goes to War

April 1775 marked the official start of hostilities between the American colonists, especially those in New England, and the Royal authorities. Although independence was not yet a declared goal, the fight for American rights resembled a war. Our favorite surgeon found himself caught in the middle of it. In May 1775, Church traveled to Philadelphia, where he discussed the military situation in Massachusetts with Congress. As head of the Committee of Safety, he signed the order for the construction of defenses at Breed's Hill and Prospect Hill. 

Breed's Hill defenses

In July 1775, he was appointed Director General and Chief Physician of the newly established Medical Department of the Army, making him head of both the hospital department at the first army hospital and the first headquarters of regimental surgeons. This prestigious appointment placed him at the peak of his career. 

Doctor Gloom?

Interestingly, Church proved to be an indifferent medical administrator and faced a barrage of complaints from the army’s regimental surgeons about his management of the medical system. He pushed back, claiming jealousy was the real motivation behind his critics, and soon asked to be relieved of his duties. Why would a renowned and highly trained surgeon (18th-century term for a physician) show any sign of failure in what should be a core skill? Perhaps our doctor had other priorities occupying his mind.

As chief army surgeon, Church was 

responsible for medical supplies

Other Things

Other clouds swirled around the standing Whig leader. In the world of espionage, these were labeled anomalies and indicators. Although they were present, it would take an overt event to start bringing things together. There were suspicions about his allegiance to the cause, particularly the cause of independence. 

At that time, there still might have been prominent Whigs who were unsure about breaking completely with Britain. But was he one of them? Yes, Church had an English wife, and his brother-in-law was a well-known Tory printer, John Fleming. However, many had connections to Britain and the Tories, so he couldn’t be seen as entirely unusual. As rebellion approached, Church gained a reputation as a notable patriot writer and poet. Still, it turns out that he sometimes responded to his own patriotic open letters in the press with “op-ed” pieces that took the Tory side! 

Advertisement for John Fleming's Printshop

As it would later be revealed, he also had at least one meeting with General Thomas Gage, which was reported, probably by the Mechanics, a spy network run by Paul Revere (see the Yankee Doodle Spies post on them). Church dismissed it—like many suspected spies do too easily. What was then unknown was that Church was in debt, some of which was caused by keeping a mistress. And she was not his first, as it turned out.

Did Paul Revere's Mechanics have 

the doctor in their sights?

A House of Cards

In July 1775, Doctor Benjamin Church’s scheme unraveled when a secret letter was intercepted and decoded. A cipher message was sent to a British officer in Boston named Major Cane through a former mistress. But Eros intervenes in strange ways—the letter was intercepted by another of the woman's ex-lovers and sent to the new Continental Army commander-in-chief, General Washington, in September. 

It took some effort to decode, but they were rewarded because it contained information about the American forces gathered around Boston. Although little of the information was critical, the message clearly showed Church’s loyalty to the King and sought instructions for further secret correspondence. A bombshell striking Washington’s headquarters couldn’t have been more explosive than this news!

King George III

A General Court Martial

During the court-martial in Cambridge that immediately followed, Church admitted to writing the letter (a typical ploy) but insisted he aimed to display the Continental Army’s strength to deter an attack while it was still low on ammunition. He believed it might also help bring about an end to hostilities. While impressing the British probably benefited Washington’s position, this belief showed Church’s ambivalence. Because there was no “espionage statute” and America wasn’t yet an independent nation and therefore could not be “betrayed,” the court, presided over by Washington, concluded that Church engaged in a “criminal correspondence with the British.”  

General Washington penned a report 

following Church's court-martial

Report to Congress

On October 5, 1775, General George Washington wrote to John Jay, the President of the Continental Congress, to notify him that a letter from Dr. Benjamin Church, the surgeon general of the Continental Army, to Lt. Gen. Thomas Gage, the British commander in chief for North America, had been intercepted. His case was then forwarded to the Continental Congress for punishment, along with this report from Washington to the President of Congress:

I have now a painful though necessary duty to perform, respecting Doctor Church, the Director of the Hospital. About a week ago, Mr. Secretary Ward, of Providence, sent up one Wainwood, an inhabitant of Newport, to me with a letter directed to Major Cane in Boston, in occult letters, which he said had been left with Wainwood some time ago by a woman who was kept by Doctor Church. She had before pressed Wainwood to take her to Captain Wallace, Mr. Dudley, the Collector, or George Rowe, which he declined. She gave him the letter with strict injunctions to deliver it to either of these gentlemen. He, suspecting some improper correspondence, kept the letter and after some time opened it, but not being able to read it, laid it up, where it remained until he received an obscure letter from the woman, expressing an anxiety as to the original letter. He then communicated the whole matter to Mr. Ward, who sent him up with the papers to me. I immediately secured the woman, but for a long time she was proof against every threat and persuasion to discover the author. However she was at length brought to a confession and named Doctor Church. I then immediately secured him and all his papers. Upon the first examination he readily acknowledged the letter and said that it was designed for his brother, etc. The army and country are exceedingly irritated.

Crime and Punishment

Because there were no actual laws or a death sentence, Church was sentenced to an indefinite prison term and kept in solitary confinement in Norwich, Connecticut. When he became ill in January 1776, he was released from jail and allowed to move around under guard. In May of that year, he was sent back to Massachusetts on bail and remained in prison until 1778, when the Massachusetts Banishment Act ordered him to be exiled to Martinique in the West Indies. Soon after, he set sail, but the schooner carrying him was never heard from again. It was believed to have gone down in a storm on the open sea.

Church would spend most of his life in prison before exile

A Spy Exposed

Doctor Benjamin Church’s case was one of the mysteries of the American Revolution. Many believed he was wrongly judged, and he certainly thought so himself. After all, his credentials, services, and pedigree were spotless. Although he admitted to certain acts, he insisted strongly that he was just keeping channels open and trying to feed the British bogus information. Torn between two sides, he may have genuinely believed his own story.

Yet he was in debt, had mistresses, and clearly had the ego to take bold action. Was his visit to British-held Boston to meet the Royal Governor and Commander in Chief, General Gage, an act of perfidy or misguided statesmanship?

Did a mistress or mistresses do him in?

Years later, the truth was revealed when scholars gained access to General Gage's files. In the early 20th century, these papers became available to historians. They contained letters with information about the rebel army—correspondence carried by Church that could only have come from him. The good doctor was definitely providing the British army with intelligence from at least early 1775, possibly even earlier. 

General Thomas Gage's files finally outed the spy

A Spy’s Motive

Why did the esteemed Dr. Benjamin Church engage in espionage? Was it because of overwhelming debt? Disputes and grudges against rivals in American leadership? Was there ambivalence about truly breaking ties with Britain? Family connections? Loyalty to the crown? Or perhaps it was for the most frustrating reason of all – simply because he could.

The Legacy Today - Military Intelligence Corps

"There is nothing more necessary than good intelligence to frustrate a designing enemy, & nothing requires greater pains to obtain."
--George Washington

The Yankee Doodle Spies series serves in part as a tribute to the United States’ first army—the Continental Army—and its initial intelligence agency. In a sense, it also honors today’s Army and contemporary Army intelligence.

Unlike today’s Army, the Continental Army lacked a holistic intelligence structure. Instead, various militia units and Continental forces scattered across the states recruited their own local spy networks and attempted to detect British and Loyalist spy networks with varying degrees of success. In 1775, Congress created a Committee of Secret Correspondence to oversee all intelligence activities – essentially America’s first intelligence entity (I hesitate to say agency). Benjamin Franklin was a member. A year later, Congress established a Committee on Spies. John Adams was a member of that one. Additionally, New York’s “Committee to Detect Conspiracies” oversaw counterespionage operations in and around New York City, famously uncovering a plot to assassinate George Washington. John Jay was the committee’s original Chairman.

                                                                                                                                                                                

John Jay

Regarding military intelligence, Washington directed much of the intelligence activity centered on the main Continental Army. He was both the consumer and the producer of intelligence. His action arm was initially under the direction of Thomas Knowlton and later Benjamin Tallmadge. Both play cameo roles in the Yankee Doodle Spies series. As commander in chief, he personally spent a considerable amount of time fretting over and developing sources of information, including spies, informants, prisoners, intercepted correspondence, and even what we today call “open source.”

Benjamin Tallmadge

But after the war, there was no comprehensive intelligence organization for most of the Army’s history. Instead, the function fluctuated. The Army eventually adopted the modern staff system with intelligence centralized around an appointed G2 and intelligence officers assigned from other Army branches. In wartime, tasks were completed effectively, but intelligence must be involved in both peace and war.

Fortunately, 50 years ago this year, the Army finally resolved the issue by establishing Military Intelligence as a branch, professionalizing its intelligence officer corps for the first time. Twenty-five years ago, the Army took it a step further by forming the Military Intelligence Corps, integrating its enlisted cadre into a professional body to enhance the quality of intelligence provided to the United States Army.

The benefits of creating the MI Branch and Corps were numerous, but foremost among them was a trained and dedicated cadre of men and women advocating for the service branch that George Washington valued so highly.