A Treacherous Love Triangle

“How can we draw the line and say at what precise point (treachery begins)…when the treachery is in progress of execution, or.. when the mind is still wavering upon it? In short, how loose and slippery becomes the ground ...  if ... we stray forth in quest of secret motives and designs.”  - Lord Mahon, History of England, 1854 

Perhaps the most infamous story to arise out of the American Revolution is the defection of Benedict Arnold. Some will argue that he was forced to do it by the consequences of his own actions, the actions of his many political enemies, his insatiable desire for money, or his bullish nature. The truth is that it was a combination of all these variables. To better understand the circumstances, let’s begin with a brief introduction for the three most famous conspirators: Benedict Arnold himself, British Chief of Intelligence John Andre, and Margaret “Peggy” Shippen.  

Benedict Arnold 

Benedict Arnold is one of the most controversial figures of the American Revolution. Born in Connecticut in 1741, Arnold was short with a solid build. He was energetic, strong willed, and had great endurance. If there was a task to be completed, Benedict put his all into it. Having descended from one of the founders of Rhode Island, Benedict was good looking and possessing a prideful charisma. He had black hair, gray eyes, and a curved nose that gave the athletic colonist a royal countenance. Benedict Arnold’s pride led him to great success as a seaborne merchant before the Revolution, and a regular duelist at the first hint of insult.  

Coming of age during the French and Indian War, Arnold served in the militia for several years. After the war he worked in the shipping business moving items, above and below board, to Canada and the West Indies. On the outbreak of the American Revolution, he led militiamen during the siege of Boston and later participated in the capture of Fort Ticonderoga. He also led soldiers in the failed invasion of Canada and participated in the failed assault on British-held Quebec, where he was wounded for the first time. Upon retreating south, he created a flotilla of gunships to hold the British advance on Lake Champlain, called the Mosquito Navy. Though the entire flotilla was destroyed, his holding action against the British delayed their advance south long enough for the British to achieve a hollow victory -- a feat that Arnold thought deserved a promotion. That promotion was denied by Congress, the first of many “insults” towards Arnold. Nevertheless, he fought exceptionally well during the Danbury Raid, led the relief force to save Fort Stanwix, and excelled at the battle of Saratoga, during which Benedict Arnold was severely wounded in the leg and sent to Philadelphia to heal and act as military commandant of the city. Arriving there, he became the target of British Major John Andre, chief intelligence officer in the New World.  

 Deeply connected to his first wife, Margaret Mansfield, who died while Arnold was fighting in the north, he threw himself wholly into the task of leading soldiers and sailors into battle. While building and commanding the Mosquito Fleet on Lake Champlain, his merchant vessel was seized by the Continental Army and sunk to create a navigational hazard to the Port of New York -- an action never repaid by Congress. His sister Hanna wrote of the ordeal, “If you ever live to return…you will find yourself a broken merchant.”  

Further complicating his time in the north, Arnold had many detractors in the Continental Congress who propagated rumors of his taking supplies and loot for personal gain in the retreat out of Canada. (however true or false these rumors were, they are congruent with the man’s personality). Arnold wrote in his defense, “I cannot but think it extremely cruel when I have sacrificed my ease, health, and great part of my private property in the cause of my country to be calumniated as a robber and thief at a time too when I have it not in my power to be heard in my own defense.”  

Arnold’s temperament became a problem as the war progressed, described thus by Dr. Benjamin Rush: “His conversation was uninteresting and sometimes indelicate. His language was ungrammatical and his pronunciation vulgar.” Another officer stated, “the fighter did not combine … any intellectual qualities with his physical prowess. Instead of engaging an interesting argument, he shouted and pounded the table.”  

These traits were not becoming of an officer who was expected to be genteel and of the upper class. On the high seas, however, these uncouth habits made for a splendid captain. During the winter of 1776, Arnold began to prepare for a post to the American Navy, asking for a commission as a commodore. This move would have allowed Arnold to collect prize money for the ships, goods, and material that he would seize -- money that would allow him to live the playboy lifestyle to which he was accustomed, finally have total autonomy over his forces (whilst at sea), and escape the privations of an overly hostile Continental Congress. Ultimately his request was denied, as he was deemed too “necessary to the cause” to be put out to sea.  

John Andre 

Picture located in the London Tower

John Andre 

In stark contrast, one of the most charismatic and unique individuals in the American Revolution was British Major John Andre. Born in 1751 to a prominent London merchant, Andre had a French lineage on both sides of his family. Like other affluent children, he was sent to Switzerland for his education and returned with the ability to speak four languages: German, French, Italian, and his native English. Growing up the son of a wealthy merchant with strong familial ties to France, he probably was taught French and English side by side growing up.  

In addition to his affinity to languages, Andre was an accomplished musician, artist, and painter. In his free time, he often read literature and wrote poetry, a skill that would aid his climb through the ranks of the British military. After leaving the family business, Andre joined the military in 1771. The next year saw him stationed in Germany, and in 1775 he was transferred to the 7th Fusiliers and shipped out to the New World. He landed in Philadelphia, tasked with moving north to British garrisons in Canada. He was captured at St. John in 1775 and spent the next year, 1776 as a “prisoner”; he gave his word to his captors that he wouldn’t escape until exchanged, and was allowed him to roam as he saw fit. Andre kept his word, never attempting an escape. Upon his exchange in late 1776, he relayed his experiences in the New World to his commanders. The skill and detail of Andre’s observations earned him a captaincy in the 26th Regiment, and later the position as aide-de-camp to General Charles Grey -- a position in which Andre served until his death in 1780.  

Thanks to his charisma as the career officer, Andre was a prominent socialite. He interacted with upper-class loyalists and attended social occasions when afforded the opportunity -- so much that throughout the winters of 1777, 1778, and 1779, he was known to host some of the most lavish balls for the officer corps and local socialites. None was more outrageous than the Meschianza, a farewell party to honor British General William Howe and his brother, Admiral Richard Howe, upon their recall to the homeland.  

These parties were a welcome distraction for British officers and loyalists alike. However, for the military cause, they provided a unique opportunity to get to know enemy officers, military styles, and force distributions. Generals Henry Clinton and George Washington had networks of spies who attended these balls, either as guests or as servants. While the army was largely male, both spy networks were composed mostly of females and bonded servants -- people who could get close to party guests and relay their secrets, habits, and movements back to the spy master’s camp.  

The success of these parties relied on the charisma of the spy and his or her ability to move information effectively and accurately. So successful were these opposing networks that treason and espionage became a major military stratagem for both sides during the later stages of the American Revolution. The most prolific example was the defection of Benedict Arnold. Assigned the head of British Intelligence in the New World, Andre was tasked with turning Arnold to the British cause -- an act that succeeded due to Andre’s familiarity with Arnold’s wife, who had an affinity for British balls. 

Margaret "Peggy" Shippen

Margaret “Peggy” Shippen was born in 1760 to a prominent lawyer in Philadelphia named Edward Shippen. The youngest of her family to survive to adulthood, she quickly became her father’s most capable and favorite child. Belonging to a prosperous family, two of her ancestors were mayors of Philadelphia. She was the granddaughter of one of Princeton’s founding trustees, and having grown up in a mansion on Society Hill, she was destined for greatness. Shippen was blond-haired, possessed delicate features, and had eyes that appeared to be blue, hazel, or gray, depending on her mood. She was incredibly intelligent in matters of business and the rules of society. Often considered the most beautiful woman in the room, Shippen garnered attention from all those whose presence she graced. Her beauty purportedly only outmatched by her intellect, Shippen’s intelligence resulted from a strong desire for education, self-improvement, and family achievement.  

Portrait of Margaret Shippen (Mrs. Benedict Arnold) -  by Major John Andre, , 1778. Yale University Art Gallery

Growing up, Shippen had the distinct advantage of having house guests such as George Washington; Benjamin Franklin, who was close friends with her grandfathers; Charles Mason and Jeremiah Dixon, famous for creating the Mason-Dixon Line; cousin Dr. William Shippen, who was the director of Penn’s Medical School until his arrest on five different charges; Benjamin Chew, chief justice in Pennsylvania and the father of a close friend; and, of course, Benedict Arnold, a dashing merchant, and her future husband. With her brilliance, drive, and upbringing, it is no surprise Shippen possessed a sharp mind and the social acumen to interact with the upper echelons of power. By the time Shippen was a teenager, her family had moved back to Philadelphia after a brief stint in the country, allowing her to bask in frivolity, gaiety, and revelry that was the British occupation during the winter of 1777.  

The Turmoil

Fancy balls were not just held for purposes of intelligence, a circumstance that mostly arose organically. They were an outlet for British officers and upper-class loyalists to comingle, take their minds off the war, and expend some youthful energy. At these events, Shippen and her close confidants were introduced to Andre. Possessing similar intellect, personal drive, and a love of the arts, dancing, and music, Shippen and Andre became quite close, with Shippen regularly attending dances and plays put on by Andre, and Andre regularly taking tea in the home of the Shippens.  

The spring campaign season of 1778 began with the retreat of the British Army out of the capital of the fledgling new country. Before shipping out of Philadelphia, Andre wrote this poem to Shippen and her three closest friends, the ladies with whom he had wintered: 

“If at the close of war and strife 

My destiny once more 

Should in the various paths of life 

Conduct me to this shore 

Should British banners guard the land 

And faction be restrained 

And Clivenden’s peaceful mansion stand 

No more with blood bestained 

Say, wilt thought then receive again  

And welcome to they sight  

The youth who bides with stifled pain 

His sad farewell tonight?”  

Genteel soldier-scholar John Andre could not have been more a juxtaposition to the hulking, brash, impetuous, and bold Benedict Arnold. Nevertheless, within a month of his arrival as military governor of Philadelphia, Arnold was a regular in the home of the Shippen family. The military occupation paired with the siege of the winter of 1777 left the city a broken shell of what it once was, with many of its upper-class residents desperate to recoup the massive amounts of income lost, including Edward Shippen and the ever-slighted and largely broke Benedict Arnold. Edward and Peggy Shippen saw the income potential of Arnold’s multiple, under-the-table (largely questionable if not downright immoral) business ventures as a means to restore the family wealth.  

One such financial endeavor resulted when Joseph Reed, a representative to Congress from Philadelphia, ordered the city’s shops closed for a week so the military could take possession of whatever was deemed necessary for the war effort. Arnold, always being the opportunist, sought out luxury goods from the upper-class citizens and bought them at bargain prices to ensure they weren’t seized by the army. This venture was funded by a previous one that involved Arnold investing in a merchant ship’s cargo, a merchant ship stuck in port and likely to be seized by the British. Using his power, Arnold requisitioned 12 wagons, with enough teamsters and laborers from the Continental Army to bring the goods from New Jersey into Philadelphia, where Arnold sold them for an enormous profit.  

By February 1779, Peggy Shippen and Benedict Arnold were engaged to be married, on two conditions. The first was that Arnold’s leg wound from Saratoga would heal satisfactorily manner. Second, he would hold estate. The former was up to chance and Arnold’s strength of will. The second came down to his fame. Having fought the majority of the war in the northern regions of the colonies, he had protected the state of New York from multiple British invasions from the north -- an act for which New York was more than willing to properly reward him. The state had seized two large tracts of land from loyalist Tories and offered them at a pittance to Arnold, on the condition that he continue to be the buffer that prevented British incursions from the North. The first property, Kingsland, comprised 130,000 acres in the Mohawk Valley. The second property was a 40,000-acre estate on Lake Champlain. This would have allowed the couple to have an unparalleled estate and prominence in the socio-political arena in the new nation. Unfortunately, one of Arnold’s most ardent adversaries, Joseph Reed, used this opportunity to levy eight charges against Arnold that heralded him as a pirate, traitor, and war profiteer. These edicts were sent to each of the leaders of the 13 colonies, Continental Congress (where Arnold had many vocal enemies), and lastly, to George Washington himself.  

Arnold and Shippen married April 8, 1779, two months before his court-martial. Ever prideful, Arnold abandoned his quest to New York and went straight for his commander in chief, George Washington, to clear his name. Hoping to avoid imprisonment or permanent disgrace, he fought the charges, which eventually were brought before Congress. After several hearings, it was deemed that four of the eight charges would be brought to court-martial. Arnold buried his profits from his under-the-table dealings in Philadelphia while (most likely) leveraging his status as a military leader to garner a 12,000-pound loan from a French merchant to purchase a property for him and a pregnant Shippen. This only fueled belief that his disloyalty furnished his lavish lifestyle.  

Under mounting pressure from Congress, their creditors, societal pressure, and a muddied reputation, the Arnolds began to actively conspire against the Continental government a month after their marriage in May 1799. The Royal Gazette describes Arnold’s plight: “General Arnold heretofore had been styled another Hannibal, but losing a leg (just the functional use of it) in the service of the Congress, the latter considering him unfit for any further exercise of his military talents, permit him thus to fall into the unmerciful fangs of the executive council of Pennsylvania.”   

At this point, Peggy Arnold, ever bright, lent her full support to her husband. Through a friendly go-between she fostered regular contact with her old friend John Andre, who would eventually attempt a mad escape to New York with traitorous documents written by her husband. Through the use of invisible ink, an underground communication network set up by Andre, and Andre’s personal skill (he created several personas to impersonate American, French, and German officers), negotiations began in earnest for the defection of Benedict Arnold. Arnold was after a large sum of money. Andre, meanwhile, was after a prize so large it would inevitably lead to the end of the war, and fate was about to provide such an opportunity.  

Between the winter of 1779 and the spring of 1780, the two armies traded blows back and forth in the north and the south. The governments of each faction were loathe to pour more resources into the conflict, and the French had yet to commit large forces to aid Washington in the north. In seven months of secret communications, Arnold told his British counterparts of Washington’s position, troop distribution, where his winter quarters were, and how Congress was looking to appropriate a loan from Holland to further the war effort. Now he was about to have the fight of his life in his military court-martial. Should he be successful, he would prove more than valuable as a traitor, and his scheming would all come to fruition. Eventually, all charges were dropped except for one, leading to an official reprimand of Arnold and a personal letter of rebuke from Washington. The insults were enough to wound the man’s pride but not enough to keep him from earning another command, one that would be essential to his future as a defector to the British.  

After being denied a naval command a second time, Arnold successfully petitioned Congress for the command of West Point, a complex of fortifications so profound they served to protect upstate New York and maintain possession of both Lake Champlain and the Hudson River. Arnold intended to give this as his dowry for his marriage to the British cause. Upon taking command of West Point, he set about to ensure that 3,000 soldiers were there, and the breastworks were as incomplete as possible (both conditions of his deal proctored through Andre). Washington, fully aware of the vital nature of the fortress and with fresh news of overwhelming defeats in the south, wanted to personally inspect the fortress that the whole American cause now depended upon. Arnold saw this as an opportunity to sweeten the pot with the British. In a secret overnight meeting with Andre, he hashed out lines of advance for the British troops to take the fortress and the commander in chief. 

During this meeting, Andre received detailed drawings of the fortifications as well as the tentative travel plans for Washington’s inspection. Once the plans were received, Andre’s first line of escape -- a sloop that had been run off by American artillery -- had been cut off. This forced him to have to change out of his uniform and try to make his way through neutral territory into New York City -- a move that should have concerned Andre, except he had befriended several of the local gangs that controlled the area. It was a win-win for him; if he was caught by gangs loyal to the Americans, he had a pass signed by Arnold himself. If he was stopped by those loyal to the British, he would use his status and familiarity to pass through to his commanders in New York.  

The Capture of Major Andre - 1780

Sadly, after a mad dash through the New York countryside, Andre ran into Americans dressed as British soldiers -- an outcome that proved fatal to him and the British cause to take West Point. Uncharacteristically, Andre revealed his true identity, resulting in his capture (out of uniform) with intimate plans to capture West Point, and a pass signed by Arnold using Andre’s alias. After some searching, for their commander in chief, couriers finally arrived to meet with General Washington, who was already touring West Point and dining with Peggy Arnold. It was not until late in the day, after inspection of the fortifications and supper with Arnold’s wife, that Washington received Andre’s packet with the maps Arnold created. Only through the network of spies Andre had set up was Arnold notified of the failure of the mission earlier in the day. This allowed him to escape while his wife knowingly entertained the officers, buying him precious time to complete his defection. 

Upon receipt of the package, Peggy Arnold instantly went into an inconsolable fit that lasted for days, and was so convincing that George Washington, Lafayette, and Henry Knox absolved her of any involvement in the plot. Due to the lost time and lack of accurate plans of the fortification, the British attack on West Point never materialized. Despite a hearty defense and multiple letters of exchange from his British commanders trying to negotiate his release, Andre was hung (a task his captors, who found him a most agreeable man, completed efficiently if with some regret) as a spy. Arnold was commissioned as a brigadier general in the British Army. And Peggy Shippen eventually joined her husband in New York, where he was still an active combatant in the war, just in a British uniform.  

Having yet another field command Benedict Arnold was back leading soldiers in combat, a role in which he had always excelled and truly enjoyed. Benedict began to make himself invaluable under the flag of the British army, he collected 1,600 soldiers and sailed south to aide General Cornwallis in the Carolina’s. The soldiers and 42 ships sailed down the coast and up the James River to capture Portsmouth, and to conduct raids through Virginia. True to form, Arnold was incredibly successful, so successful as to take the capitol of Richmond forcing a narrow escape of the governor, Thomas Jefferson. Unsurprisingly, Arnold agreed to split the profits from the captured loot with the Commodore of the British feet, of whom his soldiers relied upon for fire support and transportation. A violent row broke out between the two men, resulting in each refusing to work in coordination with each other on matters private or military. After a successful (militarily) expedition to the South, Arnold was granted an opportunity to attack Continental Army forces in his home state of New Hampshire. The goal was to shut down Continental supply lines. Benedict’s men attacked and destroyed the port of New London, accidentally setting a gunpowder store on fire, resulting in the destruction of the town. Things then took an even more violent turn, after a battlefield miscommunication, Arnold’s men attacked and successfully took Fort Griswold. After taking heavy casualties in the endeavor, the men serving under Benedict’s banner, despite orders to take prisoners, massacred the Continental forces. Going so far as to bayonet the fort’s commander directly after he surrendered his sword. Even though successful, on the battlefield, Arnold could not outrun the British defeat at Yorktown, an event that signaled the end of the war. 

Despite boasts of his returning to command 20,000 men to retake the continent, Peggy, Benedict, and their two sons left for their new home in England in December of 1781. Upon arrival in London, Benedict was introduced to the King, members of the military elite, and became intimate with the Prince of Wales. Peggy on the other hand became one of the most beautiful women in all of London, so much so the Queen suggested the members of her court shower love upon her, and General Henry Clinton authorized a pension of 500 pounds for her…”services, which were very meritorious.”  

The couple settled in a modest home on Putnam Square, where they became regular members of the London social scene. Peggy eventually bore seven children in total, five surviving into adulthood. Arnold ever seeking adventure, and riches, led a failed trading expedition into New Brunswick. A storm ran the merchant ship ashore, where the contents of her hold were stolen, leaving Benedict with a broken ship and no cargo. After several successful adventures into the Eastern Caribbean Benedict was able to bring Peggy and their children into a new home in St. John Canada. Where Benedict set up a shipping enterprise that put the family, with Peggy’s accounting prowess, in comfortable standing. Peggy made it home to visit her family one last time in 1789, it would be her last visit before Benedict and Peggy returned, financially ruined, to London in 1791.  

Never one to sit still long, Benedict soon left England for another merchant run into the Eastern Caribbean, where after a brief stay as a prisoner of the French Navy, he escaped and found his way to British lines. Where he negotiated a position to train local militia and provide supplies for British Garrisons in the Caribbean. Returning to London with modest means, he soon lost them again funding privateers in the war with the French. Never to financially recover or take the field again. In 1801 Benedict Arnold died at the age of 60, a few years later Peggy Shippen passed at the a ge of 44 in 1804. With the deaths of the Arnold’s, a chapter of history closed. One that was tumultuous and eventful. A chapter that thrust three individuals of vastly differing backgrounds and personalities into a spotlight that changed the world. 

The perfect storm of politics, war, degradation, and personal vendettas created the events leading to perhaps the most famous scandal in U.S. history. All of it started with a charismatic British officer hosting parties, putting on theatrical performances,and wooing a group of intelligent, gifted, and powerful young women. It is not unsurprising that politicians, diplomats, soldiers, and spies used the formal balls during the Revolution as means to a political end. Balls held in Boston, Philadelphia, and New York became mini-theaters of political and social dramas that exploded onto the international stage and set the tone for battle policy and foreign policy for decades to come. Had it not been for the social interaction allowed at the balls during the American Revolution, the war might have turned out differently. Washington would not have received accurate information on British strategy, and the British might not have been given the opportunity to turn Benedict Arnold -- an action that changed the course of history.