After distinguishing himself in the Battles of Saratoga in the fall of 1777, Arnold believed he had finally shamed his critics and detractors who were standing in the way of the meteoric rise he so desperately desired. His valor in combat was undeniable—even though he had acted in direct defiance of an order from his superior officer, with whom he had a personal dispute. He had been severely wounded in his left leg but refused to allow an amputation; instead, he had it set to heal, but the job was poorly done. As a result, Arnold walked with a limp for the rest of his life.
In June 1778, as the Americans were reestablishing their presence in Philadelphia—and roughly two months before Woodhull began spying in New York as Culper Senior—Washington appointed Arnold the military commander of Philadelphia. Arnold quickly realized that this new position would allow him to engage in a variety of business deals to restore his finances, which were still plagued by his numerous debts back home in New Haven. He was not particularly popular among many citizens of Philadelphia, however, and complaints were soon raised that not all of his ventures were legitimate. One vocal critic was Allen McLane, a highly respected and distinguished soldier from Delaware, who had been among the first Americans to enter Philadelphia when the British left; McLane voiced his concerns to General Washington but was reprimanded for challenging such a high-ranking officer. When Arnold learned about the complaints, he was angry that so many citizens and fellow soldiers questioned his integrity, particularly because his position was one of public service to a war-torn city. Was he not an officer of the Continental Army who was fighting for the liberty and freedom of all Americans?
This upturn in his fortunes pleased Arnold, and he lived well in Philadelphia, even under the shadow of accusations that his gains were ill gotten. Like his British predecessors, he enjoyed rich furnishings and luxurious dinners and entertainments. He even mingled with Philadelphia’s society belles, one of whom, Peggy Shippen, especially caught his attention.
PEGGY
As the youngest surviving child born into a politically prominent family, Margaret “Peggy” Shippen grew up a pampered, spoiled darling of her parents and blossomed into one of the stars of Philadelphia’s social scene. Under her father’s supervision, she received an excellent education, even dabbling in political theory, which was highly unusual for a young woman of her time but later made her a delight at dinner parties and a favorite conversant among the military officers quartered in the city.
The Shippens were devout Loyalists living in the midst of what was, in many ways, the heart of the American cause. Philadelphia had hosted the First Continental Congress in 1774, which convened in response to the Intolerable Acts imposed as punishment on the colonists by the British Parliament after the Boston Tea Party. In May 1775, the Second Continental Congress was called, and again the delegates met in Philadelphia. The city played host to several of the delegates’ meetings over the next six years, including their most famous, in 1776, which resulted in the Declaration of Independence, all while the Shippens—and many other residents who considered themselves loyal to King George—looked on in disapproval.
When the British marched on Philadelphia in September 1777 and captured it easily, the Shippens and their friends welcomed them. The winter that followed, while miserable for the Americans encamped outside the city at Valley Forge, was rather delightful for the British soldiers stationed in town. Galas and dinners were hosted in honor of the officers, who were the centerpiece of the social scene. Major John André, the dashing British poet-spy who would later be published by Rivington in New York, was one of the most sought after, and he attracted a bevy of female followers wherever he went.
Seventeen-year-old Peggy was among André’s admirers, and history hints that her attentions might have been returned. Members of the leisure class understood that flirtation was a lovely game when both parties engaged in it merely for sport; so when the British decided to abandon Philadelphia nine months later in order to shore up their defenses in New York, there were probably very few tears shed on Peggy Shippen’s pillow. The dapper André had marched away, but nature, armies, and young hearts all abhor a vacuum, and the American troops who were now pouring into the city promised their own diversions and charms for the young lady.
AN UNLIKELY UNION
Peggy Shippen found her life little changed with the arrival of the Continental Army. Her family still had wealth and prestige, and the most significant alteration to the social scene was simply the color of the officers’ jackets. Despite her family’s political allegiances, Peggy soon found herself enamored with the widowed Patriot general Benedict Arnold, even though he was nearly twenty years her senior. For his part, he was flattered by the attentions of the young and vivacious woman who remained one of the most prominent ladies in Philadelphia.
Just what the attraction was on Peggy’s side is unclear. Arnold had position and prestige, but he also had some fairly substantial debts, a military career that might be in peril due to his wounded leg, a short temper, and deep-seated insecurities. Perhaps this was precisely what made Arnold’s Samson the perfect catch for Peggy’s Delilah. Peggy was a woman with a mind of her own, and she may have realized just how much power she could wield over such a husband. He would, in essence, be her slave, bending himself to her will out of fear that she might cuckold him if she didn’t get her way. If there was one thing Arnold craved, it was admiration, and Peggy knew he thought that a beautiful young wife on his arm would win him the envy of his rivals.
Whatever the case, she captured his notice and his heart, and the two were married the following April, in 1779. Arnold’s life had never been better: His finances were improving, both through his own investments and through the fortune of his pretty new wife. He was finally garnering the kind of respect and authority he felt he deserved. Still, he was bitter because other American officers seemed to be more popular and loved by their men. Just one month after his marriage to Peggy, an indignant Arnold wrote to General Washington regarding the charges against his business practices in Philadelphia: “If your Excellency thinks me criminal, for Heaven’s sake let me be immediately tried, and, if found guilty, executed. I want no favor; I ask only for justice. . . . Having made every sacrifice of fortune and blood, and become a cripple in the service of my country, I little expected to meet the ungrateful returns I have received from my countrymen.”
CHANGE OF HEART
While Arnold was reveling in his newfound prominence and respect, Peggy was throwing grand parties that helped to raise her husband’s social profile—and his debts. The Arnolds enjoyed an extravagant lifestyle in Philadelphia, living well beyond their means, which may have contributed to Benedict’s wandering eye in terms of his Patriotic allegiances.
Despite his initial zeal for taking up arms against the tyranny of King George, Arnold had long been losing faith in the Americans’ chances at success, and the company he was keeping in Philadelphia did little to change his mind. Now it seemed he had his chance to throw in his lot with both sides and (if he played it right) emerge from the war a victor, no matter which army prevailed. In May 1779, Arnold made overtures to General Clinton in New York, by way of a Loyalist merchant in Philadelphia, as to whether he could be of service. The British did not immediately jump at his offer; after all, how often does a high-ranking enemy officer voluntarily offer to spy? Suspicions were rampant, but the proposal seemed legitimate and, if Arnold could prove himself trustworthy to the king, his intelligence would be an invaluable source of information about American strategies, plans, and plots. To test Arnold’s proposal by degrees, Major John André, the newly appointed chief of intelligence for the British army, contacted Arnold—a connection aided, no doubt, by André’s previous acquaintance with Arnold’s new wife.
The correspondence between the two men often involved Peggy. Even as she acted as a messenger between Philadelphia girls and their British lovers who were now stationed in New York, secretly carrying letters and p
arcels back and forth, she would now also act as a courier between André’s agent and her own husband. Her conduct on the first count was an open secret, which provided an excellent cover for her more nefarious role.
Arnold used a method similar to that of the Culpers when communicating with André: invisible ink and a book-based code. He based his code on two books: William Blackstone’s Commentaries on the Laws of England and Nathan Bailey’s An Universal Etymological English Dictionary. Each word was denoted by three numbers separated by a period. The first was the page number, the second was the line, and the third was the position of the word, starting from the left margin, in that line. For example, 172.8.7s stood for “troops”: page 172, line 8, seventh word in. The s at the end simply made it plural. Like the communications of the Culpers and other spies of the era, the letters of Arnold and André were often disguised as ordinary notes about family matters or inconsequential gossip addressed to or written by Peggy. In between the lines, written in some form of invisible ink, were the real messages.
Despite the similarities in technique between the two spy rings, the Culpers were operating with several advantages. First, they had an added layer of security: Not every member or satellite was aware of the identities of the others in the ring. Arnold and André and their various go-betweens knew the names of everyone with whom they were dealing, which meant a higher risk of detection should someone be caught. Second, Arnold and André could communicate only with each other, but the Culpers had developed a more complex network that allowed Woodhull, Brewster, or Roe to add intelligence en route to General Washington, confirming or correcting the initial reports, and making the information more detailed when it finally reached its intended destination.
Third, the Culpers were able to operate in a wider social circle because the members were citizens from all walks of life. Townsend gathered information from soldiers around the city and sailors at the dock; Agent 355 charmed strategic details out of high-ranking officers at soirees; Rivington repeated gossip and plans overheard in his shop; Woodhull enhanced these reports with his own observations of troop activities on Long Island and recounted what shop owners were saying or if there was an uptick in lumber sales and ship repairs; Roe learned whatever news was shared when tongues loosened in his tavern; and from the water Brewster spied on British naval movements. The Arnolds and André were limited to the upper tier of Loyalist social circles for their intelligence.
EVERY MAN HAS HIS PRICE
Arnold’s double-dealings had to be sidelined in the autumn of 1779 when suspicions fell on a number of Loyalists still residing and working in Philadelphia. Because Arnold had married into one of the most prominent Tory families, he, too, found himself forced to prove his allegiance to the Continental Army and the American cause.
Further complicating matters and frustrating Arnold was the fact that he faced a court-martial for some of his business dealings in the city. Never mind that the trial had initially been his idea when the concerns were first raised; he had hoped that just such an event would be an excellent opportunity to publicly shame his critics and exonerate himself. Now, it just seemed to add to his stress by bringing his actions under close scrutiny—an uncomfortable prospect for anyone leading a double life.
The hearing went forward, however, and Arnold conducted himself brilliantly. On January 26, 1780, he was found guilty of two minor charges; the rest were dropped. It was a tremendous moral victory for Arnold, and he wasted no time or expense in spreading the word that he had prevailed over his detractors. To make his happiness complete, six weeks later Peggy gave birth to their first child, a boy named Edward Shippen Arnold, after the baby’s maternal grandfather.
The celebration was soon dampened, however, when the Continental Congress conducted a kind of self-audit and ruled in April that Arnold owed the government more than one thousand pounds for undocumented expenses from the unsuccessful invasion of Quebec he helped to lead in 1775. The records showed a substantial sum tied to Arnold for which there was no accounting or receipts; according to practice, the amount due was his own responsibility.
The investigation humiliated Arnold—and also put him in a financial bind. Shortly after the audit, he struck up a correspondence once again with the British. General Clinton was especially interested in expanding his grasp on New York beyond the boundaries of Long Island and Manhattan, and was eyeing the Hudson Valley as a means of controlling the land north of the Hudson River as well as the harbor. He would handsomely reward Arnold for his assistance, but Arnold and Peggy were still locked in Patriot Philadelphia, which wasn’t nearly so rich a grounds for the intelligence Clinton and André desired. Despite his willingness to sell what he knew, the damage that Arnold was able to inflict upon the American cause was somewhat limited by his current capacity and location. Clinton wanted to see his spy situated somewhere much more significant for the Crown’s goals of reestablishing authority over as much land, population, and key transportation and resource channels as possible, and he urged Arnold to seek new opportunities and a new command.
For the past year, Arnold had found life in Philadelphia quite to his liking, but now he was fed up. The bill from Congress for the invasion of Quebec was as humiliating as it was beyond his ability to pay. He had heard that the command at Fort West Point was available, and it seemed the perfect solution to his various woes. While he may not have relished the thought of moving to a remote outpost, the thought of being in absolute authority in his own fort away from Philadelphia must have appealed to his pride. He could quit the city, assume control of the strategic fort, and at precisely the right time turn it over to the British. He would then collect his reward and enjoy a life of leisure as the man who had made the king’s victory over the rebellion possible. Away in New York, General Clinton, too, recognized the potential of West Point; it was situated fifty-five miles north of Manhattan, on a sharp turn of the Hudson River. From there, it was possible to control the access of ships to the rest of the river, thereby limiting or opening the movement of troops, supplies, and goods for trade. It was, in many ways, the key to the rest of the state. Through Major André, he urged Arnold to press his case for the command of the fort.
Washington resisted the petition at first. Arnold had resigned his position in Philadelphia after the Quebec payment insult, and despite his acquittal on all but two minor charges resulting from the court-martial, his conduct in those matters had still been disappointing. Washington had personally written a strongly worded letter to Arnold chastising him for such behavior not long after the verdict was handed down, despite which Arnold had commenced with his very public celebrations of the outcome. Still, West Point needed an experienced man at its helm, and much of Arnold’s combat and strategy experience had been in upstate New York. Washington mulled over the matter even as Arnold and several of his allies lobbied heavily for the appointment.
With a permanent departure from Philadelphia on his mind, Arnold set off for New Haven in order to settle his affairs in that city, as well as to begin quietly transferring his cash assets to London banks. He deliberately routed his travels so that he could stop and inspect West Point on the way under the guise of wanting to get a sense of the state of the fort to better prepare for taking command. He secretly sent off whatever information he was able to gather to André with the implied promise that much more would follow should their plan succeed and he be given control in the coming months. Initially, the price he named for his treachery was ten thousand pounds, in addition to his out-of-pocket costs and losses (which makes Woodhull’s occasional requests to General Washington for fifty pounds to reimburse members of the Culper Ring seem humble, paltry, even laughable). But Arnold knew the British had the money and he was certain they would pay as much for the information as for the sheer satisfaction of humiliating the Americans.
Just a few weeks later, however, whether from discovering that his debts in Connecticut were far worse than he had anticipated, from finding
Peggy’s influence greatly diminished with his geographical separation from her, or simply from losing heart, Arnold suddenly grew panicked, even paranoid. In a letter to André dated July 11, 1780, he complained that he was not being trusted and hinted that he would put a stop to the whole deal unless things changed to his satisfaction. The next day, he wrote again, this time doubling his price to twenty thousand pounds, overtly offering to surrender the fort, and insisting that a portion of the reward be tendered as a down payment for his services.
In all fairness, Arnold’s anxiety was not unfounded. He was, in fact, being spied upon by order of General Clinton because the British did not consider him altogether trustworthy; after all, if he changed his loyalties once, what was to stop him from playing the turncoat again? But his course was set and he was determined to carry it out, certain that he would emerge as victor in the end.
CHAPTER 12
Negotiations and Treachery
Benedict Arnold’s treason was well under way when the French fleet arrived in Newport during the summer of 1780. Observing that Washington was actively working on several covert plans to outmaneuver the British, Arnold tried just as actively to undo them in secret. Fortunately for Washington, the deep secrecy surrounding the Culpers kept the ring out of Arnold’s reach, but the success of the spies’ tip and Washington’s ruse had alerted Benedict Arnold. He knew he would need to infiltrate or stop the ring were his betrayal to be successful. Little did he know that members of the very ring he was attempting to ensnare were removed from him by just a few degrees of separation.
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