Benedict Arnold’s story is often told as if he woke up one morning and decided to become a traitor. That is a neat way of teaching history, but it does not do justice to the truth. Men rarely betray their country out of a single moment of madness. More often it builds slowly, fueled by pride, resentment, money troubles, and the sting of being overlooked. For Arnold, all those ingredients had been simmering for years by the time September 1780 rolled around.
At Saratoga in 1777, Arnold had been the hero. He was bold, decisive, and fearless, charging forward in a way that rallied men to fight when all seemed lost. The wounds he took in that battle left him crippled, but they also made his name. People cheered him in the streets, toasted him at taverns, and called him the savior of the Revolution. He expected that kind of glory to last. Instead, what followed were court-martials, accusations, and slights from Congress. He had risked everything and been rewarded with doubt and suspicion. That, to a man like Arnold, burned hotter than the musket ball still lodged in his leg.
Money played no small role. Arnold lived as if he were a gentleman of means, but he was not. He borrowed freely, speculated unwisely, and complained loudly that Congress owed him reimbursement for expenses he had laid out from his own pocket during campaigns. Instead of paying him, they investigated him. Joseph Reed, the head of Pennsylvania’s government, led the charge, accusing Arnold of corruption while he was military governor of Philadelphia. Arnold felt this was not only unfair but insulting. He saw himself as an honest man surrounded by petty politicians and backbiters. In reality, Arnold was both careless and reckless with money. He cut deals, lined his pockets where he could, and lived on a scale that made enemies jealous. His pride demanded the life of a gentleman, but his purse could not support it.
Then there was his marriage. Peggy Shippen, young and beautiful, came from one of Philadelphia’s wealthiest Loyalist families. Before Arnold, she had moved in circles that included British officers, including Major John André himself. She brought Arnold into that world, or perhaps reminded him of it. She represented refinement and status, and Arnold adored her. But she also came with expectations. To keep Peggy happy, Arnold needed more money than his army salary or his battered credit could provide. Through Peggy, Arnold kept up a connection to Loyalist society even as he wore the uniform of a patriot general. Many later accused her of planting the seed of treason in him. That is likely too simple, but there is no question she encouraged his ambition and his sense that America had wronged him.
The Debate-Arnold’s Treason: Hubris or Just Bad Luck?
Add to all of this the bleak outlook of the war in 1780. The French alliance had helped, but the British still held New York City and much of the South. Washington’s army was starving, short of supplies, and plagued by desertions. Congress seemed powerless, a bickering body of men who could not pay soldiers or officers and did not even pay attention to the sacrifices men like Arnold had made. If you were a man looking at the ledger, weighing what you had given and what you had received, it was not hard to conclude that the British were the better bet. Arnold had given his youth, his health, and his fortune to the American cause. In return he had humiliation, debt, and enemies who seemed determined to ruin him. No wonder the British promise of gold and recognition looked attractive.
It is easy to shake our heads now and call Arnold greedy, which he certainly was, or vain, which he definitely was. But imagine for a moment that you are in his shoes. You have been the hero, but the glory faded. Your leg aches with every step, and Congress, instead of honoring you, hauls you into hearings and cuts off your claims. Your creditors hound you, your lifestyle drains your purse, and your wife’s friends whisper that England treats its generals like gentlemen, while America treats them like criminals. Pride is wounded, debts pile up, and the war looks grim. In Arnold’s mind, he had every reason to think he had earned more than he got. That is not to excuse him, but it helps us understand the path that led him to September 21, 1780. His treason did not begin that night. It began years before, when his pride and his ambition curdled into bitterness.
By the summer of 1780, Benedict Arnold was no longer just grumbling. He was planning. His ambition had found its outlet in treason, and his pride convinced him it was the only way left to reclaim the recognition and fortune he believed he deserved. The linchpin of that plan was West Point, the great fortress on the Hudson River.
West Point was more than just a fort. It was the choke point of the Hudson, the artery that connected New England to the rest of the rebellious colonies. Control that stretch of the river and you could strangle the Revolution. The British had tried in 1777 with their Hudson River campaign and failed at Saratoga. But the dream never died. To hold West Point would mean splitting the colonies in half, severing Massachusetts, Connecticut, and the hotbed of rebellion from the middle and southern states. Washington himself called it “the key to America.” When Arnold received command of the post in August 1780, he was given not just a garrison but the fate of the war. That made him valuable to both sides. To the Americans, he was trusted with a crown jewel. To the British, he was the answer to their strategic prayers.
Arnold’s plan was straightforward in conception and breathtaking in betrayal. He would weaken the defenses of West Point, scatter its supplies, and leave the fortress vulnerable. When the time was right, British troops under Sir Henry Clinton would sail up the Hudson, strike swiftly, and seize it. The garrison, ill-prepared and under-strength by Arnold’s design, would fold. The Revolution would suffer a blow so crushing it might never recover. In return, Arnold demanded money and rank. He had no interest in merely defecting. He wanted a commission as a general in the British Army and £20,000 to pay his debts and secure his future. This was not the treason of ideology, it was the treason of calculation.
The negotiations had begun long before. Through secret channels, Arnold sent letters to the British in New York, using intermediaries like Joseph Stansbury, a Loyalist merchant in Philadelphia. The correspondence was carried through Peggy’s connections, couched in codes and pseudonyms. Arnold signed as “Gustavus.” The British replied under the name “John Anderson,” which would become André’s alias. The letters were written in invisible ink, disguised as business correspondence, and smuggled through occupied lines. In these exchanges, Arnold pressed his terms, haggled over price, and dangled the prize of West Point like a merchant offering goods to a buyer. One letter from the British side even noted, “The advantages are of the highest importance, and Arnold’s discontents are such that he may be secured.”
By early September, the deal was close. Arnold had tightened his command over West Point, made subtle changes that weakened its readiness, and continued to press Clinton for assurances. André, Clinton’s trusted adjutant, was chosen to seal the agreement in person. It was a dangerous move, but Clinton trusted André’s skill and charm. Arnold insisted on a meeting to finalize matters and deliver the details directly. September 21 was chosen. André would come up the Hudson aboard the sloop of war Vulture. Arnold would arrange to meet him ashore in the dead of night, using a local intermediary named Joshua Hett Smith to provide cover.
Every step of this plan reeked of treachery, yet to Arnold it felt like business. He had convinced himself he was not betraying so much as correcting an injustice. America had mistreated him. Britain would treat him better. He was not turning his back on honor; he was reclaiming it. That was the story he told himself, and perhaps the story Peggy reinforced. But history does not remember what men tell themselves. It remembers what they do.
By the eve of September 21, 1780, all the pieces were in place. The Vulture waited on the river. André was prepared to risk everything for the mission. Smith had been recruited to ferry the officer ashore. And Arnold, commander of West Point, was ready to sell it. It is chilling to think how close it came to working. If not for a cannonade on the Hudson, if not for three militiamen near Tarrytown, the Revolution might have unraveled. But that night, September 21, the plan moved from ink and whispers to action, and Benedict Arnold stepped fully into the role that would define him forever.
The night of September 21, 1780, was dark along the Hudson. Autumn was creeping into the valley, the air sharp with the scent of falling leaves and the river carrying a chill. The British sloop of war Vulture sat anchored off Teller’s Point, her guns ready, her crew tense. Below decks, Major John André waited. He was a man of polish, an officer and a gentleman, not the sort of figure one expected to sneak about like a common spy. Yet this night he had agreed to do just that. His mission was to come ashore, meet Benedict Arnold, and close the deal that would hand West Point to the King’s forces.
Arnold had arranged the logistics through Joshua Hett Smith, a local with a Loyalist background who had been helpful to both sides at different times. Smith’s role was to provide plausible cover, to ferry André ashore, and to host the meeting at his house in Haverstraw. Smith could pass through American lines without raising much suspicion, and his house was conveniently located. To Arnold, Smith was a useful tool. To André, he was the gatekeeper to the most valuable intelligence Britain could hope for.
In the dead of night, with muffled oars to mask the sound, Smith and a pair of boatmen rowed to the Vulture. André was waiting on deck. One can imagine the officer stepping into the small boat, his fine uniform hidden beneath a dark cloak, the creak of wood and the dip of oars carrying him toward the shore. It was a perilous act. If the Americans caught him, he would be considered a spy, not a prisoner of war. The risk was clear, but the reward was greater: the fall of West Point and perhaps the end of the rebellion.
On the shore, Arnold was waiting. The two men greeted each other quietly, then withdrew to the Smith House, later remembered as the Treason House. Behind its walls, the fate of the Revolution was bartered like goods in a market. Arnold provided André with detailed plans: maps of the fortress, notes on its defenses, the placement of cannon and stores. He explained how he had thinned the garrison, scattered supplies, and made the post vulnerable. The information was damning, and André knew it. Arnold also provided him with a pass, written in his own hand, authorizing “John Anderson” to move through American lines. This would be André’s shield on his way back to British territory. Without it, his mission would be suicide.
For hours they spoke. Arnold laid out his conditions, reaffirmed the price, and offered reassurances. André listened, recorded, and gathered the documents that would make his general’s plan possible. It was treason in its purest form, a general entrusted with America’s most vital fortress selling it to the enemy. Yet within the walls of the Smith House, it felt like business. Arnold thought himself clever. André thought himself lucky. Both men believed they were on the brink of victory.
But the river had other ideas. At dawn, American cannon opened fire on the Vulture from the shore batteries at Teller’s Point. The gunners, alerted to the British sloop, raked the vessel with fire. Cannonballs splashed into the water and whistled over the decks, forcing the Vulture to pull anchor and drop downriver. When Arnold and André emerged from their clandestine meeting, they discovered that André could not return to the ship. His ride was gone. He was now stranded behind American lines with incriminating papers in his possession.
Arnold improvised. He insisted André shed his uniform and put on civilian clothes. To André’s horror, this sealed his fate. He had hoped to remain in his officer’s dress, which would grant him the rights of a prisoner of war if captured. Now, dressed as a civilian with forged papers and secret documents hidden in his boot, he was a spy by every definition. Arnold reassured him, handing him the pass that would allow him to slip through checkpoints and make his way to British territory on foot. The journey would be dangerous, but André trusted Arnold’s authority to see him through. It was a fatal miscalculation.
That morning, September 21 turned to September 22, and Major John André set out overland, papers in his boot, alias in hand, and fate closing in. Behind him, Arnold returned to West Point, outwardly the dutiful commander, inwardly the man who had just sold his country. The meeting at Haverstraw was over, but its consequences were only beginning.
Treason does not happen in a vacuum. Benedict Arnold may have been the prime mover, but around him were people whose presence, choices, and fates gave shape to the conspiracy. To tell the story of September 21, 1780, without them would be to miss the human texture of the plot. There was Peggy Shippen Arnold, the young wife whose charm and connections linked her husband to the Loyalist world. There was Joshua Hett Smith, the local figure who ferried the British officer ashore and lent his house to the night’s meeting. And there was Major John André himself, the man who carried Arnold’s betrayal in his boot and paid for it with his life.
Peggy Shippen was just twenty years old when she married Arnold in 1779. He was more than twice her age, wounded, proud, and desperate to prove himself. She was beautiful, from a wealthy Philadelphia family, and known for her wit and social grace. Before her marriage she had moved in circles that included British officers during the occupation of Philadelphia, and among them was John André. They had attended the same social events, traded polite correspondence, and likely admired each other. When Arnold married Peggy, he married into more than just youth and beauty. He married into a web of Loyalist connections that stretched across occupied New York and Philadelphia society. Peggy kept up those connections, and it is through her that Arnold found a willing channel to communicate with the British. Later, when the plot unraveled, Peggy would play her part to perfection. Confronted in her quarters at West Point, she flew into hysterics, screaming, weeping, and raving so convincingly that Washington himself was shaken. Some saw her as a manipulator, others as a victim, but no one denied that she played her role with dramatic flair.
Joshua Hett Smith was another figure in the drama. He was a landowner on the Hudson, a man of shifting loyalties who seemed always to know someone on both sides of the war. Smith had been sympathetic to the Loyalist cause, but he had also cooperated with American authorities when it suited him. To Arnold, Smith was useful. He could be trusted to row a boat in the night, to host a meeting, to provide cover without asking too many questions. On September 21, it was Smith’s boat, rowed by his hired hands, that carried André from the Vulture to the shore. It was Smith’s house, later dubbed the Treason House, where Arnold and André sat together for hours plotting the fall of West Point. Smith later claimed he did not know the true nature of the meeting, though his protestations were met with skepticism. When André was captured and the plot exposed, Smith was arrested, tried, and narrowly escaped execution. His role was ambiguous, but without him, Arnold and André could never have met that night.
Then there was André himself. He was no ordinary adjutant. Polished, educated, and artistic, he had risen quickly in the British Army, becoming General Clinton’s trusted aide. He was admired even by his enemies for his charm and manners. In another world, he might have been remembered as a poet or a painter rather than as a spy. On the night of September 21, he was thrust into a role that he accepted with reluctance. “It was impossible to avoid it,” he later wrote, when accused of donning civilian clothes and disguises. He insisted he had not volunteered but had been trapped by circumstances. That may be true, but the fact remains that André stepped into the boat, accepted Arnold’s papers, and carried away the maps. He may not have wanted the role of spy, but he played it. The tragedy is that while Arnold escaped, André would hang for it.
Together, these three figures remind us that Arnold’s treason was more than a personal act. Peggy’s influence and connections helped open the door. Smith’s cooperation made the meeting possible. André’s presence gave the plan its deadly seriousness, for he was not just a messenger but the living embodiment of British interest in Arnold’s betrayal. When the plot collapsed, each of them paid a price in their own way. Peggy lived under suspicion, her reputation forever stained. Smith lived in exile, his name linked to treachery. And André swung from a gallows, his gallantry praised even as the rope choked him.
Arnold may be remembered as the traitor, but the story of September 21 is richer when we see the cast around him. Treason, like history, is never the act of one man alone. It ripples outward, pulling in family, neighbors, allies, and enemies, until the whole world seems to be caught up in its consequences. On the banks of the Hudson that night, four lives were bound together in conspiracy, and all of them would be changed forever.
Two days after that fateful meeting, the conspiracy began to collapse. Major John André, carrying the maps of West Point and Arnold’s signed pass, set out on September 22 to make his way back toward British lines. He must have felt uneasy. The Vulture had been driven off by American cannon fire, and what had begun as a covert exchange with a swift return to safety had turned into a perilous overland journey. Dressed in civilian clothes, papers hidden in his boot, and armed only with Arnold’s pass for “John Anderson,” André was a British officer forced to play the part of a spy.
At first, his luck held. He passed checkpoints, answered questions, and carried on southward toward New York. But on the morning of September 23, near Tarrytown, fate intervened. Three American militiamen — John Paulding, Isaac Van Wart, and David Williams — stopped him on the road. They were rough country men, not Continental regulars, and André must have thought he could bluff his way past them. He showed them Arnold’s pass and claimed he was traveling on business. But the militiamen were not convinced. Paulding, who had recently escaped from British captivity, wore a Hessian coat. Seeing it, André let slip his guard and asked if they were from the British side. That single mistake aroused suspicion. The men searched him and found nothing at first. Then they insisted he remove his boots. Hidden inside were the incriminating documents — maps of West Point, notes in Arnold’s hand, and the damning evidence of a traitor’s bargain.
With that discovery, André’s fate was sealed. The militiamen ignored his offers of gold and rewards, choosing instead to deliver him to American authorities. They may not have known at that moment the true scale of what they had uncovered, but they understood enough. Here was a man traveling in disguise with secret papers that pointed to treason at the highest level. Their decision to hold him, rather than take the bribe, preserved West Point and perhaps the Revolution itself.
André was brought before Colonel John Jameson, who commanded in the area. At first Jameson hesitated. The pass bore Arnold’s signature, after all. Unsure, he actually sent word to Arnold, along with a note that André had been detained. That moment of hesitation nearly cost everything. Had Washington not been en route to West Point at that very time, Arnold might have had the chance to cover his tracks. Instead, when Jameson’s messenger reached him, Arnold realized instantly that the plot was exposed. He fled without hesitation. Leaving Peggy behind, he bolted for the river, leapt into a waiting boat, and ordered the oarsmen to row him down to the Vulture. He bribed and threatened them until they complied. Before Washington arrived, Arnold was gone, safe under British protection.
Back at West Point, the scene was chaos. Washington rode in expecting to inspect the defenses. Instead, he found his trusted general missing and evidence of betrayal spilling out before him. In his papers, Washington recorded his shock and grief. He had relied on Arnold, despite whispers and accusations, and now he saw that trust had been misplaced. It was a near disaster. Had the plot succeeded, Washington himself might have walked into a British trap at West Point that very day. Instead, he was left staring at the ruins of trust, wondering how close he had come to disaster.
André, meanwhile, was not so fortunate. Taken under guard to Tappan, he was interrogated, tried, and condemned. The evidence was overwhelming. He had been captured in civilian disguise with papers concealed in his boot. Arnold’s pass made it clear that he had conspired with the commander of West Point. The board of officers, which included figures like Nathanael Greene and Marquis de Lafayette, found him guilty as a spy. André faced his fate with dignity. He requested a firing squad, the death of a soldier, but Washington could not grant it. To spare André would be to dishonor the law of war itself. On October 2, 1780, John André was hanged. Witnesses said he mounted the gallows with calm composure, declaring, “I meet my fate like a brave man.”
The contrast was stark. André faced death with courage and won sympathy even from his enemies. Arnold, safe in British lines, lived on but was despised. He was granted a commission as a brigadier general in the British Army and given his promised reward, but he was never fully trusted by his new masters. To them, as to his former comrades, he was a traitor. He had fled dishonor, only to live in it.
For Washington and the American cause, the aftermath was sobering. They had nearly lost their most important fortress. Their enemy had nearly scored a decisive blow. Yet the conspiracy’s failure rallied spirits. If Arnold’s treason had succeeded, the war might have ended. Because it failed, the Revolution endured. Arnold’s name would live in infamy, André’s in tragic honor, and Washington’s in lasting resolve.
The story of September 21, 1780, did not end with André’s noose or Arnold’s flight to the British. Its legacy stretched far beyond the banks of the Hudson. That night, in the Smith House at Haverstraw, the Revolution had faced its most dangerous moment of betrayal. The details may fade in the retelling, but the meaning has endured. Arnold’s name is still spoken as the very definition of treachery. André is remembered with sympathy, almost as a tragic victim of circumstance. Washington emerged shaken but resolute. And the Revolution, which might have died in a single stroke, survived to fight on.
For Americans of the time, Arnold’s treason was a gut punch. He had been their hero, the man who rode into battle at Saratoga and turned despair into victory. His bravery had been beyond question, his sacrifices real. To see such a man turn traitor was not only shocking, it was personal. Ordinary soldiers felt it like a betrayal in the family. Washington, who had trusted him, who had defended him against critics, was left shaken. Lafayette wrote of his sorrow that “the most enterprising man of the American army has turned traitor.” The sheer weight of Arnold’s name made the betrayal heavier. Had it been some minor officer, history would have noted it and moved on. But Arnold had been the best of them. His fall was a reminder that no one was beyond suspicion, and that pride and ambition could undo even the most brilliant reputations.
André’s fate offered a counterpoint. Where Arnold was despised, André was pitied. He had charm, wit, and grace, and even in captivity he bore himself like a gentleman. The officers who condemned him to die did so with heavy hearts, and Washington himself is said to have grieved that duty required such an end. André became a symbol of tragic gallantry, a man caught in a web of circumstance, who died with dignity for a cause not his own. To this day his story is remembered with more compassion than Arnold’s, even though both men had been engaged in the same treachery. André’s gallows became a place of mourning. Arnold’s escape became a wound that never healed.
As for Arnold himself, he lived another two decades, but never escaped the shadow of his betrayal. The British gave him money and a commission, but they never gave him trust. To them he was useful, but he was also a man who had sold out his own comrades, and no officer could entirely respect that. In London, Arnold was heckled on the streets. In Canada, where he tried to reestablish a mercantile life, he found himself despised by Loyalists and Patriots alike. He fought lawsuits, argued with partners, and lived out his days in bitterness. He died in 1801, a man of fame but not of honor. His body lies in a London churchyard, far from the land he once fought to free, then tried to betray.
The legacy of September 21 lives on not just in Arnold’s name, but in the way Americans remember treason itself. To call someone a “Benedict Arnold” is to call them the worst of traitors. The phrase has outlived centuries, carried down from schoolrooms to political speeches. It has a sting because it is personal. Treason is not just betrayal of a nation. It is betrayal of trust. Arnold had been trusted, loved, and admired. When he turned, the sense of betrayal cut deeper than if he had never been a hero at all.
Yet the night also gave Americans a reason to rally. If Arnold’s treason had succeeded, the war might have ended. Instead, it failed. West Point remained in American hands. Washington was spared from walking into a trap. The Revolution carried on, its soldiers reminded that vigilance mattered, that loyalty could never be assumed, that freedom required both courage and sacrifice. In a strange way, Arnold’s betrayal strengthened the cause it had nearly destroyed.
In Haverstraw today, the Treason House is gone, but the ground where it stood is marked. In Tarrytown, a monument honors the three militiamen who captured André, celebrating their refusal of a bribe and their loyalty to the cause. In Westminster Abbey, a plaque honors John André, erected by a grieving Britain that saw him as a victim of duty. But no statue honors Arnold. His name appears on plaques at Saratoga and West Point only because it cannot be erased from the record of those battles. In each case it is recorded without rank, a blank space where his name would have stood among heroes. That blank space may be the most fitting memorial of all. It is the mark of a man whose ambition consumed his honor.
Looking back across the centuries, September 21, 1780, stands as one of the great “what ifs” of American history. What if André had not been stopped at Tarrytown? What if Arnold’s plan had worked? The Revolution might have collapsed, and the United States might never have been born. But history is not made of what ifs. It is made of choices, and on that night Arnold made his. He chose gold over honor, resentment over loyalty, ambition over country. The choice carried him into infamy, and it carried André to the gallows. It very nearly carried Washington and the Revolution to destruction. That it did not is one of those miracles of history, where the decision of three militiamen and the well-aimed fire of a cannon saved a nation from ruin.
The lesson lingers still. Trust is fragile. Pride is dangerous. And betrayal, once made, cannot be undone. Benedict Arnold remains the eternal reminder of what happens when a man turns his back on the cause he once claimed to serve. On September 21, 1780, he crossed that line. He never came back.
DAVE DOES HISTORY 
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