A Ruined Legacy
If there was ever a man whose actions forever outweighed everything else about him, it was Benedict Arnold. During the American Revolution, he quickly became indispensable and had everything he could possibly need. However, he couldn’t stop hustling and eventually threw it all away. Many historians have deliberated over what complex motives were at the root of his betrayal—but the truth may be a lot simpler.
1. He Was A Survivor
No matter who Benedict Arnold fought for, the motivation driving most of his decisions was self-interest. Above any allegiance or moral obligation was whatever action served him the most, as he was a survivor primarily—even from the beginning. Born on January 14, 1741, in Norwich, Connecticut, he and his sister were the only ones of his parents' six children to reach adulthood, since the rest of his siblings tragically perished from yellow fever early on.
Naturally, the immense loss changed things forever.
2. His Father Was Devastated
Benedict’s father had run a thriving business, which allowed him and his family to live a prosperous lifestyle, but not for long. With the loss of most of their children, Benedict’s parents were never the same. His father turned to drinking, and it quickly drained the majority of their wealth.
And while his mother was forever nursing a broken heart, she knew she had to step up for her two surviving children.
3. His Mother Made A Call
The family’s diminishing funds meant that Benedict didn’t have many opportunities that his parents had hoped for him, including a formal schooling. Not to mention that his father’s condition kept Benedict from training in the family business. Instead, his mother, Hannah Arnold, was able to get him an apprenticeship with her cousins at their apothecary.
But the apothecary business lacked excitement—and Benedict was craving action.
4. His Opportunity Arrived
During the conflict between Great Britain and France beginning in 1755, Benedict felt drawn to serving in the army, choosing to enlist in the Connecticut provincial militia. Although his mother refused to let him do so that year, he turned 16 two years later and went against his mother’s initial wishes, joining the militia.
This time, though, his mother would have nothing to worry about.
5. He Didn’t Serve For Long
As soon as Benedict signed up with the militia, he was swept off to Lake George in New York to defend Fort William Henry from France. However, news spread that the French had overtaken the Fort in a devastating loss for the British, resulting in Benedict’s dismissal—limiting his early time in the service to just 13 days.
Unfortunately, his return home brought more tragedy.
6. He Lost His Parents
With Benedict’s father slowly declining in his alcoholism, he only had his mother to rely on, and so the two became extremely close. Tragically, though, she would pass in 1759 and leave Benedict with a broken heart. Having already lost his children, Benedict’s father’s condition worsened, and he also perished shortly after, in 1761.
After losing most of his family, Benedict threw himself into work.
7. He Made A Name For Himself
Benedict's apprenticeship with his relatives proved fruitful, as they continued to help his business endeavors. By 1762, he had set up shop in New Haven, Connecticut, selling books and continuing the apothecary trade. He was so successful that he was able to repay his relatives for their aid within the year. That same year, he bought back his old family homestead and flipped it for a profit. He was living the American Dream before America existed.
But as the world changed, he changed with it—and things were about to take a dark turn.
8. He Sympathized With Them
By this point, several significant changes by the British government had caused those in the colonies to steadily reach the point of rebellion, and Benedict was no different. As a businessman, things like the 1765 Stamp Act radicalized him enough to protest against British taxation by joining the Sons of Liberty.
His membership introduced him to a lot of important people—one, perhaps, more important than anyone else.
9. He Fell In Love
As numerous influential men—or those looking to be influential men—did, Benedict joined the local Masonic lodge, where he became familiar with New Haven’s Sheriff Samuel Mansfield. At the same time, he grew closer to Mansfield’s daughter, Margaret, and the two married on February 22, 1767, going on to have three sons in quick succession.
However, they wouldn’t see much of him.
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10. He Led His Company
Having technically served in the Connecticut militia, the American Revolution brought Benedict a new opportunity, as he was quickly elected to the rank of Captain in 1775. Shortly after the Battles of Lexington and Concord, which kicked off the conflict, he and his company left Connecticut to aid the army in the Siege of Boston.
Riding high on success, Benedict wanted more.
11. He Had An Idea
Benedict kept his eye on the prize and constantly strived to rise through the ranks, usually through the glory of battle. Upon learning of Fort Ticonderoga’s poor defenses, he proposed its seizure to the Massachusetts Committee of Safety. Taking a chance on Benedict, they commissioned him as a colonel and tasked him with claiming the Fort.
Suddenly, his absence from home took a larger toll.
12. He Won...And Lost
Riding off to upstate New York, Benedict reached Fort Ticonderoga in time to lead his men to victory—but this sadly came at a severe personal cost. While he enjoyed the American win and stayed at the Fort for a time after, his wife Margaret unexpectedly passed on June 19, 1775. Word of this didn’t get to him until he was on his way back to Connecticut.
Although his grief had been overpowering, he had no choice but to quickly return to action.
13. He Proposed Another Idea
At another of Benedict’s suggestions, the Second Continental Congress greenlit an invasion of Quebec. However, he became disappointed when they gave General Montgomery command of the expedition instead of him. Undeterred, he approached George Washington himself and proposed a second expedition against Quebec through the wilderness.
Benedict got his wish—but the journey wasn’t easy.
14. He Lost Most Of His Men Before He Even Arrived
Benedict, now a colonel in the Continental Army, took a force of 1,100 men to Quebec—on his planned route through the wilderness. Unfortunately, the hostile conditions caused 300 of his men to turn back, and 200 to perish. When he finally made it to his destination, he arrived without cannons, facing a fortified city garrisoned by hundreds of British regulars and local militia. It was an absolute disaster.
Even Benedict didn’t come out unscathed.
15. He Was Injured
When Benedict and his remaining men arrived at Quebec City they joined with General Montgomery. Together, they launched an attack on December 31—but it did not go to plan. Hundreds of men were either killed or taken prisoner, resulting in a major defeat for the Continental Army. During the battle, Montgomery perished, and Benedict sustained an injury that shattered his leg.
But his initiative and sacrifice did not go unnoticed.
16. He Was Promoted
Although Benedict was severely injured and faced a siege in which defeat became only more inevitable, he had maintained command until a replacement arrived and took over. Following the failed battle, the higher-ups honored his efforts and granted him the rank of brigadier general.
With this promotion, Benedict cultivated some key connections—and his thirst for power grew stronger.
17. He Made Powerful Friends
In his attempts to gain command and prove himself, Benedict had already rubbed shoulders with some of the Revolution's most prominent leaders. However, as a brigadier general, he received more responsibility and formed strong friendships with several generals such as Horatio Gates, Philip Schuyler, and—most impressive of all—George Washington.
Still, bitterness eventually crept in.
18. They Skipped Him
By 1777, Benedict had accomplished so much and made such a widespread name for himself that he believed he was due for another promotion. However, that year, he discovered that Congress had chosen someone else to promote to the rank of major general. This wasn't the first time he had been passed over. Benedict was so upset he penned his resignation, but Washington refused it.
This just made him all the more desperate to prove himself.
19. He Sprang Into Action
Benedict believed he deserved a promotion and traveled to Philadelphia to fight for it, but on the way, he heard that the British were attempting to take a supply depot in Danbury. Wasting no time, he gathered a militia with a couple of other generals and met the British in battle, during which his leg became injured again.
Finally, he got what he wanted—or so he thought.
20. It Was Bittersweet
To Congress, Benedict's actions in Danbury were valiant enough to earn him the rank of major general, but Benedict didn’t accept his promotion happily. Although it was initially what he wanted, Congress hadn’t reinstated his seniority over the officers promoted before him. This was the second time he tried to resign, with Washington refusing it again.
This bitterness quickly turned into insubordination.
21. He Didn’t Listen
During the two Battles of Saratoga in 1777, Benedict’s bitterness and hostility began to show more, so much so that General Gates had removed him from command for his defiance. Benedict ignored this, however, and led his men during the second battle, once again getting injured in the same leg as both previous wounds.
This time though, his injuries had serious consequences.
22. He Fell Short
The fact that Benedict injured his left leg multiple times meant that he now had to undergo risky surgery, resulting in several months of recovery. Refusing amputation, Benedict had his leg crudely set instead, resulting in his left leg being two inches shorter than his right leg—plaguing him with pain for the rest of his life.
Even after this, he didn’t let go of his grudge.
23. He Felt Insulted
Benedict disobeyed Gates’ orders during Saratoga, but in doing so, his leadership became an integral stepping stone to an American victory that day. To commemorate this, Congress mended his previous grievance and restored his command superiority, like he wanted. At the same time, he participated in the first recorded oath of allegiance—as a sign of loyalty to the United States.
Unfortunately, Benedict believed they only did this because they pitied his injury, so he remained bitter. Soon, though, he received more than a promotion.
24. He Started Scheming
In 1778, Benedict received a special appointment in response to Britain’s departure from Philadelphia. Washington made him the commander of the wealthy city—which would turn out to be “one of the worst decisions” of Washington’s career, according to historians. Benedict saw this opportunity as much more than a matter of duty and honor, though. Immediately, he started thinking up ways to make money in this position through offering protection and profiting off of army supplies.
His new job title did more than earn him money, though.
25. He Met Someone
As a result of his financial schemes and power in Philadelphia, Benedict enjoyed a lavish lifestyle and became acquainted with many of the city’s most affluent residents. One of these was 18-year-old Peggy Shippen, a judge’s daughter—who came from a family of Loyalist sympathizers. After a year-long courtship, the two married on April 8, 1779.
Still, a deep anger had rooted itself in him.
26. He Became Resentful
Benedict had lost his business years before, and since then, had been seriously injured and passed over for promotion several times. Not to mention his financial scheming in Philadelphia caught him a few corruption charges. Over time, in service of the Revolution, the chip on his shoulder only grew larger.
With this much disdain, he became the perfect target.
27. His Wife Was Connected
Benedict's wife Peggy had a group of friends who found methods of staying in contact with love interests and friends across the battle lines, despite military bans on communication with the enemy. Benedict was already a rule-breaker, and now he realized his wife was too.
It didn't take long for him to make further connections.
28. They Started Talking
By 1779, Peggy was no longer the only Loyalist sympathizer in his life, and the idea of secretly aiding the British had become much more appealing. Soon enough, through letters written in code and invisible ink, Benedict began corresponding with the British spy chief, John André, often using Peggy and her circle of women as messengers.
Then, he went even further.
29. He Told Them Everything
Within the next few months, Benedict's messages to André and subsequently, the British general, Sir Henry Clinton, would include more and more American information. He relayed sensitive details about the army, such as locations and assessments, all while negotiating how much the British could pay him in exchange.
Suddenly, things became more precarious.
30. They Were In Danger
Although Benedict’s correspondence with the British remained unknown, the similar political allegiances of his wife and her family still put them at risk. This only became more of an issue later that year, as mobs of revolutionaries rampaged through Philadelphia, hoping to root out any Loyalists.
This didn’t scare him away, however.
31. He Called Them Up
In 1780, Benedict finally had the chance for a position of greater command and responsibility, as General Schuyler considered giving him command of the West Point army post. He quickly realized that he could use this opportunity to gain further reward from the British. So, he wrote to General Clinton, telling him of the offer.
As soon as the decision was final, Benedict contacted Clinton once more—this time, with a disturbing deal in mind.
32. They Gave Him Command
That summer Benedict received command of West Point—with full intention of using it in service of the British. In his last conversation with General Clinton, Benedict offered to surrender West Point to them, depending on what he may receive in return. Seeing this new advantage, Clinton then responded to Benedict with an offer of £20,000.
However, there was one major setback.
33. There Was A Miscommunication
Benedict had named the £20,000 price himself, but he also requested compensation for his previous losses, to which General Clinton refused. Even so, Benedict accepted the general’s final offer, but delivering messages across the line had become so much more difficult that neither he nor Clinton knew the deal was finalized until a couple of weeks later.
Meanwhile, Benedict did everything he could to fail at his job.
34. He Sabotaged Them
If Benedict’s men at West Point didn’t suspect him of treachery, they likely thought he was just a horrible commander. Between ignoring necessary repairs and incompetently spreading out his forces, he would intentionally diminish their supplies, leading his men to believe he was selling them on the black market—which he likely would have no problem with.
At least they weren't onto his real plan—not yet, anyway.
35. He Lost His Ride
Benedict and André had largely been communicating through coded messages, but at last, they spoke face-to-face on September 21. When they finished, André intended to board the HMS Vulture back to New York, but the ship became damaged in an attack and had to leave early. With little alternative, Benedict issued passes for André to travel back by land.
And while this was a grave mistake in itself, Benedict gave André something that unintentionally sealed his devastating fate.
36. He Was Captured
No matter what precautions André made, crossing the line had become much more dangerous—a fact he learned as American militiamen captured him on September 23. He likely tried to talk his way out of this, but no negotiating in the world could have saved him once the men searched him and found papers containing the detailed British plans, including the surrender of West Point.
Before Benedict could do anything about it, the whole situation spiraled out of control.
37. He Panicked
The next day, Benedict received word of André's capture, and naturally, he began to panic. Still, he couldn’t show it, as he was about to have breakfast with Washington—who hadn’t arrived yet. However, a message from Colonel John Jameson appeared, informing Benedict that the documents taken from André were currently on their way to Washington.
Benedict panicked, and did what he thought was best.
38. He Fled
Realizing that he had been found out and couldn’t remain at his headquarters any longer—and with his breakfast plans now cancelled—Benedict chose to flee. He immediately ordered his bargemen to take him downriver to the anchored HMS Vulture, where he found passage to New York and safety among the British.
Most who knew him felt shocked, to say the least.
39. They Were Dumbfounded
In his career up till this point, Benedict had become a close ally to many revolutionary leaders, all of whom were in disbelief once Washington learned of the plot. Although Washington is quoted as saying, “Arnold has betrayed me. Whom can we trust now?” he allegedly remained calm amid his distressed staff.
Still, Benedict tried to justify himself.
40. He Made Excuses
From his relative safety on the British side of the line, Benedict then saw fit to speak up for himself and explain his situation. In an open letter, To the Inhabitants of America, he excused his actions as a response to a perceived corruption in Congress, a belief that America should give up the conflict, and his rejection of the Declaration of Independence.
Now with the British, he found himself unexpectedly disappointed.
41. He Received Less
Benedict had officially committed treason and become a turncoat, for which the British rewarded him by commissioning him as a brigadier general. However, this wasn’t exactly what he had asked for, and the promised £20,000 never came. His plan to surrender West Point hadn’t worked, so instead, the British gave him £6,315 and an annual £360 pension.
Although disappointed, he continued down the path he had started.
42. He Spread Chaos
One of Benedict’s first acts as a British brigadier general was the Raid on Richmond, in which he captured the city with an army of 1,600 men. He didn’t seem content with just this capture, however, as he and his men surged through Virginia, pillaging and destroying anything they wanted to.
Meanwhile, America was hunting him.
43. They Were Out For Blood
If the treasonous plan hadn’t been enough, Washington lost any feelings of mercy once Benedict published his open letter. Enlisting one of his key players, the Marquis de Lafayette, Washington ordered him to hunt down Benedict and hang him for his actions. This order lasted even beyond the end of the Revolution.
As usual, Benedict had only one option: run.
44. He Asked To Leave
By late 1781, the Revolution wasn’t looking good for the British, and Benedict knew he didn’t want to stay in the colonies. Having unsuccessfully asked once before for permission to go to England, Benedict asked General Clinton once again following the decisive surrender of Britain’s General Cornwallis. This time, Clinton said yes.
So, Benedict said goodbye to America—not realizing what he was about to walk into.
45. He Left America For Good
Despite Washington’s newfound disdain for Benedict, the general had ensured safe passage for the turncoat’s wife, Peggy. She had given birth to their second child earlier that year, so Benedict, his wife, and their children departed for England on December 8, 1781, once he received General Clinton’s authorization.
However, he didn’t exactly live the life of a hero.
46. They Didn’t Trust Him
Britain had certainly rewarded Benedict for defecting, but he was quick to learn that most in England were wary of him at best, and at worst, criticized his dishonor. As such, his numerous applications to accompany the British army or serve in the British government were always rejected.
As for his life outside the army, he returned to his usual business practices.
47. He Made Poor Decisions
Being denied any opportunity with the army, government, or even the British East India Company, Benedict and his family survived on his diminished pay. To make up for it, he returned to his roots as a merchant, but it didn’t take long for others to label him a cheat. To make matters worse, he wasn’t a stranger to filing lawsuits over some of the most trivial issues.
The British were just as quick to turn on him as his former allies.
48. They Burned Him
In 1787, the family moved to New Brunswick after Benedict escaped a lawsuit, but he wasted no time in creating new problems. Upsetting the townsfolk with his usual antics, it all culminated when he won a slander suit against a former business partner. This prompted the other citizens to burn an effigy of him in his front yard while his young family watched, causing them to return to London.
It wouldn’t be long before his story came to an end.
49. He Became Sickly
As time passed into the 1800s, Benedict's health declined further, and limited much of what he was able to do. His thrice-wounded leg constantly ached, while his other leg had suffered from gout since 1775. Eventually, his doctors diagnosed him with edema and ordered him to take some time in the countryside, where he passed on June 14, 1801.
Despite his attitude, there’s a chance he regretted his actions.
50. He May Have Felt Remorse
During the Revolution, Benedict seemed to stand behind his treasonous decision, but he might have thought differently at the end of his life—or at least, according to legend. As the story goes, Benedict lay on his deathbed and stated a desire to perish in his old uniform before uttering, “May God forgive me for ever having put on another”.
Unfortunately for him, even after his passing, he still received one last dishonor.
51. They Moved Him
Benedict Arnold’s wife and children certainly mourned his passing, and they buried him in Battersea at St Mary's Church, but any respect left for him was eventually lost. In fact, around a century later, the church was making some renovations and—due to a clerical error—accidentally relocated his remains to an unmarked mass grave.
As to why he decided to turn traitor, some are still unsure, but one theory seems more popular than the rest.
52. She Might Have Been Behind It
In life, Benedict gave many reasons why he betrayed his country in his open letter to the American public. However, historians continue to debate as to what mix of circumstances pushed him over the edge into treason. While simple resentment and ambition may be the ultimate causes, many have accepted that it all came down to his Loyalist wife, Peggy. As historian W D Wetherell put it, Benedict simply “married the wrong person”.
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