America’s First Villian: Benedict Arnold

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Benedict Arnold was a ship merchant when the Revolutionary War began in 1775. He joined the growing army outside Boston and distinguished himself through acts of intelligence and bravery. Some of Arnold’s military accomplishments include the capture of Fort Ticonderoga, the battle of Ridgefield, the siege of Fort Stanwix and actions during the battle of Saratoga. In the last battle, Arnold suffered leg injuries that halted his combat career for several years. Because of Arnold’s military accomplishments, he was promoted to the position of Major General.

In June of 1178, the British withdrew occupation of Philadelphia, and General George Washington appointed Arnold military commander of the city. As soon as Arnold got this power, he began to capitalize financially on it. Arnold was less than qualified for this position and frankly over his head, but he was close with General Washington and thus got vital appointments.

Arnold lived lavishly in Philadelphia and was prominent on the social scene. Arnold met Peggy Shippen, who was the daughter of a British loyalist who still did business with the British as the war was going on. Before being courted by Arnold, Peggy was courted by British Major John Andre during the British occupation of Philadelphia. Arnold and Peggy married on April 8, 1779. Peggy and her friends had found methods of staying in contact with past British lovers across the battle lines despite military bans on such communication.

Arnold had an extraordinarily ambitious and jealous personality. He was also greedy and a spendthrift and was heavily in debt to London financiers. Arnold was distrusted and disliked by military officials on both sides of the war. General Washington was one of the few people who genuinely liked Arnold, but Arnold thought Washington had betrayed him, Because of politics and Arnold’s personality, he was passed over for higher military positions numerous times.

Why did Arnold think Washington betrayed him? Well while Arnold was in charge of Philly, he was accused by Philly officials of using his authority to make a profit, which he totally was and was court marshaled for it. General Washington gave him the lightest of reprimand, which was a letter written by Washington debunking Arnold’s actions. Because of this, Arnold thought Washington betrayed him. Arnold was quite the sensitive fellow, right?

John Andre, while also being a Major in the British army, was also head of the British espionage system. Because of his relationship with Peggy, he encouraged her to get Arnold to give vital info to the British. Peggy egged on Arnold and also collaborated in his treason. Peggy was mainly a courier passing along letters from Arnold to Andre, who was in New York City.

An essential fact to remember is that Arnold was giving information to the British before his Court Marshall hearing! These Arnolds ain’t loyal, ill tell you. By July of 1779, Arnold was supplying the British with troop locations and strengths as well as passing on the site of supply depots. Arnold wasn’t doing all of this for free of course. Arnold was negotiating a compensation package for himself for all his excellent intel. Arnold first offer was $ 10,000 and indemnification of his losses.

Phillip Schuyler, a General with the Continental army, approached Arnold about giving him command of West Point. West Point was a strategic Military base along the Hudson River Valley. The British were very keen on having control of Westpoint. Arnold seeing a chance to negotiate for more money, now asked for $ 20,000 and indemnification of his losses. In exchange, Arnold was supposed to give up the total surrender of Westpoint. Arnold took control of Westpoint and also reached an agreement with the British for $ 20,000. (straight cash homie) Arnold immediately began weakening Westpoint’s defense and military strength. Arnold and Andre met in September of that year, where Arnold handed Andre Plans to take over West Point. On Andres trip back to NYC, his ship was attacked, and he was forced to get back to NYC on land. While Andre was making his way to NYC, he was caught by continental army militiamen, and the papers between him and Arnold were discovered.

Arnold was set to have breakfast with General Washington when he got word that Andre was captured, more importantly, he also found out that his correspondence with Andre was captured too. Arnold immediately left and fled to NYC. Arnold wrote a letter to Washington asking for him to give safe passage to Peggy to go to her family in Philly, Washington obliged. (unaware of Peggy’s actions in the treason). Washington offered a trade to the British. Washington would give Andre back to the British in exchange for Arnold, (and a 1780 first round draft pick j/k). General Clinton, who was in charge of the British military operations in America, refused the offer ( the first round pick was too rich for his blood ) and Andre was hanged by the Continental Army. Washington then sent men into NYC to try to capture Arnold, but he was able to escape to Virginia. Arnold officially switched sides and was now a Brigadier General in the British Army. The British only paid him $ 6,315, and a pension because well, Arnold’s plan failed. Arnold led a British army into a few battles with the continental and has some success, but his new side never fully trusted him because well he was just fighting for the other side a few months ago.

Arnold was never given an important military command with the British. Arnold eventually moved his family to London, where he found no job and a mixture of contempt and admiration. Arnold then moved his family to Canada where he reentered the shipping business, Arnold was even more disliked in Canada than London, and he had to return to London. When the war between France and England started (again!), Arnold tried to reenter Military service, he was rebuffed. Arnolds shipping ventures eventually failed, and he died in 1801, virtually unknown.

Mistakes Were Made:

The name Benedict Arnold lives in infamy in American History as synonymous with the word “traitor.” Benedict’s name was even dropped in Ice Cube’s diss record to N.W.A “No Vaseline.” Some Historians say Arnold simply married wrong and that’s what led to his betrayal of his country. Though Peggy did play a part in Arnold becoming a traitor, I think it was more a perfect storm of events i.e., Arnold being passed over for promotion, Arnold severely injuring his leg in battle, Arnold’s ambition and wanting to live the good life, his enormous debt to the British, all of that led to his becoming a traitor.

The saying, “You can’t have your cake and eat it too,” perfectly sums up Arnold’s situation. Arnold, being disgruntled, instead of just quitting and leaving the Continental Army, tried to play both sides and unsurprisingly got caught. Arnold didn’t or couldn’t foresee that going to the British, though probably his only option at the time, limited his future actions. The British never fully accepted him, and he was held in contempt by a lot of folks. Arnold could never go back to his home country and died as a nobody, far from the grand ambitions Arnold had when he was a general in the Continental Army. Who knows if Arnold had stayed, we might be talking about him as one of the founding fathers, a member of Washington’s cabinet, hell even a famous Broadway play may be named after him. Instead, I’m writing about Arnold as America’s first villain, principally because he was focused on the short term issue of a money grab and couldn’t foresee how his actions would destroy him and his families legacy. Arnold wanted his cake and eat it too, and mainly got neither.

Originally published at on July 7, 2019.

recovering Lawyer, History buff who wants to share my knowledge with the world . To teach them lessons from our past. see all of the stories on

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