Benedict Arnold: Connecticut's Traitor
A Hidden in the Oak
*This article was originally published by Yankee Institute.
Time heals all wounds — except for New Londoners. Then again, their grievance is understandable.
Since Sept. 6, 2013, Flock Theatre, a theater company, has organized the annual “Burning of Benedict Arnold” festival, in which hundreds of participants parade down Bank Street, accompanied by a fife and drum corps, and merrily burn an effigy of the infamous American traitor on the city’s waterfront. The festival has gained international attention and is a day of “theatrical catharsis.”
Ironically, the (mostly) light-hearted affair commemorates a tragic chapter in the Revolutionary War, when British troops led by Arnold — once a Major General in the Continental Army — raided and razed New London. The siege, on Sept. 6, 1781, destroyed “more than 140 homes, shops, warehouses, and other buildings,” according to Connecticut History.
This is not lost on festival organizers, as a play recounts the horror inflicted on 18th century New Londoners. Indeed, Arnold’s effigy burning is not new, but a resurrected tradition that lasted until the American Civil War. One of the earliest dramatizations occurred on Sept. 30, 1780, five days after Arnold defected to the British, when Philadelphians paraded a “two-faced Benedict Arnold with the Devil shaking money in his ear,” Connecticut History notes.
Yet Arnold’s military derring-do for the independence cause, prior to his betrayal, cannot be understated. Along with Ethan Allen’s Green Mountain Boys, Arnold and his men captured Fort Ticonderoga in May 1775, securing not only an “important cache of artillery,” but also the Americans’ first offensive victory. Two years later, he was lauded as a hero for defeating the British during the Battle of Saratoga, which convinced France to support the Americans in the war. This alliance proved vital in Britain’s eventual defeat and surrender at Yorktown in October 1781.
Arnold risked life and limb for America. In fact, his actions inspired his countrymen to continue fighting at pivotal junctures, when despair gripped Congress and the Continental Army. As Ron Chernow in Washington: A Life explains, Arnold was “an officer who was dedicated root and branch to the cause and who acted courageously on his own initiative.”
So why did he betray the Revolutionary cause? After all, this is the same man who, despite reeling from Congress passing him over for military promotions, “girded on his sword and galloped toward the scene of the action” when British soldiers landed in his home-state Connecticut in April 1777, according to God Save Benedict Arnold: The True Story of America's Most Hated Man by Jack Kelly. Three years later, however, he ordered New London’s burning.
Today, Benedict Arnold’s name is synonymous with betrayal. This is the story of how Connecticut’s son turned into one of America’s greatest villains.
‘Are All Americans Asleep?’
Benedict Arnold was born in Norwich, Conn., on Jan. 14, 1741, into a prominent, respected family, descended from “the Rhode Island equivalent of royalty.” One of his ancestors — also named Benedict — served as the colony’s first governor in the mid-to-late 17th century, according to Smithsonian Magazine.
Yet tragedy, both circumstantial and self-inflicted, ravaged the family. Many of Arnold’s siblings did not survive into adulthood due to yellow fever, “calamitous events that triggered alcoholism in his father,” according to Mount Vernon. The alcoholism worsened the Arnolds’ financial situation, as his “drinking led to bankruptcy when Benedict was fourteen” which proved to be a “traumatic event that overshadowed his childhood,” Chernow notes. To help with family expenses, the young Arnold was apprenticed to work for a relative who was a pharmacist. At 18 years old, as if the family did not witness enough hardship, his mother passed away.
Early biographies depict Arnold as a “nasty little boy” and a “traitor from the cradle,” but Kelly notes these descriptions, spread after he betrayed his country, are akin to the apocryphal fable of George Washington chopping down a cherry tree. He certainly was mischievous and intelligent, attending Yale before the financial misfortunes. But the early hardships and his family’s financial setbacks turned him into a “headstrong young man who was obsessed with status and money,” according to Washington: A Life.
He also sought the thrill of adventure. As a young teenager, the colonies were consumed by the Seven Years’ or French and Indian War (1754-1763), which pitted the British and French empires against each other in the New World. After years of land disputes, the war officially began in a skirmish led by 22-year-oldLieut. George Washington. (The war, however, was truly global, with fighting on five continents. Future Prime Minister Winston Churchill and the U.K.’s National Army Museum believed it can be claimed as the “original” world war.) The conflict “fed his young imagination,” as Kelly states; the16-year-old Arnold joined the Norwich militia and marched to the New York frontier to save Fort William Henry on Lake George, according to Kelly. However, the militia arrived too late — the fort was lost. Arnold and the militia saw no fighting. They promptly returned home.
In the following years, Arnold opened a successful apothecary business in New Haven, but he also became a sea captain, traveling to Canadian and Caribbean markets in an age of piracy. However, the often “impetuous and overbearing” man “often resorted to duels, and was litigious when libeled,” which only heightened his pugnacious reputation, as Chernow describes. Yet he still strove to be a man of honor and a gentleman, as he was an “admirer of the refined and wealthy men who influenced events,” according to Kelly.
Overburdened by large debts from the Seven Years’ War, the British Parliament sought to recoup losses by enacting various regulatory and tax laws — such as The Currency Act, the Stamp Act and the Sugar Act, to name a few. Arnold’s business ventures were directly affected, fueling an ire against the mother country. Ever combative, he ventured into radical politics, joining the Sons of Liberty and smuggling goods to circumvent the onerous laws. When he heard about the Boston Massacre, during which British soldiers killed five colonists on March 5, 1770, Arnold was scornful, writing to a fellow merchant, “Good God, are Americans all asleep and tamely giving up their glorious liberties?” By 1775, prior to the Battles of Lexington and Concord, he rose through the ranks in the Connecticut militia, elected as a captain.
In short, Arnold seemed to be a true believer — and not merely a pure opportunist for financial gain (though that was certainly present). As Kelly suggests:
“Yet Arnold could smell the future. Something fundamental was about to happen, something that could not only alter his life but shape the destiny of the country. He had always felt an irresistible urge, almost a mania, to climb, to acquire, to become somebody. Here was an opportunity even grander, a chance to play a role in history, a chance for immortality. He never hesitated.”
When the Revolutionary War commenced, the captain — who had limited military training — left New Haven with 60 men and a portion of the city’s gun powder for Massachusetts; there, he received a commission and a new rank as colonel. Outmanned and outgunned, the colonists needed armaments fast to ward off the British laying siege of Boston. The future traitor hatched a daring solution. According to Kelly’s biography:
“[Arnold] had often traded along the corridor that ran from Montreal down Lake Champlain and the Hudson River to New York City. The forts at Ticonderoga and Crown Point, twelve miles apart on the western shore of Lake Champlain, had served as important outposts before 1763, when the French still held Canada. Arnold told Joseph Warren [then President of the Massachusetts Provincial Congress] that 130 cannon, maybe more, lay unused at Ticonderoga and that the fort was in ‘ruinous condition.’ It could not hold out an hour against a determined force of fighters.”
En route to Fort Ticonderoga, Arnold met the Green Mountain Boys led by Ethan Allen. Born in Litchfield, Conn., Allen was a “frontier populist,” as Kelly describes, which clashed with Arnold’s sensibilities. Nevertheless, after sizing each other up, both men made an “uneasy alliance” despite “objections of some of Allen’s men.” On May 10, 1775, Arnold and Allen, along with more than 80 men, raided and seized the fort without any deaths. The surrender proved enormously consequential, as the artillery cache was transported to Boston and utilized by the Continental Army with much success. The British evacuated the city in March 1776, only several months after the colonists were fortified by the artillery.
Yet, even in victory, Arnold was disappointed by the disorder exhibited by Allen’s men, who celebrated by pillaging and drinking the fort’s liquor. He remained at Fort Ticonderoga until June, when 1,000 Connecticut men and a general, commissioned by Congress, arrived to reinforce it, according to American Battlefield Trust. The colonel took “umbrage,” resigning his commission and began the trip back to New Haven. However, he would not arrive in time before his wife, Margaret, passed away at 31 years old on June 19. The news was heartbreaking for him and their three sons. However, he would not grieve for long, choosing instead to “bury his anguish” to fight with the colonists.
‘A Cripple in Service of My Country’
In a letter dated June 13, 1775, Arnold laid out to the Continental Congress his daring vision of capturing the British-occupied, walled-city of Quebec. An attack of this magnitude could “discourage the enemies of American liberty, and, in a great degree, frustrate their cruel and unjust plan of operation,” Arnold wrote, adding that there were also plenty of “provisions of every kind” in the city.
Eliminating the northern threat was alluring, particularly to Gen. George Washington. The Continental Army general approved a two-pronged surprise attack led by both Arnold and Gen. Richard Montgomery, which the pair began marching toward in the fall of 1775. It was a near “impossible trek” through Maine’s harsh wilderness that was “slowed by heavy rains, swollen streams, and fierce raids,” according to Washington: A Life. Food supplies were so limited that Arnold’s “starving troops devoured soap and candles and gnawed on boiled moccasins,” Chernow notes. However, under Arnold’s inspiring though strict command, the troops eventually arrived at Quebec. Washington was mightily impressed by Arnold’s fortitude under harsh conditions, calling him an “enterprising and persevering spirit.” As Chernow suggests, the general was confident Arnold and Montgomery would succeed. However, what transpired on Dec. 31, 1775, was an unmitigated disaster: Montgomery was killed, and Arnold escaped near-death — or at least a lost limb — when a musket ball tore through his knee. The failed attack was a “severe setback for Washington, whose first strategic plan had misfired,” according to Chernow.
Despite the injury, Arnold gained a reputation as a courageous leader, which only grew after he stalled British advancements from Canada into New York during the naval battle at Valcour Island in October 1776. However, he also made enemies among Continental Army officers. As Mount Vernon recounts, “Arnold brought complaints against Moses Hazen which led to his court-martial. Afterwards, Hazen leveled counter charges. Arnold also became involved in conflicts with both John Brown and James Easton.”
This may have not served him well when, in February 1777, the Continental Congress appointed five subordinates to major general, a rank which Arnold felt he deserved. Disgruntled, he tendered his resignation, though Washington refused since he “valued Arnold’s derring-do and keen taste for combat” and believed he was “one of the few generals who seemed not to arouse Washington’s competitive urges or suspicions,” according to Chernow. The hurt Arnold relented to his commander’s pleas; yet this slight against him “curdled,” which greatly served as a bedrock for his later betrayal, as described in Washington: A Life.
Still, Arnold reported for duty. Only a few months later in April 1777, he established a roadblock in Ridgefield against British forces marching through Connecticut. On April 27, the forces clashed with Arnold’s troops, who experienced “the fiercest of the fighting,” according to Connecticut History. This was the only inland battle fought in Connecticut throughout the American Revolution.
His popularity, however, reached its zenith among the patriotic populace during the Battle of Saratoga in the fall later that year. Led by Gen. John Burgoyne, the British claimed multiple victories while advancing south from Canada into New York before meeting American forces, under the command of Gen. Horatio Gates, outside the village of Saratoga. If successful, the British could have isolated New England from the other colonies, effectively dividing the Continental Army and supply routes. Yet on Sept. 19, 1777, Burgoyne’s soldiers were halted by Arnold and his men, who “anticipated the British maneuver” and inflicted “roughly twice” the casualties, despite losing the ground, according to Mount Vernon.
The ill-fed and ill-supplied British clashed again with a reinforced American army on Oct. 7. According to American Battlefield Trust, Arnold exhibited enormous courage “riding out in front to rally the troops” to capture a strategic point, Breymann Redoubt, which was defended by 200 Hessian (or German) mercenaries. During the action, the same leg injured at Quebec was shot. As Chernow describes, “doctors wanted to amputate the maimed limb, but [Arnold] scoffed at this as ‘damned nonsense’ and refused to muddle on as a single-legged cripple.” He walked with a pronounced limp for the rest of his life. However, he emerged as a great patriot in one of the most decisive battles of the American Revolution. (Today, there is a boot monument at the battle site that reads, in part, “In memory of the most brilliant soldier of the Continental Army who was desperately wounded on this spot.” Arnold’s name is conspicuously and purposefully absent.)
The laurels from his countrymen were not sufficient to ease his swelling resentment. Nor when he was appointed major general or as military commandant of Philadelphia after the British Army’s evacuation in June 1778, both with Washington’s support. It was in Philadelphia Arnold faced accusations that he exploited his position for riches and when he met the 18-year-old Margaret “Peggy” Shippen, whose family had a “distaste for the radical patriots who were waging an undeclared war on Philadelphia’s upper classes,” according to Smithsonian Magazine.
A court-martial, which he demanded, further aggravated Arnold since he was found guilty of “two relatively minor counts of misconduct” and let off “with a mild reprimand,” as Chernow notes. But he felt betrayed by Washington, who remained neutral during the ordeal, believing that the general “withheld the unconditional support he merited,” according to Washington: A Life. As Arnold wrote in a May 5, 1779, letter to Washington:
“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 of my countrymen, but as Congress have stamped ingratitude as a current coin I must take it. I wish your Excellency for your long and eminent services may not be paid of [sic] in the same coin.”
Feeling ostracized by his commander, his honor damaged, mounting debt from his extravagant spending and marriage to an “enthusiastic Loyalist,” Arnold was ripe for apostasy.
‘Treason of the Blackest Dye’
A happy wife is a happy life, as the adage asserts, and life with Peggy Shippen was no different.
Prior to meeting Arnold, the young woman certainly relished balls and Philadelphian high society — but she was also well-educated in “all of the womanly arts, like needlework, dancing, and music” and “displayed an early passion for following news and politics,” as described by the New York Historical Society. An eligible, attractive, intelligent woman, Peggy no doubt received much attention from potential suitors vying for her hand. After all, she was “trailed by rumors of having fraternized with British officers” and befriended Major John André, the British intelligence officer and later Arnold’s contact, according to Chernow.
Experiencing this life while the British occupied the city may have stoked Loyalist sympathies; American control pushed her over the edge. She resented the Revolutionary War since it “forced her family to flee from Philadelphia” for a time and “reduced her beloved father to a cringing parody of his former self,” Smithsonian Magazine notes. She missed the old life.
Yet the Continental Army, like the British Army, held balls and parties and invited wealthier families like the Shippens in 1778. It is probable that Peggy and Arnold met on one of these occasions. They quickly fell for each other. She was “captivated by his stature as a decorated war hero who seemed to be poised for further greatness,” the New York Historical Society notes; meanwhile, Arnold wrote passionate love letters (albeit with recycled prose from a previous infatuation).
Peggy’s family, however, was “not thrilled” by Arnold’s ties to the American Revolution. Nevertheless, the pair married on April 8, 1779.
To what extent Peggy’s Loyalism influenced Arnold’s eventual defection is uncertain, but it was evident in his actions. Her husband certainly harbored bitter grievances over the skirted promotions, and increasingly “expressed disappointment and pessimism about the prospects of the United States,” according to Mount Vernon. The debt only compounded his anger toward what he viewed as an “ungrateful” army for his heroic contributions, as noted by History.com. Still, those took years to boil. Yet less than a month after their marriage, Arnold established relations through an emissary with Peggy’s friend André, then in the British-controlled New York City.
The British aimed to capture West Point along the Hudson River to divide the colonies. Even Washington recognized the fort as the “the most important Post in America.” A military strategist with a bone to pick, Arnold offered André — and the British — the fort. His price: 6,000-pound sterling and a commission in the British Army. The latter accepted.
First, Arnold had to position himself accordingly, and did so by exaggerating his limp in front of Washington at least on one occasion, while lobbying for a “sedentary post” since he “could no longer ride horses for long or undertake active commands,” according to Washington: A Life. The general suspected nothing, commissioning the hero of Saratoga to take command of West Point on Aug. 3, 1780.
Washington ordered Arnold to bolster the fort’s defenses, which the latter feigned, “pretending to embark on a whirl of improvements at the fortress, while continually weakening them,” Chernow notes. In one near catastrophe of history, Washington told Arnold that he would be traveling in secret through the Hudson Valley en route to Hartford, Conn. Acting on his animus toward his former commander, Arnold “relayed this letter to his British accomplices, listing places Washington would spend the night,” as described in Washington: A Life. He even devised a scheme to have the general captured at West Point; however, the letter was delayed. Therefore, Washington, unbeknownst to him, escaped capture on the trip.
But Arnold’s treasonous designs were not over. On Sept. 21, 1780, he handed André — who slipped behind enemy lines under the pseudonym of “John Anderson” — information on West Point’s “troop strength and artillery, along with the minutes of a September 6 war council sent to him by Washington,” according to Chernow. André tucked the papers in his boot and began the return trip to the British ship, the Vulture, moored in the Hudson River. However, on Sept. 23, three American militiamen fortuitously detained the British agent and found the documents.
Two days later, on Sept. 25, Washington and his entourage were to arrive, and Arnold was to breakfast with them at the Beverley Robinson House, which stood on the opposite side of the Hudson from West Point and where he resided. During the meal, Arnold received a private report about André’s capture. It was now or never: he had to escape lest his betrayal be discovered, and he be executed as a traitor. According to Chernow, Arnold excused himself “said goodbye to his wife, left the house abruptly, and disappeared,” fleeing to the Vulture. Meanwhile, Peggy — ever the dutiful wife or, in this case, an accomplice — distracted Washington and others by acting deliriously, which they simply took for madness and not a ruse.
When Washington eventually realized Arnold’s betrayal, he called it “Treason of the blackest dye.” Yet, still believing Peggy’s innocence, he agreed to let her return to Philadelphia to be with her family. André was hanged on Oct. 2, 1780.
Now in British territory, Arnold penned his “Letter to the Inhabitants of America,” released on Oct. 7, in which he disingenuously explains why he betrayed the American cause, and how patriots have been “duped” by its alliance with “the insidious” French, the enemy of the Seven Years’ War. He writes, in part:
“I lamented therefore the Impolicy, tyranny, and Injustice, which with a Sovereign Contempt of the People of America, studiously neglected to take their Collective Sentiments of the British proposals of Peace, and to negotiate under a suspension of Arms, for an adjustment of differences, as a dangerous Sacrifice of the great Interest of this Country to the Partial Views of a Proud, Antient, and Crafty Foe. ...the Insidious offers of France, I preferred those from Great Britain, thinking it infinitely wiser and safer to cast my Confidence upon her Justice and Generosity, than to trust a Monarchy too feeble to establish your Independency, so Perilous to her distant Dominions; the Enemy of the Protestant Faith, and fraudulently avowing an affection for the liberties of mankind, while she holds her Native Sons in Vassalage and Chains.
He concluded that Britain would offer benefits — rights, tax exemptions, among others — as a conciliatory gesture if the colonies abandoned their fight, adding, “In short, I fought for much less than the Parent Country is as willing to grant to her Colonies, as they can be to receive or enjoy.”
There was no mistake: Arnold, once the hero of many crucial battles that spurred on the American pursuit for independence, had turned — and for good.
The Ninth Circle
If Arnold exited the Revolutionary War after André’s execution, that would be one thing. He would still be a villain of American history, but he cemented himself as the villain by leading attacks against his own countrymen. As one Pennsylvania Packet editorial titled “To the Traytor [sic] General Arnold” published Sept. 25, 1781, encapsulates:
“But, as if your crimes were not yet sufficient, when I find you slaughtering your countrymen, and carrying on the ravages and devastations of the war with a degree of inveteracy never before heard of; I stand confounded and shocked at the thoughts of such a viper ever being brought into the world.”
Though Washington ordered efforts to abduct him, all of them were foiled. On Jan. 1, 1781, Arnold — now a commissioned officer in the British Army — sailed along the James River toward Richmond laying “waste to colonial plantations and settlements,” according to American Battlefield Trust. A few days later, he arrived in the Virginian capital with almost no resistance as the militia’s defense folded rather quickly, and demanded supplies from Gov. Thomas Jefferson, which the Declaration of Independence’s author refused. In response, Arnold ordered Richmond to be burned — and his men obliged. Eventually, after several skirmishes with Col. Sampson Mathews’ men, Arnold retreated and left Virginia on Jan. 19.
Like Richmond, Arnold also led the British forces to destroy New London and capture Fort Griswold in September that year. However, on Oct. 19, 1781, American forces accepted the surrender of Gen. Lord Charles Cornwallis at Yorktown, effectively ending the war. In the aftermath, Arnold, Peggy and their two sons fled to England. At first, he was treated rather well. He enjoyed a royal audience with King George III and “received compensation for his losses in America” and “large grants of land in Canada,” according to The Tragedy of Benedict Arnold by Joyce Lee Malcolm. But he was in exile; and the British public treated the Arnolds with contempt, hissing at them in public and never “fully trust[ing] or respect[ing]” him, as Malcolm notes.
Even Silas Deane — another Connecticut native who nursed a maligned reputation despite having been instrumental in the American Revolution — refused to meet with Arnold publicly. (Deane’s reputation was restored after his death; read more about his contributions here.)
Arnold lived unhappily for the remainder of his days. Unpopular, he failed to obtain commissions in the East India Company. When he moved to Canada in 1785, Arnold had moderately successful business ventures, but “Debts, disputes, and litigation soured his acceptance in St. John,” according to God Save Benedict Arnold: The True Story of America’s Most Hated Man. After six years, the Arnolds moved back to London, and he returned to a life he knew before the Revolutionary War: sailing to various markets across the Caribbean.
Nevertheless, Arnold was constantly in debt and the financial woes weakened his health. According to family legend, the American traitor, on his deathbed, asked to be clothed in his Continental Army uniform, saying, “Bring me, I beg you, the epaulettes and sword-knots which Washington gave me; let me die in my old American uniform, the uniform which I fought my battles. God forgive me for ever putting on any other.”
He died on June 14, 1801, at 60 years old, “tormented with despair and regret,” as Malcolm states.
Whether Arnold made peace with God is between him and the Creator of All Things. Perhaps one day, if by His grace we are welcomed into eternal glory, we may be shocked to find him in that celestial company. Yet if Dante Alighieri’s Inferno were adapted with American characters, Arnold would certainly reside in the deepest circle of Hell, which is reserved for traitors like Judas Iscariot, Brutus and Satan.
Ultimately, Arnold’s betrayal is puzzling. Regardless of his motivations, for a man profoundly concerned about any slight to honor and reputation, he singlehandedly destroyed the family name himself — more than his alcoholic father ever did in his own lifetime. If he had remained with the Americans, he would have been one of the most extolled soldiers of the war. But he chose exile, becoming a man with no country and no admirers.
There are plenty of “what ifs” swirling around Arnold’s life, even “what if his first wife had survived the war, avoiding Peggy’s Loyalist influence?” But that is a hard game to play because, in the end, Arnold’s faith in the American cause was killed like the “seed sown among thorns” to quote The Parable of the Sower, “who hears the word, but then worldly anxiety and the lure of riches choke the word.”
It pays to have faith. To remain committed to principles and truths. To sacrifice for one’s brethren and country. Those are the heroes we remember. Arnold’s life, meanwhile, is an American tragedy, the prime example of how vanity, selfishness and deceit damn those who cultivate those qualities.
As the country celebrates our Independence, may we remain vigilant and never lose hope in our neighbors, our communities, our states and our country. In the end, hope fosters the good in others. Despair and bitterness, like Arnold exhibited, lead to destruction.
Till next time —
Your Yankee Doodle Dandy,
Andy Fowler
What neat history do you have in your town? Send it to yours truly and I may end up highlighting it in a future edition of ‘Hidden in the Oak.’ Please encourage others to follow and subscribe to our newsletters and podcast, ‘Y CT Matters.’
This is a favorite new read. Gave me clarity on the actions of Benedict
Arnold.