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Rebels, bastards and broken things: The real American Revolutionaries

Updated: Sep 22, 2020

"Rebellion, on the contrary, breaks the seal and allows the whole being to come into play. It liberates stagnant waters and turns them into a raging torrent."

- Albert Camus, The Rebel

I was sweating in strange places the day I marched myself from 55th street in all the way to 66th and 3rd in Manhattan. It was the middle of August and for whatever reason I decided to walk. For me it was a pilgrimage, hiking to the location of the martyrdom of America’s first saint. The Upper East Side had belonged to rows and rows of apple orchards owned by the Livingstons and the Rutgers, the Vanderbilts and Rockefellers of the late 1700s. The tallest building in Manhattan was Trinity Church and the city ended near Barclay Street, where Kings College (now Columbia) once stood. The rest of Manhattan Island was home to farms, estates or claimed by the wilderness. At the time half the city had been burned down in the great fire of 1776, set by some “good honest fellow” as General George Washington had put it, although the identity of the arsonist remains a mystery. It was that same year the American general had been forced out of New York City after suffering his most devastating defeat of the war so far at the Battle of Long Island. His Excellency was indecisive about burning the city after his army left but it seemed someone had made the decision for him. Having full command of the city, the British began using the apple orchards on Manhattan as a staging point for attacking the now demoralized and defeated American soldiers hiding further up north. Rutgers mansion, which sat on the same property as the apple orchard, was used as a barracks. Just as the embers of the great fire were beginning to cool, a young man was captured carrying sensitive information regarding the British strength and numbers, and now was to be marched up to the so recently hushed and serene apple orchards of Rutgers. It seemed the apple trees provided the British with the perfect opportunity to hang traitors, as the former schoolteacher turned Army captain Nathan Hale was soon to find out.

Map of Manhattan in the 1770s showing the damage of the Great Fire of 1776.

As I trudged through the blistering heat of the city I was hoping I hadn’t been confused as to the location of Hale’s execution, since there are apparently several sprinkled around the city, however considering death is a one time deal I figured I’d settle on just one. Conquering my unhealthy perspiration and disarray I finally arrived at the spot of Hale’s hanging. 66th Street is narrow but otherwise not unique city block on the Upper East Side of Manhattan. 3rd avenue is bustling and busy, and stretches all the way down to the Bowery. Where the two streets meet, concrete lines the earth, and the buildings scrape the sky. Businessmen in black suits and dog walkers in sweatpants walk side by side, smartphones firmly in hand. A far cry from the tranquil and almost desolate apple orchard it had once been, and that is not a bad thing. Looking at the Starbucks with its impressionable hipsters and caffeine addicts, drinking over the resting place of America’s first spy, I was reminded of how much the city and the country have changed. New York City is the center of the financial world. Down by Wall Street and Battery Park, where a statue of King George III once stood gleaming in gold on a ten foot marble pedestal now stands the bronze sculpture of the charging bull, a symbol of a nation’s changing priorities. Over by Fulton Street, where prostitutes would haggle and ply their trade now stands the site of the worst terrorist attack in modern history. And down by Pearl Street where slaves from Africa had once been bought and sold reminds us that residents of lower Manhattan have been subjected to terror on more than one occasion. All this history is unmarked in New York however, where it is one of the only places I know of that has no problem literally burying the past and building right on top of it (as was done with the former slave cemetery on Chambers Street). Though this history is important if we are to make a plan for the future. History does not repeat itself but it does have excellent continuity, and stories like Nathan Hale’s can help clear the misconceptions of what the founding of this country meant and who it was fought by and what it means for us today.

The Great Fire of 1776 destroyed half of New York City. It would take over a century to fully recover.

Nathan Hale was twenty-one years old at the time of his execution, just two years younger than I was standing there over two hundred years later. Only a short time earlier, Nathan was wandering the Yale campus under the stars alongside his friends William Hull and Benjamin Tallmadge. In just five years, Hale would be hanged as a spy, Hull would be a captain in the infant Continental Army and Tallmadge would be head spymaster and confidant to George Washington himself. However on a cool clear night in 1771, the three men were mischievous college students looking for something to occupy their time other than their studies. “I had not much occasion to study during the first two years of my collegiate life,” wrote Tallmadge. “Which I had always thought had a tendency to make me idle.” After spending some time at a local tavern, the men decided to address their academic idleness more directly by smashing a few windows around campus. One might find it strange based on their subsequent achievements, but none of these men would earn any special honors while they were away at university. They weren’t gifted learners, as we now call them, but they were revolutionary thinkers as well rebellious and charismatic young men. Besides window breaking, Nathan and his friends enjoyed their drinking and card playing, not to mention the company of local young women. None of these interests took away from their pedagogy however. Nathan was deeply interested in taking on education as a career, and often debated contemporary topics with his classmates. Lucky for him and his friends, corporal indulgences could traverse cerebral pleasures. During the 18th century it would have been taboo and even illegal to educate one’s daughters. However Nathan Hale and Benjamin Tallmadge, two men studying to become educators, both advocated and debated publicly for the education of women while at Yale, to the admiration and delight of the female attendees. Once they became schoolmasters they put their words into practice, educating (and occasionally seducing) the women of Rhode Island and Connecticut. It was also during Hale’s teaching career he was possibly the first American to publicly advocate for independence from Britain and the creation of a new republican government. However it seemed that despite having discarded idleness on the Yale schoolyard, both Tallmadge and Hale once again found it in while tutoring. Fortunately for them relief would come with the impending war. As the violence between the colonial Americans and the British escalated in 1775, Nathan would join the army and later become a captain, seeing action during the siege of Boston and later at devastating Battle of Long Island in 1776. Nathan became one of the more knowledgeable and well liked officers in the Continental Army. He was a revolutionary as well as a soldier, and so was recommended for a group of experienced rangers led by Thomas Knowlton, known as Knowlton’s Rangers. The Rangers were typically tasked with reconnaissance and intelligence gathering and eventually would become known as the first Special Forces unit in the United States military.

When the Americans were licking their wounds after Long Island, Washington needed information about his enemy’s intentions, strength and movements. Spying was difficult work and in the 18th century it was considered a dishonorable occupation. It was a job for rakes and cutthroats. Someone who wanted to make a few bucks and didn’t necessarily care for what they had to do. It was more honorable to meet the enemy on the field, face to face, than it was to sneak around amongst them. Therefore the job was almost always given to someone who could not be trusted to carry out the job reliably. This made Washington’s job impossible considering the army itself was already on the edge of desolation. Right now, spying not only seemed like a suicide mission but would also damage the personal integrity of whoever volunteered. Washington eventually went to Knowlton’s Rangers looking for thrill seekers but was out of luck. He could not find any officer or a soldier to volunteer to spy on the British in New York. Until Nathan Hale. William Hull, Nathan’s friend from Yale tried to talk him out of it. “In the progress of the war, there will be ample opportunity to give your talents and your life, should it so be ordered, to the sacred cause to which we are pledged,” said Hull to his friend. “By one fatal act, you crush forever the power and the opportunity heaven offers.” William’s old comrade could not be convinced. “I will reflect,” Nathan said as he grabbed William’s hand. “And do nothing but what duty demands.” Retrospective foreboding omens aside, no one knew that the mission was doomed from the start. Nathan was perhaps one of the most conspicuous looking men in the army. He was very tall (over six foot), very handsome according to his contemporaries and he had a very noticeable mole on his neck of which he had always claimed was evidence of his fate: death by hanging. Nathan also had scars on his forehead from the flash pan of his musket. Any British soldier that came close enough to him would be able to recognize those marks and where they had come from. This all not to mention the Continental Army had been pushed further up north to Fort Washington (now the location of the George Washington Bridge), by the time Nathan had arrived on Long Island. Any information he could have provided would have been useless. Nathan was to land at Huntington on Long Island and make his way to Manhattan Island, making notes and gathering any information he can along the way and then return some time later. And he was almost successful until he was betrayed and captured on his way back. The mission was a failure. Accounts vary, but Nathan’s famous final words (“I only regret, that I have but one life to lose for my country”) were most likely never uttered by him. The captured spy’s former classmate William Hull put the words into Nathan’s mouth later on. In an effort to preserve his friend’s memory, William Hull made him into a legend. News of Nathan’s death was delivered to the American camp by British engineer and captain John Montresor, and received by Alexander Hamilton; another recently former student at Kings College, now turned full American Revolutionary. Hamilton never finished his degree, instead he formed a militia known as the Hearts of Oak and dropped out of Kings College to do what higher level education is meant to do: teach one to think critically and independently while standing up for what you believe in.

Statue of Nathan Hale on the CIA campus. His purported final words surround the base.

Although I equate faith with the abdication of one’s ability to think freely and critically, Nathan Hale was a man of deep Christian faith, drilled into him at a young age by his father. During his captivity he requested a minister to which he was declined. He then asked for a Bible of which he was also declined. Despite having his spiritual comfort withheld Nathan did not waver, then again it wasn’t salvation he was dying for. Nathan Hale was never a martyr for his Christian faith, as one of his biographers M. William Phelps so firmly believes, and none of his purported final words, however apocryphal ever mention god or spirituality. His body was never exhumed, or parts of it left conveniently intact after fermentation, as is the practice with sainthood in the Catholic Church. Nathan Hale’s faith is not what made him exceptional. In fact his faith is what would have made him unexceptional. Just ask Nathan’s brother Enoch, who chose the Church over the Revolution and whom you have undoubtedly heard of. Nathan Hale was a patriot, an American, a student and a teacher, who when confronted with extraordinary circumstances, stood up for what he believed in despite what it may mean for his well being, his family name and even his own personal integrity. He paved the way for two centuries of American patriotism, not just in the way he died but also in the way he lived.

Statue of Nathan Hale outside of City Hall in New York City. One of the supposed, but less likely locations for his executions.

The American Revolution is not an event reserved for the powdered wigs of old intellectuals arguing whether the national symbol should be a turkey or an eagle. Nor was it exclusive to a band of hard worked farmers who decided to abandon their plow after being pushed too far. It was lived and fought, in many cases by students, ruffians and contrarians, like Nathan Hale who challenged the way things were with what ought to be. It’s twenty one year old Yale student Nathan Hale who stands venerated in bronze at the entrance the CIA headquarters in Virginia, a reminder to all who work in American intelligence why they do what they do. And it was Nathan who decided on his own accord to advocate for women’s education, and argue in favor of independence and republican government. It was also twenty two year old Yale student Benjamin Tallmadge who became Chief Spymaster to General Washington, setting up the Culper Spy ring on Long Island and helped uncover General Benedict Arnold’s betrayal. It was twenty two year old William Hull who was recognized by Washington and Congress for his bravery at the Battle of White Plains, Trenton, Saratoga and Monmouth. It was the twenty-five year old son of a South Carolina slaveowner John Laurens who in spite of his own family and his own state severely criticized the practice of slavery and recruited slaves to fight for their freedom through the American cause. It was nineteen year old college drop out Alexander Hamilton, who formed the Hearts of Oak to defend Manhattan Island from British invaders, became George Washington’s most trusted advisor, held a bridge at the Battle of Monmouth (however impractically), stormed the redoubts at Yorktown and became one of the most influential American of the early Republic. They were all rambunctious, salacious, open-minded students turned rebels, who often acted recklessly with little regard with their own safety to form the keystone of the revolutionary process. They were young men who knew when to put down their books and pick up a gun, knowing full well what was worth living with and dying for. We should be asking the same thing of students today, not in terms of violence, but in terms of confrontation and active civil participation. We should be compelling students to challenge and properly defend their own beliefs, before challenging those of others. Winning a war of ideas takes confrontation, not of the person who holds the idea, but of the idea itself. Shouting someone down or ignoring them is not a recipe for victory. If you genuinely believe your ideas are superior to someone else’s you shouldn’t be afraid of defending them.

Many who take no interest in learning history, but enjoy lecturing others on their supposed knowledge of the subject, are unwilling to believe that colonial Americans challenged or even raised certain questions such as societal status quo, slavery or the education and suffrage of women. That is because they want to believe in an American history that fits their own narrative, one that has no place for people that look different from themselves, or that America would not have had the capacity to think that deeply. However to believe in such a history is to believe that America never had a revolution at all. The creation of the United States did not initially answer all of its questions correctly, and I don’t mean to say that from 1776 to today we have always acted in accordance with our founding principles. The revolution laid a foundation of liberty and equality that allowed for the growth for such movements such as abolition and women’s suffrage, it did not grant them outright. It allows for men and women to build on the previous generation’s concept of liberty with their own. History never runs in a straight line however, and that battle isn’t always a winning one. None of these men were perfect, and to lie on their behalf would only leave their work unfinished. Unfortunately many of these revolutionaries died before their time, and with each death the revolution grew less revolutionary, making room for an older more conservative reactionary to take their place once the dust had settled. However these men could only put the revolution on hold for a time, until it came bursting through once more during America’s first Civil War.


- Washington's Spies: The story of America's First Spy Ring by Alexander Rose

- Nathan Hale: The Life and Death of America's First Spy by M. William Phelps

- Alexander Hamilton by Ron Chernow

- Under the Guns New York: 1775-1776 by Bruce Bliven Jr.

- American Revolutions: A Continental History, 1750-1804 by Alan Taylor

- Renegade Revolutionary: The Life of General Charles Lee by Philip Papas

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