Chapter I

A Natural Rebel with Much to Prove

Alexander Hamilton, a brilliant young immigrant from the Caribbean, made his dreams come true in America in spectacular fashion and in relatively short time. America, like Hamilton, overcame the odds to reach its full potential, but only after a great deal of heartache and struggle, winning its independence after eight years of bitter conflict. When he first stepped on the shores of America in the summer of 1773 not long before the American Revolution, few young men seemed so unlikely to reach such soaring heights as Hamilton.

For such reasons, Hamilton embraced the totality of the American dream and a heady new nationalism like a holy shroud, and quickly distanced himself from his dark West Indian past. Despite his future successes, the emotional pain of that dark past of a troubled life never left him. With a chip on his shoulder from the snubs and humiliations of his past because of his low social standing, the young man made for a natural revolutionary who fit neatly into the mainstream of angry Americans determined to shake off the bondage of the mother country.

Hamilton’s unpleasant early life in the Caribbean was no fault of his own. Hamilton’s father, James—a Scottish aristocrat and aspiring merchant with little business savvy—deserted the family and was not seen again. James Hamilton was the fourth of eleven children from the family estate at Ayrshire, southwest Scotland. However, a branch of the Hamilton family had been centered in the township of Hambleton, England. Handsome and personable, Hamilton’s father was a Scottish nobleman and proud of it, but at the same time was a ne’er-do-well, whose Caribbean business ventures too often went awry. He never married Hamilton’s mother, the considerably younger Rachel Faucette-Lavien, and their informal relationship represented the relatively loose morality of West Indian Creole society. She was a feisty woman of French Huguenot descent. Strong-willed and a force to be reckoned with, Rachel hailed from a respected family who owned a small sugar cane plantation on the Caribbean island of Nevis. Having the greatest influence on Alexander’s life than anyone else, she was a remarkable woman of moral courage and intelligence, and ahead of her time in many fundamental ways.

Before James Hamilton’s arrival, Rachel Faucette’s first husband had resulted in an ill-fated and disastrous relationship for the spirited young woman. When she was only sixteen, Rachel had been swept off her feet and married a Dane, Johann (John) Michael Lavien, more than ten years her senior, in 1745. Rachel eventually realized her grave mistake. Around 1750, after about a half decade of marriage, she struck out on her own way rather than endure a loveless, perhaps even abusive, relationship. Rachel simply left, after her husband had used up her inheritance that had once been a “snug fortune.” Rachel ended her relationship much like her mother Mary did before her, who had gained a legal separation from her husband.

A fancy dresser with an outsized ego, Lavien (Lavine in Alexander Hamilton’s spelling) was a German-Jewish merchant from Copenhagen, Denmark. Like most ambitious transplants from the cities of western Europe, he had aspired to seek his fortune in the West Indies and become a sugar and cotton planter and small slave-owner on the Danish island of St. Croix. Lavien also hoped that Rachel would return to him, but her independent spirit and ways dictated otherwise, which resulted in a personal vendetta from an embittered husband.

After having been an apprentice with a leading Glasgow businessman and textile merchant in the growing linen industry, James Hamilton had been working for a St. Christopher (better known as St. Kitts) mercantile firm that had extensive ties to Glasgow, including sugar refineries. James first met Rachel in the Leeward Island of St. Kitts. She had briefly moved from St. Croix with son Peter Lavien, her only legitimate child, born in 1746, to rejoin her mother, who was living with a large landowning planter on the island of Nevis. However, Rachel returned to St. Croix, where she supported herself by renting out her three slaves (Flora, Esther, and Rebecca inherited from her grandmother), and by a small sewing business. Under pressure from debtors and her vindictive husband who had her imprisoned at the main fort in Christianstead (the capital of St. Croix) for adultery, the persecuted Rachel fled to the English island of St. Kitts in 1750, abandoning all that she had known, including her son Peter: a drastic step that now made a legal separation from her estranged husband impossible and would doom any future children (James Hamilton, Jr., and Alexander Hamilton) as illegitimate.

Destiny seemed to have ordained a fateful meeting on St. Kitts between Rachel and James Hamilton in the early 1750s. Because divorce was such a rare and expensive undertaking at this time, and remarriage was now not possible for Rachel in legal terms under convoluted Danish law on St. Croix, Alexander’s mother (although legally still married to Lavien) lived an unconventional lifestyle with James Hamilton. Under the circumstances, it was impossible for Rachel to legitimize their relationship and common law marriage in legal terms. She lived with James for perhaps as many as fifteen years, a period in which he was unable to acquire riches in the Caribbean. Born around 1718 and raised in his landed family’s Kerelaw Castle, which overlooked the port town of Stevenston, Scotland, James had grown up with the finer things in life. Like most West Indies planters, James had planned to retire in his native homeland after he made his riches in the Caribbean.

The two were polar opposites. Rachel’s dominant traits were not only practicality and commonsense but also intelligence, while James was more of a dreamer that ensured some “indolence.” However, James Hamilton was blessed with a pleasing personality and charming ways. Fortunately for him, Alexander Hamilton benefitted from this union by gaining the most admirable qualities of each parent. Even by Caribbean standards, this common-law marriage was scandalous, but less so if on the mainland, when Alexander Hamilton—the couple’s second son after James, Jr.—was born in Charlestown, the capital of Nevis in the British Caribbean, on Saturday, January 11, 1755. Lacking the work ethic necessary to succeed but burdened with a sense of entitlement of a proud Scottish nobleman, James, Sr. dealt the hard-luck Rachel another severe blow. After having failed as a husband like in his business ventures, he deserted the family in 1766. After having brought his common-law wife and two sons from Nevis to St. Croix’s busiest port, Christiansted, Hamilton disappeared for good. Alexander never saw his father again.1

After nearly a decade of having fled St. Croix, Lavien filed for divorce in 1759 in order to protect his one legitimate heir, Peter Lavien, while ensuring that Alexander and James were declared bastard and “whore children,” who could never legally inherit any of his property. With the 1759 decision of the judge sitting on the Danish divorce court, Lavien was allowed to remarry, unlike Rachel. Rachel had been disgraced by her husband’s wrath, including what might well have been trumped-up charges of adultery that caused her to be jailed in Christiansted for a short period.

As sad fate would have it, Alexander Hamilton paid a high psychological and emotional price for all of these unfortunate developments, and the unconventional nature of his mother’s relationship with his father, and his illegitimate status. This was especially the case in the port of Christiansted, where his mother had suffered her greatest setbacks and humiliations, weighing heavily on a woman valiantly struggling against the odds. As a result, Alexander’s first education came in the school of hard knocks.

Although from a broken family herself and not raised by her father, Rachel had found the long-term relationship with the affable Scotsman, relatively secure. Alexander certainly benefitted from this early stability of a nuclear family. Despite being destined to experience hard times in the Caribbean, Alexander never lived in a lower class dwelling. Before relocating to St. Croix with James Hamilton in the spring of 1765, Rachel had lived with him in a stone waterfront home located on the foreshore of Gallows Bay in the port of Charlestown on Nevis’ southwestern side near the Customs House. Situated on the main street that ran parallel to the bay and near Anglican Churches, Rachel had inherited this property from her father. The large, two-story house stood on a flat, sandy plot of land located not far from the luminous blue-green wide bay.2

Because of the family’s dysfunctional past, young Alexander suffered from the inevitable social backlash while growing up on St. Croix, especially after his father’s departure. He was forced to fight for his reputation, name, and honor in Christiansted’s streets, learning firsthand about the harshness and unfairness of the outside world, hard lessons that he never lost and wounds that never disappeared. Rather remarkably, however, he never held any resentment or bore a grudge toward his “charming scamp of a father,” for abandoning the family. In social terms, the Celtic background of the family of Alexander’s Scottish father was distinguished and respectable, which was so vitally important in class-conscious eighteenth century society and especially to a young man without a stable family life. The distinguished heritage became a source of pride for Alexander in his dark moments.

Despite the hardships brought about by his father’s hasty departure when he was ten, and his mother’s upcoming death from yellow fever on February 18, 1768, when he was only thirteen, Alexander developed a tough-mindedness, hardened exterior, and resiliency that served as an emotional and psychological buffer for protection, qualities that served him well in meeting life’s stern challenges in the future. Cruel twists of fate and adversity shaped a young Hamilton out of necessity into a responsible individual mature well beyond his years. With a passion and ample justification because he had suffered in this class-based environment, the ever-egalitarian Hamilton long denounced the rigid artificiality of class distinctions and aristocracy on both sides of the Atlantic. He sincerely believed that non-aristocratic “blood is as good as that of those who plume themselves upon their ancestry.”3

The place of Alexander’s birth, Nevis, lay in the Queen’s Leewards, consisting of five tropical islands situated amid turquoise waters. Only thirty-five square miles in size, Nevis was positioned near its oddly shaped sister island of St. Kitts (first known as St. Christopher and about twice Nevis’ size), from where James Hamilton hailed. These two islands rose up from the same mountain range that had been thrust upward from the ocean’s floor millions of years ago.

Alexander Hamilton’s life at the port of Charlestown, Nevis, till age ten, and then later Christiansted, St. Croix, to age seventeen, was filled with the sights and sounds of the busy wharf and dock: noisy fishermen and sailors from around the world; the sight of large numbers of black slaves; stately royal palms and orange trees loaded with ripe fruit; flocks of low-flying brown pelicans flying low over blue waters in search of unwary fish; lucrative island commerce from nations around the world; and African slaves gathering at the town’s marketplace every Sunday to sell their produce. Towering above Charleston, Nevis was distinguished by snow-covered Mount Nevis, which dominated the island’s center. Standing at 3,200 feet above sea level and often obscured in clouds, this imposing mountain towered over a green carpet of sugar cane plantations that covered the fertile lowlands. Christopher Columbus had allegedly christened this picturesque island Nuestra Señora de las Nieves (Our Lady of the Snows) because of the extinct volcano’s frigid peak. Bustling Charlestown was the island’s largest and busiest port.4

In an environment that was the antithesis of the traditional backgrounds and native environments (mostly small farms or larger Southern estates near the east coast) of the other Founding Fathers, the beauty of Nevis and St. Croix contrasted sharply with the harsh realities of life—including slavery’s horrors—on these tropical islands. He had seen men, women, and children sold on the auction block. The horrors and agonies of slavery left a deep impression upon young Hamilton, who became a hater of slavery and a diehard abolitionist. In fact, Alexander’s early experiences that confirmed the humanity of slaves—which had been denied by so many whites—allowed him to stand high above most of his fellow Founding Fathers in moral terms.

Rachel became the owner of five full-grown female slaves after her mother’s death, which had allowed her to inherit two additional slaves who were likewise hired out. She assigned a young slave boy named Ajax to Alexander as a body servant. Charlestown prospered as the island’s primary slave market, part of the lucrative international mercantile system. Besides the endless source of cheap labor performed by the unfortunate Africans in the broad fields, the rich volcanic island soil, warm weather, and bright sunshine all fueled the island’s primary cash crop of sugar cane. Nevis was covered by flowing cane fields that stretched as far as the eye could see. The sprawling planter estates were dotted with rounded stone windmills that provided the wind energy, along with slave labor, that crushed the green stalks into cane juice.5

The basic core of Hamilton’s personality, including his hated of slavery, was formed in his personal struggles and humiliations on St. Croix. The world of the Danish West Indies shaped and molded the man destined to become one of America’s most unforgettable Founding Fathers, although that significant influence has been long minimized by generations of historians. Ironically, St. Kitts would send much-needed supplies to General George Washington’s Army during the first two years of the American Revolution, which might have been a source of pride to Hamilton, while serving his country.

Distinguished by a sound business sense, financial smarts, strong will, and work ethic, Rachel was tough and resourceful out of necessity. The independent-minded Rachel was autonomous to a degree not usually seen in a woman at this time. She defied a patriarchal society’s lowly expectations, especially when on her own. After James Hamilton abandoned the family and was seen no more, the irrepressible Rachel was primarily responsible for providing for herself and two sons, Alexander and James, Jr., by her own resourcefulness and brainpower to create a decent life for the hard-luck family on St. Croix. A bright woman who had mastered the art of survival on her own, Rachel was a skilled businesswoman who continued to defy convention. Her entrepreneurial sense and never-say-die spirit were passed down to her precocious son, who was destined to put these admirable qualities to good use on American soil.

A hard worker, Rachel successfully operated a small store from her rented two-story house (the upstairs was the residence and downstairs was the business) at No. 34 Company Street in Christiansted. Rachel’s wealthy brother-in-law, James Lytton, paid the rent and donated the Spartan furnishings. He might also have contributed the silver utensils and porcelain water basins and plates owned by Rachel. Conducting a profitable business to support her family unlike the fumbling James at a time when women seldom operated an independent business enterprise, she sold a variety of goods imported from the American colonies through the import-export mercantile firm of David Beekman and Nicholas Cruger of New York City. These imports, especially salt pork and flour, were sold by Rachel to plantation owners, who exclusively grew crops of sugar cane to utilize all available acreage. In addition, Rachel’s good looks and stylish dress at age thirty-six did nothing to hurt business among admiring male customers.

Most importantly, Alexander learned at an early age how to effectively manage and operate the store, gaining an understanding of financial matters and becoming an expert at accounting. Hamilton also learned the advantages of promptly paying debts while working by his mother’s side and gaining a well-honed knowledge for business. Meanwhile, his enterprising mother also gained income from the five slaves, whom she continued to rent out. Despite its small size, Alexander’s Caribbean world was cosmopolitan and lively, thriving at the crossroads of imperial destinies and mercantile ambitions of the major European powers. Sailing ships from around the world docked at the Caribbean’s major ports, including those in St. Croix. Christiansted was the thriving commercial center, situated on St. Croix’s north central side, while Frederiksted was located on the island’s west side. Named in honor of Danish kings, these bustling towns were laid out and built in traditional Danish-style, with whitewashed homes and buildings gleaming in the Caribbean sunshine.

Hamilton saw little romance on the tropical islands of either Nevis or St. Croix, only the harsh realities of what was often a short life in the hell of the tropics, especially from the ravages of disease. Because of the stain on the family name and the geographic-social constraints for future advancement, Hamilton’s ambitions were early frustrated. Therefore, he soon found a satisfying refuge in books, including thirty-four volumes owned by his mother. These books were almost certainly bought or donated by her well-to-do brother-in-law, James Lytton, who had married her sister Ann. This small library, which almost certainly included the Holy Bible, was a rare luxury for a relatively young woman of only modest means, speaking well of Rachel’s intellectual abilities and foresight in regard to her sons. Hamilton viewed St. Croix’s eighty-four square miles and three hundred eighty sugar plantations as little more than a prison that confined his growing ambitions and dreams.6

Processing bills of lading, bookkeeping, accounting, and tabulating funds as a teenage apprentice at the mercantile firm of Beekman and Cruger (eventually to become Kortright and Cruger which continued to be based in the great mercantile center of New York) was a dead-end occupation for Hamilton’s lofty aspirations. His mother had secured this entry position for Alexander since he was eleven, when his education in business continued unabated after having worked at his mother’s store: a wise decision that ensured the young man a livelihood and mentor, Nicholas Cruger. Rachel had done all that she could to place her precious son in a professional position, and she succeeded admirably in her mission.

Rachel died on February 19, 1768, of a yellow fever epidemic at age thirty-eight, thanks in part to an excessive bleeding procedure prescribed by her physician. The same epidemic nearly took Alexander’s life, and he was fortunate to have survived. Thankfully, to provide Alexander with some consolation, social humiliation did not follow Rachel in death because of her past social indiscretions. She was buried at nearly St. John’s Anglican Church, and the religious-minded young man envisioned her good soul ascending to heaven, where it belonged, contrary to the harsh opinions of most self-righteous people in Christiansted.

Then, as if not enough tragedy had marred Alexander’s life, Rachel’s still vindictive Danish husband Lavien suddenly returned and laid claim to his wife’s meager estate because she had not left a will. With evil intent in his personal war that never ended against Rachel and her memory, he deprived Alexander and his brother, now orphans and on their own, of their inheritance, which included Rachel’s five adult female slaves. Alexander and James continued to suffer only because they were illegitimate. Again, the relentless Lavien was determined that everything was to go to his legitimate son of Rachel, Peter. The court agreed, and all of Rachel’s estate went to Peter. The two young men were then placed under the legal guardianship of Peter Lytton, a cousin in his early thirties. However, during the summer of 1769, a troubled Peter Lytton committed suicide, leaving his estate to his black paramour, Ledja, and their mulatto children. Then, less than a month later, wealthy brother-in-law James Lytton also died: still another stunning setback for the forlorn Alexander and James, Jr., whose fortunes continued to spiral downward at a rapid rate. Displaying the strength of character long demonstrated by his mother, as if he were compensating for his wayward father’s shortcomings, Hamilton channeled the family setbacks and humiliations to his maximum advantage. He developed an uncanny ability to turn negatives into positives, with reversals only strengthening his will to succeed in life. Hamilton was consumed with his great dream, to escape the Caribbean at the first opportunity, because he hated “the groveling and [lowly] condition of a clerk,” as he lamented in a letter dated November 11, 1769, at age fourteen.7

Alexander finally benefitted from a decent break in life. While older brother James Hamilton, Jr., became an apprentice to a carpenter, Alexander was taken in by the family of wealthy merchant Thomas Stevens on King Street, after his mother’s death. Alexander also gained a best friend in the merchant’s son, Edward “Ned” (also “Neddy” as Hamilton penned in letters, including the one on November 11, 1769) Stevens, who was near his own age. The two young Creoles were much alike, even sharing a hatred of slavery. But this promising son of one of Christiansted’s leading merchants left for America to complete his education. In November 1769, while languishing as a teenage apprentice to Beekman and Cruger, where he had been working before Peter Lytton’s death, Hamilton worked long hours at the company’s headquarters near the busy wharf. Alexander’s desire to escape from St. Croix was so strong that he wrote his best friend, Ned Stevens, who was studying at King’s College (now Columbia University) in New York City, that he had “to confess my weakness,” which was a soaring ambition.8 Significantly, in regard to his future ascent in life, the many “harrowing experiences of his youth did not embitter Hamilton against the world [but] instilled in him an inflexible resolution to conquer it” rather than be conquered.9

Year after year, Hamilton engaged in thankless employment for Nicholas Cruger, a New York City merchant of Dutch heritage, at King Street’s lower in downtown Christiansted. Here, at the company’s store and large warehouse near the wide harbor and the wharf, Hamilton demonstrated his considerable talents and superior abilities over an extended period. Nicholas Cruger, Alexander’s boss, was the son of a leading mercantile and political family of New York City, which had elected two Cruger mayors. Nicholas was a junior partner of St. Croix’s most lucrative exporter of sugar and molasses to England’s thirteen colonies. Hamilton now had connections to New York City, where he was eventually bound, while putting his French to good use, because of the firm’s business links to the French West Indies, especially St. Domingue (the future Haiti).

Blessed with a strong work ethic and stamina for long hours of labor, Hamilton’s knowledge of finance and commerce became more refined. In 1769 when Hamilton was fourteen, and after having worked as a clerk for around three years, David Beekman departed the firm. He was replaced by New Yorker Cornelius Kortright. However, Hamilton’s lowly status did not change at Kortright and Cruger.

But then an opportunity unexpectedly developed. Hamilton’s promise increased in Cruger’s eyes when he excelled by taking charge and making smart decisions, after excelling at extra responsibilities far beyond a clerk’s duties. This golden opportunity to demonstrate the full extent of his abilities came by accident. Despite only being sixteen, Hamilton suddenly benefitted from rising from a lowly clerk’s position in October 1771 to become a very effective manager during Cruger’s temporary absence. With his trademark boundless energy and savvy in money matters, Hamilton had even improved the business by making tough decisions, including having to fire the company’s attorney and ship captain who had drained the company’s profits. Cruger imported the same commodities, including fine “Philadelphia flour” that Rachel had sold at her provisioning store, whose goods supplied the sugar planters. But after effectively managing the firm’s St. Croix business operations like a veteran manager many years his senior, Hamilton returned to his former clerk position when a recovered Cruger reappeared to take over.

Since he was mostly self-taught, Hamilton continued to read and write as he grew older, nursing a desire to become a distinguished man of letters, perhaps as a ticket out of the detested tropics and bleak island exile. He became more ambitious when a newspaper was established in Christiansted in 1770, which fueled his literary efforts. In early April 1771, he wrote a romantic poem, which was published in St. Croix’s primary English newspaper. Displaying no bitter feelings about the family’s abandonment, Alexander also wrote a riveting letter to his wayward father, who was living somewhere in the southern Caribbean, about a tropical hurricane’s devastation of St. Croix.

Hamilton’s hurricane letter was republished in the Royal Danish American Gazette on October 3, 1772. At age seventeen, Hamilton drew widespread attention for his masterful prose and colorful vocabulary distinguished by a precocious blend of passion, religion, and wit that seemingly could only have been written by an older (cynical and worldly) and more experienced writer. As demonstrated in the past, he proved himself adept as thoroughly with poems treating sexual topics as he was with religious themes. The sermon-like hurricane letter reminded readers of the supreme folly of man, who was deserving of such divine retribution for earthly sins. Hamilton’s words had a dramatic impact on the upper-class elite of St. Croix, even garnering the governor’s attention. With his promise and intelligence so bright, a group of benevolent local backers, almost certainly organized by Reverend Hugh Knox and no doubt including men like his employer Nicholas Cruger and his guardian Thomas Stevens, decided to send Hamilton to America to further his education by studying medicine. Doctors were always needed on the disease-ridden tropical island, where yellow fever had taken so many lives, including Hamilton’s own mother. Hence, young men from the islands, like Hamilton’s good friend “Neddie” Stevens now a student at King’s College, studied medicine in America.10

Reverend Knox’s personal and spiritual influence in assisting Hamilton to fulfill his dreams can hardly be overestimated. Arriving on St. Croix in early 1772, the enlightened Scottish Presbyterian minister who had been educated in divinity at the College of New Jersey (later Princeton University), became not only Hamilton’s mentor but also his savior. As the pastor of the Scottish Presbyterian Church in Christiansted, Knox’s influence resulted in Hamilton’s spiritual turn to religious poetry, and then to more lofty writing pursuits. From Knox, born among the Irish Presbyterians of Ulster Province, north Ireland, and his extensive library, Hamilton gained not only a greater spiritual faith, but also an early education in Enlightenment ideologies and philosophies. Desiring for this gifted young man to succeed in life beyond a lowly clerk trapped on a remote island, the handsome Knox played the key role in paving the way for Hamilton to go to America to fulfill his lofty ambitions. After he secured Knox’s letters of introduction to friends in America and learned of the availability of donated funds in America for continuing his education, the opportunities in America beckoned to the young Hamilton as never before.

On a day that he never forgot, Alexander Hamilton walked out along the same lengthy Christiansted wharf from which he and his family had arrived from Nevis in the spring of 1765 less than a decade before. When he finally sailed away from tiny St. Croix and the Caribbean forever in summer 1773 with few possessions, he had no desire to ever return to the place of so much personal suffering and pain. Hamilton left behind almost too many pained memories to count and no regrets.

Most of all, the young West Indian wanted nothing more than a new place and identity to start anew, because he was determined to make a name for himself. At only age eighteen, he was now highly motivated to prove wrong and show up all the haughty upper-class individuals who looked down upon him and his mother with such arrogance and disdain by gaining more distinction than all of them put together. Small wonder that this dreamy young man had early turned to reading, studying history, and writing as a comforting buffer against harsh realities of life in the Caribbean. He was smart, confident, and self-reliant, which boded well for whatever he embarked upon in America.

Phoenix Rising

After embarking upon a three-week journey from St. Croix and experiencing a close call when the ship had caught fire on the open sea, eighteen-year-old Alexander Hamilton landed on the mainland of British America in the summer of 1773. He arrived at the port of Boston, Massachusetts, with high hopes for a brighter future. Hamilton never saw the Caribbean again. He was fiercely motivated to excel in this new environment, despite being a perfect stranger to America and without a friend in this new world. Without family or social connections, he would have to excel on his own in a strange land that he had never seen before. But he had a soaring ambition and keen intelligence that were destined to serve him well in the days ahead. The humiliations of St. Croix failed to diminish his sense of optimism and hope for a brighter future. In fact, the family reversals and social embarrassments in the Caribbean had only fueled his desire to succeed at any cost. As fate would have it, he had entered a world as turbulent as his own past, because of stirrings of a people’s revolution were in the air.

Unlike anything seen on St. Croix, Hamilton found that America was a brewing cauldron of revolutionary sentiments fueled by heady Age of Enlightenment idealogy. He immediately journeyed south from Boston to New York City to pick up his allowance from his St. Croix backers for his education at the headquarters of Kortright and Company. Here, his friend Ned Stevens (the only person that he knew in America) studied at King’s College, and this was where Cruger’s associates lived. However, making an excellent initial impression with his smart dress, erect carriage, and winning personality, Hamilton easily cultivated new friends and associates. Hamilton met a radical merchant named Alexander McDougall, one of the leading Sons of Liberty, in New York City. On July 6, 1774, McDougall was destined to give a rousing speech that galvanized patriot support and greatly impressed Hamilton. Already an anti-establishment man with a long list of personal grievances against the ruling elite and upper class that he detested on St. Croix, Hamilton soaked up the fiery revolutionary sentiment of America and its heady egalitarian promise. Without the rise of this brewing conflict and his arrival in America occurring at exactly the right time, Hamilton would very likely have remained an obscure unknown individual lost to the pages of history.

Hamilton finally began to study at Elizabethtown (today’s Elizabeth), New Jersey, located just southwest of New York City on Newark Bay. The town was founded in 1664 and named after Queen Elizabeth I. Reverend Hugh Knox, his benevolent St. Croix mentor and chief supporter who had early recognized the young man’s potential, had given him introductory letters that allowed his entry into the Elizabethtown Academy. He did not have any relations in American nor hard currency except for the letters of credit secured from the Kortright and Company in New York City. Hamilton only had great expectations and winning ways in abundance to propel himself upward and onward. Here, just northwest of the northern edge of Staten Island and just west of the Hudson River, Hamilton thrived in his preparatory studies before gaining entry to college. More importantly, he excelled in the vibrant social world of Elizabethtown, where he made invaluable connections and lifelong friends of the social, political, and professional elite, including many attorneys: William Livingston, Elias Boudinot, William Alexander (Lord Stirling, who was of noble Scottish blood like Hamilton), and John Jay. Significantly, all of these men were destined to play leading roles in the struggle for liberty.

After six months of study at the academy (a prep school) thanks to Knox’s letter of introduction, Hamilton’s plan to attend school at the College of New Jersey (now Princeton University), a center of Presbyterian revolutionary sentiment, failed. Hamilton’s excessive academic ambitions required an accelerated course of study, which he boldly proposed to the school’s head, Scotland-born John Witherspoon. Hamilton’s proposal was rejected by letter from the board of trustees. Not deterred by the setback, Hamilton then applied to New York City’s King’s College (today’s Columbia University), where friend Ned Stevens studied, partly because he had new sponsors, such as William Alexander, who served on the college’s governing board. In addition, Hamilton was sufficiently urbane to thoroughly enjoy the bustling life of New York City, the throbbing economic center of America, compared to the dreary New Jersey backwoods of remote Princeton. To Hamilton’s delight, despite the fact that this educational institution was Anglican and Loyalist, King’s College accepted his plan to embark upon an accelerated course of study. He had finally fulfilled his desire to proceed on the fast track by the fall of 1773. More importantly, Hamilton’s rejection at Princeton thrust him into the heart of the swelling tide of revolution and among leading New York City patriots.

Only age eighteen, Hamilton had also targeted New York City because this was where the Cruger family had long conducted business. Hamilton possessed personal contacts through Kortright and Company, whose representative in St. Croix was Kortright and Cruger, which managed his educational allowance. In lower Manhattan, he boarded with an Irish immigrant tailor named Hercules Mulligan, and his wife Elizabeth. A handsome Irishman with blue eyes, Mulligan hailed from Coleraine, County Antrim, Ulster Province, north Ireland. The son of an accountant, he had migrated to America with his Scotch-Irish family at age six. Educated at King’s College and an Episcopalian born on the Emerald Isle in 1740, Mulligan was an influential leader of New York City’s Sons of Liberty and an active member of the New York Committee of Correspondence. Mulligan’s brother was a junior partner in the firm of Kortright and Company, while his father operated an accounting business, where he had once worked as a clerk: an experience shared by Hamilton in St. Croix. Hamilton and Mulligan were both gregarious and became fast friends.

Even more multi-cultural than the Caribbean, New York City was swept with a flood of new Enlightenment ideas about the meaning of freedom. Without hesitation, Hamilton had sided with the Americans in their quarrel against England, embracing a new patriotism and a nascent nationalism. Hamilton also continued to receive enlightened Presbyterian lessons (first learned from Reverend Knox in St. Croix) that emphasized the sacredness of republicanism and egalitarianism. Thanks to his dual educations from the New York Sons of Liberty and the egalitarian teachings of Presbyterianism, Hamilton quickly evolved into a champion of America’s destiny with a passion. Across America, a heightened sense of morality and religious faith, especially Presbyterianism, lay at the heart of the rise of republicanism.

Strengthened by Knox’s spiritual and liberal teachings before he had departed St. Croix, Hamilton’s Presbyterianism and his father’s faith from Scotland of the Great Awakening fused with the righteousness of revolutionary defiance toward Great Britain’s threats and dominance. The timely fusion was a natural fit for Hamilton, as he became a diehard revolutionary and nationalist. After all, he already had a considerable chip on his shoulder in regard to exploitive, arbitrary aristocratic authority and the abusive class structure on both sides of the Atlantic. Proving that he was very much his mother’s son, he naturally took to opposing the autocratic abuses of the ruling elite and wealthy planters, who had long arrogantly flaunted their high social standing to young men of a lower class like Hamilton.

After experiencing a freer life in an invigorating new land that was larger and more dynamic than he had imagined, Hamilton’s patriotism soared higher in the excitement of the times. His growing sense of nationalism had been fueled by meeting with the leading revolutionaries of New York City like McDougall. Born in Scotland, McDougall gave his most patriotic speech at the New York City Common, known as “The Fields,” near King’s College in July 1774, denouncing the harsh trade sanctions imposed by the British government on Boston, after the Boston Tea Party. But he was outdone by a slight, unknown teenager, who was a college student and an unknown to the people of New York City. Evidently without preparation, Hamilton took the stage and delivered a masterful speech on America’s behalf—which advocated a strong pro-Boston Tea Party stance and a commercial boycott of British goods—that left the crowd spellbound by its oratorical brilliance.

Quite by accident, the leaders of the Sons of Liberty had suddenly found a gifted spokesman. In another case of excellent timing, Hamilton needed New York City—America’s second largest city after Philadelphia—as much as New York’s relatively small group of zealous revolutionary leaders, needed a gifted writer, captivating street speaker, and deep thinker in the escalating propaganda war for the hearts and minds of citizens. After all, America’s largest commercial center was largely a Tory city. New York’s powerful provincial legislature consisted of faithful Loyalists with extensive political, economic, and personal connections to England. If not outright active Tories, many New Yorkers remained neutral, desiring only to stay out of the encroaching conflict. By contrast, the band of enthusiastic New York City revolutionaries, including their bright shining star named Hamilton, represented “the most daring spirits and the loftiest minds of the colony.”11

After New York City had grown into America’s major metropolis, Theodore Roosevelt, in 1906, concluded without exaggeration how “the purest and ablest New Yorkers were to be found in the ranks of the revolutionists…. The young men of ardent, generous temper, such as Alexander Hamilton, John Jay and Gouverneur Morris” played key roles in leading the way to revolution for New York’s patriots.12

Rising Up Against England’s Might

Like so many others of his day who fought for America, Hamilton had no prior military or political experience, but these class-based limitations did absolutely nothing to dim the young man’s ardor or confidence. Nevertheless, and as he had prophetically predicted to “Neddie” Stevens in regard to an armed conflict as a younger man (at age fourteen) in St. Croix in November 1769, Hamilton saw the encroaching war as an opportunity to earn distinction and win the respect from his peers to ensure his advance in a revolutionary society dedicated to equality.13

Of all the Founding Fathers, Hamilton was a man without a past (as he preferred under the circumstances) when he first arrived in New York City. America’s struggle offered the best chance of his life to literally reinvent himself into an entirely new man. Thanks to his own natural inclinations combined with the heady influence of New York City’s Sons of Liberty, Hamilton envisioned a people’s republic where anyone could rise on merit rather than social standing and wealth as on his detested St. Croix. Indeed, of “all the Founding Fathers, Hamilton was especially suited to fight for a new society where men could live together free of ancient customs and outworn prejudices” that had made his life difficult in St. Croix.14

Because he hailed from a faraway speck of a tropical island that was considered foreign to most Americans, especially because it was located in the Danish West Indies, Hamilton wanted to prove that he was a true American and republican. After his early July 1774 “Fields” speech that displayed his oratory skills that had mesmerized the crowd, Hamilton demonstrated his patriotic worthiness by advocating for American rights and an enthusiastic support for the First Continental Congress, and America’s liberty with brilliant writing that flowed so effortlessly from his hand. Clearly, even as this early date, Hamilton was demonstrating that he was a formidable dual threat—by way of pen and oratory—in the propaganda war to defy British dominance.

Hamilton gained greater public notice as a hard-hitting pamphleteer (under the appropriate name of “A Friend of America”) in an influential and timely piece of thirty-five pages published entitled “A Full Vindication of the Measure of Congress,” in December 1774. With analytical clarity, attorney-like precision, and a masterful style, Hamilton made the case that “Americans are entitled to freedom,” and systematically eviscerated the anti-Congress arguments of the gifted Loyalist writer and Anglican rector Samuel Seabury of Westchester, New York. In “A Westchester Farmer,” the Yale and Oxford man had wielded highly effective propaganda that dealt a severe blow to the patriot cause.

At this time, when a masterful rebuttal was needed to bolster patriot sentiment, especially in New York City, Hamilton was still a member of the student literary society at King’s College on the northern edge of New York City. A systematic dismantling of a brilliant writer who was a privileged, pompous Anglican clergyman and just the kind of authority figure that an outlier and natural rebel like Hamilton loved to mock and reduce in size, utilizing cleverly worded insults that packed powerful punches.

After Seabury answered his pamphlet, Hamilton then reentered the pamphlet war by releasing an even more hard-hitting attack in eighty pages, published on February 23, 1775, The Farmer Refuted. He especially emphasized his two greatest intellectual strengths, economics and politics, which revealed the immense depth of his knowledge and even prophetic insights that relatively few Americans had embraced at this time. Ever the optimistic visionary, Hamilton emphasized America’s future greatness and special destiny, if only the colonists would unite in their resistance against a common foe. Hamilton’s writings in his two masterful “Farmer” essays were broadly appealing and presaged central arguments later included in the Declaration of Independence, that many people believed that John Jay, a leading revolutionary and New York delegate of the First Continental Congress, was the author.

Hamilton early coveted the privilege of battling for the liberties of a freedom-loving people, joining the Sons of Liberty in February 1775 not long after his twentieth birthday. Thanks to his hard-hitting style on behalf of America in speech and pamphlet, he became “the darling” and “boy wonder” of the most diehard revolutionaries, especially the Sons of Liberty, in New York City. While still only a student in college, Hamilton had evolved into a respected patriot leader entirely in his own right.

Like Hamilton on his father’s side, Alexander McDougall was of Scottish descent, which represented another example of the importance of the extensive Celtic and Presbyterian contributions to America’s struggle for liberty. After all, the Scottish peoples’ own dream of independence had been crushed by English military might, and in many respects the fight in America was very much a continuation of an ancient war between Celtic people and Anglo-Saxons. For centuries, the English had become masters in the brutal art of smashing desperate liberation bids and budding nationalism among the Celtic people in Wales, Ireland, and Scotland: bloody lessons not lost to the immigrant sons of these conquered Celtic regions now living on American soil. Born on the island of Islay, Scotland, McDougall would form the First New York Regiment, and lose his beloved soldier son in America’s disastrous Canadian Campaign during the winter of 1775–1776.

Hamilton’s passion for independence early caused him to take the initiative in other ways besides masterful writing and fiery speechmaking. Hamilton enlisted in a volunteer infantry company of Manhattan men and boys known as “the Corsicans” under Captain Edward Fleming, a British Army veteran, with the news of the first clashes at Lexington and Concord, Massachusetts, in April 1775. He then gained invaluable knowledge about artillery from an experienced gunner, who almost certainly had served in the British Army like Fleming.

The ever-opportunistic Hamilton saw greater future possibilities for himself in service with the artillery arm than in the infantry. After learning about the proper useage of artillery from one of “the Corsicans,” therefore, he then helped to organize a volunteer artillery company, known as the “Heart of Oaks,” from a group of students in his literary society at King’s College in late 1775. Along with school mates Nicholas Fish and Robert Troup, former members of “the Corsicans,” and although still too young to shave, Hamilton wore a fancy and tight-fitting green uniform coat with a stylish brown leather cap distinguished by the words, “Liberty or Death.” He carried a flintlock pistol and a powder horn with his name carved in it. He also etched symbols on the powder horn that represented the true path to future success from his readings of Sir Francis Bacon. Hamilton’s hand-carved designs emphasized his motto of always looking forward to a brighter future, including the visualization of goals. He, therefore, carved a unicorn, which symbolized personal aspirations, with the design of a five-petal flower from the Hamilton family coat of arms on the hindquarters. After studying military manuals, meanwhile, he drilled his fifty student-gunners of the Heart of Oaks volunteer company on the grassy, open grounds of the churchyard of nearby St. Paul’s Church each morning before class at King’s College.

Then, May 10, 1775, Hamilton bravely intervened to quell an angry mob to save King’s College president Dr. Myles Cooper, who had been accused of Loyalist activities. Employing his masterful oratory before Cooper’s locked door, Hamilton bought time for the panicked president to escape in the nick of time. Clearly, even as a leading Sons of Liberty revolutionary in New York City, Hamilton had not lost his compassion or humanity for a Loyalist. Meanwhile, he continued his effective writing on behalf of the patriotic cause, including condemning the Quebec Act, because it extended the boundary of French Catholic Canada south and all the way to the Ohio River to infringe on America’s ambitions, especially colonies like Virginia, to extend farther west. Hamilton’s forceful arguments were printed in two essays published in the New-York Gazetteer, New York City. Not long thereafter, the native West Indian continued to demonstrate his skill with the pen with articles in the New York Journal. He produced a stunning total of fourteen essays in as many weeks under the pseudonym of “Monitor.” As usual, Hamilton emphasized how it was a conspiracy of corrupt and evil men of Parliament in London who were conniving to economically and politically enslave the American people.

Revealing that he was also a man of action, Hamilton was then part of a daring night raid that captured a large number of British cannon at the Grand Battery, located just south of rectangular-shaped Fort George at the southern tip of lower Manhattan Island, on the warm night of August 23, 1775. At the imposing artillery bastion—which contained two dozen large caliber cannon that faced New York harbor and had long protected the city from attack by water—Hamilton and more than a dozen King’s College volunteers played a role in rescuing the guns. With the sixty-four-gun British warship Asia close and seemingly about to send forth a shore party to take possession of the cannon, Hamilton and his comrades hauled off twenty-one of the precious guns. He risked his life in helping to evacuate cannon from the battery while under cannon-fire from the warship and musketry from soldiers manning a British patrol boat. On his own and ignoring the danger, Hamilton then returned to the battery and then coolly retrived his musket, misplaced by his friend Hercules Mulligan, that had been left behind.15

He resumed his studies at King’s College, but the drilling and training continued unabated on the grounds of St. Paul’s Church throughout the fall of 1775. When he left King’s College in January 1776 after around two years of study, Hamilton was determined to go his own way, despite not having formally graduated. Wartime requirements beckoned Hamilton, and he left his studies behind without regrets, because he knew that this people’s revolutionary provided unprecedented opportunities for a gifted young man on the rise. Long seen as a haven of Loyalists, King’s College was transformed into a hospital by the patriots. Ironically, the same classrooms where Hamilton had sat as a student were turned into prison cells for rebels, after the British captured New York City later in 1776.

At this time, the stern requirements of the revolutionary struggle called, and Hamilton’s days as one of America’s most effective pamphleteers and a Corsican and Hearts of Oak militiaman were over. Hamilton wanted to see action even to the point of rejecting lofty positions that guaranteed social connections and advancement. “I am going into the army,” he wrote on February 18, 1776, and Hamilton’s life would never be the same. Clearly, the young man was not a soulless mercenary type in this regard. When he was offered a prestigious position on the staff of his old friend Brigadier General William Alexander (Lord Stirling) through his friend Elias Boudinot, Hamilton declined. This was a surprising decision for any young officer except Hamilton, who was a true outlier in this regard. He utterly detested the concept of taking a subordinate role, although a staff officer’s position could provide a path to upward mobility on the coattails of a successful general.

Hamilton was determined to fulfill his ambition for active field command rather than staff duty. In consequence, he turned his sights on becoming a captain as a battery commander, after New York City friend Alexander McDougall, former ship captain and Sons of Liberty leader, recommended him as the commander (captain) of the New York artillery unit in February 1776. This artillery unit was to be raised by the New York Provincial Assembly to protect the city. Hamilton, consumed by revolutionary zeal and patriotic sentiment, was eager for action to prove his worth to one and all.

However, he lacked the necessary experience, and officers’ commissions only seemed to be awarded to well-known members of New York City’s social and political elite, and not to recent immigrants from a small Caribbean island or a young man fresh out of King’s College. This new artillery unit was the only battery that represented New York City, providing high visibility and widespread recognition for stirring accomplishments, if demonstrated on the battlefield. Even though he was an idealist in regard to America’s struggle, the young man from the West Indies had no illusions about the cost of fighting for freedom, and wrote on February 18, 1776, with his usual flair: “perhaps ere long [I] may be destined to seal with my blood the sentiments defended by my pen. Be it so, if heaven decree it. I was born to die and my reason and conscience tell me it is impossible to die in a better or more important cause.”16 Revealing that intellectual reasoning applied to scrutinizing his own motivations even in the midst of a sacred struggle for liberty, Hamilton excused his burning ambition to excel on the battlefield as just a common feature of human nature that was largely beyond his control: “The desire for reward is one of the strongest incentives for human conduct,” he wrote.17

An enigma and perhaps the most complex Founding Father, Hamilton was a rare blend of a man of action and scholarly intellectual. He was “one of the first Americans of the War of Independence to unlimber a cannon” in the name of America.18 However, despite the majority having no military experience themselves, the well-dressed aristocrats of the New York Provincial Assembly had to be convinced that this recent immigrant and a smooth-faced college student could command the respect of his older American-born volunteers to gain distinction on the battlefield for the city and assembly. Influential patrons continued to speak up in his behalf to support this young man unknown to Americans only a few months before. These included John Jay, of Huguenot descent, and Colonel Alexander McDougall, who was the son of a “Scots milkman.” But even this support was not enough to win Hamilton the coveted position; he would have to do it himself. As so often in the past, Hamilton then applied his can do aptitude for overcoming obstacles. He studied long and hard for the examination required to secure the coveted position. Improving upon what he had already learned as a college student outside of the classroom on the training ground of King’s College, Hamilton shortly became an expert in artillery, the army’s most technical arm, at a time when few Americans knew anything about it.

Hamilton’s graceful manners and dignified style revealed a confident natural leader of men, including those who were much older, and a proper gentleman that were viewed as so important in colonial and colonial society: requirements for the right kind of leadership in the eyes of New Yorker leaders, who also placed faith in McDougall’s and Jay’s vote of confidence. His diverse range of abilities also impressed the patriotic members of the New York Provincial Assembly. At age twenty-one, Hamilton won the appointment to command the New York “Provincial Company of Artillery” with the rank of captain on March 14, 1776. Hamilton became one of the youngest captains in America’s militia. Most importantly, he proved that he adhered to his own words that had been read by large numbers of Americans in a recent pamphlet: “the law of nature which gives every man a right to his personal liberty, and therefore confer no obligation to obedience.”19

Exhibiting a dashing style and a meticulous eye for detail that in part made him a good commander, Hamilton wore a splendid blue uniform coat newly made at a New York City tailor shop. Hamilton had always been a sharp dresser when he could afford to be, and he now continued his distinct style as a proud New York artillery officer. His captain’s fine uniform was very likely made at Hercules Mulligan’s tailor shop on Water Street in lower Manhattan, located near the wharves along the East River. Hamilton became a model officer, who would never lord over his men like most military leaders of the day. Assisted by Mulligan in scouring lower Manhattan, Hamilton had recruited a good many Irish and Scots to serve in his battery, including illiterate immigrants, and an occasional Dutchman with roots in the former New Amsterdam Colony. Hamilton’s artillery unit, the New York Provincial Company of Artillery, soon contained sixty-eight gunners, whom he trained intensely to become some of the best artillerymen in the service. These artillerymen wore blue coats with white shoulder belts of leather and brass buttons to reflect the “smart” appearance that Hamilton required of himself.

Hamilton was described by a Pennsylvania officer as “under middle size, thin in person, but remarkably erect and dignified in his deportment. His hair was turned back from his forehead, powdered and collected in a club behind. His complexion was exceedingly fair, and varying from this only by the almost feminine rosiness of his cheeks … as to figure and colour, an uncommonly handsome face [and] when in conversation it easily assumed an attractive smile.”20

The young officer was determined to prove himself, after having mastered the artilleryman’s art and win distinction on the battlefield. He had dressed and equipped his cannoneers, now some of the best-uniformed soldiers, who wore buckskin pants, in America, by using the remaining college funds provided by his St. Croix sponsors. Hamilton developed into a highly respected commander: Hard-working, conscientious, and always concerned for his men’s welfare to ensure their loyalty and full support.21 His well-honed business experience from his St. Croix days paid invaluable dividends in organizing and supplying his New York battery.22

Week after week, Hamilton trained and prepared his young New York artillerymen to oppose the finest British regulars in defending New York City. But he still found time to study the books to continue his education, while transforming his men into a very good artillery unit distinguished by its “appearance and the regularity of their movements.” He proved to be an ideal and popular commander, who early gained the respect of his gunners. Hamilton realized that it was only a matter of time before Great Britain launched a mighty expedition with the mission of crushing the rebellion. Ironically, as revealed in his late 1774 writings, when he was more naïve but still amazingly prophetic, Hamilton had been convinced that only “the grossest infatuation of madness itself [could cause the English monarchy to] enforce her despotic claims by fire and sword.” Then, in his The Farmer Refuted in early 1775 and with the keen insight for which he was becoming known, Hamilton “may have been the first in print to maintain that Britain could not win the war” in the end.23

Dramatic Meeting at Bayard’s Hill

On the orders of General William Alexander (Lord Stirling), Hamilton and his New Yorkers fortified some of New York’s highest ground on the north side of the city on Bayard’s Hill, hoping to stop British warships from sailing north up the Hudson. Young Captain Hamilton first met General George Washington there in lower Manhattan in mid-April. The austere Virginian and member of the Virginia elite with extensive French and Indian War experience inspected the newly built defensive bastion on Bayard’s Hill known as Fort Bunker Hill, bristling with a dozen cannon, which overlooked the city and the wide Hudson that led north to Albany, New York. Like Lord Stirling and New Englander General Nathanael Greene who had offered him a staff position that was also rejected, Hamilton made a highly favorable impression on the commander-in-chief. Looking and acting anything but like a recent immigrant from the West Indies as carefully cultivated, Hamilton garnered Washington’s compliments for him and his New York gunners for their “masterly manner of executing the work.”24

However, at this point in the conflict, Hamilton’s real war was now not on a battlefield against the British but rather against the mismanagement of authorities, who denied his gunners vital supplies. Knowing the importance of keeping up the spirits of his New York artillerymen, Hamilton fought for a fair share of supplies, including rations, and pay for his gunners: equal to that of Continental artillerymen. In an impassioned letter on May 26, 1776, to the provincial congress of New York in seeking equal treatment for his artillerymen, Hamilton made a righteous appeal to justice in his usual diplomatic style: “I am not personally interested in having an augmentation [of pay] because my own pay will remain the same that it now is; but I make this application on behalf of the company, as I am fully convinced such a disadvantageous distinction will have a very pernicious effect on the minds and behavior of the men. They do the same duty with the other companies and think themselves entitled to the same pay.”25

Hamilton’s First Combat as Artillery Commander

On his own initiative or perhaps under direct orders, Captain Alexander Hamilton laid plans to launch a daring night raid with the arrival of warmer and less rainy weather just after mid-June, after the spring rains had stopped. Envisioning a surprise attack, he targeted the British defensive position around the lighthouse at the northern end of Sandy Hook, New Jersey, south of New York Harbor and just southeast of Staten Island. Situated at the entrance of New York harbor, Sandy Hook, a thin peninsula that thrust north from the New Jersey mainland, was a strategic position. Hamilton struck in the darkness in an assault in which he carefully coordinated the fire of his New York artillery pieces and infantry attackers. Conducting his first offensive strike, the young captain mixed musketry with artillery fire of approximately one hundred men, taking advantage of the darkness and the element of surprise. But the enemy’s defensive position was too strong to be overcome. Hamilton revealed his trademark hard-hitting style: “I continued the attack for two hours with [his New York] fieldpieces and small arms, being all that time between two smart fires from the shipping [British warships just outside Sandy Hook] and the [defensive position around] the lighthouse, but could make no impression on the walls” of the British defensive position. This sharp clash at Sandy Hook has become one of the forgotten fights of the American Revolution.

Meanwhile, Washington was placed in a no-win situation by the rising chorus of demanding politicians of the Continental Congress and the impossible mission of defending New York City. Because Manhattan Island was surrounded by a network of waterways, Washington was unable to develop an adequate tactical solution for defending the city. Nothing could counter the powerful Royal Navy, which guaranteed that America’s largest city would fall, after England had dispatched the largest fleet and expeditionary force ever set forth, under General William Howe. On June 28, and not long after he returned from his Sandy Hook raid, Hamilton watched the execution of Irishman Sergeant Thomas Hickey in lower Manhattan, near the Bowery, for his role in a plot to murder General Washington in a city swarming with Loyalists. Hamilton fully approved the execution that he hoped would cow “those miscreants,” the large Tory population of New York City.

In early July, General William Howe finally made his first tactical move, disembarking thousands of British and Hessian troops onto Staten Island from warships of his brother Lord Richard Howe’s fleet. Hamilton and his gunners saw their first action on July 12, barely a week after the signing of the Declaration of Independence in Philadelphia. The spirits of Hamilton and his men were high, after Washington announced the issuing of the declaration to his troops assembled on the New York City Common, where the native West Indian had made his impassioned speech two years before. Still smarting from having recently lost his purse containing his officer’s pay, (which happened on July 6, perhaps from too much drinking from America’s first Fourth of July celebration), Hamilton might have been in a bad mood. If so, he was presented with an opportunity to finally unleash his wrath on the enemy.

Two British warships, the Rose and the Phoenix of the powerful fleet of Admiral Richard Howe, the brother of General William Howe, caused panic on Manhattan Island by sailing up the Hudson to probe the strength of the American defenses, including Fort Bunker Hill. Nothing could stop the two warships that demonstrated the tactical superiority and skill of the British Navy: an ill-omen for American forces in regard to attempting to defend a city surrounded by waterways. From this high point on Manhattan Island, Hamilton gave the command to fire. His men opened up with their guns at the British vessels. King George III’s sailors returned fire upon Hamilton’s earthen fort atop the commanding heights. Because of inferior artillery in terms of caliber, Hamilton’s resistance proved largely ineffective, allowing the two warships to continue sailing up the broad Hudson. Several New York artillerymen were injured when the barrel of one Hamilton’s guns exploded, most likely because the barrel was defective because of age or inferior quality. Contrary to the opinions of some historians, Hamilton was not at fault for what was nothing more than an accident.

With an elaborate defensive network protecting New York City that Washington attempted to hold in the hope of inflicting another defeat like at Bunker Hill (Breed’s Hill just outside Boston)—if General Howe was foolish enough to order frontal assaults as on that bloody day last June—the British wisely refused the bait of launching infantry attacks. Unfortunately, feeling that he had to face the British Army’s might—now swollen to forty-two thousand men to outnumber Washington’s Army—partly because this upcoming confrontation was a “point of honor” and under political pressure from the Continental Congress to defend New York City, Washington was already in serious trouble long before the first shot in the showdown for New York City was fired in anger. He had dispersed his troops over a wide area to defend Manhattan and Brooklyn, which Hamilton correctly believed was indefensible. In fact, this precocious young man sensed the fast-approaching disaster, because Washington had divided his army, which was now separated across a sizeable body of water, the Upper Bay just below the East River.

Finally, Howe struck when he felt the opportunity was right. The Royal Navy sailed from Staten Island and landed thousands of troops on the southern end of Long Island at Gravesend Bay. After coming ashore via new, innovative landing crafts on the warm morning of August 22, Howe’s troops then skillfully maneuvered inland. Around seventeen thousand British and Hessian soldiers marched seven miles to the northeast to outflank American defensive positions, and eased themselves into an ideal position to strike Washington’s rear south of Brooklyn Heights, to catch the badly outnumbered homespun rebels by surprise. Lord William Howe’s professional troops struck a powerful blow that sent the American forces reeling on August 27 during the battle of Long Island.

Meanwhile, maintaining his longtime defensive position on Manhattan Island to the northwest, Hamilton and his New York gunners from atop Bayard’s Hill, the highest point in the city, listened to the battle roaring on Long Island. Washington was driven to new levels of frustration by the rout. The embarrassing defeat—a new low for the novice Continental Army and the largest battle to date—showed that the amateurs in rebellion (this was Washington’s first experience in commanding an army in a sizeable battle) were no match for well-trained troops led by experienced, professional leaders.26

After the survivors of the disastrous battle of Long Island were transported west in flat-bottomed boats by Colonel John Glover’s New England mariners across the mist-covered East River on the night of August 29 to Manhattan Island’s safety during the narrow escape, Washington still attempted to hold the strategic island, which only guaranteed the same inevitable bleak results, because of the Royal Navy’s vast superiority. However, the sound arguments of his top lieutenant, General Nathanael Greene, had convinced the commander-in-chief otherwise. Washington wisely decided to abandon New York City before it was too late, because the British Navy could land large numbers of troops north of Washington at anytime to trap his army on Manhattan Island. At a commanders’ conference on September 12, it was decided that the army of ill-trained troops, who were no match for redcoat regulars, should retreat north up the Hudson to the easily defendable high ground of Harlem Heights.

Two young officers who would win distinction in the years ahead played key roles in protecting Washington’s withdrawal (“I was among the last of our army that left the city” bragged Hamilton for good reason) northward up Manhattan Island. After sailing up the East River, Howe’s forces landed at Kip’s Bay, around nine miles southeast of Harlem Heights, on a Sunday that Washington never forgot. What happened at Kip’s Bay was an alarming reminder of what could also happen on the island’s west side along the Hudson, because of the Royal Navy’s strength and capabilities: the British could land large numbers of troops at will north of Washington’s Army to cut-off escape from Manhattan Island. Here, at this natural indentation located on the island’s east side above New York City, a heavy cannonade of nearly eighty guns from Admiral Howe’s warships and the unnerving sight of thousands of British-Hessian troops rowing toward shore in barges caused a rout of the raw New England soldiers on September 15, 1776. Without losing a single soldier, Howe succeeded in negating the American riflemen in defensive positions—the old Bunker Hill formula for success—with a massive artillery bombardment.

But two highly capable young officers had restored a measure of honor to the Continental Army during the dismal withdrawal. As a strange fate would have it, the destinies of Hamilton and Aaron Burr were already intertwined on the American stage by the time of the retreat to Harlem Heights. Despite now wearing Continental officer uniforms of blue, one of these promising men was destined to take the other’s life in a little more than a quarter century. Hamilton’s New York battery had been now reduced in firepower, after having been forced to leave their heavy guns behind, at Fort Bayard, after Washington had issued orders for New York City’s evacuation. Therefore, Hamilton now commanded only three light guns of his reduced New York battery.27

A historian before he became the nation’s twenty-sixth president in September 1901, Theodore Roosevelt emphasized the value of the Hamilton-Burr connection in protecting Washington’s vulnerable rear during his withdrawal north from New York City. Washington’s “divisions, on their retreat, were guided by a brilliant young officer, Aaron Burr, then an aide-de-camp to [General Israel Putnam, while the army’s] rear was protected by Alexander Hamilton and his company of New York artillerymen, who in one or two slight skirmishes beat off the advance guard of the pursuers.”28

During the cheerless withdrawal north to Harlem Heights, and assisted by Burr’s knowledge of the road leading north, Hamilton repeatedly rose to the challenge of protecting the army’s rear, demonstrating leadership abilities noticed by his superiors, including Washington. As planned, Washington took good defensive position on the commanding ground of Harlem Heights just over a dozen miles north of New York City. He naturally hoped that Howe would commit the folly of assaulting the fortifications situated atop dominant terrain. Fulfilling his rearguard role for the army, young Captain Hamilton was one of the last Americans to reach the safety of the new defense line. Forced to drag their guns because artillery horses had been lost, he and his New York gunners arrived after dark on another warm September night with their two New York cannon, after one of his guns broke down and had to be left behind, along with the artillery unit’s baggage. Only because the British pursuit lacked vigor, Hamilton was fortunate not to have been captured.

Here at the rocky plateau known as Harlem Heights, including bluffs ascending to a height of around sixty feet, was a panoramic view of the southern end of Manhattan Island, where Hamilton selected a good position in Washington’s newly constructed defensive line and carefully placed his two light guns for the best fields of fire. Even the survivors of the Kip’s Bay disaster were emboldened by Washington’s high ground defensive position brimming with artillery, including Hamilton’s New York guns. Washington again viewed Hamilton’s organization skill and military bearing at his new defensive position that had been bolstered by light earthworks to protect his two cannon. Washington was impressed by what he saw.

But Howe had learned his Bunker Hill lesson well on June 1775, and never forgot his frightfully high losses. He refused to take the bait of attacking the formidable Harlem Heights, although fighting did erupt on September 16. Once again, the Royal Navy landed large numbers of Howe’s troops north of Washington’s stationary position to negate the high ground advantage. The out-maneuvered revolutionaries were once again forced to withdraw north from Harlem Heights toward Manhattan Island’s upper tip, when the leaves of October had already turned to their autumnal hues of red and gold, especially the maples, to reveal a natural beauty that seemed to mock America’s sinking military fortunes and the creeping darkness that surrounded the increasingly vulnerable life of an infant republic.

Rising to the Challenge at White Plains

After being forced to depart from his excellent defensive position along Harlem Heights, Washington retreated farther north to White Plains, New York. Here, he fortified another good high ground position, presenting Howe with still another formidable defensive array. But Chatterton’s Hill, part of a ridge looming at around one hundred eighty feet in height at this point on the vulnerable American right and overlooking the Hudson River just to the west of Washington’s main defensive position, was a vulnerable point of this weak defensive line. Washington had massed most of his troops on the high ground to the east, forcing Howe to look elsewhere to strike.

Therefore, correctly ascertaining a good tactical opportunity west of the Bronx River on October 28, Howe ordered the capture of the vulnerable Chatterton’s Hill. Positioned on the high ground overlooking the Bronx River, Hamilton had a bird’s eye view of the surrounding countryside. He became alarmed by the dire threat posed by the advance of Howe’s troops in fording the Bronx River, that flowed between Chatterton’s Hill (to the west) and Washington’s main line (to the east), and then Howe’s surge up the hill in a bid to turn Washington’s right flank. Responding quickly to the day’s most serious threat to the defenders of Chatterton’s Hill, who numbered only about a thousand, Hamilton immediately ordered two of his light guns dragged into an excellent firing position on a rocky ledge of the hill that overlooked the river. From this elevated vantage point, Hamilton opened fire on the German Hessians, crack mercenary troops led by highly capable professional officers, in the river valley below, who were attempting to cross the river by wading and ascending the commanding elevation.

Just as the Hessians seemed about to overrun Chatterton’s Hill, out-flank Washington’s Army, and win the day, Hamilton’s timely and accurate fire proved effective in turning the tide. With well-aimed fire, combined with an eruption of musketry from the Delaware and Maryland Continentals who protected the flanks of his New York cannon, Hamilton stopped the determined Hessian attempt to turn Washington’s weak right flank. With only two guns, Hamilton’s leadership decisions and quick actions saved the day. Despite this, Howe’s resurgent troops eventually captured the hill, forcing Hamilton to retire to save his two guns. However, the resistance effort fueled by Hamilton’s guns helped to convince Howe to conclude his offensive effort on October 28. Young Captain Hamilton basked in his sparkling success which for once allowed Washington to inflict more losses than he suffered, in an inversion of the usual formula of the disastrous New York Campaign. At only age twenty-one, Hamilton reveled in an impressive battlefield performance.

After so many American reversals around New York City, the euphoria stemming from the signing of the Declaration of Independence had evaporated among patriots by the fall of 1776. New York City had been lost and Washington had been defeated in a series of battles during the nightmarish New York Campaign. Washington could not hold Manhattan due to the powerful Royal Navy, thousands of well-trained British and Hessian troops, and General Howe’s tactical skill. Before withdrawing to the mainland, Washington left large numbers of troops at the five-pointed star-shaped earthen walls of Fort Washington. Located on the high ground known as “Mount Washington” that dominated Manhattan Island’s northern end and overlooked the Hudson River, the ill-fated Fort Washington represented the Americans’ last fatal grip on Manhattan.

Nested on the commanding high ground located between Harlem Creek to the east and the Hudson, this massive fort in Upper Manhattan had been named after the commander-in-chief. Fort Washington stood across the wide Hudson from Fort Lee, New Jersey, just slightly to the southwest. But its inevitable dismal fate was only a matter of time, proving the folly of Washington’s strategic plan of fortified posts. Fort Washington’s fall and the capture of more than two thousand of the army’s best Continental troops on November 15, 1776, represented still another bitter defeat and a stunning blow to the reeling homespun revolutionaries. Then, after Fort Lee’s fall on November 20, Washington had no alternative but to withdraw southwest through New Jersey, as desertions skyrocketed during this exceptionally dark period for America’s fortunes.29

Winning Glory along the Raritan River

Reinforced by another ten thousand troops for his invasion of New Jersey after Fort Lee’s capture, a supremely confident Howe then turned his sights on vulnerable Philadelphia, America’s capital. General Howe followed Washington’s reeling army deeper through the lowlands of New Jersey, pushing southwest across a landscape bathed in bright autumn colors of perhaps during what could have been the last autumn for the independent republic, if the British and Hessians continued their winning ways. Washington implored General Charles Lee, who commanded a separate portion of the Continental Army, to watch over the New York Highlands, to join him. The Virginian now envisioned making a united stand on the Raritan River, one of New Jersey’s major rivers, near New Brunswick in north central New Jersey and southwest of New York City. But the cunning Lee, who had ambitions of replacing Washington as commander-in-chief, refused to march south to Washington’s assistance. Washington and his ever-dwindling band of soldiers were now on their own to make the best out of a very bad situation that continued to get worse, while retiring to avoid certain destruction from what appeared to be an unbeatable opponent.30

During the long withdrawal toward Philadelphia to the southwest, Hamilton led his New York artillery past the Elizabethtown Academy, New Jersey, where he had once studied with visions of a bright future on America soil without the horrors of war. During this period of gloom, he was described by an officer as “small, slender, and with a delicate frame.” But these undistinguished outward appearances of this serious-minded and intense young man were deceiving, a characteristic that Washington had already learned, and would soon see again.

After crossing the Raritan River on the “New Bridge” and reaching New Brunswick, nestled on the river’s south bank, Washington gained the protection of a river between him and his pursuers. But because of massive desertions, he lacked the necessary strength to make a defensive stand. Consequently, Washington planned to continue his retreat toward eastern Pennsylvania and Philadelphia. The wooden bridge spanning the Raritan River had been erected in early 1776 to replace the ferry, providing Washington with an easy means of crossing the river with his ragtag army. After the motley collection of the remaining troops crossed over the wide Raritan that was tidal at this point, they hurriedly removed the large wooden planks to prevent Howe’s troops from crossing. Therefore, only a nearby ford now offered Howe a good crossing point. Consequently, this key location needed to be defended to buy precious time.

In a timely defensive stand on the south bank of the Raritan to protect Washington’s withdrawal south toward Trenton, New Jersey, on November 29, Hamilton’s leadership abilities and skills as an artillery commander were once again demonstrated. Fortunately for Washington and his retreating men, Hamilton had transformed his artillery command into “a model of discipline” by this time. Here, along the high riverbank, Hamilton’s two blazing six-pounders kept the encroaching British and Hessians at bay hour after hour. Animated by the hot action and his heavy responsibility to hold fast in the army’s rear, the energetic captain in his neat-fitting blue uniform was everywhere at once, shouting instructions and instilling confidence among his New York gunners, who hoped to hold Howe’s legions at arm’s length.

The twenty-one-year-old artillery officer bought precious time, helping to save Washington’s depleted army as it limped slowly toward eastern Pennsylvania and an unknown fate. Imploring his New York artillerymen to fire faster and more accurately from their protected ledge of high ground along the Raritan, Hamilton experienced one of his finest days. He encouraged his New York cannoneers to maintain a blistering fire, resulting in a lengthy duel with a row of British artillery.

With Hamilton commanding his New York guns with skill, Colonel Henry Knox’s faith in his young battery commander was well-rewarded. He had placed his trust in what Hamilton could accomplish against the odds in a true crisis situation. Meanwhile, to the southwest, Captain Hamilton’s barking guns were beautiful music to Washington’s ears, providing him with a sense of relief that his vulnerable rear was now well-protected during the long withdrawal to Princeton, New Jersey. Most importantly for an extended period, with his accurate covering fire, Hamilton had succeeded in keeping an aggressive enemy at arm’s length, while Washington led his weary survivors south toward Princeton. All of this was accomplished at great risk to himself and his New York gunners. With the enemy drawing closer, Hamilton ordered his men to switch from cannonballs to canister to dissuade Howe’s finest light troops from crossing the at the ford: a wise decision that bought more precious time for Washington’s army to farther slip to safety.

After a job well done, Captain Hamilton became the talk of a thankful army, because his defiant last stand ensured that the Continental Army would escape to live and fight another day. Having seen Hamilton’s spirited defense of the Raritan ford in a critical situation, Washington sent one of his aides back to the front for the express purpose of learning the name of the officer who commanded the guns at the ford, because Colonel Knox had ordered the timely placement of Hamilton’s guns after Washington departed. Wishing that he had a good many more fighting men of Hamilton’s caliber after Knox had sung the young man’s praises, Washington was “charmed by the brilliant courage and admirable skill” of the young artillerist, who always performed at his best in the greatest crisis situation. Not having seen the action at the Raritan ford, Washington later informed Congress in an early December letter about the sudden appearance of “several parties on the heights opposite Brunswick and were advancing in a large body towards the crossing place [and] we had a smart cannonade,” in which the trusty Hamilton had played the leading role.31

Captain Hamilton’s impressive battlefield accomplishments seemed to contradict a placid façade, boyish handsomeness, and slight physique which gave little hint of the hard-fighting qualities and fiery nature of the “Little Lion” that lay just beneath the calm surface. Hamilton was described by an older and much larger soldier, who could hardly believe his eyes, as “a mere stripling [who wore in jaunty fashion] a cocked hat pulled down over his eyes,” while leading his artillerymen with skill and boldness.32

Equally shocked by the sight of the boyish Hamilton and his powder-grimed gunners when they reached Princeton after their spirited defiance along the Raritan, another one of Washington’s men marveled at the finely uniformed commander who so often skillfully led the New York battery, which “was a model of discipline; at their head was a boy, and I wondered at his youth, but what was my surprise when he was pointed out to me as that Hamilton of whom we had already heard so much.”33

With a look that was guaranteed to win the hearts of the ladies, Hamilton was fine-boned, slender with an erect military bearing, and of only medium height. With reddish-brown hair and an “almost pretty face,” and one that was “never to be forgotten,” wrote one woman, Hamilton’s appearance gave little clue of the depth of the boldness of this young officer, who would fight to the last artillery round and last man if necessary. He performed so well and audaciously, but not recklessly, on the battlefield that onlookers, military and civilian, were amazed by his growing list of martial exploits that gained the admiration of the army’s senior leaders, including Washington. Captain Hamilton was indeed Washington’s feisty “Little Lion,” whose roar was familiar to a large number of British and Hessian troops.

But Captain Hamilton’s military gifts were manifested in other ways. Two years before his defiant stand along the Raritan, Hamilton had already outlined that strategy that would eventually result in the defeat of the British Army. As an undergraduate student at King’s College and barely out of his teenage years, he had written with prophetic vision and wise insight in making a bold claim that England could not win this war: “The circumstances of our country put it in our power to evade a pitched battle [because] it will be better policy to harass and exhaust the [British] soldiery by frequent skirmishes and incursions than to take the open field with them, by which means they would have the full benefit of their superior regularity and skills. Americans are better qualified for that kind of fighting which is most adapted to this country than regular troops.”34

Surprise Attack at Trenton

Meanwhile, Washington’s gloomy retreat though New Jersey continued unabated during America’s darkest hour to date. Washington finally took a tenuous defensive position on the Delaware River’s west bank on the Pennsylvania side, after crossing the brownish river just ahead of the pursuit of Lord Charles Cornwallis, Howe’s capable top subordinate. But with time running out for the enlistments of so many Continentals at year’s end, Washington’s situation was becoming even more critical. Knowing that a victory was desperately needed to lift the patriots’ flagging spirits after so many recent reversals, Washington decided to launch a daring strike on the early morning of December 26: the kind of wise guerrilla-like strategy that Hamilton had advocated in his masterful The Farmer Refuted, written while a King’s College student even before he had ever seen a battle.

Washington was presented with a golden tactical opportunity, after Howe decided that the campaign of 1776 was over, before delivering a knock-out blow. He therefore established winter quarters and an over-extended line of defensive posts that stretched across New Jersey and all the way back to New York City. A lover of high living, the aristocratic Howe returned to New York City to enjoy urban delights, including his mistress. Washington took full advantage of the suddenly more favorable situation. He outlined his audacious battle plan at a commanders’ conference to his top lieutenants and other officers, including Captain Hamilton. Hamilton had been recently stricken with a “long and severe fit” of illness, in his own words. Unable to perform any duty, he had been bedridden “in the back room” of Colonel Knox’s headquarters at the John Chapman House, located on the north side of Jericho Mountain in Bucks County, Pennsylvania.

Despite the risks involved in such an audacious strike that called for a risky river crossing and a lengthy march of nine miles south to Trenton amid the dead of winter, the young man had literally willed himself out of the sickbed in order to get back on his feet just for the opportunity to lead his New York artillerymen (now reduced to fewer than thirty followers) in the upcoming operation. At this time, his splendid performance during the long New Jersey retreat, especially in the defense of the Raritan ford, was still the talk of the army.35

In a critical situation, Washington was now going for broke because he had no choice. It was now literally a case of do or die for the patriot cause. He planned to transport his remaining Continentals to the east side of the Delaware River in order to launch a surprise attack on the sizeable Hessian garrison of Trenton by sunrise of December 26. Quite simply, this was Washington’s last opportunity to reverse the fast-declining fortunes of a dying revolution. A desperate Washington hoped to vanquish the seasoned and well-trained professional Hessian soldiers, which had proved impossible in the past. Fortunately, Washington could count on some very good men, including Captain Hamilton, for undertaking his supreme challenge. The stoic soldiers who now remained by Washington’s side were now the very backbone of the resistance effort and quite literally America’s best and brightest like Hamilton, after the mass desertions and casualties.

In the fast-fading daylight of a bleak Christmas Day, Washington’s ragtag revolutionaries assembled in silence on the Delaware’s west bank. Here, they prepared to cross the ice-clogged river at McConkey’s Ferry about nine miles above Trenton. Not long after the sun dropped in a frozen sky that brought the first harsh offerings from a winter storm that had suddenly descended over the Delaware River Valley, the first of Washington’s soldiers began to cross the swift Delaware in Durham boats. These sturdy wooden boats were manned mostly by Colonel John Glover’s mariners from the Massachusetts seacoast, especially the fishing port of Marblehead that overlooked a beautiful bay. After Washington’s ill-clad infantrymen had been rowed across the Delaware’s swirling waters following much effort by Glover’s hardy men during the tempestuous night, the first of Colonel Henry Knox’s eighteen guns were pushed and pulled onto the wide bottoms of the ferry boats for the perilous crossing not long after midnight.

Wearing a makeshift cape fashioned from an old blanket for slight protection against the icy rain, snow, and biting cold of late December, Captain Hamilton made sure that his six-pounder guns and battery horses were aboard the ferry boat. Hamilton’s guns were transported safely across the angry Delaware without incident during the nerve-racking crossing, when the Durham boat was rocked by chunks of ice slamming into its side. Hamilton must have wondered about the strange course of his life that had brought him to this crossing on one of the coldest of nights of the year and so far from the tropical warmth of his native Caribbean. During his St. Croix exile, he had prophetically dreamed about winning glory and distinction, writing in his November 11, 1769, letter to his good friend Edward Stevens, “I wish there was a war”: a great dream of youth that had come true, but one that perhaps Captain Hamilton now regretted, given the circumstances.

While a mixture of snow, rain, and sleet poured down across a landscape already shrouded in a fresh blanket of snow, Hamilton attempted to stay warm as best that he could amid the howling December winds. He fondly recalled the warm ocean breezes and blue turquoise waters glittering in the Caribbean sunshine during the grueling ordeal. The young man often showed his love for his New York cannon, even “patting [the barrel of one], as if it were a favorite horse or a pet plaything,” wrote one amused older officer.36 Hoping to exceed his Raritan River exploits, Hamilton was encouraged by the resolve of his stoic men and his commander’s adherence to guerrilla-like tactics that he had long advocated. Bolstering his confidence for a successful outcome at Trenton, Hamilton believed that Washington’s remaining Continental soldiers, tough and seasoned regular troops, were “ready, every devil one of them” for the great challenge that lay ahead.37

After eight hours of high anxiety on a nightmarish night, Washington finally transported all 2,400 of his best men (mostly Continentals) and artillery pieces across the Delaware under Knox’s supervision while sleet and snow poured down. Once safe on the small plot of flat ground on the river’s eastern bank, Hamilton quickly mustered his New York gunners, who were now wet and cold. Then, he went to work getting his guns and half-frozen men for the advance east up high ground from the river to eventually gain the road that led the nine miles south over the white expanse to Trenton’s northern edge.

Finally, Washington gave the word for his hopeful troops to move out in the blackness. Hamilton led his New York artillerymen up the timbered hill shrouded in snow. After pushing east up the ascending terrain, now white with freshly fallen snow, to gain the high ground above the Delaware, the soldiers of the lengthy column continued east before turning south down the Scotch Road that led to Trenton. The first major natural obstacle encountered by Washington’s troops on the march south was the heavily wooded environs of Jacob’s Creek. Here, the unfamiliar terrain descended sharply into the narrow creek valley, a deep gorge cut by the now-raging watercourse, amid the silent woodlands. With much effort and as gently as possible, Hamilton and his gunners eased their cumbersome artillery pieces down the steep slope leading to the creek, after Washington’s column of infantrymen had churned up the ground, making it more slippery for weary soldiers and horses.

With Hamilton working beside his men and shouting orders, the New York artillery pieces were hauled across the creek’s freezing waters, after much effort. Hamilton’s gunners, including their captain, who was not mounted like Washington at the head of his troops, got their feet wet while crossing the swollen stream. After gaining the high ground on the creek’s south side, the lengthy column moved out once again, heading south during a trek toward Trenton. At the small community of Birmingham, New Jersey, Washington divided his column into two divisions to strike Trenton from two directions.

General John Sullivan, a hard-fighting Presbyterian of Scottish heritage like Hamilton, commanded the First Division. Commanding his division of mostly New Englanders with skill, General Sullivan, who had been taken prisoner at the battle of Long Island but was exchanged shortly before the battle of Trenton, was ordered by Washington to march southwest to gain the snow-covered River Road that paralleled the Delaware and then entered Trenton’s southwestern edge. Meanwhile, Washington and Hamilton remained at the head of General Nathanael Greene’s Second Division. Part of the brigade commanded by his old friend Lord Stirling (William Alexander), Hamilton’s New York battery was placed in front of Greene’s column. Hamilton’s guns were in an advanced position in the column to occupy the strategic high ground at the town’s northern edge to command Trenton nested in the river valley below to the south, once the vanguard of Greene’s column reached its objective. Once in position, the two arms of Washington’s pincer movement were then to close tightly around the three regiments of Colonel Johann Gottlieb Rall’s Hessian brigade in the river valley. But besides the disproportionate amount of artillery, the key to Washington’s masterful battle plan was to strike as closely to sunrise as possible, although his delicate timetable had been ruined by the time-consuming river crossing and the raging storm that had slowed the march south.

After trekking nine miles and finally reaching the strategic high ground at Trenton’s northern edge, Washington and Hamilton rejoiced that all three Hessian regiments had been caught by surprise. Knowing that the key to the battle’s outcome now depended upon placing all of Colonel Knox’s artillery, including Hamilton’s New York State battery, in a row along the commanding high ground that overlooked Trenton, Washington and Knox ordered the guns into their elevated positions atop the freshly fallen snow. At the head of Greene’s column, Hamilton shouted to his gunners to hurriedly unlimber their cannon on the windswept heights.

Finally, after getting the field pieces through the snow, the New Yorkers placed their guns in their assigned positions at the head of Queen Street, just east of King Street. These two parallel main streets ran through Trenton, from north to south, and down the slope to the Delaware. Once his field pieces were aligned on the heights and his cannoneers took careful aim at their targets below in the town situated on the banks of the Delaware, Hamilton gave the order to fire. The young artillery officer from King’s College described how, “one of the first groups [of Hessians] was cut down by” the fire from his New York guns.38

As he had fought during the defensive stand against the odds along the Raritan River, Captain Hamilton also excelled in the stiff challenges of urban combat. Contrary to myth, the Hessians were not drunk for a late night celebration. Instead, they were ready to fight back with great spirit. Therefore, the showdown at Trenton was one of the hardest-fought battles of the American Revolution. To inflict additional damage on the Knyphausen Regiment (Colonel Rall’s rightmost, or easternmost, command) that had hurriedly aligned along Queen Street, Hamilton aggressively employed his guns like “flying artillery.” Demonstrating tactical skill and flexibility, he ordered some guns pushed south down the snowy street, easing closer to the splendidly uniformed members of the Knyphausen Regiment to provide greater assistance to Washington’s charging infantrymen battling in the snow-covered streets, their first experience in urban warfare. Then, exploiting the opportunity to the fullest, the tactically astute captain played a key role in the Hessians’ encirclement. Such aggressive tactics made the surrender of Rall’s fusilier and grenadier brigade inevitable. The brave Colonel Rall had fallen from his horse, mortally wounded by riflemen in the bitter street fighting, while leading a daring counterattack west and back into the heart of Trenton.39

Sealing the fate of the Hessian brigade, Captain Hamilton had no idea at this time that his effective artillery fire was made possible by a precious reserve of black powder (many infantrymen’s muskets were wet and unable to fire in the snowstorm) that had been smuggled to America from the same tropical islands where he had been raised. Clearly, the many ironies of Hamilton’s life were played out in a variety of ways at Trenton, where America’s struggle for liberty was revitalized by Washington’s remarkable victory. But that promising life had almost come to an abrupt end at Trenton, where he had “narrowly escaped [Hessian] cannonballs, which whizzed by his ears” on this day of destiny.40

Washington Strikes Again: Princeton

Emboldened by his elimination of an entire seemingly invincible Hessian brigade (along with its dynamic Colonel Rall who had never previously known defeat on American soil) at Trenton and to continue to fan the flames of a rekindled resistance effort to restore faith in the revolution’s prospects, Washington decided to again cross the Delaware on December 30. With his fighting blood up after his Trenton success, he planned to strike again at the college town of Princeton, garrisoned by the British, to make a mockery of the British claim that New Jersey had been subjugated and that the war was all but over. Picking off isolated New Jersey garrisons offered the tantalizing possibility of forcing the British to withdraw all the way back to New York City.

However, Lord Charles Cornwallis, bent on revenge after the sharp setback at Trenton that had caught him by surprise, reinforced Princeton on January 1, 1777. Cornwallis believed that he now had Washington trapped on the river’s east side at Trenton, which he reached the following day. Washington made a defensive stand on high ground above Assunpink Creek on the south of Trenton, repelling Cornwallis’ attack by massive artillery fire, including from Hamilton’s guns. After having left Princeton too lightly defended following what has been called the Second Battle of Trenton (also known as the Battle of Assunpink Creek), Cornwallis never expected that Washington would then dare to launch a strike in his rear, however.

Displaying tactical audacity after leaving campfires burning and sentinels in place to fool Cornwallis who remained on the Assunpink and confident that his opponent would be easily destroyed with the sunrise, Washington then stole a march on Howe’s most capable top lieutenant by pushing north in the night to deliver an audacious attack. Under cover of darkness, he skillfully sidestepped Cornwallis’ advanced force by easing quietly to the right, marching a dozen miles upon Princeton. To maintain silence while stealthy passing by Cornwallis’ troops, the wheels of Hamilton’s New York guns were wrapped in rags and blankets. Washington’s nighttime maneuver was masterful, and reminiscent of his daring strike on Trenton. Just outside Princeton on the morning of January 3, the advance of Washington’s troops, under Scotland-born General Hugh Mercer, then ran into a seasoned brigade of redcoats on the march to link with Cornwallis. Appreciating the irony, Hamilton entered the fray at Princeton, where he had first attempted to enroll as a student at the prestigious college not long after his arrival in America.

Exploiting the tactical advantage gained by Washington’s troops in hurling the British rearward like at Trenton, Hamilton and New York gunners of a “model” artillery command went into action with high spirits. But they shortly faced a formidable challenge at Nassau Hall, which was the College of New Jersey’s and the town’s largest building. Located just south of the Post Road, this sturdy structure was now filled with hundreds of British soldiers, who found timely refuge there. They had been hurled rearward by General Sullivan’s attackers, but the Britons were now determined to hold firm. To reduce the defensive bastion after setting up his guns in the yard of the college and at close range, Hamilton opened up with his six-pounders on the rear of Nassau Hall, which no doubt brought some personal satisfaction to the young man who never forgot a slight from his so-called social superiors.

Almost as if to eliminate that embarrassing setback from his memory, with Princeton rejecting him only a few years before, Hamilton’s guns continued to unleash a hot fire at Nassau Hall, where British soldiers returned musketry from windows, from which panes of glass had been knocked out. Solid iron projectiles from Hamilton’s two field pieces tore through the walls and bounced off rear walls around the defenders. A cannonball from one of Hamilton’s guns that relentlessly pounded the main building scored a direct hit, tearing through the wall of the prayer hall (chapel) of the stately building and hitting the large portrait of King George I. Allegedly, the iron projectile symbolically struck the monarch’s head, tearing it from the large painting that had been long revered like a sacred relic. Later, Washington learned of Hamilton’s direct hit, perhaps from the captain himself.41

More importantly, the accurate fire directed by Hamilton at Nassau Hall had a decisive effect in breaking the defenders’ spirit and will to resist, forcing hundreds of British soldiers to surrender. A white flag waved from one of the windows. Then, in one American sergeant’s words, “a haughty crabbed set of men” in red uniforms surrendered, to Hamilton’s delight, because of what his guns had achieved.42

Again catching British leadership, especially Cornwallis, by surprise, Washington won the day at Princeton. Captain Hamilton enjoyed the sweet taste of victory, basking in the two remarkable successes that had turned the tide of the revolution, thanks to Washington’s adherence to unorthodox tactics that he had long advocated. Washington was hearing more about this dynamic young artillery officer, who had risen magnificently to every challenge. Hamilton later concluded with glee that Washington’s bold “enterprises of Trenton and Princeton [represented] the dawning of [a] bright day which afterwards broke forth with such resplendent luster.”43

With Cornwallis in pursuit, Washington retreated to the west, after burning bridges to slow the redcoats bent on revenge. He then led his army into winter quarters at Morristown, New Jersey, where Hamilton once again took to a sick bed out of urgent necessity after the winter campaign’s rigors. Providing some consolation to him during his illness, he basked in his recent accomplishments. At the battles of Trenton and Princeton, Captain Hamilton continued to demonstrate courage, leadership ability, and tactical skill that caught the notice of the Continental Army’s officer corps. During the Trenton-Princeton Campaign that reversed the revolution’s course when it seemed all but impossible to do so, Hamilton’s feats and dynamic leadership style continued to be the talk of the army. Contrary to myth, he had first become known to Washington for intelligence and exceptional promise through Colonel Joseph Reed, Washington’s adjutant general, during a prisoner (for officers) exchange mission in which he played a role in September 1776. However, because of his youth and recent immigrant background, Hamilton had still needed an influential patron to sing his praises as a highly capable officer and a proper gentleman.

Colonel Henry Knox, Washington’s young chief of artillery from Boston who had most closely seen Hamilton’s potential and promise at the Raritan, Trenton, and Princeton, was that man. The scholarly Knox, a self-educated man with a can-do attitude and innovative mind, closely identified with Hamilton, including with the young man’s difficult past in the West Indies. Much like Alexander’s family’s abandonment by hard-luck James Hamilton, Knox’s own father had left his family, suddenly sailing off to the West Indies to leave his responsibilities behind. Knox and Hamilton, therefore, had been forced to work at young ages to provide for their families, gaining worldly experience, maturing out of necessity, and learning the meaning of responsibility. Not surprisingly, Knox had taken an early interest in the bright artillery officer under his command, because they were very much kindred spirits and self-made men of outstanding promise. For good reason, in a letter to Washington at a later date, Hamilton described how, “General Knox has the confidence of the army and is a man of sense.”44

Recognizing talent and ability, General Nathanael Greene, Washington’s top lieutenant, had also praised the young Hamilton to the commander-in-chief, especially after seeing him in action at Trenton and Princeton.

This steady flow of favorable accounts praising Hamilton’s abilities and talents had been passed on to the commander-in-chief for some time. At his always-busy headquarters, Washington needed such a dynamic young man with a lively intellect and outstanding abilities (seemingly boundless) on his personal staff. Washington had also seen for himself what Hamilton could accomplish during the recent campaign. He understood that Hamilton, brilliant and assiduous, was a very special officer of unlimited promise. Consequently, only three weeks after his surprising victory at snowy Princeton, while settled into winter quarters in a protective valley at Morristown (and with a staff vacancy open after George Baylor’s departure to cavalry service), Washington inquired about “the suitability” of young Hamilton as an aide-de-camp to serve on his small staff, where the demands were disproportionately large and challenges endless.

In a formal setting that reflected proper protocol, Washington then met with Hamilton, after he had been invited to a dinner at headquarters. Like everyone else, the commander-in-chief was greatly impressed by the young man with refined manners, gentlemanly behavior, and boundless charm. Washington realized that this was exactly the kind of gifted officer who he needed on his personal staff. After all, Hamilton was nothing short of a “boy genius,” which had been recognized by the Continental Army’s top leaders. Indeed, and even more than Washington now realized, because “of all the founding fathers, Hamilton best understood the full breath of the Revolution—from war to politics to organization” at every level.

Consequently, Hamilton shortly received a coveted personal invitation (Washington’s note of January 20, 1777) to become a member of the general’s personal staff at his headquarters and to join the elite group of young staff officers of his “family.” However, this was not an easy decision for the young man. He still lusted most of all for independent command, in part because he knew that “the regiments of artillery were multiplied [and] I had good reason to expect that the command of one of them would have fallen to me….”45

And, if Hamilton gained command of a regiment, then he envisioned eventually winning command of a brigade and a corresponding brigadier general’s rank. After having previously refused to take aide-de-camp positions for two generals, Hamilton gave Washington his answer only after deliberation that took some time (nearly six weeks that included the period when ill), because he was not looking forward to a desk job that would deprive him of battlefield opportunities. Joining Washington’s staff ensured an advance from the rank of captain to lieutenant colonel: a significant increase in rank for a mere youth of twenty-two and recent immigrant lacking social standing and wealth in America. This was the kind of fast track advancement that Hamilton relished, although he had been a frustrated clerk working at a desk in a dead-end position in St. Croix only four years before.

However, he correctly sensed Washington’s best qualities, and instinctively knew that he could rise higher, if the Virginian succeeded in winning this war for America’s heart and soul. Despite his serious initial reservations, Hamilton finally made up his mind. As Hamilton emphasized in his own words from a letter and directly contrary to innermost inclinations, he was bound by a deep sense of patriotism and admiration toward Washington “to accept his invitation to enter into his family.”46

In his general orders of March 1, 1777, Washington officially announced that Hamilton “is appointed Aide-De-Camp to the Commander in Chief, and is to be respected and obeyed as such.”47 No longer a captain of a New York battery (state service) and after he turned over his command to a faithful lieutenant, Hamilton’s star was on the rise, after becoming the nineteenth man who had been appointed to Washington’s staff since July 5, 1775. Serving with Washington at his headquarters was considered to be the highest honor and a great opportunity. But this would only remain true as long as Washington was successful on the battlefield or just avoided decisive defeat. The young man’s career was about to soar to unprecedented heights, far beyond what anyone (including Washington and Hamilton) could imagine, especially at a time when many Americans, including those in high places, doubted Washington’s leadership and tactical abilities. With his New York battery now depleted by disease, losses, enlistment expirations, and desertions, Hamilton was fortunate to have been presented this golden opportunity to accept such a prestigious position. Clearly, this lofty position on Washington’s staff represented an example of Hamilton doing what he had to do to get ahead, especially in regard to proving his worth and value to the leader of America’s revolutionary resistance effort. Fortunately, for Hamilton, this peoples’ revolution and its egalitarian nature allowed talented men to rise up on their own ability, despite the lack of social standing or wealth. Hamilton was at the right place, right time, and now with the right person in charge to make a name for himself. He was now in a position to excel as never before. But Hamilton could not imagine that by linking his fortunes with Washington, he was about to begin “one of the most important and creative associations in American history.”48