Alexander Hamilton - Ron Chernow (2005)

Chapter 2. HURRICANE

Even in the languorous tropics, Hamilton, while clerking at Beekman and Cruger, was schooled in a fast-paced modern world of trading ships and fluctuating markets. Whatever his frustrations, he did not operate in an obscure corner of the world, and his first job afforded him valuable insights into global commerce and the maneuvers of imperial powers. Working on an island first developed by a trading company, he was exposed early on to the mercantilist policies that governed European economies.

Beekman and Cruger engaged in an export-import business that provided an excellent training ground for Hamilton, who had to monitor a bewildering inventory of goods. The firm dealt in every conceivable commodity required by planters: timber, bread, flour, rice, lard, pork, beef, fish, black-eyed peas, corn, porter, cider, pine, oak, hoops, shingles, iron, lime, rope, lampblack, bricks, mules, and cattle. “Amid his various engagements in later years,” John C. Hamilton said of his father, “he adverted to [this time] as the most useful part of his education.”1 He learned to write in a beautiful, clear, flowing hand. He had to mind money, chart courses for ships, keep track of freight, and compute prices in an exotic blend of currencies, including Portuguese coins, Spanish pieces of eight, British pounds, Danish ducats, and Dutch stivers. If Hamilton seemed very knowing about business as a young adult, it can partly be traced to these formative years.

Located above the harbor at the elevated intersection of King and King’s Cross Streets, Beekman and Cruger ran a shop and an adjoining warehouse. A pleasant stroll down the sloping main street would have brought Hamilton, freshened by sea breezes, to the hectic wharf area, where the firm maintained its own dock and ship. While the clerk inspected incoming merchandise, some of it contraband, the air was thick with the sweet fragrances of sugar, rum, and molasses, hauled in barrels by horse-drawn wagons and ready for shipment to North America in exchange for grain, flour, timber, and sundry other staples. The neutral Danish island served as a transit point to the French West Indies, converting Hamilton’s ease in French into a critical business asset. As a rule, the merchants of St. Croix were natives of the British Isles, so that English, not Danish, functioned as the island’s lingua franca.

Beekman and Cruger furnished Hamilton with a direct link to his future home in New York, which carried on extensive trade with St. Croix. Many Manhattan trading firms dispatched young family members to the islands as local agents, and Nicholas Cruger was a prime example. He came from one of colonial New York’s most distinguished families. His father, Henry, was a wealthy merchant, shipowner, and member of His Majesty’s Royal Council for the province. His uncle, John Cruger, had been a long-standing mayor and a member of the Stamp Act Congress. While this blue-blooded clan had distinct Anglophile tendencies, time was to expose a split. Nicholas’s brother, also Henry, based in Britain, was elected a member of Parliament from Bristol beside no less august a personage than Edmund Burke. Nicholas himself was to side with the rebel colonists and revere George Washington. One wonders whether he functioned as Hamilton’s first political tutor. He also exposed Hamilton to a prosperous, civic-minded breed of New York businessmen, who stood as models for the elite brand of Federalism he later espoused.

From the outset, the young Hamilton had phenomenal stamina for sustained work: ambitious, orphaned boys do not enjoy the option of idleness. Even before starting work, he must have developed unusual autonomy for a thirteen-year-old, and Beekman and Cruger would only have toughened his moral fiber. Hamilton exuded an air of crisp efficiency and cool self-command. While his peers squandered their time on frivolities, Hamilton led a much more strenuous, urgent life that was to liberate him from St. Croix. He was a proud and sensitive boy, caught in the lower reaches of a rigid class society with small chance for social mobility. His friend Nathaniel Pendleton later said of his clerkship that Hamilton “conceived so strong an aversion to it as to be induced to abandon altogether the pursuits of commerce.”2 On November 11, 1769, in his earliest surviving letter, the fourteen-year-old Hamilton vented the blackest pent-up despair. Written in elegant penmanship, the letter shows that the young clerk felt demeaned by his lowly social station and chafed with excess energy. Already he sought psychic relief in extravagant fantasies of fame and faraway glory. The recipient was his dear friend and lookalike Edward Stevens, who had recently begun his studies at King’s College in New York:

To confess my weakness, Ned, my ambition is [so] prevalent that I contemn the grovelling and conditions of a clerk or the like to which my fortune &c. condemns me and would willingly risk my life, tho’ not my character, to exalt my station. I’m confident, Ned, that my youth excludes me from any hopes of immediate preferment, nor do I desire it, but I mean to prepare the way for futurity. I’m no philosopher, you see, and may be jus[t]ly said to build castles in the air. My folly makes me ashamed and beg you’ll conceal it, yet Neddy we have seen such schemes successful when the projector is constant. I shall conclude [by] saying I wish there was a war. Alex. Hamilton.3

What prophetic aspirations Hamilton telescoped into this short letter! The boy hankering for heroism and martial glory was to find his war soon enough. He betrayed a stinging sense of shame that the adult Hamilton would studiously cloak behind an air of bravado. Of special interest are his intuitive fear that his outsized ambition might corrupt him and his insistence that he would never endanger his ethics to conquer the world. Despite some awkwardness in the writing, he appears surprisingly mature for fourteen and springs full-blown into the historical record.

He had ample opportunities to exercise his many talents. In 1769, David Beekman quit the business and was replaced by Cornelius Kortright—another New Yorker with another prestigious name—and the firm was reconstituted as Kortright and Cruger. In October 1771, for medical reasons, Nicholas Cruger returned to New York for a five-month stint and left his precocious clerk in charge.

A sheaf of revealing business letters drafted by Hamilton shows him, for the first time, in the take-charge mode that was to characterize his tumultuous career. With peculiar zeal, he collected money owed to the firm. “Believe me Sir,” he assured the absent Cruger, “I dun as hard as is proper.”4 The bulk of the correspondence concerns a sloop called the Thunderbolt, partly owned by the Crugers, that carried several dozen miserable mules through churning seas in early 1772. Hamilton had to direct this cargo safely along the Spanish Main (South America’s northwestern coast), then brimming with hostile vessels. Hamilton did not hesitate to advise his bosses that they should arm the ship with four guns. He said flatly to Tileman Cruger, who oversaw family operations in Curaçao, “It would be undoubtedly a great pity that such a vessel should be lost for the want of them.”5 When the ship docked with forty-one skeletal, drooping mules, Hamilton lectured the vessel’s skipper in a peremptory tone that someday would be familiar to legions of respectful subordinates: “Reflect continually on the unfortunate voyage you have just made and endeavour to make up for the considerable loss therefrom accruing to your owners.”6 The adolescent clerk had a capacity for quick decisions and showed no qualms about giving a tongue-lashing to a veteran sea captain. So proficient and eager to lead was he that he must have been slightly deflated when Nicholas Cruger returned to St. Croix in March 1772.

Hamilton’s apprenticeship provided many benefits. He developed an intimate knowledge of traders and smugglers that later aided his establishment of the U.S. Coast Guard and Customs Service. He saw that business was often obstructed by scarce cash or credit and learned the value of a uniform currency in stimulating trade. Finally, he was forced to ponder the paradox that the West Indian islands, with all their fertile soil, traded at a disadvantage with the rest of the world because of their reliance on only the sugar crop—a conundrum to which he was to return in his celebrated “Report on Manufactures.” It may be that Hamilton’s preference for a diversified economy of manufacturing and agriculture originated in his youthful reflections on the avoidable poverty he had witnessed in the Caribbean.

While Kortright and Cruger mostly brokered foodstuffs and dry goods, at least once a year the firm handled a large shipment of far more perishable cargo: slaves. On the slave ships, hundreds of Africans were chained and stuffed in fetid holds, where many suffocated. So vile were the conditions on these noisome ships that people onshore could smell their foul effluvia even miles away. On January 23, 1771, during Hamilton’s tenure, his firm ran a notice atop the front page of the local bilingual paper, the Royal Danish American Gazette: “Just imported from the Windward Coast of Africa, and to be sold on Monday next, by Messrs. Kortright & Cruger, At said Cruger’s yard, Three Hundred Prime SLAVES.”7 The following year, Nicholas Cruger imported 250 more slaves from Africa’s Gold Coast and complained that they were “very indifferent indeed, sickly and thin.”8 One can only imagine the inhuman scenes that Hamilton observed as he helped to inspect, house, groom, and price the slaves about to be auctioned. To enhance their appearance, their bodies were shaved and rubbed with palm oil until their muscles glistened in the sunlight. Some buyers came armed with branding irons to imprint their initials on their newly purchased property. From the frequency with which Nicholas Cruger placed newspaper notices to catch runaway slaves, it seems clear that the traffic in human beings formed a substantial portion of his business.

By the time Hamilton arrived on St. Croix, the burgeoning slave population had doubled in just a decade, and the planters banded together to guard against uprisings or mass escapes to nearby Puerto Rico, where slaves could secure their freedom under Spanish rule. In this fearful environment, no white enjoyed the luxury of being a neutral spectator: either he was an accomplice of the slave system or he left the island. To remove any ambiguity in the matter, the government in Copenhagen issued a booklet, “The St. Croixian Pocket Companion,” which spelled out the duties of every white on the island—duties that would have applied to Hamilton starting in 1771. Every male over sixteen was obligated to serve in the militia and attend monthly drills with his arms and ammunition at the ready. If the fort fired its guns twice in a row, all white males had to grab their muskets and flock there instantly. On days when renegade slaves were executed at Christiansvaern, the white men formed a ring around the fort to prevent other slaves from interfering. Any slave who attacked a white person faced certain death by hanging or decapitation—death that probably came as a blessed relief after first being prodded with red-hot pokers and castrated. Punishments were designed to be hellish so as to terrorize the rest of the captive population into submission. If a slave lifted a hand in resistance, it would promptly be chopped off. Any runaway who returned within a three-month period would have one foot lopped off. If he then ran away a second time, the other foot was amputated. Recidivists might also have their necks fitted with grisly iron collars of sharp, inward-pointing spikes that made it impossible to crawl away through the dense underbrush without slashing their own throats in the effort.

It is hard to grasp Hamilton’s later politics without contemplating the raw cruelty that he witnessed as a boy and that later deprived him of the hopefulness so contagious in the American milieu. On the most obvious level, the slave trade of St. Croix generated a permanent detestation of the system and resulted in his later abolitionist efforts. But something deeper may have seeped into his consciousness. In this hierarchical world, skittish planters lived in constant dread of slave revolts and fortified their garrison state to avert them. Even when he left for America, Hamilton carried a heavy dread of anarchy and disorder that always struggled with his no less active love of liberty. Perhaps the true legacy of his boyhood was an equivocal one: he came to detest the tyranny embodied by the planters and their authoritarian rule, while also fearing the potential uprisings of the disaffected slaves. The twin specters of despotism and anarchy were to haunt him for the rest of his life.

Like Ben Franklin, Hamilton was mostly self-taught and probably snatched every spare moment to read. The young clerk aimed to be a man of letters. He may already have had a premonition that his facility with words would someday free him from his humble berth and place him on a par with the most powerful men of his age. The West Indies boasted few stores that sold books, which had to be ordered by special subscription. For that reason, it must have been a godsend to the culture-starved Hamilton when the Royal Danish American Gazette launched publication in 1770. The paper had a pronounced Anglophile slant, reflecting the fact that King Christian VII of Denmark was both first cousin and brother-in-law to King George III of England. Each issue carried reverential excerpts from parliamentary debates in London, showcasing William Pitt the Elder and other distinguished orators, and retailed gossipy, fawning snippets about the royal household.

Having a potential place to publish, Hamilton began to scribble poetry. Once his verbal fountain began to flow, it became a geyser that never ceased. The refined wit and pithy maxims of Alexander Pope mesmerized the young clerk, and just as Pope wrote youthful imitations of the classical poets so Hamilton penned imitations of Pope. On April 6, 1771, he published a pair of poems in the Gazette that he introduced with a diffident note to the editor: “Sir, I am a youth about seventeen, and consequently such an attempt as this must be presumptuous; but if, upon perusal, you think the following piece worthy of a place in your paper, by inserting it you’ll much oblige Your obedient servant, A. H.” The two amorous poems that follow are schizophrenic in their contrasting visions of love. In the first, the dreamy poet steals upon his virgin love, who is reclining by a brook as “lambkins” gambol around her. He kneels and awakens her with an ecstatic kiss before sweeping her up in his arms and carrying her off to marital bliss, intoning, “Believe me love is doubly sweet / In wedlock’s holy bands.”9 In the next poem, Hamilton has suddenly metamorphosed into a jaded rake, who begins with a shocking, Swiftian opening line: “Celia’s an artful little slut.” This launches a portrait of a manipulative, feline woman that concludes:

So, stroking puss’s velvet paws,

How well the jade conceals her claws

And purrs; but if at last

You hap to squeeze her somewhat hard

She spits—her back up—prenez garde;

Good faith she has you fast.

The first poem seems to have been composed by a sheltered adolescent with an idealized view of women and the second by a world-weary young philanderer who has already tasted many amorous sweets and shed any illusions about female virtue. In fact, this apparent attraction to two opposite types of women—the pure and angelic versus the earthy and flirtatious—ran straight through Hamilton’s life, a contradiction he never resolved and that was to lead to scandalous consequences.

The next year, Hamilton published two more poems in the paper, now re-creating himself as a somber religious poet. The change in heart can almost certainly be attributed to the advent in St. Croix of a Presbyterian minister named Hugh Knox. Born in northern Ireland of Scottish ancestry, the handsome young Knox migrated to America and became a schoolteacher in Delaware. As a raffish young man, he exhibited a lukewarm piety until a strange incident transformed his life. One Saturday at a local tavern where he was a regular, Knox amused his tipsy companions with a mocking imitation of a sermon delivered by his patron, the Reverend John Rodgers. Afterward, Knox sat down, shaken by his own impiety but also moved by the sermon that still reverberated in his mind. He decided to study divinity at the College of New Jersey (later Princeton) under its president, Aaron Burr, an eminent divine and father of the man who became Hamilton’s nemesis. It was almost certainly from Knox’s lips that Alexander Hamilton first heard the name of Aaron Burr.

Ordained by Burr in 1755, Knox decided to propagate the gospel and was sent to Saba in the Dutch West Indies. This tiny island near Nevis measured five square miles, had no beaches, and was solitary enough to try the fortitude of the most determined missionary. Rough seas girded Saba’s rocky shores, making it hazardous for ships to land there. As the sole clergyman, Knox resided in a settlement known as the Bottom, sunk in the elevated crater of an extinct volcano; it could be reached only by climbing up a stony path. Knox left a bleak picture of the heedless sinners he was assigned to save. “Young fellows and married men, not only without any symptoms of serious religion…but keepers of negro wenches…rakes, night rioters, drunkards, gamesters, Sabbath breakers, church neglecters, common swearers, unjust dealers etc.”10 An erudite man with a classical education, Knox was starved for both intellectual companionship and money. In 1771, he visited St. Croix and was received warmly by the local Presbyterians, who enticed him to move there. In May 1772, he became pastor at the Scotch Presbyterian church at a salary considerably beyond what he had earned inside his old crater.

After the lonely years in Saba, the forty-five-year-old Knox felt rejuvenated in St. Croix. Humane and tolerant, politically liberal (he was to fervently support American independence), opposed to slavery (though he owned some slaves), and later author of several volumes of sermons, he held a number of views that would have attracted Hamilton. In his earliest surviving letter, he defended his confirmed belief that illegitimate children should be baptized and argued that clergymen should rescue them from their parents instead of rejecting them. He departed from a strict Calvinist belief in predestination. Instead of a darkly punitive God, Knox favored a sunny, fair-minded one. He also saw human nature as insatiably curious and reserved his highest praise for minds that created “schemes or systems of truth.”11

Then an illegitimate young clerk with an uncommon knack for systematic thinking stepped into his life. Knox must have marveled at his tremendous luck in discovering Hamilton. We do not know exactly how they met, but Knox threw open his library to this prodigious youth, encouraged him to write verse, and prodded him toward scholarship. An avuncular man with a droll wit, Knox worried that Hamilton was too driven and prone to overwork, too eager to compensate for lost time—a failing, if it was one, that he never outgrew. In later years, Knox liked to remind Hamilton that he had been “rather delicate & frail,” with an “ambition to excel,” and had tended to “strain every nerve” to be the very best at what he was doing.12 Knox had an accurate intuition that this exceptional adolescent was fated to accomplish great deeds, although he later confessed that Alexander Hamilton had outstripped even his loftiest expectations.

Among his other gifts, the versatile Hugh Knox was a self-taught doctor and apothecary and a part-time journalist who occasionally filled in for the editor of the Royal Danish American Gazette. It may have been at the newspaper office, not at the church, that he first ran into Hamilton. That Knox moonlighted as a journalist proved highly consequential for Hamilton when a massive hurricane tore through St. Croix on the night of August 31, 1772, and carved a wide swath of destruction through nearby islands.

By all accounts, the storm struck with unprecedented fury, the Gazette reporting that it was the “most dreadful hurricane known in the memory of man.” Starting at sundown, the gales blew “like great guns, for about six hours, save for half an hour’s intermission…. The face of this once beautiful island is now so calamitous and disfigured, as it would beggar all description.”13 The tremendous winds uprooted tall trees, smashed homes to splinters, and swept up boats in foaming billows and flung them far inland. Detailed reports of the storm in Nevis, where the destruction was comparable—huge sugar barrels were tossed four hundred yards, furniture landed two miles away—confirm its terrifying power. Nevis had also been struck by a severe earthquake that afternoon, and it seems probable that Nevis, St. Kitts, St. Croix, and neighboring islands were deluged by a tidal wave up to fifteen feet high. The devastation was so widespread that an appeal for food was launched in the North American colonies to avert an anticipated famine.

On September 6, Hugh Knox gathered the jittery faithful at his church and delivered a consoling sermon that was published in pamphlet form some weeks later. Hamilton must have attended and been inspired by Knox’s homily, for he went home and composed a long, feverish letter to his father, trying to convey the hurricane’s horror. (It is noteworthy that Hamilton was still in touch with his father more than six years after the latter’s departure from St. Croix. That James Hamilton resided outside the storm area suggests that he was in the southern Caribbean, possibly Grenada or Tobago.) In his melodramatic description of the hurricane, one sees the young Hamilton glorying in his verbal powers. He must have shown the letter to Knox, who persuaded him to publish it in the Royal Danish American Gazette, where it appeared on October 3. The prefatory note to the piece, presumably written by Knox, explained: “The following letter was written the week after the late hurricane, by a youth of this island, to his father; the copy of it fell by accident into the hands of a gentleman, who, being pleased with it himself, showed it to others to whom it gave equal satisfaction, and who all agreed that it might not prove unentertaining to the public.” Lest anyone suspect that an unfeeling Hamilton was capitalizing on mass misfortune, Knox noted that the anonymous author had at first declined to publish it—perhaps the last time in Alexander Hamilton’s life that he would prove bashful or hesitant about publication.

Hamilton’s famous letter about the storm astounds the reader for two reasons. For all its bombastic excesses, it does seem wondrous that a seventeen-year-old self-educated clerk could write with such verve and gusto. Clearly, Hamilton was highly literate and already had a considerable fund of verbal riches: “It seemed as if a total dissolution of nature was taking place. The roaring of the sea and wind, fiery meteors flying about it [sic] in the air, the prodigious glare of almost perpetual lightning, the crash of the falling houses, and the ear-piercing shrieks of the distressed, were sufficient to strike astonishment into angels.”

But the description was also notable for the way Hamilton viewed the hurricane as a divine rebuke to human vanity and pomposity. In what sounded like a cross between a tragic soliloquy and a fire-and-brimstone sermon, he exhorted his fellow mortals:

Where now, oh! vile worm, is all thy boasted fortitude and resolution? What is become of thine arrogance and self sufficiency?…Death comes rushing on in triumph, veiled in a mantle of tenfold darkness. His unrelenting scythe, pointed and ready for the stroke…See thy wretched helpless state and learn to know thyself…. Despise thyself and adore thy God…. O ye who revel in affluence see the afflictions of humanity and bestow your superfluity to ease them…. Succour the miserable and lay up a treasure in heaven.14

Gloomy thoughts for a teenage boy, even in the aftermath of a lethal hurricane. The dark spirit of the storm that he summons up, his apocalyptic sense of universal tumult and disorder, bespeak a somber view of the cosmos. He also shows a strain of youthful idealism as he admonishes the rich to share their wealth.

Hamilton did not know it, but he had just written his way out of poverty. This natural calamity was to prove his salvation. His hurricane letter generated such a sensation—even the island’s governor inquired after the young author’s identity—that a subscription fund was taken up by local businessmen to send this promising youth to North America to be educated. This generosity was all the more remarkable given the island’s dismal state. The hurricane had flattened dwellings, shredded sugarcane, destroyed refineries, and threatened St. Croix with prolonged economic hardship. It would take many months, maybe years, for the island to recover.

The chief sponsor of the subscription fund was likely the good-hearted Hugh Knox, who later told Hamilton, “I have always had a just and secret pride in having advised you to go to America and in having recommended you to some [of] my old friends there.”15 The chief donors were probably Hamilton’s past and present bosses—Nicholas Cruger, Cornelius Kortright, and David Beekman—plus his guardian, Thomas Stevens, and his first cousin, Ann Lytton Venton. Possibly aware of Hamilton’s early (indeed, abiding) interest in medicine, the business community may have hoped to train a doctor who would return and treat the many tropical diseases endemic to the island. Doctors were perpetually scarce in the Caribbean, and Edward Stevens was already in New York preparing for such a career.

In the standard telling of his life, Hamilton boards a ship in October 1772 and sails off to North America forever. Yet a close study of the Royal Danish American Gazette and other documents raises questions about this usual chronology. Hamilton may have been the “Juvenis” who published a poem, “The Melancholy Hour,” in the Gazette of October 11, 1772. This brooding work—“Why hangs this gloomy damp upon my mind / Why heaves my bosom with the struggling sigh”—reprises the theme of the hurricane as heavenly retribution upon a fallen world. On October 17, the Gazette ran an unsigned hymn in imitation of Pope that incontestably came from Hamilton’s pen and was later cherished by his wife as proof of her husband’s religious devotion. Entitled “The Soul Ascending into Bliss,” it is a lovely, mystical meditation in which Hamilton envisions his soul soaring heavenward. “Hark! Hark! A voice from yonder sky / Methinks I hear my Saviour cry…. I come oh Lord, I mount, I fly / On rapid wings I cleave the sky.” There is a third poem by Hamilton that has been overlooked and that appeared in the Gazette of February 3, 1773, under the heading: “Christiansted. A Character. By A. H.” In this short, disillusioned verse, Hamilton evokes a sharp-witted fellow named Eugenio who manages inadvertently to antagonize all of his friends. The poem concludes: “Wit not well govern’d rankles into vice / He to his Jest his Friend will sacrifice!”16 The discovery of this poem, possibly influenced by an event in the life of Molière, bolsters the supposition that Hamilton spent the winter of 1772–1773 in St. Croix, although he could have mailed Hugh Knox the verse from North America.

To understand this transitional moment in Hamilton’s life, we must introduce yet another figure into the convoluted saga of his early years: his first cousin Ann Lytton Venton, later Ann Mitchell. So incalculable was Hamilton’s debt to her that on the eve of his duel with Burr, as he contemplated his life, he instructed his wife: “Mrs. Mitchell is the person in the world to whom as a friend I am under the greatest obligations. I have [not] hitherto done my [duty] to her.”17 Why this guilt-ridden homage to a figure who has lingered in the historical shadows?

Twelve years older than Hamilton, Ann Lytton Venton was the oldest daughter of Rachel’s sister, Ann. Like so many figures in Hamilton’s family, she led a checkered life. In her early teens, she married a poor Christiansted grocer, Thomas Hallwood, and promptly had a son. After one year of marriage, Hallwood died. In 1759, Ann married the somewhat more prosperous John Kirwan Venton, who bought a small sugar estate. By 1762, his business had failed, and their home and effects were seized by creditors. The couple decamped to New York, leaving an infant daughter with Ann’s parents. The Ventons evidently faltered in New York and were drawn back to St. Croix in 1770 after the suicide of Ann’s brother Peter and the death of her father, James Lytton. If John Kirwan Venton hoped to lay hands on Ann’s inheritance, he was foiled by the foresight of his father-in-law, who left two-sevenths of his estate to Ann but specifically excluded Venton from the money, calling him “unfortunate in his conduct.”

At this point, the Venton marriage dissolved in acrimony, with Ann and her daughter occupying Peter’s house in Christiansted while John took refuge in Frederiksted. After the hurricane, John Venton filed for bankruptcy again and posted a notice to his creditors. No less mean-spirited than Johann Michael Lavien, Venton also placed the following threatening ad in the Gazette of May 15, 1773: “JOHN KIRWAN VENTON forbids all masters of vessels from carrying Ann Venton, or her daughter Ann Lytton Venton off this island.”18 Defying this warning, Ann Venton and her daughter fled to New York, a brave act that would have reminded Hamilton of his mother flouting the odious Lavien. To secure her inheritance, Ann entrusted the eighteen-year-old Hamilton with a power of attorney that allowed him to collect payments from her father’s estate due on May 3 and 26 and June 3, 1773. It may well have been after receipt of this money that he boarded a vessel bound for Boston, leaving the West Indies forever. Perhaps in gratitude for his assistance or else plain affection for her exceedingly bright cousin, Ann Lytton Venton repaid Hamilton by becoming a benefactor—quite likely the principal benefactor—of his voyage to North America and subsequent education. If so, Hamilton repaid the favor by aiding Ann financially in future years. He always felt under a more compelling obligation to her than to anyone else from his early years, and we may know only a fraction of the vital services that she rendered him.

What a world of scarred emotion and secret grief Alexander Hamilton bore with him on the boat to Boston. He took his unhappy boyhood, tucked it away in a mental closet, and never opened the door again. Beside the horrid memories, this young dynamo simply was not cut out for the drowsy, slow-paced life of slave owners on a tropical island, and he never evinced the least nostalgia for his West Indian boyhood or voiced any desire to return. He wrote two years later, “Men are generally too much attached to their native countries to leave it and dissolve all their connexions, unless they are driven to it by necessity.”19 He chose a psychological strategy adopted by many orphans and immigrants: he decided to cut himself off from his past and forge a new identity. He would find a home where he would be accepted for what he did, not for who he was, and where he would no longer labor in the shadow of illegitimacy. His relentless drive, his wretched feelings of shame and degradation, and his precocious self-sufficiency combined to produce a young man with an insatiable craving for success. As a student of history, he knew the mutability of human fortune and later observed, “The changes in the human condition are uncertain and frequent. Many, on whom fortune has bestowed her favours, may trace their family to a more unprosperous station; and many who are now in obscurity, may look back upon the affluence and exalted rank of their ancestors.”20 He would be the former, his father no less unmistakably the latter.

As Alexander sailed north toward spectacular adventures, his father sank ever deeper into incurable poverty. Documents located in St. Vincent reveal that James Hamilton had wandered to the southern end of the Caribbean, almost to the coast of South America. On the tiny, secluded island of Bequia, located just south of St. Vincent, he had entered into a program set up by the British Crown to encourage impoverished settlers. Bequia is the northernmost of the Grenadine Islands, an isolated spot, seven square miles in size, of soft hills, jagged cliffs, and sandy beaches. On March 14, 1774, James Hamilton signed a contract that gave him twenty-five acres of free woodland property along the shore of Southeast Bay. In this lovely but menacing place, a stronghold of indigenous black and yellow Caribs and runaway slaves, James Hamilton chose a spot on public land reserved for a future fortification. Bequia was the sort of distant, godforsaken place that could have attracted only somebody who had exhausted all other options. The deed for James Hamilton’s land purchase tells its own tacit tale of woe; it made clear that his twenty-five acres were “not adapted for sugar plantations” and had been set aside “for the accommodations of poor settlers.”21 Under the grant, James Hamilton didn’t have to pay a penny for the first four years but had to stay on the island for at least one year. A 1776 survey shows him sharing seventy acres with a man named Simple, and they are the only two people listed on the roster of poor residents. There must have been days when it was hard for James to believe that he was the fourth son of a Scottish laird and had grown up in a fogbound castle. The descent of his life had been as stunning and irrevocable as the rise of his son in America was to seem almost blessedly inevitable.