Alexander Hamilton

by Ron Chernow

  Because the Elizabethtown Academy supplied many students to Princeton, we can deduce something about Hamilton’s preparatory studies from that college’s requirements. Princeton applicants had to know Virgil, Cicero’s orations, and Latin grammar and also had to be “so well acquainted with the Greek as to render any part of the four Evangelists in that language into Latin or English.”2 Never tentative about tackling new things and buoyed by a preternatural self-confidence, Hamilton proved a fantastically quick study. He often worked past midnight, curled up in his blanket, then awoke at dawn and paced the nearby burial ground, mumbling to himself as he memorized his lessons. (Hamilton’s lifelong habit of talking sotto voce while pacing lent him an air of either inspiration or madness.) A copious note taker, he left behind, in a minute hand, an exercise book in which he jotted down passages from the Iliad in Greek, took extensive notes on geography and history, and compiled detailed chapter synopses from the books of Genesis and Revelation. As if wanting to pack every spare moment with achievement, he also found time to craft poetry and wrote the prologue and epilogue of an unspecified play performed by a local detachment of British soldiers.

  Hamilton’s attendance at the Elizabethtown Academy brought him into the immediate vicinity of the younger Aaron Burr, who had attended the same school several years earlier. Burr’s brother-in-law, jurist Tapping Reeve, sat on the academy’s board of visitors and had been a vital force behind the school’s creation. By an extraordinary coincidence, Burr spent the summer of 1773 in Elizabethtown, right around the time Hamilton arrived. Hamilton might have seen this handsome, genial young man sauntering down the street, gliding by in a boat along the town’s many inlets, or hunting in the nearby woods. As we shall see, they probably also met in the drawing rooms of mutual friends.

  Hamilton always displayed an unusual capacity for impressing older, influential men, and he gained his social footing in Elizabethtown with surpassing speed, crossing over an invisible divide into a privileged, patrician world in a way that would have been impossible in St. Croix. Thanks to the letters from Hugh Knox, he had instant access to men at the pinnacle of colonial society in New Jersey. He met William Livingston and Elias Boudinot, well-heeled lawyers and luminaries in the Presbyterian political world, who exposed him to the heterodox political currents of the day. They were both associated with the Whigs, who sought to curb royal power, boost parliamentary influence, and preserve civil liberties.

  Unquestionably the most vivid figure in Hamilton’s new life was fifty-year-old Livingston, a born crusader, who had abandoned a contentious career in New York politics to assume the sedate life of a New Jersey country squire. As work proceeded on Liberty Hall, his 120-acre estate, Livingston took temporary quarters in town, and Hamilton may have lodged with him during this interlude. Livingston was the sort of contradictory figure that always enchanted the young Hamilton. A blueblooded rebel and scion of a powerful Hudson River clan, Livingston had spurned an easy life to write romantic poetry, crank out polemical essays, and plunge into controversial causes. Tall and lanky, nicknamed “the whipping post,” the voluble Livingston tilted lances with royal authorities with such self-righteous glee that one Tory newspaper anointed him “the Don Quixote of the Jerseys.”3

  Like many Presbyterians, Livingston had gravitated to political dissent while opposing Tory efforts to entrench the Church of England in America. Two decades earlier, he had spearheaded a vitriolic campaign to block the establishment of an Anglican college in New York, which, he warned, would become “a contracted receptacle of bigotry” and an instrument of royal power.4 After their campaign failed and the school received a royal charter as King’s College in 1754, Livingston and his friends founded the New York Society Library to provide safe alternative reading matter for students. (Hamilton would take out books there.) An opponent of the Stamp Act and subsequent measures to saddle the colonies with oppressive taxes, Livingston was to attend the Continental Congress and the Constitutional Convention and become the first governor of an independent New Jersey in 1776.

  A gregarious man, William Livingston conducted Hamilton into a much more glamorous society than the one he left behind. Though benefiting from Livingston largesse, Hamilton was never mistaken for the family help, and he befriended the Livingston children, including the cerebral Brockholst, who was later an eminent Supreme Court judge and already friendly with Aaron Burr. There were also dazzling Livingston daughters to ravish the eye. As one of Burr’s friends observed of Elizabethtown at the time, “There is certainly something amorous in its very air.”5 Hamilton observed the courtship of the beautiful, high-spirited Sarah Livingston by a young lawyer named John Jay. (So regal was Sarah Livingston’s presence that when she later attended the opera in Paris, some audience members mistook her for the queen of France.) A special rapport sprang up between Hamilton and another Livingston daughter, Catharine, known as Kitty. She was the type of woman Hamilton found irresistible: pretty, coquettish, somewhat spoiled, and always ready for flirtatious banter. Judging from a letter Hamilton wrote to her during the Revolution, one suspects that Kitty was his first romantic conquest in America:

  I challenge you to meet me in whatever path you dare. And, if you have no objection, for variety and amusement, we will even make excursions in the flowery walks and roseate bowers of Cupid. You know I am renowned for gallantry and shall always be able to entertain you with a choice collection of the prettiest things imaginable....You shall be one of the graces, or Diana, or Venus, or something surpassing them all.6

  It is hard to imagine that Alexander Hamilton slept under the same roof as Kitty Livingston and didn’t harbor impure thoughts. In this sociable world, Hamilton also befriended Livingston’s brother-in-law, William Alexander, a bluff, convivial man known as Lord Stirling because of his contested claim to a Scottish earldom. An extravagant spendthrift, he was already swamped with debt when he met Hamilton. A decade earlier, the handsome, round-faced Stirling had constructed a thousand-acre estate at Basking Ridge, adorned with stables, gardens, and a deer park in imitation of the country houses of British nobility. Like Livingston, Lord Stirling was a curious amalgam of reformer and self-styled aristocrat. He rode about in a coach emblazoned with the Stirling coat of arms and possessed a princely wardrobe of 31 coats, 58 vests, 43 pairs of breeches, 30 shirts, 27 cravats, and 14 pairs of shoes.

  If Aaron Burr is to be trusted, Lord Stirling drank his way straight through the American Revolution as a brigadier general, plied by his aide-de-camp, James Monroe, who served as his faithful cupbearer: “Monroe’s whole duty was to fill his lordship’s tankard and hear, with indications of admiration, his lordship’s long stories about himself.”7 Burr’s barbed commentary doesn’t do justice to the bibulous Lord Stirling, who would win renown in the battle of Brooklyn. He was a literate man with eclectic interests, including mathematics and astronomy (he published a monograph on the transit of Venus), and a cofounder of the New York Society Library. Of special relevance to Hamilton’s future, he was a leading proponent of American manufactures. He bred horses and cattle, grew grapes and made wine, and produced pig iron and hemp. Lord Stirling had one final attraction for Hamilton: he also had enchanting daughters, especially the charming Catharine, always called “Lady Kitty.” She was to marry William Duer, the most notorious friend in Hamilton’s life.

  The third and most enduring tie formed by Hamilton was with Elias Boudinot, a lawyer who later became president of the Continental Congress and who owned copper and sulfur mines. A balding man with a jowly face and a smile that radiated benign intelligence, Boudinot was an innkeeper’s son and, like Hamilton, descended from French Huguenots. Such was his piety that he became the first president of the American Bible Society. As an organizer of the Elizabethtown Academy, he had pushed for the admission of “a number of free scholars in this town” and would have embraced heartily a poor but deserving youth such as Hamilton.8

  As a regular visitor to Boudinot’s mansion, Boxwood Hall, Hamilton was expose
d to a refined world of books, political debate, and high culture. Boudinot’s wife, Annie, wrote verse that George Washington complimented as “elegant poetry,” and this bookish family gathered each evening to hear biographies and sacred histories read aloud.9 Hamilton’s friendship with the Boudinots was so intimate that when their infant daughter, Anna Maria, contracted a fatal illness in September 1774, Hamilton kept a vigil by the sickly child and composed an affecting elegy after she died. This poem highlights a notable capacity for empathy in Hamilton, who dared to write it in the voice of the grieving mother. Since Hamilton had at least one sibling who had died in infancy or childhood, the poem may have summoned up memories of his own mother’s hardships:

  For the sweet babe, my doting heart Did all a mother’s fondness feel; Careful to act each tender part And guard from every threatening ill.

  But what alas! availed my care?

  The unrelenting hand of death,

  Regardless of a parent’s prayer

  Has stopped my lovely infant’s breath—10

  Later on, friends would comment on the almost maternal solicitude that Hamilton showed for friends or family members in distress. As a young man in a constant rush, scarcely pausing for breath, Hamilton did not dally in Elizabethtown for more than six months. Nevertheless, this fleeting period may have left its imprint on his politics. He hobnobbed with wealthy, accomplished men who lived like English nobility even as they agitated for change. These men wanted to modify the social order, not overturn it—a fair description of Hamilton’s future politics. At this juncture, Hamilton’s New Jersey patrons rejected national independence as a rash option, favored reconciliation, and repeatedly invoked their rights as English subjects. Far from wanting separation from the British empire, they favored fuller integration into it. Britain remained their beau ideal, if a somewhat faded one. Hamilton later admitted to having had a “strong prejudice” for the British viewpoint while at Elizabethtown and apparently leaned toward monarchism. Like his mentors, he would always be an uneasy and reluctant revolutionary who found it hard to jettison legal forms in favor of outright rebellion.11 Mingling with Presbyterians may also have influenced his politics. The denomination was associated with the Whig critique of the British Crown, while Anglicans tended to be Tories and more often supported British imperial policy toward the colonies and an established church.

  As Hamilton contemplated his next educational step, there were only nine colleges in the colonies to consider. William Livingston and Elias Boudinot sat on Princeton’s board of trustees—Livingston was such a trusted friend of the former president Aaron Burr that he had delivered his eulogy—and it would have been impolitic, not to say rude, for Hamilton to resist their entreaties to at least scout out the college. The school already had a contingent of West Indian students, and President John Witherspoon was so eager to augment their numbers (or tap the money of rich sugar planters for professorships) that he had issued a rousing newspaper appeal the previous year, an “Address to the Inhabitants of Jamaica and the Other West Indian Islands on Behalf of the College of New Jersey,” wherein he discoursed “on the advantages of his college for the education of West Indian youth.”12 Founded in 1746 as a counterweight to the Church of England’s influence, Princeton was a hotbed of Presbyterian/Whig sentiment, preached religious freedom, and might have seemed a logical choice for Hamilton. Hercules Mulligan contends that Hamilton told him that “he preferred Princeton to King’s College because it was more republican.”13 Indeed, the school bubbled with such political ferment that it was denounced in Tory quarters as a nursery of political radicalism. President Witherspoon confessed that “the spirit of liberty” ran “high and strong” at Princeton.14

  Little more than a coach stop between New York and Philadelphia, the rural hamlet of Princeton was hemmed in by thick forests. For Presbyterians eager to produce new ministers to fill rapidly expanding pulpits, this isolation was a protective measure that shielded students from urban temptations. The school stood in the throes of a religious revival when Hamilton applied. Hercules Mulligan said that he accompanied his young friend to this rustic outpost and introduced him to Witherspoon, but William Livingston and Elias Boudinot, as trustees, would have provided any needed introductions.

  An eminent theologian, born in Edinburgh, Witherspoon was a husky man with an oddly shaped head that narrowed at the top and bulged out in the middle. Garry Wills has called him “probably the most influential teacher in the history of American education,” and Princeton under his tutelage produced a bumper crop of politician alumni: a U.S. president, a vice president, twenty-one senators, twentynine congressmen, and twelve state governors.15 He was to sign the Declaration of Independence and minister to the Continental Congress as its first clergyman. By no coincidence, Princeton outpaced all other colleges by sending nine alumni to the Constitutional Convention. Witherspoon could be intimidating on first encounter. Pugnacious and outspoken, he had an unsettling way of erupting in strange twitches and fidgets. Hamilton, with his rock-hard ego, held his ground with the college president. Witherspoon examined Hamilton orally and was impressed by his fully fledged intellect. Then Hamilton made an unconventional proposal. According to Hercules Mulligan, Hamilton informed Witherspoon that he wanted to enter the college and advance “with as much rapidity as his exertions would enable him to do. Dr. Witherspoon listened with great attention to so unusual a proposition from so young a person and replied that he had not the sole power to determine that but that he would submit the request to the trustees who would decide.”16 One feels here the vastly accelerated tempo of Hamilton’s life, which was likely due to the chronic impatience fostered by his belated start in life.

  When Witherspoon had taken over at Princeton a few years earlier, he had set about to stiffen its lax admissions requirements and might have frowned on Hamilton’s special timetable for that reason. Mulligan blamed the trustees for rebuffing the proposal, saying that two weeks later Hamilton received a letter from Witherspoon “stating that the request could not be complied with because it was contrary to the usage of the college and expressing his regret because he was convinced that the young gentleman would do honor to any seminary at which he should be educated.”17 In fact, there had been a precedent for Hamilton’s brash request: Aaron Burr had tried to enter Princeton at age eleven and was told he was too young. He had then crammed for two years and cheekily applied for admission to the junior class at age thirteen. In a compromise, he was admitted as a sophomore and graduated in 1772 at sixteen. Hamilton may have learned about this experience from Burr himself or through their mutual friend Brockholst Livingston.

  In weighing Hamilton’s demand, Witherspoon and his trustees may have been deterred by the recent experience of a young Virginia scholar who had entered as a sophomore in 1769 and worked himself into a state of nervous exhaustion by completing his bachelor’s degree in two years instead of three. His name was James Madison, later Hamilton’s illustrious collaborator on The Federalist Papers. Fond of Witherspoon and too weak to travel after graduation, Madison had lingered in Princeton for a year to study privately with “the old Doctor.”18 When Madison finally returned to Virginia in the spring of 1772, he was still so debilitated from his intense studies that he feared for his health.

  While applying to Princeton Hamilton may have decided to “correct” his real age and shed a couple of years. If he was born in 1755, he would have been applying to college at eighteen, when fourteen or fifteen was often the standard minimum age for entrance—a highly uncomfortable state of affairs for a wunderkind. (Gouverneur Morris had entered King’s College at age twelve.) Prodigies aren’t supposed to be overaged freshmen. To be sure, Madison had entered Princeton at eighteen, but he was considered slightly old for a newcomer and skipped to sophomore status. If Hamilton trimmed two years from his age, one can sympathize with him. After all, while Aaron Burr was delivering a commencement speech at Princeton the year before, Hamilton, a year older, was still trying to figure out an es
cape route from Cruger’s countinghouse on St. Croix. For a precocious young man in his predicament, lying about his age would have been a pardonable lapse.

  Spurned at Princeton, Hamilton ended up at King’s College. He did not lack sponsors. Lord Stirling, who had inherited a town house on Broad Street in lower Manhattan, had long sat on the college’s governing board and raised money for it. Hamilton’s life was now set moving in a new direction. This nomadic, stateless boy found a home in the best possible city for a future treasury secretary, a city in which commerce always held an honored place. He was to be immersed in a heady world of business, law, and politics, and he made valuable contacts in the merchant community.

  Had he gone to Princeton, Hamilton might well have been radicalized sooner in the revolt against Britain, but that is arguable. Instead of with Witherspoon, Hamilton studied under one of the most ardent Tories in the colonies, Dr. Myles Cooper, the president of King’s. Attendance at King’s placed Hamilton in a city with a vocal Tory population, the bastion of British colonial power. At the same time, being in New York was also to lead to firsthand contact with tremendous revolutionary ferment and exposure to some of the colonies’ most eloquent agitators and outspoken newspapers. The virulent clash of Tories and Whigs in New York was to sharpen all of the conflicting feelings in Hamilton’s nature, enabling him to sympathize with the views of both patriots and Loyalists. In fact, by rejecting Alexander Hamilton, President Witherspoon and his associates at Princeton unintentionally thrust the young West Indian straight into the thick of the combustible patriotic drama in a way that would have proved impossible in a sleepy New Jersey country town.