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Authors: John Ferling

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For more than a year after James Hamilton abandoned them, Rachel and her sons lived in a two-story house in Christiansted. Her brother-in-law paid the rent and provided some of the furnishings. The family lived upstairs, and Rachel opened a general store on the lower level. She had inherited two additional slaves, bringing the total of her adult chattel to five, and all were likely hired out. An inventory completed when Alexander was thirteen showed that Rachel possessed several silver utensils, porcelain plates and basins, and a small library. While she and the boys lived austerely, they were not impoverished.

The future may have held promise, but Alexander was star-crossed. Early in 1768 both he and his mother fell ill with a virulent fever that ravaged St. Croix. Alexander survived. Rachel, only thirty-eight, perished. Jefferson had been fourteen when his father died. Hamilton was one year younger when he was effectively orphaned. Jefferson had been left with a mother with whom he apparently could not develop close emotional ties. Hamilton was left with no one.

It may have seemed as if things could not be worse, but soon they were.
The Laviens, father and son, resurfaced during the probate of Rachel’s estate. They wanted everything. To get it, they gave new life to the unseemly allegations that had been aired in court years earlier during the divorce proceedings. Nine months after Rachel’s death, the probate court awarded her entire estate to Peter Lavien, the son she had abandoned eighteen years before. Nothing of Rachel’s was left to Alexander and his sixteen-year-old brother. The boys were placed under the guardianship of a member of their aunt’s family. James was quickly apprenticed to a carpenter. Alexander, who might also have been earmarked for a life as a tradesman, was spared that fate. Perhaps before Rachel’s death in February, certainly before the probate decision in November, Alexander had obtained work as a clerk for the trading firm of Beekman and Cruger—soon to become Kortright and Cruger—the New York–based company that had supplied the groceries his mother sold. As he was already employed, Alexander was not apprenticed. He continued to work for the firm’s Christiansted office while living in the home of Thomas Stevens, a merchant who, together with his wife and five children, resided in Christiansted.

Hamilton worked for the company for five years. He was called a “clerk,” but his work was multifaceted. In time, he kept the books, monitored shipments, stayed abreast of inventory, managed a shop and warehouse, and tended to busy ship captains. He oversaw the acquisition of commodities to be sold on St. Croix and other islands in the West Indies—mostly food, wine, livestock, and African slaves—and the sugar and its by-products that were exported to Europe and Great Britain’s mainland colonies. His employment proved to be an important training ground. Hamilton subsequently referred to his years with the company as “the most useful of his education,” as he learned the value of organization and discipline, perfected his command of French, and discovered how to work with others, especially impatient, bustling businessmen.
15

Hamilton was busy, his work was varied and challenging, and he bore considerable responsibilities. Yet, he was unhappy. His formal education appeared to have come to a crashing halt before his fourteenth birthday. In addition, as he was unlikely to ever accumulate sufficient capital to open his own company, the door to upward mobility seemed permanently closed to him. He spun “Castles in the Air,” as he put it, dreaming of a new lease on life.
16
More than anything, this scarred adolescent’s passion appears to have been to gain renown, to surpass in distinction all those who had sneered at his mother and had looked on him with supercilious airs.

It is striking that both Jefferson and Hamilton, in their earliest surviving letter, spoke of their ambition. Jefferson, nearly seventeen, wrote of his yearning to go to college so that he might flourish in whatever he chose to do.
Hamilton, nearly fifteen, yearned to escape his dead-end job and attain a higher standing. He presumed that attending college was beyond all hope. One way out of his trap, he thought, was to make useful contacts. Another was to gain fame as a soldier. But peace prevailed. Soldiering was a dim hope unless someone started a war. “I wish there was a War,” he declared.
17

Three years after Hamilton wrote that letter, his fortunes improved. Glib and precocious, and extraordinarily bright, he caught people’s attention. Older, successful men were often impressed by this industrious, enterprising, and responsible young man. Hamilton found several patrons, including Thomas Stevens, with whom he lived, and each of the three men who were his employers, Beekman, Cruger, and Kortright. However, no one was more important to him than the Reverend Hugh Knox, a Scots-Irish Presbyterian minister who took a church on St. Croix some twenty years following his graduation from the College of New Jersey, later known as Princeton. Hamilton was about seventeen when he met Knox. Quickly impressed, the pastor appears to have become something of a tutor. Knox made available his library and probably provided some direction to Hamilton’s reading. He additionally helped Hamilton, who had begun to place short poetic compositions in the local newspaper, refine his writing skills. Knox’s mentoring paid off. Hamilton published a dramatic and florid account of a hurricane that punished the island in the summer of 1772.
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Hamilton’s writing helped convince his well-wishers to subsidize his college education in North America. He probably had no more than six years of schooling, two or three fewer years than most students spent preparing for admission to college, but colleges sometimes admitted deficient though promising students. If it was found that he lacked adequate preparation, Hamilton’s patrons were willing, at least for a time, to underwrite his study in a preparatory school. They pooled their money, and in the fall of 1772 Hamilton sailed alone for mainland America to find his destiny.

Nearly thirty years old when Hamilton sailed, Jefferson had negotiated the shoals of youth, though his passage to maturity had been neither easy nor painless. At age nineteen, Jefferson had plunged into legal studies with Wythe. He planned to remain at Wythe’s side for six or seven months, after which he would complete his training through self-study while living at Shadwell.

Jefferson remained at Shadwell for a year, but in the fall of 1763 he abandoned the rural seat and returned to the capital. He may have concluded that he needed Wythe’s systematic guidance. Or, Shadwell may have seemed dismayingly isolated to a single young man fresh from three years in Williamsburg. Albemarle County was remote and primitive; a century later, a visitor
described it as “wild” with “rugged and broken” roads that led to scattered homes and plantations.
19
Jefferson may also have been bothered by the constant distractions of life on a working plantation. After moving back to Williamsburg, he lived and studied with Wythe for two years, deep into 1765, reading, helping his mentor prepare for court appearances, and observing him before judges and juries.

These were not Jefferson’s happiest years. He found his legal studies less than exhilarating, and complained that law books were “dull” and riddled with “jargon.” Furthermore, most of his friends from college were settling into married life and the greater independence of adulthood.
20
A groomsman at many of their weddings, Jefferson appeared to be envious. They seemed blissful. He was miserable, suspended somewhere between adolescence and adulthood. That he was unsuccessful in winning the affections of his first love, Rebecca Burwell, hardly improved his state of mind.

He met Rebecca in 1762, around the time he first took up his study with Wythe, and his infatuation with her was almost surely a factor in his decision to return to Williamsburg in 1763. When they first met, Rebecca was sixteen and living at her uncle’s estate near the capital. Jefferson was immediately captivated and obsessed. He must have seen her infrequently, mostly in the episodic social whirl of the town, but he could not stop thinking of her. He waxed on about her in letter after letter, confessing: “I think of her too often, … I fear for my peace of mind.” He asked acquaintances to tell Rebecca that she was on his mind. In one of his most curious letters, Jefferson admitted that he dreamed of building a house for himself, John Page, a friend from college, and Rebecca. Despite his endless longing, he appears to have never written to her.

Though he thought of her often, in a candid moment he acknowledged, “she never gave me reason to hope.” On two occasions in the fall of 1763 he sought to become a suitor. On the first occasion, at a ball, he carefully planned and rehearsed a few witty remarks and more serious palaver, but Jefferson failed miserably when he was alone with her. Overcome by a “strange confusion,” the best he could do was stammer “a few broken sentences, uttered in great disorder.” Later, he tried again and may even have proposed marriage, though he concocted a story of “the necessity of my going to England, and the delays which would consequently be occasioned by that.” This time he was more coherent, but Rebecca rebuffed him.
21
Jefferson’s behavior was that of an infatuated young man who was not ready to settle down, and who in fact must have feared that marriage would thwart his ambitions.

Within a few months Rebecca was engaged to another man, whom she married in May 1764. “Well the lord bless her I say!” Jefferson remarked when
he heard the news. But he was far from over her, and he was all bluster when he told a friend that he relished being single.
22
In fact, when he learned that he had lost Rebecca, he fell ill with a crippling headache that sent him to bed in agonizing pain for several days. It was his first such bout with what some believe to have been migraines and others think were cluster, or muscular contraction, headaches. Many more would follow over the next half century, and they invariably would occur during moments of great personal stress.
23

After a brief phase when he was rendered “abominably indolent,” Jefferson returned to his studies. He grew close to Wythe, his mentor, as he had with Small, which hints that both teachers not only recognized Jefferson’s remarkable intellect but also responded to his emotional needs. Jefferson came to regard Wythe as “my second father” and “most affectionate friend” as well as “one of the greatest men of the age.” Later, Jefferson spoke of his law teacher as he had of Professor Small, remarking on Wythe’s “salutary influence on the course of my life.”
24

Jefferson was twenty-two when he completed his studies with Wythe. In all likelihood, he passed the Virginia bar examination that same year, 1765, though he waited two additional years before commencing practice. A brief wait was not uncommon for freshly minted lawyers, though to mark time for two years was nearly unheard of. Jefferson returned to Shadwell and devoted the interim to additional study. He later claimed to have studied sixteen hours a day. While he may have exaggerated, Edmund Randolph, a relative, said that Jefferson was “Indefatigable and methodical” in his studies. James Madison later remarked with awe that Jefferson had studied the law “to the bottom, and in its greatest breadth.”
25

Jefferson felt no financial pressure to go to work, and while he studied rigorously, he craved leisure time. When he was about twenty-three, Jefferson spent two months traveling to Annapolis, Philadelphia, and New York. In part, he made the trip in order to receive the smallpox inoculation in Philadelphia. But the excursion was also, as his foremost biographer, Dumas Malone, characterized it, a “Great Tour,” after the fashion of British and European aristocrats. Jefferson had never been outside Virginia, and he wanted to sight-see and shop.

However, Jefferson spent most of the five years beginning in 1765 at home, leading a life that one scholar called “monastic.” He had returned to Shadwell “to reestablish himself,” as historian Andrew Burstein put it, to continue his education in preparation for his adult life. Jefferson read law, but he spent more time immersed in classical philosophy, history, natural history, and the works of leading Enlightenment writers. Jefferson once said that he had a “canine appetite” for learning; Edmund Randolph conjectured that it was Jefferson’s
intention to acquire “great literary endowments” that could enhance his writing skills. Randolph also said that Jefferson believed his pen would lead to “advantageous connections” among the best educated men in the colonies and the mother country. What is more, Jefferson must have discovered during evenings spent in sophisticated company, as when he consorted with Small, Wythe, and Fauquier, that he was ill-equipped to keep pace with the dinner conversation. More the pragmatist than many have realized, Jefferson saw his study as indispensable to his enjoyment of a genial and cultured social life.
26

Jefferson never looked back with affection on the seven or eight years following his graduation from college. Whereas John Adams allotted forty pages in his autobiography to that phase of life, Jefferson glossed over his early adulthood in a single sentence in his memoirs. Through 1767, Jefferson remained almost exclusively at Shadwell, and even after opening his legal practice, he lived at home with his mother for about ten months of each year. It must have been an extraordinarily solitary existence for so young a man, but it was one of his own choosing.

Throughout his life Jefferson had a proclivity to retreat from the hostile outside world, the scene of acrimony and despair, and sometimes of personal failings. In addition, he frequently showed the traits of an obsessive personality. In this instance, scarred by Rebecca’s rejection, he may have fixated on not only his disappointment but also his repudiation. These would be throbbing pains for any young person to bear. It is conceivable that he shrank from the risk of further misadventures, walling himself from the cruel world in the sanctuary of home.

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