Of all the original thirteen states, Virginia had perhaps the strongest claim to the first loyalty of its citizens. It had been the largest, oldest, richest, and most populous of the British colonies in North America, the one where English ideas of class, religion, and social order were the most deeply entrenched, and its role was so central to the creation of the United States of America that the country’s capital was built on Virginia’s border and four out of America’s first five presidents were Virginian.

It was also the colony in which the English ideal of rule by a landed aristocracy took root most deeply. Even as Virginia developed representative forms of government, they were dominated, as in England, by those who possessed wealth and land, or by their sons and other relatives. Since many of the early English settlers were royalists who had fled from Cromwell’s Commonwealth, the idea that Virginians were gentlemen—“Cavaliers” who had fought for the king and been defeated, as opposed to New England Puritans who had repudiated the very idea of kingship—took hold early on in the colony’s history, and helped to develop Virginia’s reputation, or at least its self-image, as a place of elegance, refinement, good manners, and genteel behavior. Certainly it produced, to the astonishment of English visitors, any number of handsome manor houses set on estates that rivaled an English county in size, and a society of a refinement that was perhaps unique in North America. Behind that gracious image, however, it was also a place where huge fortunes were made—and all too often lost—in reckless land speculation on a vast scale; where dueling was not uncommon and often fatal; where going head over heels into debt was commonplace; and where much of the principal crop, tobacco, the mainstay of its commerce with Britain, was grown, picked, and cured by slave labor, with all the moral and practical difficulties of that “peculiar institution.” By the time of the Civil War more than a third of the population consisted of black slaves (and a small minority of “freedmen”), in a state that was then 425 miles in width and over 300 miles from south to north at its widest point—bigger than some European countries.

The “First Families of Virginia” formed its aristocracy, and after an initial experiment in marrying the daughters of the more important Indian chiefs, of whom Pocahontas, who became something of a celebrity in Elizabethan England, is the best-known example, the First Families tended to marry within their own rather small social class, quickly producing, as had happened in the English aristocracy, a world in which almost anyone who mattered was related however remotely to everyone else. “Cousinage—c’est une dangereuse voisinage,” as Tolstoy wrote in War and Peace about a different slave-owning aristocratic society, and certainly in Virginia cousins and vaguely defined “kinsmen” seemed to proliferate to an extraordinary degree, linking all the First Families together in a mesh that was as hard for outsiders to unravel as Penelope’s shroud. The Lees would never have boasted of being first in this social order, nor even “first among equals”; they were too well-mannered for that. But they were widely regarded as one of the most respected and best-connected families in Virginia: wealthy, cultured, devoted to public service, patrician in the best sense of that word. Of course, as in every family, there was over time the occasional black sheep or scandal, but for almost 200 years they acquired great estates and plantations, married well, filled major public offices with credit and honor, and when necessary fought for their mother country and colony, and later for their state and country.

The first Lee arrived in Jamestown, Virginia, in 1639, only thirty-two years after the establishment there of the first permanent English colony in North America. He disembarked not as an impoverished immigrant, but as an ambitious and well-connected one. Colonel Richard Lee (“The Immigrant”) was armigerous, bearing the coat of arms of the Lees of Cotton Hall in County Shropshire, England (which oddly enough includes a squirrel eating a golden hazelnut atop an elaborate medieval helmet), who traced their descent back to a Richard Lee, high sheriff of Salop in the mid-fifteenth century, and far beyond him into the misty antiquity of Anglo-Norman genealogy, possibly to a Hugh de Lega who arrived in England with William the Conqueror in 1066, and to a Lionel de Lee who accompanied the ill-fated Richard the Lionhearted on his attempt to take Jerusalem during the Third Crusade in 1183. In short, Richard Lee was a gentleman.

He was also tough, shrewd, fearless, and skillful at climbing the rungs of the colonial political ladder. He arrived with nothing more than the “patronage” of Sir Francis Wyatt, the first governor of Virginia, and soon became attorney general, then secretary of state, then a member of the King’s Council, high sheriff, and a colonel of the Virginia Militia. He was also at various times a fur trader, an Indian fighter, a slave trader, and a tobacco planter, and went on to become one of the largest landowners in Virginia, one of the richest men in North America, and the founder of a flourishing dynasty. Two of his descendants would be signers of the Declaration of Independence; two others (Robert E. Lee and his father) generals; and one, Zachary Taylor, not only a general but a president.

Richard Lee was not just a slave trader, in the days when that was still considered a respectable business, but a slave owner on a large scale, and a major employer of “indentured servants,” mostly young British men and women who signed up for three to seven years of work without wages to pay for their passage to America, and the chance of a new life once they had completed their indenture; unlike slaves, they could not be bought and sold as chattel property. Thus, almost from the beginning, Virginia had three classes: the landed gentry; impoverished English, Irish, Welsh, and Scots who came over as their indentured servants with the intention of eventually becoming independent farmers or workmen; and black slaves. The idea of a poor man acquiring land of his own was almost impossible to achieve in Britain, or anywhere in Europe—land was the magnet drawing people all the way across the Atlantic to work under conditions not much better than those of the slaves, and forming the basis for the land speculation that so obsessed their betters. Winning “land grants” from the crown, and turning the vast, seemingly endless forest to the west—from which the Native Americans were slowly receding or being driven, or where they were being decimated by disease—into what we would now call developed real estate was an even bigger and more profitable business than growing tobacco, and Richard Lee was as successful at that as he was at all things.

He was as fortunate in his children, ten of them, as he was in business and politics; indeed the family motto might almost have been replaced by Dr. Pangloss’s famous remark in Voltaire’s Candide, “Tout est pour le mieux dans le meilleur des mondes possibles.” (“Everything is for the best in the best of all possible worlds.”) He had so much land that on his death he was able to leave large parcels of it to his children. They built impressive houses of their own on it and thus created several branches of the Lee family, all of which produced in every generation men of distinction and merit, and women who married well. By the time of the American Revolution John Adams of Massachusetts, by no means an unqualified admirer of the South, was of the opinion that the Lees had “more men of merit . . . than any other family.”

One branch of this fast-growing and mighty tree descended from the third of Richard Lee’s seven sons, Richard Henry Lee II, known in the family as “Richard the Scholar” because he was educated at Oxford University, collected one of the largest personal libraries in North America, and wrote fluently in Greek, Hebrew, and Latin. He, like his father, filled numerous colonial offices, serving in the House of Burgesses and the King’s Council. He had eight children, one of whom, Captain Henry Lee I, the father of Henry Lee II, who married Lucy Grymes, “the low-land beauty,” a distant relative of George Washington—in fact Washington admired her greatly and was widely supposed by the Lees not only to have been in love with her, but to have lost her to Henry Lee II.

Henry Lee II built a handsome manor house for himself, the Lee House, at Leesylvania, and there he and Lucy had eight children together, the first of whom, Henry Lee III, better known as Light-Horse Harry Lee, would grow up to become perhaps the most famous cavalry commander of the Revolutionary War, and a friend, trusted subordinate, and protégé of George Washington’s—it was Henry Lee III who gave Washington’s funeral oration, calling him, “First in war, first in peace, and first in the hearts of his countrymen,” a phrase that is still remembered by millions of people who have no idea who its author was.

Henry Lee III, who despite many disappointments rose eventually to become governor of Virginia and a Virginian representative in Congress, was the father of Robert E. Lee. The Lee House at Leesylvania was therefore Robert E. Lee’s “ancestral home,” which George Washington visited several times, perhaps drawn by the still beautiful Lucy, and which represented for Robert E. Lee, although more in his imagination than in reality, a whole intricately linked, gracious world of stability, wealth, privilege, good manners, and family connections all his life, even though it passed out of his family’s ownership while he was still a youth. Other great houses haunted him throughout his life, much of which was spent in modest rented quarters, barracks, and tents: Shirley, built by Robert “King” Carter, then the richest man in Virginia, its roof surmounted by a carved, gilded pineapple, the symbol of hospitality, one of the grandest and most graceful mansions in Virginia, was his mother’s home; White House, one of his father-in-law’s plantations, would play a significant part in Robert E. Lee’s adult life; Stratford, built by Thomas Lee, another son of Richard the Scholar, with an unrivaled view over the Potomac River, set on a plantation of 6,600 acres, a brick mansion of great size and harmonious design, more impressive, perhaps, than beautiful, with magnificently proportioned steps sweeping upward to the entrance and one of the most admired formal gardens in America, was where Robert E. Lee was born; and Arlington, in Alexandria, Virginia, with its white columns and its associations with George Washington, was the mansion Lee would inherit by marriage, only to have it occupied by Federal troops at the beginning of the Civil War.

Modeling himself upon “the father of his country” would represent a challenge to any young man, but in Lee’s case it was complicated by his deeply ambivalent feelings about his own father, whose role in what Freud called “the family romance” was deeply conflicted, an example to be at once copied and avoided at all costs. Light-Horse Harry Lee was one of those men whose good advice to his children was seldom matched by his personal behavior—a courageous and innovative soldier, he was in peacetime an inveterate and increasingly reckless gambler on what we would now call risky investment schemes, mostly land speculation, which invariably failed, saddling him with enormous debts. His status as a Revolutionary War hero; his bluff, hearty good looks, somewhat spoiled in later life by a tendency to put on weight; his charm and the fact that he was a Lee led people to forgive him too easily and too often for his own good—and theirs—the end result being that he was a loving but often absent father, and that he left his large family virtually penniless.

“Light horsemen” were intended to carry out daring raids, to move quickly over long distances on missions of reconnaissance, or to dismount and fight as light infantry, for they carried a short musket or pistols as well as a short, curved saber. The idea of light-horse formations had been brought to France early in the eighteenth century by one of those typically charming and ubiquitous Hungarian emigrants, Count Laszlo Bercsenyi, who introduced the French to the huszár—the traditional Hungarian light cavalryman with his short, gold-laced, fur-trimmed cape thrown over one shoulder; a fur cap; skintight embroidered riding breeches; short, tight-fitting soft boots; a curved, Turkish-style saber; and a pair of pistols. Bercsenyi’s ideas were adopted enthusiastically by the French army, and in the days when France was still the leader in military innovation and fashion they spread rapidly to other countries in the form of countless lancer, hussar, chasseur, and “light dragoon” regiments, with glamorous names and uniforms, and even more glamorous officers, unquestioned as the elite of every army until the charge of the Light Brigade at the Battle of Balaclava brought about increasing skepticism on the subject. Light cavalry was well suited to North America, where there were few opportunities for big, formal European battles. It was cheaper too—big horses consumed more fodder, and heavy cavalry uniforms and equipment were notoriously expensive (the Household Cavalry in Great Britain is the only heavy cavalry still in active service).

Henry Lee’s high spirits and taste for taking daring risks made him a perfect light-cavalry leader, and he became the talk of the army when he beat off a surprise British attack at Spread Eagle Tavern in 1778. This earned him the opportunity of becoming one of Washington’s aides-de-camp—an honor he turned down because he preferred to fight in the field, gaining himself Washington’s lifelong respect, and promotion to major. A year later he stormed Paulus Hook, a British fort at what is now Jersey City, on the lower Hudson River, a daring, if not entirely successful action that won him Washington’s “unstinted” praise, and a gold medal awarded by Congress. Washington, recognizing Lee’s special skills, then put him in charge of a mixed infantry and light-cavalry formation, something of an innovation at the time, which was “officially known as Lee’s partisan corps,” and promoted him to lieutenant colonel. He was just twenty-five. Along with Henry Lee’s dash and competence there were, however, worrisome signs of a certain lack of judgment, a dangerous side. It was one thing for him to hang a deserter who had gone over to the enemy, but quite another to have the man’s head cut off and sent with the noose still around the neck to Washington’s headquarters “much to the horror of the commander-in-chief.”

Sent south to serve under General Nathanael Greene, Henry Lee quickly proved himself to be a commander of extraordinary talent in the Carolinas, amazing both the enemy and his own superiors by the skill and speed of his raids and forays, and by the distance his men and horses covered in some of the most brutal fighting of the war—though not otherwise resembling either of them, he had many of the qualities that would make Colonel T. E. Lawrence such a gifted leader of “irregular” warriors in World War I, or Major-General Orde Wingate in World War II. His role in General Greene’s successful campaign to free the Carolinas and Georgia was a major one, and earned him the honor of carrying dispatches from Greene to Washington in time to be present at the historic moment when Lord Cornwallis surrendered his army to Washington at Yorktown.

This was, in some ways, the high point of Henry Lee’s life, or at any rate the moment before things began to go badly wrong for him. He became, in the words of Douglas Southall Freeman, “sensitive, resentful, and imperious,” apparently feeling that his services had not been sufficiently appreciated, even though he was one of the recognized heroes of the war, and the only officer below the rank of general to be awarded a gold medal by Congress, and resigned from the army in 1782, determined to win “riches and . . . eminence” in public life. It is possible that he had expected to be promoted to general, and was offended when he was not; in any event, portraits of Henry Lee III do indeed appear to bear out Freeman’s description of him, and reveal a certain degree of petulance or dissatisfaction in the downturned corners of his lips. Despite the handsome features, it does not look like the face of a man you would want to buy a horse from.

Henry Lee III seems to have begun as a charming rogue, an eternal optimist, not at first dishonest in the conventional meaning of the word, but he swiftly degenerated into a gifted and persuasive confidence man, careless with facts, convinced of the merit of every harebrained scheme he devoted himself to, always promising more than he could deliver, and apparently neither able to add and subtract nor to learn from his own disastrous experiences—in short, a well-bred crook. Members of his family eventually learned to put codicils in their wills or their financial arrangements to make sure that Henry Lee III could make no decisions regarding their property or their estates, but they do not seem to have been any less fond of him for that. Every family needs a black sheep, and that was the role of Henry Lee III in the Lee family.

At first he seemed to be stepping in the right direction after Yorktown. He married a second cousin, Matilda Lee, known as “the divine Matilda,” who had inherited from her father the great mansion of Stratford and its 6,600 acres. Their marriage at Stratford was attended by George Washington, and it appears to have been a happy match. Following in the Lee tradition of public service, he became a member of Congress and then governor of Virginia, and Matilda bore him three children, one of whom, Philip, the eldest, died at the age of ten. Already, however, his business affairs were getting in the way of his other duties, and causing alarm in the widespread Lee family. When Matilda died in 1790 she left Stratford to her children rather than her husband, so she must already have been aware of his poor judgment and unreliability when it came to money—Henry’s own father left him only “some of his lesser lands,” apparently sharing Matilda’s concern. ...