On February 5, 1808, John Baylor IV, a 57-year-old Virginia aristocrat, died in debtor’s prison in Caroline County, Virginia. When Baylor was born, in 1750, he entered a highly privileged inner circle of the Virginia gentry, a network of fewer than fifty families—closely intertwined through overlapping ties of blood and marriage—that controlled Virginia. Like his father and grandfather, he was educated in England at Putney Grammar School and Gonville and Caius (pronounced “keys”) College, Cambridge. On the morning of September 29, 1770, as Baylor, in cap and gown, paraded through the college’s ancient Gate of Humility, through which all matriculants formally entered the college and initiated their studies, his prospects could not have seemed brighter. Awaiting him in Virginia was a vast tobacco plantation and estate built upon a foundation of Croesian riches amassed by his grandfather, John Baylor II, the largest slave trader of his generation in Virginia, and expanded by his father, Col. John Baylor III, one of the colony’s largest planters. As Baylor, no doubt jaunty, happy, and more than a little proud, sauntered through the college’s hallowed entrance, he did not realize that the tobacco-centered culture that dominated Virginia for nearly a century and a half before him was no longer viable, or that the planter aristocracy into which he was born was doomed.
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John Baylor IV’s father, Col. John Baylor III (1705-72), owned nearly twenty thousand acres and more than 150 slaves and was one of the wealthiest Virginians in the pre-Revolutionary period. Robert “King” Carter (1663-1732), the undisputed richest grandee in the Chesapeake, remembered Baylor’s father, John Baylor II (1650-1720), as the “great negro seller, and in all respects the greatest merchant we had among us.” Contracting with slave-trading firms based in Bristol, England, John Baylor II imported thousands of African slaves into Virginia, and in the years just before his death, he was responsible for nearly half of all slaves shipped into Virginia for sale to planters and others eager to purchase them.
Following his return to Virginia from Cambridge, Col. Baylor quickly established himself. In 1726 Virginia Lt. Gov. Hugh Drysdale (d. 1726) gave him two land grants totaling nearly twelve thousand acres along the Mattaponi River in what later became Caroline County. It was on this vast tract that he built Newmarket plantation, which he named after the famous horse racing course at the town of Newmarket, about ten miles east of Cambridge, England. Beginning with James I’s first visit in 1605, Newmarket became Britain’s most important venue for horse racing through royal patronage, which especially flourished under Charles II, who built the first racing stables there. An avid horseman, Charles II rode in a number of races and so loved the place that he perennially held court there for months at a time, a situation later satirized by poet Alexander Pope (1688-1744), who wrote, “Newmarket’s glory rose, as Britain’s fell.”
By the 1720s, when Col. Baylor attended Cambridge, Newmarket was, as a French visitor noted, the site of the “finest horse races” in Britain and the place where “all the noblemen and persons of distinction who take an interest in this amusement go … with their horses.” Newmarket was also a popular pastime—and often a vice—for Cambridge students, especially aristocrats with time and money on their hands. Until the nineteenth century, students from noble families attending Oxford or Cambridge universities were exempt from examinations and were not even required to attend lectures. These idle young men, who “enjoyed a degree of licence that certainly would not have been tolerated in a well-regulated home,” frequented Newmarket, and “indulged in a lavish expenditure ill-suited to their years.”
Daniel Defoe (1660-1731), who had come to Newmarket in 1722 to witness the spectacle of “horse races and a great concourse of the nobility and gentry,” was appalled that so many of the socially elite “were all so intent, so eager, so busy upon the sharping [gambling] part of the sport, their wagers and bets.” So focused were they at “picking one another’s pockets,” Defoe fussed, “it might be said they acted without respect to faith, honour, or good manners.” Defoe’s point of view, however, was not shared by the British aristocracy or the gentry in Virginia, where wagering of all kinds was deeply entrenched among commoners and elite alike. (Archeological excavations at Jamestown in 2007 uncovered gaming dice dating back to the earliest years of the settlement.) Writing about the same time as Defoe encountered Newmarket, Rev. Hugh Jones (1692-1760), a mathematics professor at the College of William and Mary, observed: “The common [smaller] planters leading easy lives don’t much admire labour, or any manly exercise, except horse-racing, nor diversion, except cock-fighting, in which some greatly delight.” Invariably these fiercely competitive contests were the subject of high-stakes bets among the “gentlemen” in attendance.
Though not noble, and a mere colonial to boot, Baylor must have made himself attractive and agreeable enough to have fallen in with the elite crowd at Newmarket. He undoubtedly spent many a leisurely day there, particularly during October, November, and December, when most of the horse races were run in the 1720s. It was in this cultural milieu that Baylor, while at Cambridge, sat for his portrait in a swank royal blue suit festooned with gold buttons (Fig. 1). In the painting, he sports a fancy adult wig, and his left arm is cocked imperiously on his hip, just above a dress sword. Though a young man of only about seventeen or eighteen, he is portrayed as supremely but coolly confident, a budding master of his universe. Baylor left Cambridge before obtaining his baccalaureate degree, but a Virginia planter did not need a diploma. It was enough just to have been there. (At the time, actually taking a degree was something one usually did to become a cleric or scholar or to pursue a teaching career—possession of such a credential by a “gentleman” would have suggested overt ambition, which was not an admirable characteristic among the gentry of that period.) So it was that, in addition to his books that became the beginning of his library, Baylor brought back from England a lifelong passion for thoroughbred horses and racing that would make him one of the greatest horsemen in colonial Virginia and that would later threaten to bankrupt him.