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that he was the black sheep of the family, marked for mediocrity. While James had no formal education to speak of, two older and two younger brothers attended the University of Glasgow, and most of his siblings found comfortable niches in the world. Brother John financed manufacturing and insurance ventures. Brother Alexander became a surgeon, brother Walter a doctor and apothecary, and brother William a prosperous tobacco merchant, while sister Elizabeth married the surveyor of customs for Port Glasgow. Easygoing and lackadaisical, devoid of the ambition that would propel his spirited son, James Hamilton did not seem to internalize the Glaswegian ethos of hard work and strict discipline.
    One has the impression that his eldest brother, John, now laird of Grange, was no country squire riding to hounds but an active, enterprising man who was intensely involved in the banking, shipping, and textile business revolutionizing Glasgow. This cathedral and university town, rhapsodized by Daniel Defoe in the 1720s as “the most beautiful little town in Britain,” already breathed a lively commercial spirit of the sort that later appealed to Alexander Hamilton. 19 After the 1707 union with England, as Scottish trade with the North American and West Indian colonies boomed, merchant princes grew rich trafficking in sugar, tobacco, and cotton. In November 1737, John Hamilton took the affable but feckless James, then nineteen, and steered him into a four-year apprenticeship with an innovative Glasgow businessman named Richard Allan. Allan had executed a daring raid on Dutch industrial secrets (one that strikingly anticipates what Alexander Hamilton later attempted in bringing manufacturing to Paterson, New Jersey) and helped to pioneer the linen industry in Scotland with his Haarlem Linen and Dye Manufactory.
    In 1741, John Hamilton teamed up with Allan and three Glasgow grandees— Archibald Ingram, John Glassford, and James Dechman—to form the Glasgow Inkle Factory, which produced linen tapes (inkles) that were used in making lace. Hamilton’s partners were the commercial royalty of Glasgow, who drove about in fancy coaches, presided over landed estates, and dominated the River Clyde with their oceangoing vessels. For many years these men would tirelessly bail out the hapless James Hamilton from recurrent financial scrapes.
    The onerous four-year contract that James Hamilton signed with Richard Allan in 1737 was a form of legal bondage that obligated him to work as both “an apprentice and servant.” 20 John Hamilton paid Allan forty-five pounds sterling to groom his younger brother in the textile trade. In exchange, James would receive room, board, and fresh linen in the Allan household but no guaranteed holidays or free weekend time. John Hamilton must have thought that he was shepherding the wayward James into a promising new industry. In time, the linen industry indeed proved profitable, but during this start-up phase it was a dispiriting, moneydraining proposition. So when the apprenticeship agreement expired in 1741, James Hamilton decided to test his luck in the West Indies.
    Many young aristocrats flocked to the West Indian sugar islands, seduced by a common fantasy: they would amass a quick fortune as planters or merchants, then return to Europe, flush with cash, and snap up magnificent estates. The Glasgow countryside was studded with the country houses of winners in this sweepstakes. Great shiploads of sugar traveled from the West Indian islands to Glasgow’s “boiling houses” or refineries, and its distilleries produced brandy from that sugar. Beyond the sugar trade, industrious Scots also operated stores that sold provisions to plantations and marketed their produce. One historian has noted, “Their emporiums were crammed with full lines of European and North American goods—hardware, draperies, clothing, shoes, and what not—and much resembled warehouses.” 21 Of all the Caribbean islands, few enjoyed more