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As Alexander sailed north toward spectacular adventures, his father sank ever deeper into incurable poverty. Documents located in St. Vincent reveal that James Hamilton had wandered to the southern end of the Caribbean, almost to the coast of South America. On the tiny, secluded island of Bequia, located just south of St. Vincent, he had entered into a program set up by the British Crown to encourage impoverished settlers. Bequia is the northernmost of the Grenadine Islands, an isolated spot, seven square miles in size, of soft hills, jagged cliffs, and sandy beaches. On March 14, 1774, James Hamilton signed a contract that gave him twenty-five acres of free woodland property along the shore of Southeast Bay. In this lovely but menacing place, a stronghold of indigenous black and yellow Caribs and runaway slaves, James Hamilton chose a spot on public land reserved for a future fortification. Bequia was the sort of distant, godforsaken place that could have attracted only somebody who had exhausted all other options. The deed for James Hamilton’s land purchase tells its own tacit tale of woe; it made clear that his twenty-five acres were “not adapted for sugar plantations” and had been set aside “for the accommodations of poor settlers.” Under the grant, James Hamilton didn’t have to pay a penny for the first four years but had to stay on the island for at least one year. A 1776 survey shows him sharing seventy acres with a man named Simple, and they are the only two people listed on the roster of poor residents. There must have been days when it was hard for James to believe that he was the fourth son of a Scottish laird and had grown up in a fogbound castle. The descent of his life had been as stunning and irrevocable as the rise of his son in America was to seem almost blessedly inevitable.