Yet for all that, brokers and merchants generally were more interested in the color of the man’s money than his skin. Not that Hamilton gave a damn one way or the other. In general, he simply carried on amassing his fortune whenever an obstacle arose.

Born in 1807, either in the Caribbean or in Richmond, Virginia (his story of where he came from depended very much on whom he was talking to), Hamilton first made his mark on the historical record in 1828. In that year, the 20-year-old ran a cargo of counterfeit Haitian coin to Port-au-Prince for a consortium of New York merchants. When the Haitian authorities uncovered the criminal enterprise, Hamilton fled.

After news of the abortive expedition broke in New York, the newspapers condemned him. Most notably, the editor of Freedom’s Journal, the first African-American newspaper, cursed Hamilton for what he viewed as his disgraceful role in undermining the existence of the world’s first and only black republic. Under considerable pressure to name names, the African-American entrepreneur kept his silence and the identities of the New York merchants who had bankrolled the counterfeiting expedition were never revealed. Although still young, Hamilton apparently had learned the ways of Wall Street.

Five years later, he had shifted his focus permanently to New York, where he quickly acquired a reputation for over-insuring vessels and then arranging for them to be scuttled, which proved quite lucrative (for him, at least). Indeed, it was businessmen such as Hamilton who drove the nascent marine-insurance industry to organize itself. By 1835 all of the New York marine-insurance companies made no secret that they had collectively agreed never to insure any voyage involving Hamilton.

In the mid-1830s, the United States was in the throes of a real-estate boom, and Hamilton jumped headlong into the frenzy. He bought 47 lots of land in what is present-day Astoria. Even more impressively, he invested heavily in property in Poughkeepsie, buying several tracts of land in the town, an iconic local mansion, and a 400-foot-long wharf. In all, he gambled more than $10 million in today’s money that the boom would continue. Following the herd turned out to be the worst business decision of Hamilton’s life. He had bought at the top of the market, only weeks before what became known as the Panic of 1837. Hamilton dodged his creditors for several years, but, taking adroit advantage of new federal legislation, declared bankruptcy in 1842.

Although Hamilton had bought and sold some stocks in the 1830s, the second act of his New York business career, beginning after 1842, was defined by his Wall Street speculations. His bets did not always pay off, but they most definitely were distinguished by wile and creativity. For instance, in the mid-1840s, he dragged the Poughkeepsie Silk Company into court so that the struggling firm could be legally dissolved, leaving the cash realized from the sale to individual shareholders, including himself.