Disunion follows the Civil War as it unfolded.

Writing to Frederick Douglass in 1852, the black intellectual James McCune Smith noted Jeremiah G. Hamilton as “the only black millionaire in New York,” disparaging him for the crassness of his pursuit of wealth. But despite Hamilton’s prominence in his own lifetime, modern American historians have ignored him.

What makes Hamilton’s invisibility all the more remarkable, is that, paradoxically, he was larger than life, anything but a reticent figure lost in the background. Indeed, he left a pretty hefty footprint on the historical record: there are tens of thousands of words of newsprint about him and, in the archives, well over 50 court cases involving Jeremiah Hamilton as either plaintiff or defendant. His well-documented experience as a wealthy black man provides a unique but illuminating perspective on the possibilities and limits of black life in the nation’s largest city, before and during the Civil War.

Hamilton was a broker, a black man whose very existence flies in the face of our understanding of the way things usually were in New York in the middle of the 19th century. Far from being some novice feeling his way around the economy’s periphery, he was a Wall Street adept, a skilled and innovative financial manipulator. Unlike later black success stories who would make their fortunes selling goods to black consumers, Hamilton cut a swath through the lily-white New York business world of the mid-1830s, a domain where his depredations soon earned him the nickname of “The Prince of Darkness.” Others, with even less affection, simply called him “Nigger Hamilton.”

Hamilton first made his mark in 1828, when he was just 21, running a large sum of counterfeit coins from Canada through New York to Haiti for a consortium of prominent New York merchants. Discovered, Hamilton, aided by several fishermen, escaped and lurked around Port-au-Prince harbor for 12 days until he could surreptitiously board a New York bound vessel. After he left, the Haitian authorities confiscated Hamilton’s chartered brig, the Ann Eliza Jane, and sentenced Hamilton, in absentia, to be shot. They nailed proclamations all over the island announcing this summary verdict and offering a $300 reward for him.

By the time of New York’s Great Fire of 1835, one of the most destructive events in the city’s history, Hamilton was renting an office on Wall Street. He profited handsomely from this disaster, taking pitiless advantage of several of the fire victims’ misfortunes to pocket some $5 million in today’s currency. Within months he joined in New York’s real estate boom, investing more than $7 million in today’s dollars to buy 47 lots of land at Hallet’s Cove, in present-day Astoria, and docks, wharves and tracts of land up the Hudson River in Poughkeepsie.

No one will ever erect a statue honoring Jeremiah Hamilton. He was no saint. He was more aggressive and more ruthless toward his competitors than most businessmen. But it’s understandable: for a black man to succeed he had to be at least as cavalier about such niceties as keeping within the law as his white contemporaries. Wall Street has never been a place for the faint of heart, but, in the antebellum era, with remarkably few rules of any sort yet established, New York businessmen played hardball and, at least initially sensing an easy mark, they lined up to play with Hamilton.

Hardly surprisingly, given the prejudice against African-Americans that was a commonplace, businessmen often discriminated against Hamilton. His relationship with the insurance industry was particularly fraught. In the 1830s, the New York insurance firms all agreed to blackball Hamilton by refusing to write policies for any of his ventures. Suggestions that Hamilton had conspired to scuttle heavily insured vessels were bandied about, and almost certainly had some truth to them. In 1843, the district attorney charged him with conspiring to defraud the Atlantic Insurance Company of $50,000. Eventually the case was dropped, but not before Hamilton sensationally burst into the police office one morning and claimed that the Atlantic Insurance Company had paid someone to lure the broker down to the end of Pier No. 1 on the Hudson (then known as the North River) at 9 p.m. and then to drown him.

He had his run-ins with the stock exchange as well. In 1845, the Public Stock Exchange passed a resolution that forbade members from buying or selling any shares for Hamilton under penalty of expulsion. As one newspaper commented: “the reason for this appears to be, that said Hamilton is a colored man; and so, forsooth, his money is not to be received in the same ‘till’ with theirs. Oh, ‘the land of the free and the home of the brave.’” For all that, brokers and merchants generally were more interested in the color of the black man’s money than his skin: regardless, Hamilton simply brushed aside all obstacles placed in his way, or connived to get around them, and carried on amassing his fortune.

Hamilton also wasn’t afraid to get personal, and even physical, with his enemies. In a court case in 1843, a Justice Merrit appeared as a witness and denigrated Hamilton’s character. Unable to restrain himself, Hamilton stood up in court and claimed the only reason Merrit had damned him thus was his “refusal to lend the Justice money.” Although proceedings were adjourned promptly, Hamilton and Merrit continued abusing one another as they left the chamber, then started jostling and eventually brawling on the steps of the Tombs (the building on Centre Street housing both the prison and courts). Merrit was striking Hamilton with his cane and the latter was energetically wielding a rung he had seized from a passing cart when the police intervened.

And yet for all of the disdain he attracted, financiers had to concede, time and again, that this black man was sharp as a razor and knew exactly what he was doing. Later, in the 1850s, Hamilton would engage in a titanic struggle with Cornelius Vanderbilt, America’s first tycoon and the epitome of unabashed capitalism, over control of the Nicaragua Transit Company. The day after Vanderbilt’s death on Jan. 4, 1877, an almost full-page obituary on the front of The National Republican newspaper acknowledged that, in the context of his Wall Street share transactions, “There was only one man who ever fought the Commodore to the end, and that was Jeremiah Hamilton.” The writer neither explained who Hamilton was nor even mentioned his skin color, only elaborating that although Vanderbilt “did not fear [Hamilton] because he never feared anybody,” without a shadow of doubt “the Commodore respected him.”

There was a startling disjunction between the financial world, where the black broker relished his predatory role, pursuing aggressively whatever edge he could find in his dealings with white businessmen, and his everyday existence on New York streets, ruled by an unforgiving and demeaning racial etiquette. At work Hamilton was, to borrow Tom Wolfe’s term, a master of the universe, but for the rest of the day and night he was barely a second-class citizen. For all the distance Hamilton put between himself and other African-Americans, to white New Yorkers seeing him about town, he remained just another Negro.

Any time Hamilton ventured outside, particularly if accompanied by his wife, there was the chance of an ugly scene. Hamilton was a racist’s nightmare, and an affront to the beliefs of a majority of New Yorkers. He was very successful, associated with whites – and married to a white woman. Eliza Morris had become pregnant with Hamilton’s child when she was just 13 or 14 and he was at least twice her age. They had nine more children, and their marriage lasted for some 40 years, until Hamilton’s death.

The Civil War merely heightened the absurdity of the black broker’s existence. On Wall Street, he carried on accumulating money, caring nothing about whom he upset. Hamilton was a master at manipulating speculations in shares where the client bore any loss but Hamilton reaped any profits, arrangements that spurred the disgruntled to take him to court regularly in these years. He gave scant, if any, thought to moderating his behavior or large style. On one occasion in 1864, he imperiously demanded of a white client, anxious to be given points and included in a deal, “an acknowledgment of his kindness.” Hamilton deemed a basket of bottles of champagne and a box of 600 cigars to be suitable, but he also made it clear that he “did not want any but the very best.”

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Such cocksure behavior from a black man may have been tolerated on Wall Street, but on any other city street it was an incitement to a lynching. There were always New Yorkers more than willing to remind even this most successful of black men of his blackness and what that meant in a city rived by race. Nowhere was this clearer than in the Draft Riots that erupted in New York in July 1863.

On the second evening of rioting, somewhere between a dozen and a score of “men and boys,” turned onto East 29th Street and strode down the street as if they owned it, shouting out threateningly “68, 68, 68” – the number of the house where Jeremiah G. and Eliza Jane Hamilton lived. The white rioters kicked in the basement door and rushed up the internal stairs to the ground floor where they were confronted by the 40-year-old Eliza Hamilton — not only white but also, according to one of her husband’s obituaries, “a daughter of the Hon. Robert Morris of Philadelphia” — who told them Jeremiah Hamilton was away. No one doubted the intruders’ intentions. A curious neighbor ambled down the block to see what all the noise was about, only to have a lookout point a cocked pistol at his chest and tell him that “there is a nigger living here with two white women, and we are going to bring him out, and hang him on the lamp post, and you stop and see the fun.”

After the Civil War, in the last decade of his life, Hamilton slowed down and took on a veneer of respectability. To be sure, one obituary still damned him as “the notorious colored capitalist long identified with commercial enterprises in this city.” But others were gentler, noting that, when he died, he was “with one exception, the oldest Wall Street speculator” and emphasizing that “his judgment in banking was highly esteemed, and he was often consulted by prominent bankers.” In May 1875, Hamilton was buried in his family lot in Brooklyn’s Green-Wood Cemetery, next to two of his daughters.

Jeremiah Hamilton’s life offers a way to consider, from the unusual perspective of a black man, subjects that are seen, without too much thought, as being quintessentially white, totally segregated from the African-American past: Wall Street, the stock exchange, the Great Fire and even journalism. Benjamin Day, founder of the pioneer New York Sun in 1833, was Hamilton’s best friend. Reputedly, Hamilton wrote several articles about banking that were published in that newspaper and was so closely associated with the Sun in the late 1830s that James Gordon Bennett, proprietor of the rival New York Herald, mistakenly thought for some time that the black man had bought the newspaper.

Hamilton continually defied contemporary expectations (and those of modern historians too) about African-Americans, turning up in the most surprising of places. When Hamilton, his wife and several children went on a European tour, they stopped over in Paris in late August 1870, just as the German armies were preparing to lay siege to the city.

When Hamilton died in May 1875, obituaries called him the richest black man in the United States, possessing a fortune of $2 million, or in excess of $250 million today. He lived out the American nightmare of race in his own distinctive fashion, and it would be some time before New York City would see his like again.

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Shane White is a professor of history and an Australian Professorial Fellow at the University of Sydney. He is the author or co-author of five books, including “Stylin’,” “ Stories of Freedom in Black New York,” “The Sounds of Slavery” and, most recently, “Playing the Numbers.” He is writing a book about Jeremiah G. Hamilton.