In 1849 William Thompson, a man of genteel appearance, was arrested by the New York City police. Compared with several recent big cons–the Enron boondoggle, the subprime mortgage swindle–the scam that got Thompson into trouble with the law was astonishingly simple, and his booty so penny ante that his arrest wouldn’t merit a mention in today’s tabloids. Thompson persuaded his marks to “lend” him their gold watches as a token of their confidence in him–tokens that, in fact, he had no intention of returning. Back then, however, Thompson’s small con became notorious, first in New York City and then throughout the country. Once a mere confidence man, Thompson was touted as “The Confidence Man,” and he so relished his celebrity that he scheduled interviews with the press from his cell in the Tombs, Manhattan’s notorious municipal prison. One visitor reported that he was led to Thompson’s cell by “two country looking individuals. When they arrived at the landing in the second tier, they were accosted by our hero, who sat in the keeper’s chair, in this way, ‘Gentlemen, have either of you a cigar? I am the Confidence Man.’ ”

Why this media frenzy? At the time of Thompson’s arrest, the United States was alive with the spirit of enterprise. Vast lands were being opened to settlement, commercial farming and mercantile undertakings of all sorts. Towns and cities rose up overnight. New turnpikes, canals, bridges, dockyards and railroads gave the market a vast geographical reach. Indeed, it was during the antebellum era that the marketplace first assumed its position as the country’s lodestar. Previously most economic transactions had been local. They were conducted between people who knew and trusted each other as family members, neighbors and fellow villagers, who followed long-established routines and relied on barter or tangible pieces of gold and silver as means of exchange. But in Jacksonian America, perfect strangers separated by great distances entered more often and more freely into untried and faintly mysterious kinds of business relations. These new contractual arrangements involved untested technologies, undertakings of unprecedented size like the Erie Canal and risky investments in distant unsettled places like the Ohio Valley. In this new world, one increasingly populated by anonymous, highly mobile, self-interested people, there was nothing more precious than the confidence that these contractual promises would be kept. America was brimming over with confidence. It seemed an indigenous national instinct, a fervent faith in the notion that Americans could get rich and reinvent themselves while doing it–if one was audacious enough to take the risk of trusting a stranger. Confidence was a form of equality of opportunity open to the bold–Manifest Destiny without all the heavy breathing about democracy and divine election.

Yet even as this new economy expanded, Jacksonian Americans were plagued by a crisis of confidence. What would happen if all these strangers didn’t keep their word? What if a land broker’s Elysian field turned out to be a malarial swamp? What if your railroad shares entitled you to a stake in nothing but two streaks of rust? What if the canal in which you were an investor was nothing but a fifty-mile-long bone-dry rut? What if a town promoter’s map depicting the churches, schools, stores, hotels and theaters of a New Jerusalem in some Midwestern outback was nothing more than a figment of his felonious imagination? More disconcerting still, these dealings inveigled people in an economy lubricated by paper currencies that no one could entirely trust. What if the currency issued by some faraway bank was worth no more than the useless tract of land the banker had recklessly speculated in, leaving not only the bank’s depositors high and dry but fleecing everyone else unfortunate enough to hold the bank’s paper? What if, indeed? Who do you trust?

During the quarter-century leading up to the Civil War, commonly identified as the takeoff stage of American capitalism, there were several troughs of panic and depression: a prolonged and deep one in 1837, following years of wild land speculation, and another in 1857. That year Herman Melville published The Confidence-Man: His Masquerade, perhaps the best known if least read example of a large literature: novels, memoirs, travelogues and plays devoted to exploring the era’s crisis of confidence. Melville’s gaze, as one might expect, was a coruscating one. In his novel a con artist reappears in different guises–land agent, herb doctor, stock speculator, etc.–aboard a steamboat headed from St. Louis to New Orleans. For Melville, all of American society could be likened to a confidence game, but none of his con artist’s marks are the kind of unsuspecting folk whom William Thompson fleeced.

Melville understood that a confidence man’s thievery depends on the willing collaboration of his mark, and a successful swindle requires a world of malignant innocence where people harbor the sneaky, illicit belief that fast money can be made by skirting the moral rigors and renunciations of the work ethic. Melville’s confidence man meets men on the make whose cupidity and moral slipperiness make them ripe pickings. They are willfully credulous souls in pursuit of their own aggrandizement. Each mark’s motivation may be ingenuous, idealistic even; after all, each is merely in a footrace to catch up with the American dream, to realize his own manifest destiny, the New World’s promise of limitless opportunity for every man. Still, even the most innocent (that is to say, least calculating) mark approaches the confidence man with a certain foreboding: something feels not quite right; something shady hovers nearby–but that something is very hard to resist. In Melville’s eyes, whether in the realm of politics, religion, philosophy, literature, philanthropy or commerce, confidence was a “masquerade,” a devil’s game, a phenomenon that called into question not only the underlying premise of a market economy but the very moral and existential fabric of the self and society.

Melville’s devilish protagonist casts a long shadow, one that falls back past William Thompson–who, some have claimed, was the inspiration for Melville’s novel–to the narrator of the memoir Sheppard Lee, Written by Himself, published in 1836. Its author, Robert Montgomery Bird, was a doctor and a writer. He was admired by Edgar Allan Poe and collaborated with the period’s most famous actor, Edwin Forrest, on several successful plays. Sheppard Lee, which Bird published a year before breaking with Forrest, is a rollicking satire about the transmigration of the self in Jacksonian America. During Sheppard’s strange odyssey, all of the era’s cherished, self-congratulatory maxims about the heroic individual, equality, the work ethic and invincible optimism are mocked mercilessly. Jacksonian democracy comes in for an especially withering comeuppance, perhaps in part because Bird considered himself a Whig.

The offspring of middling farmers in New Jersey, Sheppard quickly fritters away his inheritance, the family homestead, because he is allergic to work–“dull and disagreeable labour.” Like many of his neighbors, he has a taste for get-rich-quick schemes but is not cunning enough to stay out of trouble or spot those plotting to take advantage of him. More hapless than roguish, he’s utterly lacking in the ambition and energy, not to mention the moral appetite, for hard work that is supposed to animate every red-blooded American. His situation grown dire, he tries to recoup his losses by going into politics. He thinks of it as pure charade, nothing more than inflated invective aimed at banks and aristocrats (he’s apparently joined the local Jacksonian Democratic Party), which he parrots eagerly to curry favor. He is cheated out of the spoils of office by cleverer men, and then he blithely joins the opposition party but with no better result.

Creditors hot on his trail, Sheppard, while desperately chasing a rumor about Captain Kid’s buried treasure, finds himself dead, but not truly dead. Instead, he is rescued by an act of infernal intervention: he discovers he has the power to transmigrate his soul or spirit, which up to this point has been wandering about the countryside in some hard-to-pin-down disembodied state, into the body of someone recently deceased. After some momentary disorientation, with amazing alacrity Sheppard’s spirit settles into the corpse of the deceased Squire Higginson, who, as the devil’s justice would have it, had long made a habit of mocking Sheppard’s sorry state. The Squire is a man of substance, and Sheppard’s mouth waters at the prospect of taking over his wealth and persona.

After inhabiting the Squire, Sheppard reanimates the corpses of a foppish fortune hunter, a usurious miser (clearly Jewish), a Quaker philanthropist, a Virginia slave and a melancholic slave master–a sizable slice of antebellum society. Through all these transformations some fragile residue of Sheppard remains, but even he is struck by how easily he assumes the attitudes, values, passions and idiosyncrasies of each new identity, each from a different walk of life. “What had become of me?” he asks. Sheppard’s “memoir” becomes a picaresque meditation on the self and the sacred shibboleths of his age. Rather than symbolizing that rock-solid independent, self-affirming individual so central to the ethos of democratic capitalism, Sheppard’s experience suggests that the self melts away into a series of performances staged in the theater of the marketplace. It assembles and disassembles and reassembles from moment to moment. And a self like Sheppard’s, one that is essentially ephemeral, more a working hypothesis than a fact, hardly inspires confidence, neither deep down in the individual psyche nor between one self and another. It can also be disorienting to the contemporary reader: is this really a novel of the early nineteenth century? Doesn’t all this liquefaction of the self express a sensibility more familiar to life in our so-called postmodern era? While the novel is clearly one of its time, Bird’s skill as caricaturist, his wit, irony and iconoclasm, lend Sheppard Lee an odd contemporary feel.

Why all this shape-shifting, anyway? Why doesn’t Sheppard just settle into a prosperous and respected life as Squire Higginson, a Philadelphia “gentleman”? In every transmigration–with one critical exception I will return to in a moment–Sheppard’s happiness about his new existence sours into a feeling of discontent from which he longs to escape. Although the pitfalls of each of Sheppard’s lives are distinct, his chronic unease is time and again driven by the poisonous quality of his social relationships. There is a high quotient of jealousy, resentment, envy and deception in the novel, most often the bitter fruit of the money-hunger and social pretensions exhibited by Sheppard’s “selves” as well as family members, neighbors, competitors, swindlers and con artists. All of this turns the “memoir” into a scathing sendup of social mobility, equality and democracy. Sheppard Lee’s memoir is a Tocquevillian black comedy. The chance to leave behind lowly beginnings and rise to something grander–America as the land of second chances–was one of the great promises of Jackson’s “Age of the Common Man.” However, as Sheppard never fully realizes but Bird (along with Tocqueville) conveys all too well, this race up the mountain breeds a society in which everyone is trying to put one over on others, luring them like “minnows,” a world driven by invidious social distinctions that undermine its celebrated egalitarianism.

Sheppard Lee has plenty of telling aperçus about this peculiarly American form of what Bird calls variously the “republican aristocratic society,” “chip-chop” aristocrats and the “nabobocracy.” It’s a world of bloated self-importance, of “dash, flash, and splash,” full of parvenu strivings and resentments. What counts here is money, perhaps the character of one’s profession–preferably something as far away from manual labor as possible–and maybe even what your father did, but no need to trace the roots back further since all American grandfathers “were pretty much alike, and the sooner we forget them the better.” Bird has a nice appreciation of the psychosocial and political chemistry that imparts a distinctive frisson to this admixture of faux aristocracy and democratic aspiration. The pomp, ostentation and arrogance of the rich, the supercilious airs put on to fend off reminders of the shallowness of their lineages, incite a bitter hostility in the poor, who’ve been promised equality but receive a fistful of social insult instead. All this “puerile vanity and stolid pride of the genteel and refined” exasperates the lower orders, feeding “mobocracism” and “all other isms of a vulgar stamp.” The problem for the newly risen, anxious to put distance between themselves and their lowly beginnings, is that the “cobbler is [a gentleman] or thinks himself so–which is all the same thing in America.” Looked at wrong-side out, that sunny vision of equality of opportunity and plebeian democracy that lit up the Jacksonian imagination seems a sham. No one is who he claims to be.

Democracy itself turns vile in the later stages of Sheppard Lee’s transmigrations. When he pops into the body of a wealthy Quaker philanthropist (Zachariah Longstraw), Sheppard hopes for an escape from all that devil-take-the-hindmost, self-seeking nastiness into a life of virtue (although he does slyly admit he’s game on philanthropy more for the material ease than the virtue). His life as a good Samaritan, however, turns into a nightmare. Giddy with good intentions, Zachariah starts up charities to succor “the suffering poor” while exhorting them to “economy, industry, prudence…and so forth”; tries schemes to “effect a reformation in [the] habits and feelings” of “poor wretches in prison”; and establishes schools to “keep the children of the poor out of mischief.” But every one of his naïvely conceived and self-righteous acts of do-goodism is received with howls of ingratitude by the objects of his charity: poor working women, criminals, small businessmen down on their luck, embattled marble cutters and shoemakers, even an escaped slave he hides but who then runs off with the family silver.

All that is nothing, however, compared with Sheppard’s next comeuppance. He is kidnapped by two slave catchers who, fresh out of slaves, intend to sell him down South as an abolitionist, ripe for lynching. Of course Sheppard is not an abolitionist…but then again, nobody is what they seem to be, and he’ll do. His captors do a bang-up public-relations job of inventing and inflating his abolitionist credentials; indeed, they do their job too well and democracy takes care of the rest. Although our brigands want to sell Sheppard in Louisiana, where abolitionists command top dollar, they get only as far as an election rally in Virginia, which Bird uses to provide a wicked portrait of the mob, and Jacksonian democracy, in full frenzy. Their blood up, these white male citizens are ready for rough justice right there and then, and they don’t plan on paying for it either. In a hilarious scene the kidnappers appeal to the sanctity of private property–that is, their “ownership” of the philanthropist Sheppard–but the mob isn’t buying it. Riled up by a thunderclap of fatuous democratic bluster about the sanctity of The People, they set off to do away with him.

Sheppard manages to escape by transporting himself into the body of a dead slave, and being a slave turns out to be the only incarnation that Sheppard finds inherently satisfying. At first he can hardly believe it himself. Up to this point he has invariably opted for identities (or rather stolen them; we might call him a master of identity theft) that promised some improvement in his social condition. Now the process has been reversed, and out of desperation, he finds himself at the very bottom, the despised dead end of the social hierarchy. Yet wondrous strange, he and his fellow slaves are utterly content. Indeed, only as a slave does Sheppard entirely lose touch with his former self, his “Sheppardness.” Christopher Looby’s introduction to Sheppard Lee notes the racism of these passages, about which there can be no doubt. Sheppard–whose slave name is, of course, Tom–and his mates are perfect Sambo types: happy-go-lucky, childlike, slow-witted and loyal unto death to a master as all-caring as our father who art in heaven. It is the book’s most unsettling invention, an inadvertent reminder of the identity theft that occurred beyond the confines of its plot.

According to Looby, Bird considered but ultimately abandoned a wide variety of scenarios for Sheppard’s masquerades. One would have had him reincarnate as a counterfeiter. I suspect this would come as no surprise to Stephen Mihm, whose A Nation of Counterfeiters is a brilliant description of a time–Sheppard Lee’s time–in American history that seems at once distant and familiar. Mihm’s book is a lucid history of counterfeiting in antebellum America, that dark art’s golden age, so to speak. Mihm’s central subject is the transubstantiation of money, and his and Bird’s books together make up a devil’s dictionary of a burgeoning market society, its vaunted individualism and of capitalism as a kind of necromancy.

At the outset of his book Mihm conveys the elemental strangeness of this era. Until the Civil War there was no national currency, no dollar issued by the federal government and used by everybody. Instead, there were dozens of currencies issued by state banks, railroads, canal and mining companies, and other enterprises, some used only in particular locales, many others flowing freely across state borders, from region to region. (Mihm’s book is full of striking illustrations of these monies, and someone ought to mount them as an exhibition, for they comprise colorful depictions of the nation in all its workday busyness and allegorical richness, and testify to the artfulness of their skilled commercial engravers.) All these paper currencies were a good thing too. How else would this newly emerging and rambunctious market economy lubricate all the transactions people were dying to make? The demand for more money, new money, coins but especially cash that required only a printing press to reproduce in abundance (no arduous discovering and mining of precious metals), became virtually limitless during the boom years of the 1820s and ’30s, and again after the country recovered from the collapse of the land boom in 1837 and the terrible depression that followed.

But this multitude of paper was also a bad thing. No one was minding the store. State banks, the main source of this great pandemonium of money, were chartered by their respective state governments, but the charters were essentially licenses to print because they contained no provisions for ongoing public oversight to ensure that the banks had assets on hand (gold especially) to back the notes they issued. There was even less supervision, if that’s possible, of the script issued by railroad, mining and other industrial corporations. These currencies were often not worth the paper they were printed on. They might as well have been counterfeit. And there was the rub: if what passed for legal tender was often scarcely distinguishable from funny money, what was a commercial society resting on confidence to do?

Counterfeiters knew what to do, and they did a land-office business. Flourishing especially in border areas–the Vermont-Canadian backwoods was the main site of the industry’s early period–where law enforcement, such as it was, was weakly developed (here and there counterfeiters were known to hold down day jobs as sheriffs or magistrates) and compromised by overlapping governmental jurisdictions, counterfeiting grew steadily in scope, geographic reach and organizational complexity. Like any ordinary business, it concerned itself with credit arrangements, finding reliable suppliers of raw materials, quality control, the supply of skilled labor, competitive rivalries, marketing and distribution. As the economy at large began to industrialize, so too did counterfeiting; technological innovations in engraving and printing made the counterfeiters’ product more sophisticated and harder to spot. The industry also took advantage of the dispossession of skilled artisan engravers and printers, whose small workshops had been driven under by larger firms, to recruit its own labor and “sales force.” The latter often consisted of casual and unemployed workers who became the industry’s “shovers,” passing on fake notes to unsuspecting storekeepers.

Yet counterfeiting was not simply an enterprise like any other. Mihm acutely notes that by bringing back to life the casualties of legitimate capitalism–ruined banks, unemployed engravers, dead currencies, discarded machinery–counterfeiting performed a kind of necromancy. Consequently the whole monetary system lived in a chronic state of anarchy as the anxiety about what should count as real value and what should not produced what Mihm calls a “categorical collapse,” a sense of vertigo further undermining confidence in the “real” economy. This nurtured the growth of an urban capitalist demimonde inhabited by all sorts, an underclass of the semi-employed, drifters, upper-crust slummers, young clerks looking to escape their day jobs and of course criminal types, including confidence men, who made a mockery of all the cardinal virtues of bourgeois life. Counterfeiters moved among them. They became noxious to respectable society but heroes elsewhere in this capitalist dream world of easy money.

Theirs was not the prudential capitalism of the Protestant work ethic but rather the predatory, underground capitalism of the English sea dog, indifferent to the law, risk-prone in the pursuit of overnight wealth. And like those sea dogs, counterfeiters were the cultivators of a certain romantic aura. Mihm reports on how some of the better-known counterfeiters enjoyed reputations as lovable rogues who sported ruffled shirt fronts, gold watches and fob chains, the flashy regalia of this magical capitalism. They also fancied themselves exemplars of democratic self-invention. Stephen Burroughs, one of the most celebrated counterfeiters, proudly proclaimed in his memoir, “I am so far a republican, that I consider a man’s merit to rest entirely with himself, without any regard to family, blood, or connection.”

Their many victims, among them shopkeepers and legions of ordinary customers, naturally loathed them. A whole counterindustry of counterfeit detectors emerged, its main commodity being regularly updated guides to counterfeit currency, which many a storekeeper kept close by his side as he conducted his daily business. But even the detectors had a self-interest in a thriving counterfeit industry, since without it they would have been out of work, which Mihm observes made counterfeit guides less than reliable. Moreover, because the line between real and bogus currency was so hazy, legitimate banks were ripe for extortion by “detectors” who could easily ruin their reputations. What a world–like Melville’s, like Sheppard’s, like ours. Who can you trust?

Mihm explains that the particular dilemma of counterfeit currency was solved by the financial exigencies of the Civil War. The need to raise capital and pay soldiers compelled the Union to do what the Constitution had always empowered the federal government to do: issue a single national currency good as “legal tender for all debts public and private.” Greenbacks, mainly denominated as five-dollar bills, went into circulation in the summer of 1861. Their appearance was also meant to restore confidence in the future of the national government and the financial underpinnings of the economy. Although God is now duly noted as the ultimate object of trust on the back of dollar bills, in the early days of the greenbacks real trust rested in the power and moral authority of the Union as it survived its most traumatic test and honored its pledge to make good on the paper issued in its name. Henceforth counterfeiting could be likened, at least metaphorically, to treason, and its golden age ended.

Nagging questions remain, however, questions that strike deep into the murkier regions explored by Melville and Bird and shadow the present as much as they did the days of Andrew Jackson. If capitalism is by its nature a game of confidence, at what point does speculation, the beating heart of capitalist investment and innovation, dissolve into pure chicanery, a kind of economic alchemy or gambling with loaded dice? Are fictitious value and slippery selves the currency of a normal market society, not merely its criminal underworld? Mihm might say no, so long as you have a watchman on duty–in this case a federal Treasury with the sole authority to issue and police a uniform national currency. Melville, Bird and a man named James Gordon Bennett would have disagreed. Bennett, the William Randolph Hearst of the antebellum era, was the publisher of the New York Herald, and he used the occasion of William Thompson’s arrest to editorialize about society’s true confidence men. Bennett was brutally, even demagogically, direct. Thompson was a petty swindler, he wrote, but “those palazzos” of the rich, “with all their costly furniture and all their splendid equipages, have been the product of the same genius in their proprietors, which made the ‘Confidence Man’ immortal and a prisoner at ‘the Tombs.’ His genius has been employed on a small scale in Broadway. Theirs has been employed in Wall Street…. Long life to the real ‘Confidence Man’–the ‘Confidence Man’ of Wall Street–the ‘Confidence Man’ of the palace uptown.”

Bennett would feel at home today. Everything is as he left it.