The Distinctly American Ethos of the Grifter

EVERY AGE HAS its defining minor characters, those who briefly light up the public’s imagination not for their achievements but for how they personify our anxieties and most fervent human desires. Consider the half-Chinese, half-Malay Princess Caraboo, who in 1817 was kidnapped by pirates from her native island of Javasu in the Indian Ocean and sold from ship to ship around the globe until finally she jumped overboard and swam ashore, up the Bristol Channel to the parish of Almondsbury in what is today South Gloucestershire, England. Or so went the story that kindly strangers were able to coax out of the young woman who showed up on a cottage doorstep speaking “gibberish” and wearing a dress “in imitation of the Asiatic costume,” as chronicled in a leaflet published later that year. For 10 weeks, she regaled admirers with reminiscences — of a mother with blackened teeth and a bejeweled nose, and a father of such rank petitioners approached him only on their knees — before she was exposed as a cobbler’s daughter and illiterate servant, born Mary Willcocks in Devonshire. She went on to sustain a living supplying a local infirmary with — poetic justice — leeches.

We, too, have our cheats and impostors, so many these days that some commentators have cited grift as the ascendant ethos of our time. Those indicted or convicted in the past year include the faux European trust-fund baby peeling off hundred-dollar tips even as her credit cards were denied; the mid-list Hollywood stars accused of bribing their children’s way into college; the party promoter who peddled luxury villas on a white-sand Caribbean beach that turned out to be hurricane-relief tents on a gravel lot; and the Stanford University dropout in a Steve Jobs costume touting a health care revolution via a single drop of blood. It’s easy to see these stories as symptomatic of our general miasma of fakery and doubt. Everyone is on the make; everyone is getting conned. But not all of these cases technically qualify as grift, which in its highest form goes beyond mere fraud to question and undermine the institutions that control us, the systems that keep us from getting ahead — and the world as we know it.

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The word “grift” first entered recorded usage nearly a century after the Caraboo caper, in a 1914 dictionary of American-Underworld slang compiled by Louis E. Jackson and C.R. Hellyer. Its definition is tellingly vague: “an opportunity for plying criminal talents,” suggesting not so much the pursuit of illicit profit as general delight in the act of deceit.
(Some of today’s so-called grifters are more bumblers than proper swindlers, making promises that they can’t logistically fulfill.)

• Note that there’s a distinction between grift and straight-up crime, in terms of goal and scale. Politicians and financiers may be perennially conniving, but they aren’t grifters because they’re part of the system — true practitioners of the art thrive in the margins. Grifters are small-time lawbreakers, not the kind of epic liars who leave the wreckage of lives and nations in their wake. They’re not even bad people, per se: They stand outside morality, defying the social binary of good and evil. They tend to pilfer just enough to disrupt but not devastate.

Crucially, they operate against the odds, working from the outside in. We don’t cheer when the already privileged con their way into more privilege, like those accused in the Hollywood college-admissions scandal; that’s just plain old cheating. The grifters who enter folklore, whom we revere as near heroes, choose their victims among the otherwise invulnerable: the rich and mighty, whom they bring down, if only momentarily, to scramble with the rest of us. In this, America is perhaps the rightful home of grifters, for where else in the world is so deeply identified with the possibility of transcending humble origins and becoming someone powerful and new? (Princess Caraboo, before her unmasking, twice attempted to run away and hop on a boat to America, likely in hopes of finding a more credulous following.) Ours is a land that exalts opportunity to the point of encouraging its exploitation. As the cultural critic Lewis Hyde wrote in 1998, we embrace the grifter as an embodiment of what is “actually true about America but cannot be openly declared” — like “the degree to which capitalism lets us steal from our neighbors,” or the amount of unfounded faith that the stock market demands.

GRIFTING IS ARGUABLY a natural, even inevitable byproduct of American democracy. The French diplomat Alexis de Tocqueville, casting a gimlet eye on the brash young nation in “Democracy in America” (1835-40), wrote, “When all the prerogatives of birth and fortune have been abolished, when all professions are open to all and a man’s own energies may bring him to the top of any of them, an ambitious man may think it easy to launch on a great career and feel that he has been called to no common destiny.”

But this is a delusion; with the expansion of opportunity comes a corresponding flattening of hopes, as ever more people compete for the same limited number of spots. And because nothing appears to stand in the way of success in this brave new world (at least the utopian vision of it), no acknowledged social or systemic bias, we are expected — nay, mandated — to rise, our worth measured not only by the height but the speed of our ascent. Failure is wholly individual; we are allowed to blame no one but ourselves if we fumble. No wonder de Tocqueville sensed despair in even the wealthiest Americans he met:
“It is odd to watch with what feverish ardor the Americans pursue prosperity and how they are ever tormented by the shadowy suspicion that they may not have chosen the shortest route to get it.”

It’s the shortest route that calls to the grifter, who recognizes that for someone starting from a position of disadvantage, the American dream sometimes requires cutting corners. Even in the archetypal rags-to-riches story, Horatio Alger’s novel “Ragged Dick” (1868), no riches are actually obtained — only the chance to work toward riches. The main character, a teenage bootblack living on the streets, may be frugal and mostly honest (apart from a few small cons, including posing as a tax official to cajole fruit from an apple seller), but he can’t get a “respectable” job until, in a stroke of luck, he rescues a child, who happens to be the son of a benevolent merchant, from drowning. The reward is a foot in the door, a position on the lowest rung of the firm, with years of toil to follow. Ragged Dick is willing to work hard and put his fate in the hands of his social superiors because he trusts the system; the serious grifter does not. For what is a grifter but an ordinary person “living more clearly than the world permits,” as the American writer Patricia Highsmith scribbled in a notebook in 1949, imagining a character predisposed to crime — and foreshadowing the antihero of her 1955 novel, “The Talented Mr. Ripley.”

In this turbulent era, there’s almost a nostalgic appeal to the grifter, who rejects the raw deal of birth.

Like Ragged Dick, Tom Ripley starts out as a pretend tax official, reaping ill-gotten gains, and must rely on the kindness of strangers for his entree to a loftier sphere. After a chance encounter on the street, he is recruited by the rich father of Dickie Greenleaf, a distant acquaintance, to go to Europe, all expenses paid, and fetch the wayward scion home. From the beginning, his journey is framed in terms of American myth: On the ship over, he feels possessed of a new life, “as he imagined immigrants felt when they left everything behind them ... left their friends and relations and their past mistakes, and sailed for America. A clean slate!” Money and a mission have cleansed him of his sins — less his petty scams than the greater crime of having been born without means. Once he’s charmed his way into Greenleaf’s company, however, Ripley is reminded of the precariousness of his position, in contrast with his comrade’s dilettantish ease, achieved without effort, simply underwritten by his father’s fortune. No matter how talented Ripley is, he can never have that surfeit of self-belief. When he finally takes on Greenleaf’s identity (having bludgeoned the callow heir to death), he makes an explicit callback to his transformation on the voyage:
“This was the clean slate he had thought about on the boat ... This was the real annihilation of his past and of himself ... and his rebirth as a completely new person.”

Highsmith read de Tocqueville shortly before writing the novel, and in Ripley she plumbed the peculiarly American discontent of the middle-class striver, close enough to poverty to fear it and far enough from wealth to both desire and despise it. The historian Karen Halttunen, in her 1982 study “Confidence Men and Painted Women,” points out that by the 19th century in America, the label “middle class” had come to define not a static, in-between group but those of no fixed class, “suspended between the facts of their present social position and the promise, which they took for granted, of their economic future.” The heyday of grifting, from the 1900s to the stock-market crash of 1929, was a time of preternatural abundance; Herbert Hoover, accepting the Republican Party’s nomination for president in 1928, predicated an imminent “triumph over poverty.” But not everyone benefited:

• The next year, earners in the top 10 percent took in nearly half of the nation’s income, while those in the top 1 percent took in nearly 15 percent.

Such statistics are uncannily close to those in our own time, which may explain the resurgence of (or, at least, renewed interest in) the con. Grifters work the gap, and this one keeps getting bigger — because it doesn’t exist by happenstance; it’s a structural flaw in the free-market economy, a perfectly legal and socially sanctioned dynamic: the tendency for wealth to accrete to those who already have it, who can wield the power to generate more. Early American grifters profited from both a weak central government and the speculative nature of America as a country still coming into existence, with unfixed borders and newfangled paper money that was largely symbolic and occasionally worthless, issued by private banks without the bullion to back it up. A similar uncertainty haunts us now, as we attempt to redefine ourselves as a nation. In this turbulent era, there’s almost a nostalgic appeal to the grifter, who so glibly shakes off the shackles of identity and rejects the raw deal of birth. It reminds us of that bygone age of boundless possibility, when the distance between tall tale and reality was shorter, and a poor immigrant boy like, say, Andrew Carnegie could rise from lowly factory worker to industrial titan, eventually becoming, in 1901, the richest man in the world. We still want to believe those stories, now more than ever.

OURS IS A CURIOUS time of both peak cynicism and peak gullibility. News is fake unless it comes from sources that espouse our worldview, in which case even the most preposterous conspiracy theory is seen as ironclad truth. Never have we been so suspicious or more ready to expose and accuse, and yet daily we accept fictions as the basis of reality, from the posturings of bots and provocateurs on Twitter to the radiantly lit, commercially sponsored posts of Instagram influencers for whom there is no distinction between the personal and the corporate, to the seemingly innocuous deceptions of friends who obsessively filter photos and curate their feeds to present a better version of themselves. We live in constant suspension of disbelief, what the American anthropologist Michael Taussig has called “this silly if not desperate place between the real and the really made-up.” This makes us easy prey for — perhaps even complicit with — grifters who play off our communal, mimetic desires. As the linguist David Maurer wrote in his 1940 study “The Big Con,” the grifter is “really not a thief at all because he does no actual stealing. The trusting victim literally thrusts a fat bank roll into his hands.”

In fact, the best grifts approach performance art. (The critic Luc Sante, in an introduction to the 1999 reprint of Maurer’s “Big Con,” frames the ruse as “a form of theater ... staged with minute naturalistic illusionism for an audience of one, who is moreover enlisted as part of the cast.”) The trajectory of the poseur, Russian-born heiress Anna Delvey, nee Sorokin, who was convicted in April on several felony counts of grand larceny and is currently serving four to 12 years, recalls a 1983 stunt pulled by David Hampton, a middle-class black teen from upstate New York and a rarity in the history of known American grifters, who tend to be white.
(This may be because the burden of doubt is still too high for people of color, who often have trouble getting their feet in the door no matter how lofty their credentials; Linda Taylor, a Chicago woman immortalized by politicians in the 1970s as the archetypal “welfare queen,” won notoriety for mining government programs directed toward the poor — in other words, for fitting into a negative stereotype, rather than upending it.)

Pretending to be the son of the actor Sidney Poitier, Hampton sweet-talked his way onto elite college campuses, stole a student’s address book and cold-called wealthy white Manhattanites whose names were listed in them.

He introduced himself as a classmate of their children and said that he’d been mugged. His shining detail:

• He told his marks that the assailant had stolen not just his money but his thesis — on criminal justice.

The gambit didn’t yield much material reward beyond food, temporary shelter and a little cash. But Hampton certainly pranked the sensibilities of the white liberals he targeted, knowing that they would probably be at once suspicious of him and so ashamed of that suspicion — of betraying unconscious racist undertones — that they would overcompensate and welcome him into their homes, wine and dine him and invite him to sleep under their roof. News clippings about him later inspired John Guare’s play “Six Degrees of Separation,” which premiered at Lincoln Center in 1990, prompting Hampton to sue, claiming plagiarism of his life. He lost.

Grifters, for all our grudging admiration, rarely come to happy ends. Hampton’s tricks were glorified onstage, but he died alone and impoverished at 39, after spending his last days in an AIDS hospice. Sorokin may be negotiating with Hollywood — her shape-shifting is the subject of two upcoming projects from Netflix and HBO (under the helm of Shonda Rhimes and Lena Dunham, respectively) — but she remains in a prison cell, under threat of deportation to Russia for having overstayed her visa. Failure is built into grift; after all, if you get away with it, you’re no longer on the outside — you’re part of the system. What is the ultimate grift but to make good on your unlawful rewards and prove that you deserved them all along? We call that an American success story. We call that leaning in.