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.”