The allure of the grifter is a curious phenomenon, especially within the cultural landscape of America. We aren’t captivated by those who merely cheat to gain more when already privileged; the college admissions scandals are a stark example of simple dishonesty. The grifters who truly capture our imagination, who edge into folklore and are almost admired, are those who daringly target the seemingly untouchable – the wealthy and powerful. They temporarily disrupt the established order, bringing the mighty down to the level of the everyday person, even if just for a fleeting moment. Perhaps America, with its deep-seated belief in transcending humble beginnings, is the perfect breeding ground for the grifter. Where else is the narrative of rising from nothing to something powerful so ingrained? This inherent belief in opportunity, however, can be easily twisted into an environment ripe for exploitation. As cultural critic Lewis Hyde aptly noted, we embrace the grifter because they embody a hidden truth about America, something “actually true about America but cannot be openly declared,” like the darker side of capitalism or the often-blind faith demanded by the stock market.
Grifting can be seen as an almost inevitable outcome of a democratic society, particularly within the American context. Alexis de Tocqueville, in his insightful observations of early America in “Democracy in America,” remarked on the nation’s boundless ambition. He noted that when traditional barriers of birth and wealth are removed, and all professions are theoretically open to everyone, ambitious individuals believe a great career is easily attainable. However, this perception is often misleading. The expansion of opportunity brings increased competition, and the path to the top becomes ever more crowded. In this ostensibly meritocratic world, where systemic biases are downplayed, the pressure to succeed is immense. Worth is measured not just by achievement, but by the speed of ascent. Failure, then, becomes solely an individual burden, with no room to blame societal structures. Tocqueville astutely observed a sense of unease even among wealthy Americans, noting their “feverish ardor” in pursuing prosperity and their constant worry of not having chosen the most efficient route.
It is this “shortest route” that appeals directly to the grifter. They recognize that for those starting at a disadvantage, the idealized American Dream often necessitates bending the rules, or even breaking them. Even Horatio Alger’s famous “rags-to-riches” narrative, “Ragged Dick,” highlights this. The protagonist, a bootblack, is indeed frugal and mostly honest, but his path to even the chance of riches isn’t purely through virtuous hard work. He engages in minor cons and ultimately relies on a stroke of luck – rescuing a wealthy merchant’s son – to get a foot in the door. This stroke of luck provides him only with an entry-level position, requiring years of further labor. Ragged Dick believes in the system and is willing to climb the ladder conventionally. The true grifter, however, fundamentally distrusts this system. As writer Patricia Highsmith, foreshadowing her character Tom Ripley, wrote in her notebook, a grifter is simply an ordinary person “living more clearly than the world permits.” They see the inherent unfairness and choose to operate outside of its confines.
In our current, often turbulent times, there’s almost a nostalgic appeal to the figure of the grifter. They reject the hand they were dealt at birth, refusing to be limited by societal expectations or economic disadvantages. Like Ragged Dick, Tom Ripley, in “The Talented Mr. Ripley,” begins his journey with petty scams, impersonating a tax official. His entry into a higher social sphere depends on the generosity of a wealthy stranger. He is hired by Dickie Greenleaf’s father to retrieve his son from Europe, a mission funded entirely by Greenleaf’s wealth. Ripley’s journey is presented through the lens of the classic American immigrant myth. On his voyage, he envisions a complete transformation, a “clean slate,” much like immigrants leaving behind their past for a new life in America. Money and a mission offer him a chance to erase his past, not just his minor cons, but the larger “crime” of being born without privilege. However, once immersed in Greenleaf’s affluent world, Ripley is starkly reminded of his precarious position compared to Greenleaf’s effortless ease, a product of inherited wealth. No matter how talented, Ripley can never possess that innate sense of entitlement. When Ripley ultimately assumes Greenleaf’s identity after killing him, it’s a deliberate echo of his earlier transformative experience on the ship. This act becomes the “clean slate” he initially imagined, a complete erasure of his past self and “his rebirth as a completely new person.” The grifter, therefore, embodies a complex figure, one who challenges societal norms, exposes vulnerabilities within systems of power, and reflects a darker, more opportunistic side of the much-celebrated American Dream.
