Why We’re So Obsessed with Grifters

Last week, all anybody who was anybody in New York media circles could talk about was the story of Anna Delvey — since branded the “SoHo grifter” — the faux-German (and real Russian) “heiress” who managed to convince half of New York City to lend her outrageous amounts of money. Living in impossibly expensive hotels, hiring a “a svelte, ageless Oprah-esque figure” as her personal trainer, commissioning a PR firm to throw her a birthday party studded with the great and the good, recruiting a starry-eyed hotel concierge as her de facto companion, Delvey managed to pull off the ultimate con: making people think she mattered. As told in New York Magazine’s grippingly outlandish account, Delvey didn’t just rob people of their money. She robbed them, far more importantly, of their attention.
But how Delvey’s grifter strategy relied not on personal charisma, nor on physical attractiveness, nor on an ability to convince people to care about her, specifically. Rather, it seems, Delvey was successful because she recognized the purely transactional nature of her social sphere. People want to be around other people who matter. Delvey insisted — consistently, zealously, despite all evidence to the contrary — that she mattered.
In the wake of Delvey’s rise to notoriety, other grifter stories have come into the public eye. There’s the case of the “Vogue grifter,” magazine assistant Yvonne Bannigan, who allegedly bilked about $50,000 from Grace Coddington, Vogue’s creative director at large. There’s the case — a decade old, newly viral — of the “hipster grifter” Kari Ferrell, who served nine months in a Utah jail for stealing a total of $60,000 from assorted Williamsburg-based victims. (In the aftermath of the Pressler piece’s virality, New York has helpfully provided the listicle “6 Incredible Scammers You Need to Know.”)
But what is it about these stories that make them so captivating to the public imagination? Why are we so obsessed with grifters?
Related archetypes like the con artist or the gentleman thief have a long and storied cultural history. There’s the impossibly debonair Cary Grant in Hitchcock’s To Catch a Thief, Steve McQueen (and later, Pierce Brosnan) in The Thomas Crown Affair, the entire cast of several versions of Ocean’s 8. They’re mildly, tantalizingly transgressive: Watching them steal jewels or priceless art or wallets provides a certain vicarious, aspirational thrill. Surviving by their wits and their wiles, these figures offer us a glimpse of a life we want but can never have. If only we were as crafty as Cary Grant, as charming as Steve McQueen, maybe we too could be rubbing shoulders (or picking pockets) with the one percent.
But the truly great grifter stories — about people who steal not just objects but also identities, people whose goals are as much about acceptance into hallowed social spheres as they are about the material benefits derived from them — cut much deeper. Sure, reading about Anna Delvey provides some of the vicarious thrills we get from heist movies — who wouldn’t want to jet off to a $7,000-a-night Moroccan resort? But more fundamentally, the story lays bare the ridiculous nature of the system that allows her to flourish.
Delvey’s story implicates not just herself, but also all the cutthroats, bootlickers, hangers-on, and heel-snappers around her. There’s the Chinese collector Michael Xufu Huang, who is so rich that he can lend Delvey a couple thousand dollars and then forget all about it for months. There is the unnamed Futurist — Delvey’s ex-boyfriend — whose presence lends her a degree of legitimacy while he talks up his nonexistent app at dinner parties. There’s the hotel concierge who rationalizes away Delvey’s various inconsistencies the minute Delvey whisks her away to meet Macaulay Culkin. It would be incredibly easy for any one of these people to figure out that Anna Delvey is not who she says she is. And yet they persist. Delvey is someone who is “always seen at parties,” and so they, with little emotional attachment to Anna-the-person, determine that Anna-the-persona must be someone worth knowing. Delvey offered her marks a fantasy of identity—a chance to be the sort of people who hang around with the sort of person Anna Delvey pretended to be.
The grifter, unlike the gentleman thief, doesn’t succeed because she is particularly clever. Rather, she succeeds because everybody around her is particularly stupid. A heist film is exciting because of how difficult and complex the heist is to pull off. A grifter story is exciting because of just how simple it is to fool people who want to be fooled — how easily the house of cards is constructed before it collapses.
The great grifter narratives — Patricia Highsmith’s The Talented Mr. Ripley, or the excellent John Guare play turned Will Smith film, Six Degrees of Separation — are not, fundamentally, about grifters. They are about societies in which human relationships run on capitalist economics, in which all human interaction is fundamentally transaction. The grifter essentially operates an emotional Ponzi scheme.

In writing my own novel, Social Creature — a modern-day, New York–set, female-led reimagining of the Ripley story for the Instagram age — I became fascinated by the way in which the grifter represents a fundamental and universal truth. In a place like New York City, we are all faking it. We all perform our identities; we all create our own personae. We all participate in the meaningless rites of accruing “social capital” — whether it’s posting selfies on Instagram or checking into a high-end room at 11 Howard or getting that svelte, ageless, Oprah-approved body. And we all suffer from imposter syndrome: the sneaking suspicion that, one day, everybody will find out who we truly are. The irony is, of course, they won’t — they’re too busy worrying we’ll do the same to them. The grifter just figures out how to make the subtext of our lives, well, text. She doesn’t so much deceive us about herself as show us what we truly want.

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