Inside The Mind Of A Scammer

With a new Netflix miniseries about New York’s infamous fake heiress Anna Delvey out this month, Charlotte Roberts asks why we’re so enduringly obsessed with con artists

By Charlotte Roberts

20 February 2022

rom Leonardo DiCaprio’s portrayal of notorious ‘60s grifter Frank Abagnale in Catch Me If You Can, to the Jennifer Lopez-led Hustlers, which tells the story of a group of real-life strippers who fleeced their wealthy clients in the late Naughties, con artists have long been a source of fascination – particularly when they are female.

And our modern, social-media-led world has no shortage of contributors to this profession. Witness The Cut’s notorious 2019 piece ‘I Was Caroline Calloway’ – a revenge essay by Calloway’s former friend Natalie Beach, detailing her ghostwriting role with the infamous Instascammer – or the year before, ‘How Anna Delvey Tricked New York’s Party People’, which unpicked the exploits of the so-called ‘Soho Grifter’.

The latter article forms the basis of a soon-to-be-released (11/02/22) Netflix miniseries Inventing Anna. For those who need their memory refreshing – and don’t mind spoilers – in 2014, socialite Anna Delvey landed in New York, fresh from an internship in Paris with edgy fashion bible Purple. Ostensibly, the purpose of her trip was to create “a dynamic visual arts centre”. For this, she planned to lease the historic Church Missions House on the corner of Park Avenue South and East 22nd Street, a space she envisaged housing a bar, galleries, studios, restaurants and a members club. The project would cost tens of millions.

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“The scale of her scam was made even more riveting by her detachment and indifference”

Enter a cohort of young art world New Yorkers, all with money to invest, all instantly charmed by this Russian/German – no one was exactly sure – heiress. No one was exactly sure, either, how she had accumulated the vast wealth that facilitated the lavish lifestyle she was living.

Delvey was actually the fictitious creation of the then twenty-something Anna Sorokin, who by dealing mainly in cash and utilising a series of fraudulent loans and wire transfers, made her lavish lifestyle a reality. Super deluxe trips were documented to her thousands of Instagram followers, and her look became ubiquitous: large shades, coy smile, enveloped in luxury sweats. The fact that it turned out to all be smoke and mirrors only added to the allure.

Following the court case of 2018, in which the details of her lucrative scam were revealed, Delvey’s infamy only grew. The Cut’s profile was to be the first of many. We were, in equal measure, obsessed and appalled: the scale of her scam made even more riveting by her detachment and indifference. She barely blinked at her trial, yet still managed to court the press while simultaneously cementing her status as a zeitgeist icon.

Social media was fizzing with fascination, and Instagram accounts dedicated solely to her courtroom outfits quickly went viral (not since Winona had someone’s courtroom attire been so intensely raked over). Delvey was in some ways the perfect anti-heroine of the millennial era; a greedy, multi-faceted symbol of success, failure and remove. She hustled, exploited the system and momentarily triumphed while we, her rapt audience, lapped it up.

“Female success has become synonymous with the hustle”

What is it about con artists of Delvey’s ilk that we find so captivating? Even with her eventual conviction for theft of services and grand larceny in 2019, there seems to be a dearth of contempt for her. Sure, we wouldn’t actually do it, but there was a general feeling of admiration for her, even celebration.

Perhaps, in a world where we are plagued with reads of women as victims, depictions of female agency – and arguably, inner rage – seem almost defiant, anti-establishment. Cons such as Delvey’s, reframed as rebellion, offer access to a fantasy world. If we weren’t impeded by our morals, would we be able to do what she did? If we were less obedient, would our limits know no bounds?

In her book, The Confidence Game, psychologist Maria Konnikova explores the mindset of the scammer, asserting that “it feeds on the desire for magic, exploiting our endless taste for an existence that is more extraordinary and somehow more meaningful”. She suggests that scammers “aren’t actually seeking deception”, just “a reality that is somehow greater than our everyday existence”.

There is an element of seduction and magic in the scam, a delicious quality that allows us to simultaneously absorb the fantasy of the narrative and appreciate the performative nature of the con. Fuelled by the dominant ideology that wealth is the ultimate path to success, the pull of these women lies perhaps in their sheer audacity: as much as we think we could do it, these women have actually gone through with it. And more to the point, got away with it – for years.

What can we learn from the psychology of these ‘celebrity’ con artists? Former FBI agent, psychologist and intelligence consultant Jack Schafer has spent years conducting interviews with con artists. He suggests that women may have an inherent advantage due to certain neurological differences.

“There’s a left and the right side of your brain,” he says, “and in the middle there’s something called corpus callosum that is a bundle of nerves that transmits info from left to right, and scientists have found that women have a denser corpus callosum than men.” This neurological super highway integrates our emotional thinking and logical thinking, making for smarter, speedier, more sophisticated decision-making — what we might call women’s intuition.

A successful con also relies on highly attuned powers of persuasion and the ability to gain someone’s trust.

“It’s a matter of building rapport with people,” says Schafer. “If I get someone to like me, they will be willing to do things for me, maybe even go out of their way for me. The job of a con artist is to set an illusion of a friendship.”

And, he says, there’s a literal formula to it: proximity x (frequency + duration) x intensity = friendship. Any relationship you’ve ever had follows this formula, Shafer argues. “If there’s no proximity, you have to increase frequency, duration and intensity.”

Many of the techniques scammers use to create a sense of connection are taught in executive coaching, such as ‘mirroring’ (whereby subtly mimicking someone’s body language makes them feel closer and more similar to you) or simply sustained eye contact.

“One of the intensifiers is intense mutual gaze, I hold my eye contact and turn my head but maintain eye contact,” explains Schafer.

Konnikova argues that we commit these minor social cons every day, subconsciously feigning shared affinities or dislikes to create a sense of common ground and friendship. Schafer agrees we’re all scamming our way through life to an extent: “Think about going on a first date, what do you do? Present your ‘best’ self. That’s a form of manipulation.”

Female success has also become synonymous with ‘the hustle’, which only exacerbates the scam mentality. An evolution of the girl boss narrative of the 2010s, we’re encouraged to regard ourselves as a commodity and develop a marketable personal brand. Isn’t that what Anna Sorokin did – to an extreme – when she created her alter-ego, Delvey?

Con artists like Delvey ascend rapidly in worlds often far removed from the ones they grew up in; they succeed by creating an illusion of a lifestyle. It’s a game we’re all playing on social media: we present ourselves as simultaneously successful, pretty, likeable and productive, against a reality that is actually increasingly demanding and precarious.

Participating in modern womanhood, we’re required to tap into a scam mindset, cultivating a carefully judged persona and keeping it alive with just the right amount of self-belief and narcissism. The truth is, there’s a little bit of Delvey in all of us.

Header image by: Gong Jian

The Short Stack

Perhaps we’re fascinated with female scammers because, in a world of constant hustle, we secretly admire their audacity. But we’d never side-step our own morals….would we?

By Charlotte Roberts

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