With a new Netflix series set to put ‘Soho Grifter’ Anna Delvey back in the spotlight, and two shows in the works about recently convicted Silicon Valley fraudster Elizabeth Holmes, we examine what lies behind society’s collective obsession with the female con artist
The first week in January marked an important resurgence for grifter season. Elizabeth Holmes, the Steve Jobs-obsessed, maniacally disciplined blonde with a wardrobe of black turtlenecks and a cavernous DC accent, was found guilty of fraud, concluding a high-profile trial that captivated Silicon Valley and chronicled the missteps of Theranos, her now-defunct blood-testing start-up. (The company raised nearly a billion dollars from venture capitalists and private investors before Holmes was accused of fraud. She recently reached a settlement with the Securities and Exchange Commission which required her to pay a fine and relinquish control of the company, among other penalties.)
Theranos was an octopus — alien, fluid, poisonous, brilliant and flexible enough to suggest squeezing enormous bulk through tiny holes. Ultimately, it was based on nothing, yet according to John Carreyrou — the journalist who exposed Theranos in the Wall Street Journal — Holmes’ belief in her own significance bordered on sociopathic zealotry, once exclaiming at a company party, “The miniLab is the most important thing humanity has ever built.” The 37-year-old now faces up to 20 years in prison.
Elsewhere, Anna Delvey, the young woman with a sulking expression and vague European drawl who was found guilty in 2019 of theft of services and grand larceny, was back in the public eye, thanks to the promotional tour of a new Netflix series. Inventing Anna, due to hit the streaming platform early next month, chronicles the life of Delvey (real name Sorokin) as she convinces the superficial people and institutions of New York City that she is an heiress with an inheritance in the millions.
Nicknamed the Soho Grifter, Delvey has been celebrated as a sort of Bling Ring icon, throwing a spotlight on people who seem to have more money than substance. “What are you bitches, broke?” she’s attributed as saying in the article that made her famous following a decade, if not more, of steadily inclining materialism that laid the groundwork for financial and status-adjacent avarice. It would be easy to charge sexism here, and others have. But there is something else going on, summed up by a pithy phrase Delvey’s attorney Todd Spodek uttered in her defence: “Anna had to fake it until she could make it.”
What’s most interesting about the scammer du jour is that she is a woman. Long-chronicled are the men who carved out the genre — Billy McFarland, Jho Low, Frank Abagnale Jr — but women are rarely credited for their inclination to scam.
“Women are also naturally presumed to be devious and two-faced,” says Tori Telfer, author of the new book Confident Women: Swindlers, Grifters, and Shapeshifters of the Feminine Persuasion. “Think of Hamlet’s bitter complaints about women to Ophelia — ‘God has given you one face, and you make yourselves another’ — or the way people think about Eve.”
Yet, when we hear about con women, she says, it surprises us. “The most famous con artists are men, and they are really held up for being clever and almost business-minded, so we tend to think that cons are still the domain of men because sharpness and cleverness are not attributes we ascribe to women.”
Confidence artists also speak to us in ways other criminals do not — “they get to be artists!” — says Telfer, and we fall for them because they are typically charming and likeable. “The fact that we like con artists so much is probably the greatest con of all time. They are breathtakingly selfish, and don’t we all kind of wish we could be breathtakingly selfish sometimes?”
Closer to home, Mair Smyth, a woman who claimed to have descended from Irish royalty and had moved to America “under political asylum”, found herself some $70,000 (€61,700) richer by a man with whom she claimed to be best friends. His name is Jonathan Walton, an Emmy award-winning TV producer. He retells the story on his weekly podcast Queen of the Con: The Irish Heiress (from iHeartRadio and AYR Media).
“I’m a happily married gay man,” Walton tells listeners in the opening of his podcast’s first episode. “But here I am, parked out front of this woman’s place at five o’clock in the morning, just trying to catch a glimpse of her... I haven’t seen her in months, and as hard as I try, I just can’t get her out of my mind.”
Walton first found himself in the company of Smyth back in summer 2013, when his Los Angeles apartment building lost access to a shared pool over a repair dispute, and he hosted a residents’ meeting to discuss it. One of the guests introduced herself as Mair Smyth. A well-heeled and charismatic networker, she was working the room, Walton recalls, everyone commenting on her “exotic” Irish accent. She was beguiling, majestic even, and had a framed copy of the Irish Constitution hanging on her wall. Her great-great-uncle was one of Ireland’s founders, she explained, proudly pointing out his signature. She also claimed to be heiress to a vast €30m fortune, except that three of her cousins — Fintan, Tristan and Diarmuid —were seemingly doing all that they could to keep her from it. Everyone adored her, so few questioned when stories began not making sense or unpaid loans steadily piled up.
In the end, Walton accidentally found out he’d been swindled. Not taken seriously by police, he took to the internet and discovered he wasn’t alone. He and other victims united to bring the woman calling herself Mair Smyth (one of the 23 aliases, including ‘Marianne Andle’ and ‘Marianne Welch’, she used to scam people, Walton would later discover) to justice, exposing a con stretching from LA to Belfast, and taking in witchcraft, a fake cancer diagnosis, fraud and blackmail in the process.
In today’s terms, figures like Smyth, Sorokin and Holmes are highly aspirational. As women’s conferences and #Girlboss networking events might have told me had I attended them, it’s precisely the kind of deluded misapprehension that, when used correctly, acts as a manifestation for hard work. It’s the stratagem that secured Holmes a New Yorker profile, a viral Ted Talk and ensured no glassed-over expressions when she said live on CNN, “First they think you’re crazy, then they fight you, and then all of a sudden you change the world.”
How we react to a female grifter is more reflective of a woman’s place in society rather than our own preconceived notions. As Telfer explains in her book, we are less likely to believe a woman would be in a position of power, so female con artists are far more likely to use sob stories to paint themselves as helpless, vulnerable and trustworthy. They shrewdly use the most widely understood tool in their arsenal — systemic oppression — to their advantage, because any woman, con or not, knows that the key to her success is likeability. Without it, she is nothing. Con artists know this, as do the creatives that portray them.
In the 2019 film Hustlers, a mild drama about a ring of strip-club dancers who drug male clients and cheat them out of tens of thousands of dollars, we see Jennifer Lopez, Cardi B and Constance Wu recover the fortune that “Wall Street bankers robbed from hard-working Americans”. In an era where the female sexual narrative has been reclaimed, the Bechdel-test approved feature film sees a group of survivalists call the shots after a series of more conventional avenues fail in a culture stacked against them. It’s a crucial distinction, one necessary to carry their story as likeable protagonists, and a reminder that not all scams (lest the ones where rich assholes are conned, because instinctively and accurately, rich assholes have generally benefitted from conning the rest of the country) are created equal.
The average person is also aware of the huge amount of control every woman must wield on a daily basis — in the home, on their appearance, for the family — and thus respect the eschewing of a misogynistic narrative to play into her own lap. Women are societally hardwired to provide all things for all people, and to consider a female con artist at work is to consider a woman finally committing to an activity that is solely for herself. It’s overdue, applaudable even, in a world that’s stacked up against the idea of a woman breaking through her glass ceiling.
And this was only more obvious in times gone by, such as in 1848 when the Fox sisters gained popularity by convincing audiences that they could communicate with spirits via a series of mysterious clicking and rapping noises, or in 1868 when Victorian influencer’ Madame Rachel made a name for herself selling toxic beauty products and services to rich women in exchange for ‘female loveliness’.
We’re also aware of the womanly con artist’s talents, and jealous of them. It’s tempting to think we could be her, to completely give in to our most rudimentary social desires — status, power, wealth, money, admiration, control. And, in fact, most of us attempt just that, in less severe, less transgressive ways. We reinvent ourselves on social media, change our ways each new year, and hyperbolise stories to appear more grandiose and exciting. But we rarely let ourselves go all the way, such is the power of the social contracts we must adhere to.
But this is a good thing, largely, the consistent conforming and respecting, despite some of our wilder interests looking to break free from the shackles involuntarily placed upon us. Although you may forgive us for suppressing a small sigh of disappointment at the realisation. Perhaps this is why the female con artist finds it so easy to secure a sympathetic, captivated audience. She performs a service as much as we do, making an offer we couldn’t refuse.
Debuting in March, a series chronicling Holmes’ life, titled The Dropout (referencing how the protagonist, much like the supernova-adjacent entrepreneurs she admired, dropped out of an Ivy League school to pursue a pitch), will drop on Hulu, with Amanda Seyfried in the role of Holmes. A separate project, Bad Blood, similar only in story, has also been announced by Apple, starring Jennifer Lawrence as Holmes and directed by Adam McKay. Both women will bow toward the altar of Big Scam, an inclination which comes often in this shiny, stories-based, albeit hollow new world, such are the mythologies of profit, reinvention and spectacular ascent. They’ll also aim to convey a life rather than embody it, overpromising and luck pushing, provoking schadenfreude and admiration in equal measure.
It’s said that the desire to scam is borne out of the belief that you are special enough to disobey the rules, like a hot girl skipping a club queue or a CEO securing tickets to a sold-out game. The desire for special treatment, if history has taught us anything, is both extremely powerful and showing no signs of dissipating.
This brings us to the point that scammers, con artists and petty thieves aren’t actually always bad people. They’re just like us — braver or more idiotic versions, you decide — faking it until they make it, boasting simply the willingness to step on the shoulders of good guys, the kind of whom are destined to finish last.