How con artists became the new tier of celebrity

Written by Hannah Keegan

Hannah Keegan is Stylist’s Deputy Features Editor. You can find her on Twitter at @HannahKeegan.

As ‘fake heiress’ Anna Delvey plots her comeback and Theranos founder Elizabeth Holmes prepares to be sentenced for the biggest medical fraud in history, Stylist explores how con artists became a new tier of celebrity.

There are so many versions of Elizabeth Holmes, the former CEO and founder of the now-defunct and potentially criminal blood-testing company Theranos, that it can be difficult to keep up. There’s the badass tech boss, low-voiced and intense, dressed in an unchanging black turtleneck (a nod to her hero Steve Jobs), a thick coat of liner smudged across her eyelids. There’s the fleece-wearing, Silicon Valley disruptor (depicted by Amanda Seyfried in Hulu series The Dropout). And last summer, the wide-eyed, angelic Holmes – all blonde curls and sweet smiles – spotted walking into court, a demure pencil skirt stretched over her growing baby bump. This is a woman who knows how to shapeshift. Such is her power to morph between carefully crafted characters, a former employee once said: “She could convince me of anything.”

This week, Holmes will be sentenced following her conviction in January on four counts of fraud. At its height, her company, which falsely claimed it could conduct 200 medical tests (for vitamin D deficiency, thyroid disease, you name it), from a half-inch vial of blood, was worth an estimated $9 billion (£7.7bn). She’d raised nearly $1 billion (£852 million) in funding to found the start-up in 2003, dropping out of Stanford University in 2004. She alone was worth $4.5 billion (£3.8bn), while her company’s board stacked with powerful men (including former secretary of state Henry Kissinger, who dedicated a profile to her achievements in Time magazine, praising her “fierce and single-minded dedication”). Before her demise, Holmes could count the Clintons among her many admirers. People would often describe her in breathless, exaggerated terms. “Striking, ethereal, iron-willed,” wrote Kissinger, even going as far as to compare her to a member of a monastic order for her unfaltering commitment to her cause.

Theranos founder Elizabeth Holmes faces sentencing this week

People believed Holmes was a genius, on a par with Zuckerberg and Jobs, until – quite suddenly – she wasn’t. In 2015, a reporter at the Wall Street Journal began to uncover that her company’s lofty claims were false. Most of Theranos’s tests were not conducted on the company’s top-secret Edison machines (they could only carry out 12 of the listed 200 tests, it turned out), but with standard blood-testing technology – and even then, lab conditions were so chaotic, results came back wildly different to those drawn in doctors’ offices. Holmes had built billions on lies and bravado, with the true scale of the damage impossible to calculate: the symptoms that may have gone ignored, the medical decisions that were made based on false results and serious illnesses that could have spiralled out of control if those results were believed.    

And yet, miraculously, Holmes has remained a figure of brilliance to some. If you search her name on Spotify, you’ll find playlists dedicated to her. Fan clubs termed ‘The Holmies’ have assembled on TikTok: “In this house, girl bosses support girl bosses,” says one user in a video, smiling to the camera. To her army of admirers, she’s an example of the underdog who almost won, a woman unabashedly out for herself; the best kind of villain. “I love how she fooled the world, specifically the male-dominated business world,” Rachel Soh, another fan, tells me. “She ended up on the cover of Forbes when it could have been another boring man.” To them, it’s simple: she’s a ball buster, a feminist icon, #Goals. There’s even merchandise, with Theranos-branded lab coats, mugs and T-shirts all selling for extortionate prices on Etsy and Poshmark (at the time of writing, an Elizabeth Holmes fleece would set you back over $7,000). 

But it isn’t just Holmes who has provoked this strange, half-winking support and fascination. You might remember Anna Sorokin (aka Anna Delvey), the fake German heiress who lived at the Mercer Hotel, ate at the Michelin-starred Le Coucou every night and stole hundreds of thousands of dollars along the way, landing her a prison sentence of up to 12 years (of which she served less than two). Upon her release in February last year, a Netflix drama based on her life, Inventing Anna (produced by Shondaland and starring Julia Garner), was already in the works, while Emma Corrin played Delvey on the West End stage during a hit run in Anna X, a fictional two-hander heavily inspired by Sorokin’s life.  

Sorokin herself is now accumulating the profits of selling her story – a reported $320,000 has made its way into her bank account for her involvement in the Netflix series Inventing Anna – while fashion editors continue to drape her in fancy gowns. 

To extract a phrase we’re all familiar with, the regard for these women smacks of hero-worshipping. But why do we flock to their tales, desperate for details and juicy nuggets? What makes some villainous women seem so admirable to us? According to Dr Tim Holmes, a lecturer in criminology at Bangor University who has written extensively about con artists, we’re often impressed by the extent of their success. “Even when we frown on the crimes, it’s hard not to feel a sense of dumb-founded awe at their sheer scale: the people they fooled, the fortunes they amassed, the reputations they built. We call this the long con,” he says. 

There’s also the fact that when a criminal isn’t outwardly violent, it can be easy to overlook the depravity of their methods: they’re not killing anyone, right, so it’s fine? “There’s this idea that con artists aren’t violent criminals because they don’t have to be,” adds Dr Holmes. “They’re intelligent enough to be able to convince people purely through charisma and personality and so they’re thought of as the top of the criminal hierarchy.”

Elizabeth Holmes merch is widely available on sites such as Etsy, Anna Delvey reportedly hired a Stylist for her court appearances

He references the fact that Jordan Belfort, the egotistical fraudster who inspired The Wolf Of Wall Street, today makes his living as a motivational speaker, teaching people how to be persuasive. “He’s selling the exact tools he used to scam because they’re attractive qualities. Yes, they can be used for crime, but what else can they get you? A promotion? Better relationships?” You only have to look at Elizabeth Holmes’s fellow Silicon Valley CEOs to see this at work: Elon Musk was charged with securities fraud in 2018 and yet he still runs Tesla.

Among some of these villains, there’s also the peculiar sense they were ‘one of the people’, despite the wealth they accumulated. Anna Sorokin, in a Robin Hood-esque fashion, stole from those who could afford it – banks, hotels, affluent friends. Holmes, meanwhile, was insistent on maintaining an image of modesty, telling journalists her San Francisco apartment was the size of “a mattress” (the $5,000-a-month rental may have been modest for a billionaire, but she certainly wasn’t slumming it). She maintained that she slept just four hours a night and kept only bottled water in her refrigerator, omitting the fact she had a personal publicist on a retainer of $25,000 a month and flew only on a private plane.

But did the truth ever really matter anyway? To them or to us? These women were creatures of their own invention; they cultivated mystery and intrigue and boldness – things society has valued for a long time. Tori Telfer, author of Confident Women, which examines female “swindlers, grifters and shapeshifters” references a woman named Cassie Chadwick, who was arrested for stealing millions of dollars in the early 1900s: “She swindled a bunch of bankers in America, and people were obsessed with her. They made fake $20 bills with her face on them. One pharmacist actually sold a snake oil called Cassie Chadwick Nerve Tonic, which was supposed to make you bold like she was.”

There is a New York Magazine article about Holmes from 2016, a time when she had already been banned from operating a medical lab, with the headline: “Proof that if you’re chic enough, a little federal investigation doesn’t matter.” As things crumbled, Holmes was still embraced by New York society, still invited to high-profile media events, Birkin bag on arm, and still held up as an example of excellence. Female entrepreneurship! Success! Feminism! It was a narrative many wanted to believe so badly, they were willing to be co-conspirators in helping her create it.

For her ability to skilfully manipulate bigwigs, Holmes is often called a ‘millennial Madoff’ in reference to the ‘financial wizard’ Bernie Madoff. Convicted in 2009, Madoff ran the largest Ponzi scheme in US history, was worth an obscene $64 billion (£54.6bn) and was, at one point, chairman of the NASDAQ stock exchange. “Bernie Madoff was The Institution; he was The Man,” says Dr Holmes. “He actually joked people should have spotted him sooner, whereas Elizabeth Holmes tricked The Institution into funding her, simply because she had an idea.” This was all part of her Robin Hood charm; her fans wish she’d got away with it. “You expect a businessman to be corrupt,” Dr Holmes adds, “But do you anticipate the same level of corruptness from a woman?”

And even when the scam isn’t clever, you’re still left with the sheer brazenness. This is something that struck journalist Vicky Baker, presenter of the BBC podcast Fake Heiress, as she dug into the techniques Sorokin used. “What she was doing – depositing cheques she knew would bounce and withdrawing the money before the bank could notice – wasn’t exactly smart. You or I could do it. But it’s outrageous and bizarre and yet somehow relatable. You find yourself putting yourself in Anna’s shoes, and asking, could I do this? Could I get on a private jet and promise to pay later? Would I have the guts?”

Now, as Holmes’s fate hangs in the balance (she faces 20 years in jail after being convicted of four counts of fraud in January), it raises the question: is the world willing to finally condemn her? If we look to the past for answers, there isn’t much hope; Anna Sorokin has been on the cover of several magazines since her release this year and, just this week, appeared on Woman’s Hour to “correct the narrative about her”, as she puts it. 

“I don’t see Holmes having a comeback,” says Telfer. “What she did was so awful. She’s lucky more people weren’t hurt.” Harsh sentencing would certainly set a precedent among the Silicon Valley CEOs who move through the world unscathed by the crimes they commit, but it might displease the fans that have been rooting for her all along.

“The best type of con woman will vanish – they don’t want the spotlight,” says Telfer. But that hinges on us – our outrage, our fascination, our obsession. Would we ever let her?

Images: Getty; Etsy

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