What is It About Con Artists? How the American Dream Can Go Wrong

slightly blurry image of woman with dark hair looking into distance — Pexels

Just take one look at your favourite streaming service, and it’s clear: we’re at a height of glamorizing and obsessing over true crime and tales of swindlers. Many of the stories being fictionalized and made into movies and TV series — and starring some of the biggest names in Hollywood — are all about the real-life tales of true crime.

However, there’s always the discussion to be had of whether or not this is ethical, which is a valid argument to make. When we dramatize these stories, we are popularizing alleged and convicted criminals and giving them notoriety and fame, having famous actors play them, and, in some cases, allowing them to profit off our misplaced curiosity.

But, more recently in pop culture, there seems to be more of a penchant to focus on the con artist genre of true crime (ahem, The Tinder Swindler). When it comes to famous scammers and con artists, the victim is rarely ever one person and the con artist’s intentions are often complex — did they do it for the money, or were they just overly passionate about an idea?

To explore these questions, we’re looking at two famous cases of two women, and their rise and fall as con artists in the public eye.

‘Inventing Anna’ Delvey

Anna Sorokin, better known as Anna Delvey, was a fake German heiress who conned her way into New York’s elite society. What started as fancy parties, runway shows and designer clothing became something much bigger. Once she got a taste for that life, it seems that she felt she belonged there — and came up with a way to stay there. The only issue was she didn’t have the money to make it happen. She never had the money to begin with.

Portrayed by Julia Garner in the iconic Shonda Rhimes’ Netflix series Inventing Anna, which was based on the New York Magazine article by Jessica Pressler, Delvey often repeats the same infamous line: “I’ll wire you a transfer.” She was able to con her way into elite circles of art collectors, designers and tech moguls who funded her lifestyle and allowed her to continue to keep spending and making money.

As the show dramatizes, after a romantic relationship with the founder of a tech startup, she was determined to start her own company: the Anna Delvey Foundation. It was meant to be an exclusive SoHo House-like club that would have an extensive art collection, hotel rooms and restaurants. She had powerful, well-known and well-connected men on her team advising her and advocating on her behalf to secure loans on the basis that her trust fund was overseas and would be available once she turned 25. While she was building up this business, she was living in luxury hotels paid for with promises of wire transfers that never came.

Eventually, Delvey’s lies started caving in on themselves. The 11 Howard, the hotel she was living in for the most amount of time, realized she didn’t have a credit card on file and her wire transfer hadn’t come through. She jumped from hotel to hotel, each quickly realizing the same thing, as she racked up tens of thousands of dollars in unpaid bills. She was eventually homeless and tried to manipulate friends to let her stay at their homes, but she had lost everyone.

Delvey was eventually arrested and charged with grand larceny and theft of service. She spent 2019–2021 in prison, and now faces possible deportation. However, she did earn a check from the Inventing Anna series, most of which she used to pay back money she owed.

From ‘Dropout’ to billionaire to fraud

Elizabeth Holmes was a 19-year-old college dropout, but not in the way you think. Like the Mark Zuckerburgs of the world, she came up with an idea — but unfortunately that’s all it ever turned out to be.

Basically, Holmes wanted to recreate the concept of the blood test — allowing patients to get tested with a single prick of blood at a lower cost. It was a revolutionary idea and, if successful, it would have changed the medical field significantly.

Portrayed by Amanda Seyfried in the Hulu series The Dropout, which was based upon the ABC podcast of the same name, Elizabeth Holmes created a name for herself before being outed as a fraud. She built her company, Theranos, from the ground up, investing the college fund her parents had for her and convincing some important people to invest in her idea. What began as a small team of scientists, engineers and Holmes, within a decade turned into a multi-billion-dollar corporation in Silicon valley with hundreds of employees.

As The Dropout depicts, Theranos employees became unwilling pawns in Holmes’ fraud. They believed in the company and its values so deeply they were willing to look past the sketchy rules she had in place. Employees signed NDAs when signing on to the job, they were tracked within the workplace, certain employees weren’t allowed to discuss their work with other departments, and if they questioned anything they saw they were simply let go, replaced and threatened with legal action if they talked about their jobs.

Two such employees, Erika Cheung and Tyler Schultz, whose grandfather was a board member of Theranos, became the employees who took down the company. With the help of Wall Street Journal writer John Carreyrou, they provided the necessary information that Theranos wasn’t running tests on their own machines, but they were using already-existing third-party machines and altering blood tests to get the results they needed to show their investors. Their technology was years away from actually working.

After the article came out exposing this fraud, Theranos slowly began to crumble. Their labs were finally tested and deemed unacceptable and eventually the company shut down. Elizabeth Holmes faced 11 different charges, but was found guilty of only four earlier this year. She is currently free on bond as she awaits sentencing.

Did the ‘American Dream’ fail them?

When thinking about these two women and their motivations, it seems like their dreams of grandeur might have been connected to the idea of the “American Dream” – the concept that anyone can achieve anything they put their mind to. What do these two women have in common other than their infamous rise and fall occurring around the same time across the same country? They both had an idea. They weren’t simply doing what they did for the sake of stealing money.

Although, yes, Anna Delvey did live a luxury lifestyle by using other people, it seems that many of these people were already rich, and may have let her get away with it for so long because they had enough to spare. While we certainly don’t condone crime, it’s interesting to think about how she came up with an idea that impressed some of the most brilliant minds in elite society. Delvey was backed by real estate moguls, Wall Street bankers and famous restaurateurs who all believed in her idea and advocated on her behalf. The only thing she didn’t have herself to see through the idea was the actual capital. She put in the work, created a business plan and was working to connect with and convince the right people she was worth investing in.

Elizabeth Holmes’s story, on the other hand, is a bit more complicated. Yes, she defrauded some of the biggest names in history (like Rupert Murdoch and Larry Ellison) out of investments in her company, but more importantly, she also deceived patients. Allowing her technology, which she knew to be inaccurate, to run blood tests on actual patients was horrible behaviour. Although it’s not justified, the belief in an idea and wanting it to work allows people to rationalize certain things.

In the HBO documentary The Inventor: Out For Blood in Silicon Valley, behavioural economist Dan Ariely uses a metaphor that may help explain her behaviour. If someone is attached to a lie-detector test and is given the opportunity to steal money while lying, the test will detect it. However, while still attached to the lie-detector test, if given the chance to steal money for a charity of their choice, the test no longer detects it as a lie. Because they believe what they’re doing is right.

While false blood tests did actual harm to people, it’s possible that Holmes thought she was changing the world for the better with her technology, and had it succeeded it, would have been true. Delvey thought she was starting a business that, in her elite circles, meant something. It would’ve meant that someone who made their way over to America on their own was able to work their way up and create something that people would kill to be a part of. These women, both in their early 20s at the time, were able to con their way through some of the most brilliant and famous minds of the century.

Although con artists exist on an everyday basis, there’s something about the magnitude of their ambition and crime. Money comes and goes and some people are so rich, it’s possible that they don’t even notice it going. But there’s a difference between someone stealing money and someone funding an idea. Sometimes it lies in determining if the idea is worth it instead of the woman behind it.