The Growing Obsession With Those Who Game the System

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Scammer. Grifter. Con artist. Opportunist. Antihero. There are a lot of terms that have come to define people who attempt to game the system at a high level. Whether it’s Anna Delvey infiltrating the elite of Manhattan, Billy McFarland creating the disastrous Fyre Festival, or Elizabeth Holmes touting an innovative but ultimately entirely ineffective and possibly dangerous new blood test, our culture is obsessed with individuals who trick their way to the top. These larger-than-life stories are the subjects of best-selling books and magazine articles, popular documentary films, movies, and even binge-worthy TV dramas like the Shondaland Netflix series Inventing Anna, which chronicles the rise and fall of Delvey. But why are we so interested in the classic tale of the scammer?

“It’s relatable,” explains Jenner Furst, who directed and produced the 2019 Hulu documentary Fyre Fraud with Julia Willoughby Nason. “I think people are so fascinated and drawn to these types of stories that we see ourselves in both sides. We see ourselves in the duped, and we see ourselves in the duping.”

The director, who also helmed the 2021 Amazon documentary series LuLaRich, about clothing company LuLaRoe’s billion-dollar leggings marketing scam, adds, “In a sense, the scammer becomes the avatar for the average person who is maybe too afraid or has enough morality not to experiment with this type of behavior. So, it’s a way to vicariously live it out. We always assume that we know better, that our morality is stronger, that we’re smarter, but ultimately why these stories are so impactful — and why films we’ve made like Fyre Fraud or LuLaRich are impactful on a large level — is because of how relatable they are. This is us. There isn’t just a cadre of really bad, immoral people out there; we all share these traits, and we all share this gullibility. We can all be preyed upon and/or be the predator at any given point.”

Indeed, there’s a certain level of vicariousness that comes with a story like Delvey’s. Claiming to be a rich, glamorous German heiress, Delvey often bragged all over Instagram about her life overflowing with designer fashion, boutique hotels, and invites to society’s coolest parties.

In reality, Delvey was actually Anna Sorokin, a 20-something Russian immigrant who, after landing in New York City, went on to scam private jet companies, hotels, and banks, including an employee from the latter who gave her $100,000 that she never paid back. Delvey — uh, Sorokin — was consequently arrested, tried, and convicted in April 2019 on a host of charges, including larceny and theft of services, and then sentenced to four to 12 years in prison. She was released on parole last year for good behavior but was then quickly snatched up by ICE and now awaits deportation.

But when we examine her high-society heyday, who wouldn’t be wooed by that? Who hasn’t wanted to fly on a private jet or live in a five-star hotel for months on end or fly to Marrakech with a group of girlfriends? Except most of us don’t have the means for that sort of high-end existence — nor do we have the capacity to fake it. Reading about these stories or watching them on-screen, then, allows us a window into intriguing worlds and distant possibilities.

“There’s a simplicity to Anna’s scam that makes it hit the right balance between it being relatable and completely outlandish,” explains BBC journalist Vicky Baker, who created the popular podcast Fake Heiress, which followed Anna’s life and crimes, with Chloe Moss and producer Sasha Yevtushenko. “She took something so simple — ‘what if I just pretend to be rich?’ — and ran with it with no concern for the consequences. It’s the sort of story where you put yourself in the shoes of the protagonist and the victim, and I think that really adds to the appeal. You can buy into the fantasy.”

Stories like Delvey’s and McFarland’s also raise the question of how an individual operates within the systems of society. What structures or rules exist that encourage someone to scam the system but also allow people to be easily duped by the scam? While Delvey committed real crimes — and has been punished for them — some view her actions, which undercut a social subsection built by and for only a select few, as potentially justifiable. “You’re assuming the other people who are in this world are already justified in being there,” Baker says of New York’s high society. “But are they? [It’s] interesting to think about. There are some people who view Anna as a sort of antihero because she was showing how elite society can be fake and how a lot of people talk hot air when puffing up their own projects, as she did. I don’t view her as an antihero — I never wanted to glamorize what she did. She committed crimes. But it’s interesting to see how the story lands with people in general.”

“With the kinds of stories that Julia and I are committed to telling, we don’t believe in singular villains,” Furst adds. “We believe in systems. … It’s convenient to imagine a world in which individuals are so powerful that their good actions and their bad actions are so singularly important that it changes reality for the rest of us. But the reality is, we are all operating within a system, and it’s our belief that the system itself creates this behavior on both sides. Because ultimately the system does not have enough legitimate opportunities nowadays for people to have abundance and financial security and true contentment. So, there are all these scams peddling a quick fix to an intractable problem. That creates a wonderful window for the scammer to take advantage of people, whether they’re millennials going to a festival or stay-at-home mothers who are trying to make extra money.”

Journalist Jessica Pressler, who penned the Anna Delvey exposé “How Anna Delvey Tricked New York’s Party People” for New York magazine — which serves as the basis for Inventing Anna, on which Pressler was also a producer — agrees that these stories expose larger systems and also the issues that exist within those systems. While Pressler confirms that Delvey did things that were “absolutely wrong,” she’s also aware that the issues are more complex than one individual’s behavior.

Rachel DeLoache Williams with Anna Delvey on holiday in Morocco, a trip for which Williams eventually footed the entire $62,00 bill thanks to Delvey’s swindling. (Rachel DeLoache Williams)

“I think that one of the things that’s very satisfying about these stories is that when somebody games the system, you see that there is a system,” Pressler says. “You maybe knew it all along, but you really see it. It doesn’t put an end to the system, but it just makes it a little bit less threatening because it brings it to light in a way. … [These scammers] expose the cracks in our society in some strange way.”

But does Pressler, who broke Delvey’s story wide open, consider her an actual scammer? “I have used the word ‘grifter,’” Pressler says. “It’s a little more elevated. But is it dismissive? Sure. Because, yeah, it is definitely an umbrella term to describe what she did, but it doesn’t describe who she is. With Anna, I’ve never really landed on whether or not there’s a brilliance there or just a willingness to kind of tolerate awkwardness, to just kind of be there and let everyone say you’re a rich heiress, but really you’re just a gardener. To that end, I still don’t know the intent, and we’re never going to know because only she knows. She did things that were absolutely wrong — she lied to people and took their money. But did she intend to pay it back? I don’t know. We still don’t know, right?”

On a psychological level, many well-known scammers, like Delvey and McFarland, have been termed narcissists, which, on its deepest level, manifests via inflated self-importance, an excessive need for attention and admiration, and a lack of empathy for others. Furst, for instance, describes McFarland, who was interviewed for Fyre Fraud, as “an extremely intelligent, malignant narcissist who is sick and suffering through his daily life and needs the excitement and intensity of the scam in order to find meaning.” But psychiatrist and Psycom editorial board member Jean Kim, MD, says that there’s more nuance to how we classify people like McFarland. She notes that many so-called scammers exhibit traits of antisocial and/or narcissistic personality disorder, both of which can lead to grandiosity and entitlement. There’s also a feeling that they are special and can break any rule without concern for other people’s feelings or for the consequences.

“There’s controversy in the field of psychiatry about how to characterize people with what are traits of antisocial personality disorder, which is considered a pathological condition with a complex backdrop of baseline neurobiology and disordered upbringing,” Kim explains. “Are these people morally culpable for the harm they cause others if, on some level, they can’t help but behave without empathy or conscience? Where is the line between someone who has a ‘disorder’ and someone who just has traits and is just a jerk?”

She continues, “For now, we generally say yes, we should hold these behaviors as negative and requiring culpability, but it’s a murky and difficult moral quandary that our field has admittedly not adequately sorted out or figured out how to communicate to the lay public — even though there is great public concern and demand for more understanding about sociopathic and narcissistic behavior nowadays. In the end, they present with personalities that serve themselves above all else, without compunction for consequences until something externally holds them accountable.”

Juliet Lam Kuehnle, a licensed therapist and the owner of Sun Counseling & Wellness, adds that many of the individuals who pull off scams have a natural sense of confidence and charisma along with any psychological disorders. In other words, they’re likable and believable. They’re so likable, in fact, that it can be deeply satisfying to see them eventually get caught.

“We tend to think our day-to-day lives are pretty mundane, so these stories feel surreal and intriguing,” Kuehnle says. “The things these people have done are so different from our lived experiences that we get very interested in the details. It can truly feel fascinating to learn how bold, relentless, and clever these people are because it seems so far-fetched. Also, these people tend to be charming and outgoing, and it’s natural to get drawn into that vibe — and then we actually like to witness the downfall. We can even have a neurological or dopamine response when someone we may have admired on some level fails or receives consequences because it elicits pleasure. We also talk a lot about impostor syndrome, and though many of us suffer from it, this is the real-life story of a true impostor who has been found out, so it’s very compelling.”

Anna Delvey — born Anna Sorokin — is led away after being sentenced in Manhattan Supreme Court on May 9, 2019 following her conviction on multiple counts of grand larceny and theft of services. (Timothy A. Clary/Getty Images)

Many dubbed 2018, when Pressler’s article on Delvey arrived, the “summer of scam.” Endless articles were written celebrating “scammer season,” and the sudden influx of people taking advantage of others seemed to be all anyone could talk about. Fyre Festival had captivated Twitter users the year before, and McFarland was sentenced to six years in federal prison in May 2018. In June 2018, Holmes was indicted along with former Theranos chief operating officer Ramesh Balwani on nine counts of wire fraud and two counts of conspiracy to commit wire fraud. (Early this month, Holmes was acquitted of four of those counts related to patient fraud, with the jury deadlocked on three investor-fraud counts, but found guilty of four charges for defrauding investors.) Since then, numerous other scams have made headlines, some more infamous than others. Baker’s BBC podcast is titled Fake Psychic and centers on a fraudulent medium in the U.S. Although con artists have existed for centuries, they seem to thrive in today’s world. Furst has a clear answer for why: social media.

“On social media, we’re selling an identity, and we’re buying an identity from someone else,” Furst explains. “That person could be a family member, a friend, or a stranger. We’re all engaging in this transactional economy of social media every day, so the grifter has a wonderful foundation in which to scam. They do it through a false illusion on social media, through a series of dog whistles or lucky charms or some bread crumbs to the pot of gold you hope you’re going to have for your life, through using FOMO or other tools or convincing you you’re missing out on something. If only you could discover the secret they’ve discovered, your life would be better. Social media is the perfect vehicle for that. … We know from Fyre Fraud that story would not have even happened without social media. It’s a cancerous outgrowth of everything that is social media.”

Still, there’s a lot we can learn by turning over the stories of scammers. TV shows like Inventing Anna are entertaining and compelling, but they’re also a lens through which to see ourselves. Today’s con artists may be buoyed by social media, but their tales are as old as time. And whatever we call them, they’re endlessly fascinating because they reveal far more than a simple scam.

“There are some old-fashioned moral lessons to seeing these types of stories. Like an Aesop’s fable, we learn the lesson that deception catches up with you, and eventually lies will crumble beneath you, and you will be held criminally accountable,” Kim says. “However, there’s also the frustration of seeing how long it took to catch these people, and how much they got away with through their sheer nerve and chutzpah, and realizing how much that also matters in our society and how much others right now may be doing the same thing and getting away with it. Stories like these hold a mirror to what we value and believe when we talk to con people.”