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From Fyre Festival to Anna Delvey, con artists and grifters fascinate us for the same reason Trump does

We need to be willing to admit that we have ennobled the art of scam, not the art of the deal.
Image: Billy McFarland, right, at the Fyre Festival in 2017. McFarland was later convicted of fraud and sentenced to six years in prison.
Billy McFarland, right, at the Fyre Festival in 2017. McFarland was later convicted of fraud and sentenced to six years in prison.Netflix

The American dream of wealth hinges on the possibility of one big event making you rich — but, despite the occupant of the Oval Office, it’s a false projection of what it means to be a successful entrepreneur. Instead of the day-to-day grind that can make a small business successful, the myth hinges on assuming the only skill needed to get rich quick is the quick and easy patter of a con man.

Raising money to start a business is always about selling a fictional future; that’s the easy part of the dream. But the grittier, dirtier part isn’t what anyone is enamored with: Fundamentally, even when we love what we do, we hate having to go work. People often want the success and the money without the effort that goes into earning either.

And, while, con artists often tap into that desire in their victims, what we don’t discuss as often is how many people envision themselves in the role of the scammer instead of the scammed. Despite all evidence that the grifter will get caught, there’s no shortage of new con artists.

It’s shiny white kid scammer season again, and America is ready to embrace a new crop of con artists with sympathetic profiles, deep dives into why they did it and minimal engagement with the messages being sent. We love the idea of people being conned as long as the con artist is attractive, sympathetic and charming; we love it so much we ignore the warning signs until they are unavoidable.

The ones profiled in the media are young, charming, fast-talking and, every time, the justifications for their behavior are the same: they’re “good kids” who didn’t mean it; it’s not that they wanted to hurt anyone, they just wanted the money, the access to celebrity or the insta-fame. But by justifying their behavior in some way, we ignore that they not only take their victims’ money, but also often put those people at risk of long-term, harmful consequences.

They know what they’re doing is wrong, and they just don’t care. And the excuses persist well past youth — even all the way to a presidency.

Still, whether it’s the Anna Delvey scam or the fraudulent Fyre Festival, the Madoff Ponzi scheme or the Junk Bond King, we find the inner details of those who fleece others to line their own luxury suit pockets fascinating enough to yield books, documentaries and even a genre of fictional media ranging from “Leverage” to the entire “Ocean’s” series.

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Individuals who are affected by these kinds of scams in real life get angry and engender some sympathy — though, in the case of people scammed by the Fyre Festival and even Delvey, there was as much schadenfreude for their victims as anything — but there’s not the societal disdain for those perpetrators as for smaller-scale actors, like those who commit welfare or disability fraud, who are rarely as telegenic.

Then, instead of profiles into their origins, we’re ready to call them welfare queens. We don’t grudgingly admire their work, we want them hunted down and punished severely. We don't even resent corporate welfare — which is fundamentally more expensive with fewer restrictions — in the way that we resent those who try to get enough money from the state to live, even though welfare fraud occurs in less than 2 percent of cases today.

Why are we so fascinated by the creators of the most harmful schemes, and so ready to jail someone for trying to create a better life for their kids by lying about their address, or collecting enough food stamps to afford more than peanut butter and cereal?

American vulnerability to fraud is rooted in exceptionalism — a belief that it can’t happen to us (until it does). Similarly, the American dream hinges on a fantasy that we’re all just temporarily bereft millionaires. So perhaps when we see people who look like us, who struggle like us, taking risks for essentially mundane rewards and getting caught, we resent them for reminding us that even the fantasy of being a great grifter is unreasonable.

We want them punished for our own ambivalence about confronting the fact that class mobility is largely a myth, and their seeming unwillingness to accept it. Without being willing to examine why we resent others for taking the minor risks that hurt few people but mythologize those who take big ones that hurt many, we will all continue to find ourselves getting ripped off.

As the next crop of scammers is being lured by the attention they are guaranteed to receive in the press, we need to be willing to admit that we have ennobled the art of scam, not the art of the deal. And we need to ask ourselves why preserving the dream of great wealth that comes easily is so important that we grudgingly respect even those who come by it illicitly.