Why we can't get enough of hustlers, scammers, fraudsters, and bulls*** artists

Those tuned into the world of influencers have spent much of this week devouring and dissecting an article by journalist Natalie Beach about her (one suspects former) friend, American influencer Caroline Calloway.

Even those with no prior knowledge of the duo have found themselves sucked into a deep dive on the intricacies of their relationship, which began as a college friendship and evolved into a business arrangement of sorts as Natalie helped to hone Caroline’s Insta persona with clever captions and then began co-writing/ghostwriting her memoir, for which Caroline reportedly received a deal of $500,000, with an advance of €100,000.

In short, the book never materialised, as Caroline withdrew from the process.  There was also the small matter of a planned tour of ‘creativity workshops’ costing $165 which were shambolic – those that happened were not quite as advertised while others never materialised at all.  She has been lambasted on social media, branded a ‘scammer’, and Beach’s article in The Cut this week has added fuel to the fire.

Calloway has been compared to both Billy McFarland, the orchestrator of arguably the biggest festival flop in history – Fyre Festival – and Anna Delvey (real name Sorokin), the 28-year-old fake heiress who is currently languishing in prison having been found guilty of theft of services and grand larceny.  So audacious, and intriguing, were their antics that McFarland has been the subject of no fewer than two documentaries while both HBO and Netflix are each reportedly serialising Sorokin’s story. 

It seems we simply cannot get enough of the true stories of hustlers, scammers, fraudsters and bulls*** artists.  In the age of Donald Trump, deepfake, and the alternate-yet-co-existing universe that is Instagram, it’s hardly surprising we’re so enthralled by cautionary tales of ordinary people being duped by those who are not quite who they appear to be; the ultimate chancers.  If you’re not careful, it seems, you can end up with Trump in the White House or you may well find yourself knifing your mother’s dream boyfriend in the eye when he turns homicidal – a la Dirty John.

The story of John ‘Dirty John’ Meehan provided the benchmark for the modern scammer narrative.  Having met wealthy businesswoman and mother of two Debra Newell on an internet dating site, Meehan posed as an anaesthesiologist, and charmed her into marriage within a few weeks.  A litany of abuse, manipulation and gaslighting ensued before (SPOILER) Newell’s younger daughter fatally stabbed him in the eye in a car park in self defence. 

LA Times journalist Christopher Goddard chronicled the terrifying tale in the Dirty John podcast, which was downloaded 10 million times in its first six weeks.  A documentary followed as well as a series, which was picked up by Netflix and starred Eric Bana and Connie Britton as John and Debra.  Meehan’s intricate web of increasingly audacious lies was astounding, but perhaps even more astounding was Newell’s inability, or reluctance, to see through them.

Meehan was certainly a charming sociopath, and blinding charm is often cited as the most notable trait exhibited by scammers, at least initially.  Billy McFarland was routinely described as charming and great fun to be around, even by those who suffered mentally and financially when Fyre Festival all came tumbling down, literally, around them.

Such was the power of his personality that McFarland persuaded some of the biggest influencers of 2017 – among them Bella Hadid and Kendall Jenner – to promote a luxury festival on a remote island which did not have the infrastructure to support it.  A promo video was shot of them partying on the island with champagne and yachts, creating a vision that would never materialise, which they then sold to their followers on social media.

Months later, even as a thunderstorm raged and ravaged the tents and facilities, and bus loads of celebrities and influencers (some of whom had paid thousands) were dumped on the woefully unprepared site, McFarland’s employees and contractors battled to fulfil his vision, even though the man himself had effectively scarpered.

Their incredulity, not only at McFarland’s gall, but also their own inability or unwillingness to extricate themselves from a project which was clearly doomed from the start, was writ large on their faces as they recounted the sorry tale for Netflix’s Fyre Festival documentary.  McFarland kept them, the investors, and the festivalgoers on board with a litany of lies and promises which they all chose to believe over their gut instincts and, in the end, their own eyes. 

Illustrating the extent of McFarland’s hold over them was the story of one senior employee, who had worked with McFarland for six years, who claimed that he (the employee) was prepared to perform a sexual act on a customs officer in order to get four 18 wheeler trucks of Evian water delivered to the festival and ‘save’ it.

Those who were duped by fake heiress Anne Delvey (real name Anna Sorokin) were similarly held her in thrall, although more so due to her ability to flash the cash than an engaging personality.  She had arrived in New York with a credible back story, selling herself as a German heiress with a trust fund, who set up camp in a boutique Soho hotel, and set about ingratiating herself into the upper echelons of society.  All it took was flashing multiple $100 bills, and a grand plan to launch a club.  Much like McFarland, fke it till you make appeared to be her modus operandi. 

A litany of unpaid hotel bills amounting to tens of thousands caught up with her, however.   She also left a friend in Marrakesh with a bill of $62,000 (more than said friend was paid in a year).  And then there was the small matter of bank fraud.  Those who associated with Sorokin were completely taken in by her.  They had no reason to doubt her as she flaunted those $100 bills, wore the requisite designer threads, and possessed the carefree attitude one would expect from a wealthy heiress.

How she managed to get away with it is summed up in an article in The Cut.  “Anna looked at the soul of New York and recognized that if you distract people with shiny objects, with large wads of cash, with the indicia of wealth, if you show them the money, they will be virtually unable to see anything else,” wrote Jessica Pressler.  “And the thing was: It was so easy.”

Sometimes, however, the scammers are celebrated.  Hustlers, which hit the big screen this weekend, tells the true story of a pair of New York strippers who scam Wall Street bankers out of their cash via credit card fraud.  Set in 2007 before the financial crash, it stars Jennifer Lopez and Constance Wu as the strippers, sympathetic characters just making a fast buck in a life short on opportunity. 

There’s a grey area, it seems, between which scammers earn our sympathy and which provoke fear.  Either way, our fascination shows no sign of abating. It’s only a matter of time before somebody serialises the Calloway/Beach saga.  Watch this space.

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