The Seduction of Scammers: Why we remain riveted with stories of people who play with our millions

Why do remain interested with people like Elizabeth Holmes, Anna Delvey and Caroline Calloway? Nothing satiates our hunger more than watching a trainwreck.

As I’m writing this article, Elizabeth Holmes is facing federal charges on wire fraud in San Jose for her role as the CEO of Theranos.

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A once-lauded start-up turned debacle, Theranos ruined the lives and health of a large swathe of customers that believed in their pitch that they could diagnose diseases through a drop of blood with the use of a machine.

It was easy to be bought in by the mythos. Holmes was a prodigiously gifted 19-year-old with Stanford University-cred. She pretended to speak in a low, deep voice, wore black turtlenecks like her idol Steve Jobs, and pretended to own a pet wolf, which, for all in intents and purposes, was merely a husky.

She is also, crucially, white. Managing to fool investors from Rupert Murdoch to head honchos at Walmart, this was someone who had her eye on the prize, although what that prize was is becoming increasingly hard to fathom.

When the story broke, when the book was released, and when the subsequent documentary was aired, tongues were wagging. Since then, other scamming stories have grabbed our attention: fake-heiress Anna Delvey and wellness “guru” Caroline Calloway comes to mind.

What is it about these “scammer queens” that gets our attention, especially since we can be so easy to scam?

I’ve lost track of horror stories I’ve heard during the pandemic of people that have been scammed. Thankfully, no one has come forward with tales of large-scale fraud on the level of Holmes. (I have a feeling that if I asked some people I usually talk to for interview tidbits I might be blocked for life.)

The little things continue to astound me: people bored at home, shopping online for purchases that never make it home. Or if they do, they’re vastly different from the advertised product.

“I think people are embarrassed when this happens to them,” said a friend I spoke to, on condition of anonymity. “You do end up looking very stupid in hindsight.”

She knows this, she says, because she had been fooled. “I bought a pricey handbag online from an Instagram re-seller. It arrived and I immediately realized something was wrong. I couldn’t complain because I had nothing to stand on.”

In a series of Instagram stories that went viral and (and was eventually followed by a full article), Ingrid Chua called out Instagram re-sellers for promoting “VIP gift bags” from Chanel.

A quick perusal showed that these gift bags amounted to nothing more than the free gift-with-purchases you get after buying, for example, a perfume, or a special edition holiday set at the Chanel cosmetics counter.

“The authenticity claims made by resellers of their Chanel GWP or “VIP” bags are an attempt to dupe clueless buyers,” she concluded.

The story ruffled feathers on both sides: aggrieved Instagram re-sellers caught in their lies were quick to refute, while those who had purchased, and who enjoyed the feeling of owning a Chanel purse suddenly realized they had been fooled.

3

Scammer sisters

Between 2013 and 2017, Anna Sorokin, under the name Anna Delvey pretended to be a German heiress.

She stayed in hip boutique hotels in New York, paid for at first by connections by generous friends she had successfully scammed, and then by overdraft fees.

She also shopped at designer stores, and courted wealthy members of New York’s art collecting scene into something called “The Anna Delvey Foundation.” This private member’s club and art foundation, of course, did not exist, and she was subsequently evicted from all those hotels, and eventually sued.

Caroline Calloway—described by Wikipedia as “an American internet celebrity known for posting Instagram photos with long captions”—dips in and out of the news occasionally.

First, there was an essay written by collaborator Natalie Beach that went viral. It described their toxic relationship in which Beach felt she had been used on Calloway’s meteoric rise.

Calloway responded by upping the ante, promoting herself like a writer-savant, complete with “creativity workshops” and essential oils sold through her website, like a one-woman Fyre Festival.

All these actions were met with derision, and yet I felt that only Holmes got burnt of our anger because, of course, she had been playing with the hopes and health of people.

Delvey and Calloway comparatively hurt fewer people, so there’s a distance. We can be curious bystanders without actually being part of it. Calloway also has not been sued for anything.

Curiously, the reactions to notable Filipino scammers have been less kind. Kathleen Poblete faked a UP Law Degree and catfished hapless men, giving rise to the moniker “Kathfish.” People were outraged, yes, and then we quickly moved on to the next news cycle.

Are we, as Filipinos just used to our own fooling us? Or did we just miss the enjoyable glamor that comes with watching a train-wreck involving people like Sorokin playing with millions?

Maybe we also see something in these people. The need to improve and change our own lives. If this country can’t help us, we might as well get there ourselves.

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