Flirty chat to suicide in hours: The deadly new wave of AI-powered sextortion scams targeting American teens

Ben Gillenwater is an IT expert with 30 years of experience and the creator behind the “family IT guy” accounts on social media, where he shares tips with parents on how to protect their kids online from harmful content, predators, and addictive algorithms, among other virtual risks.

But most importantly, Ben is a dad. Five years ago, he gave his 5-year-old son an iPad, the results of which were so disturbing, it launched him into his current role as a full-time content creator dedicated to protecting children from the dangers of the digital world.

On this episode of “Relatable” with Allie Beth Stuckey, Ben dives into the online perils facing today’s children — including one so sinister, it’ll forever change the way you think about child predators.

When most people think of online groomers, they picture creepy men in basements posing as minors in an effort to lure children into secretly meeting up with them. But some groomers have no intention of ever making physical contact with their victims. Their sole intention is to get rich off of creating chaos and ruining lives from afar.

Gillenwater gives the example of Jordan DeMay — a 17-year-old high school student from Michigan, who tragically died by suicide in 2022 after falling victim to a sextortion scam.

“Good kid, good family, good school records, had a girlfriend,” he says.

Then one day, an attractive girl messaged him on social media and struck up a flirtatious conversation that culminated in her sending nude photos. Jordan was asked to return the favor, and when he did, it was revealed that the images of the girl were stolen or fake and that she was actually a Nigerian gang. The two brothers behind the operation — Samuel and Samson Ogoshi — threatened to blackmail DeMay by sending his explicit photos to his family, friends, and school contacts if he didn’t wire them money, spurring DeMay to take his own life.

This entire sextortion scam — from initial contact to DeMay’s suicide — occurred in less than six hours.

DeMay’s tormentors, says Gillenwater, are part of a broad network of Nigerian cybercriminals called “the Yahoo Boys.” They’re the same people behind the Nigerian prince scams that have conned hundreds of thousands — perhaps even millions — of people into wiring money with fake promises of huge inheritances or riches, only to demand endless upfront "fees" that leave victims with nothing.

Whether they’re posing as wealthy princes or attractive women, their strategy is the same: “identify weakness in people,” Gillenwater says.

Back in the '80s and '90s when the digital world was just ramping up, these cybercriminals were able to dupe people using only “poorly worded emails,” but today, thanks to advances in technology, their predatory empire is built on “very well-worded and well-informed AI-powered hunting programs,” meaning their schemes have only gotten darker and more effective.

“Teenage boys specifically are targeted for this [sextortion scam] in particular, and they exploit their biology,” says Gillenwater.

“What they do when establishing the initial connection is they study all of your friends on Instagram and gather up your whole network so they know everybody you go to school with ... everybody you go to church with ... every family member ... that's how they blackmail you is they're going to send your naked photo to all those people,” he explains.

Sadly this nefarious kind of operation isn’t exclusive to Nigeria.

“There's South American gangs, there's Asian gangs, there's African gangs, there's European gangs. It's a very high-profit, very low-effort endeavor, part of which is automated,” says Gillenwater.

But cybercriminals are just one threat in the vast, dark web of online child predation. In the next part of the interview, Gillenwater dives into some shocking statistics regarding the “traditional creep,” who targets vulnerable kids online for sexual exploitation.

To hear more and learn tips that will help you protect your kids online, watch the full episode above.

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