The Most Iconic Grifters Of The Internet Age

The IRL scams that led to URL infamy.

Nobody wants to get conned, but it sure as hell makes for riveting entertainment to see grifters’ expansive playbooks come to light. Grifting is a nuanced art — expanding from politics to “spiritual leadership” to lying CEOs. Ahead, we’ve gathered the most iconic grifters whose IRL lies spun out into URL infamy.

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Elizabeth Holmes

Elizabeth Holmes’ plan to become Steve Jobs with an X chromosome blew up in her face when investigations began surrounding her revolutionary blood testing company, Theranos. Long story short, a little federal agency called the Securities and Exchange Commission got involved, charging her with deceiving investors by "massive fraud" through false or exaggerated claims about the accuracy of the company's blood-testing technology, including nine counts of wire fraud and two counts of conspiracy to commit wire fraud for distributing blood tests with falsified results.

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Billy McFarland

Billy McFarland’s scamming led to one of the most iconic days on the internet. Rich people stranded on a tropical island, an open-faced cheese sandwich from hell — Fyre Festival, baby! The architect of the most cursed music festival of all time, along with his co-conspirator, Ja Rule, were sued for $100 million in a class action lawsuit. McFarland was quickly arrested and charged with wire fraud in Manhattan federal court, where he plead guilty to two counts of wire fraud and was sentenced to six years in federal prison.

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Caroline Calloway

An Instagram influencer turned accidental grifter, Caroline Calloway got into hot water when her "Creativity Workshop Tour" fell through, refunds for ticket holders went missing, and her assistant and former friend Natalie Beach ran to The Cut with a searing tell-all. Unfortunately for Beach, her essay catapulted Calloway to a much wider demographic and canonized her as part of the internet zeitgeist.


Anna Delvey

Anna Sorokin concocted the It Girl identity Anna Delvey and convinced gullible (and wealthy) downtown Manhattan elites that she was a German heiress. She defrauded hotels, restaurants, and trust-fund kids in an instantly iconic grift that’s spawned television adaptions of her story at both Netflix and HBO.

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Andrew Keegan

A ‘90s teen heartthrob has allegedly turned to one of the oldest grifts of all-time: “spiritual leader.” Keegan founded the religion Full Circle in 2011, and although he says it’s not a cult, he’s described as the group’s “ultimate decision maker.” Take from that what you will.

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Martin Shkreli

The “pharma bro” with a lump of coal for a heart! Shkreli was the CEO of the pharmaceutical firms Retrophin and Turing Pharmaceuticals when Turing obtained the manufacturing license for the antiparasitic drug Daraprim and price-gouged it from $13.50 to $750 per pill. Life came at Shkreli fast, and two years later he was charged and convicted in federal court on two counts of securities fraud — both unrelated to his Turig controversy — and was ultimately sentenced to seven years in federal prison and up to $7.4 million in fines.

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The Original Bling Ring Crew

Los Angeles teens Rachel Lee, Nick Prugo, Alexis Neiers, Courtney Ames, and Diana Tamayo took their celebrity obsession to new heights when they robbed A-list celebrities blind in 2008 and 2009. The Bling Ring stole roughly $3 million in cash and belongings from Lindsay Lohan, Paris Hilton, Megan Fox, Orlando Bloom, and more. Without them, we’d never have Emma Watson as Neiers saying “I wanna rob!” in Sofia Coppola’s Bling Ring. Culture as we know it wouldn’t have existed!

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The Vogue Staffer Who Stole From Grace Coddington

Media salaries are famously meager, but ex-Vogue staffer Yvonne Bannigan’s money moves landed her three years probation. Bannigan was arrested and charged for stealing from top editor Grace Coddington, allegedly racking up $53,564 in unauthorized purchases on Coddington’s card. Not only that, Bannigan allegedly pocketed a $9,000 commission from selling Coddington’s personal belongings on TheRealReal. As they say: reduce, reuse, recycle!

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Donald Trump

From being Twitter’s most infamous sh*tposter and a reality television star to the President of the United States... the ultimate grift.