5 Crazy Fraud Cases True Crime Fans Will Love

Welcome to True Crime Tuesday where we review, recommend and generally obsess over everything crime-related.

The true crime obsession has been in full swing for awhile now with new documentaries coming out left right and centre. The internet is full of opinions on every new trailer (see: Joe Berlinger’s first trailer for Extremely Wicked, Shockingly Evil and Vile), and batshit crazy stories like Abducted in Plain Sight are inspiring some of the best memes of the last decade.

The latest sub genre of true crime is fraud cases. Highly public fraud cases like the Enron scandal and Bernie Madoff’s massive Ponzi scheme were all over the news in their time and even inspired their own documentaries and films. We’ve always been fascinated by people who are somehow both smart enough and dumb enough to pull off million dollar schemes that fool thousands of people at a time. How do they start? Why don’t they know when to cut their losses? How do they finally get caught?

Here are some of the latest fraud cases that have had us all on the edge of our seats.

Fyre Festival
The disaster that was Fyre Festival was all over social media back in 2017 starting with the now-iconic tweet of the pathetic piece of bread and sliced cheese. We all had an idea that some big music festival had…not gone well, but most of us didn’t know the extent of it. Until both Netflix and Hulu graced us with their documentaries Fyre and Fyre Fraud, respectively.

On a high level, it just seemed like a bunch of rich people lost money they probably can afford to lose anyway. But the story of Fyre founder Billy McFarland was a lot more complicated—and frankly, riveting—than that. McFarland was delusional from the very beginning but somehow he managed to convince well-known (Ja Rule) and experienced (Andy King) people that his vision for a luxury music festival was possible. It wasn’t that his idea was bad, it was just that his timeline and execution were extremely unrealistic. Even when the festival was one day away, one of the headliners (Blink 182) had cancelled, and it was clear they wouldn’t be able to accommodate the festival attendees, McFarland still refused to admit defeat. He’s now serving a six year prison sentence after pleading guilty to a wire fraud charge.

Theranos
If you haven’t heard of Theranos and Elizabeth Holmes yet, there’s plenty of material to get you started. From articles in The New Yorker and The Wall Street Journal and a book (Bad Blood: Secrets and Lies in a Silicon Valley Startup by journalist John Carryrou) to an HBO documentary (The Inventor: Out for Blood in Silicon Valley) and a podcast (The Dropout), there’s no shortage of coverage. Elizabeth Holmes started out with an idea for creating a device that could test for hundreds of diseases with only a pin prick of blood. She dropped out of Stanford to found Theranos, a company she claimed would change healthcare—and the world.

Silicon Valley is full of crazy ideas. Some of them work out and some of them don’t. But Holmes was so sure of her idea (despite feedback from respected scientists that what she had in mind could not be done), that she was able to convince rich and powerful people to invest in her vision. Going from the youngest and wealthiest female billionaire in America to an accused felon, Holmes is currently awaiting trial on wire fraud charges. She has plead not guilty but the evidence against her is pretty extensive. We clearly haven’t had enough of her story yet either as both Jennifer Lawrence and Kate McKinnon are set to portray Holmes in different upcoming projects about the scandal.

Anna Sorokin
Anna Sorokin, also known as Anna Delvey or “The Fake Heiress” and “The Soho Grifter” was recently found guilty on four counts of theft of services, three of grand larceny and one of attempted grand larceny. She had spent months swindling New York bars, restaurants, hotels and banks out of more than $200,000. Rachel DeLoache Williams, a photographer for Vanity Fair was one of many people sucked into Sorokin’s lies. As a victim of grand larceny connected to a trip to Marrakech that Sorokin tricked her into paying for, Williams testified at the trial.

Sorokin was accused of falsifying documents from international banks showing accounts abroad with a total balance of approximately €60 million. She claimed to be starting an art foundation and misrepresented who she was in order to get “in” with NYC’s elite. Eventually, the money ran out and she was arrested on fraud charges. Sorokin’s lawyer told GQ she was using a courtroom stylist during her trial (which isn’t unusual), but the person she hired was actually a celebrity stylist. Both HBO and Netflix are working on a series about her life and Sorokin is reportedly delighted and hopes either Margot Robbie or Jennifer Lawrence plays her.

College Admissions Scandal
There may not be any podcasts or documentaries (yet), but following the college admissions scandal as it unfolds in the news is riveting enough all on its own. In March, over 160 people including celebrities like Lori Loughlin and Felicity Huffman were charged with fraud for paying hundreds of thousands of dollars to get their kids admitted to college. Loughlin’s daughter, Olivia Jade, already “works” as an Instagram and Youtube influencer landing partnerships with Sephora and HP (both brands have since dropped her). She talks openly in one Youtube video about how she isn’t interested in school and is only there to party. Still, her parents wanted her to go to a top university anyway.

Loughlin and her husband, fashion designer Mossimo Giannulli have been charged with conspiracy to commit mail and wire fraud and money laundering. They allegedly paid $500,000 to William “Rick” Singer, who is the man accused of being the mastermind behind the entire scheme, to get both their daughters into USC as recruits to the crew team even though neither of the girls had ever rowed crew in their lives. Although Huffman chose to plead guilty to her charges immediately, Loughlin and Giannulli plead not guilty claiming they didn’t know what they were doing was illegal. It will be interesting to see how that defence works out for them.

Gypsy Rose Blanchard
It’s easy to start thinking that people who commit fraud must be sociopaths and delusional, but others like DeeDee Blanchard, are truly mentally ill. For years, Blanchard lied to the world, her daughter Gypsy Rose, and herself, claiming Gypsy had everything from cancer and epilepsy to a severe sugar allergy. She took donations from people who genuinely wanted to help Gypsy and the two even lived in a house that was built for them for Habitat for Humanity. But the thing was, Gypsy wasn’t sick at all.

The documentary Mommy Dead and Dearest and Hulu’s The Act tell the story of Gypsy Rose’s sheltered life and how her mother not only made her think she was deathly ill, but actually did things to cause illness a lot of the time. DeeDee suffered from Munchausen’s by proxy, a psychological disorder where a person makes up or exaggerates medical symptoms of a child in their care in order to gain attention and sympathy. Eventually Gypsy started to figure out she wasn’t as ill as her mother claimed and she decided to do something about it. While DeeDee did commit fraud with all the money she took from people, she was never charged and no one really found out the extent of what she did until after she died.

Courtney Hardwick

Courtney Hardwick

Courtney Hardwick is a freelance writer based in Toronto. Her work has appeared on AmongMen.com, 29secrets.com, therichest.com, and ELLECanada.com.  When she isn’t writing about relationships, and the best TV shows and books you should really already know about, she is working on her novel. She hopes to have it published by 2025. You can follow her on Twitter @Courtooo.

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