Like everyone else recently, I am completely obsessed with scams and scammers from Theranos and Elizabeth Holmes to Fyre Festival and the downfall of Caroline Calloway. I will never find anything funnier than Ja Rule claiming he was “hoodwinked” and “bamboozled” by Billy MacFarland and I have voraciously read and watched everything I can get my hands on.

One con that really caught my eye was Anna Sorokin, who managed to stiff multiple top hotels in Manhattan and leave a string of bounced checks and elaborate lies behind her. I had read a few articles about her, but was excited to dive into My Friend Anna by Rachel Deloach Williams, a friend who testified in the trial after Anna stuck her with over $60,000 in credit card charges during a trip to Morocco. Rachel was very clearly someone who had kept and catalogued exhaustive details about her experience, but sometimes the book felt too bogged down in those details. While no stone was left unturned, I didn’t need to read every single text that they sent each other. Additionally, there was a huge amount of descriptive detail felt very “Vanity Fair” and seemed intentional to convey Rachel’s sophistication, love for photography, and privilege - but ultimately made her a less sympathetic narrator. While Anna was very clearly a criminal that manipulated Rachel and stole from her, I had a hard time watching Rachel stay friends with her after a relatively short amount of time as close friends and a huge number of red flags.

If you were interested in this scam and knowing more about who Anna was as a person, I strongly recommend this book! It does give you the closest look at who she was as a person, not just what she did, although like all scammers, she is still a bit of an enigma.

More Scams:

In terms of other famous scammers and their crimes, there are so many recent documentaries, books and podcasts that I recommend.

• Bad Blood by John Carreyrou follows the story of wunderkind Elizabeth Holmes as she rises to fame and then infamy through her medical testing company, Theranos. You don’t need medical knowledge to understand as the author does a great job of explain not only the science, but also the Silicon Valley dynamics that allowed her to become a billionaire and overnight international success.

• Fyre Fest Documentaries - there were two documentaries that came out within days of each other. The Hulu doc Fyre Fraud and the Netflix’s Fyre: The Greatest Party that Never Happened. While there are some repeat interviews in both films, they offer different perspectives on what happened and the people it impacted. Interestingly, the Netflix film was also produced by Jerry Media who did the marketing for the festival, which I always found a little bit suspect?

• If you love some “influencer” drama, nothing is better than Caroline Calloway’s failed creativity workshops in the winter of 2019. While less of a scam and more of a massive failure in planning and execution, followed by several scams, the situation first came to light in this Twitter thread by writer Kayleigh Donaldson. Calloway’s inability to admit any fault and deal with the fallout as badly as possible made her into one of the most ridiculous internet characters out there. Warning - Calloway has become more and more problematic with time and her current feed and content is often offensive and overtly sexual.

• Scam Goddess - I’ve mentioned this podcast before in the Monday Missive, but nothing is better if you are truly obsessed with scams! From small grifts to giant embezzlement plots and Ponzi schemes, there is something for everyone, plus the host Laci is hliarious!