WEBVTT

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Welcome back to the Jeep Dive. It is January

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24th, 2026. And, you know, just let that date

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sink in for a second. We are nearly a decade

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removed from the initial arrest that sparked,

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I mean, a thousand headlines. And yet the algorithm,

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and let's be honest, our own curiosity, it just

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won't let this story die. No, it won't. We are

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talking. inevitably, about the enigma that is

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Anna Delvey. Or Anna Sorokin, if we're going

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by the birth certificate. Though at this point,

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I think the two identities have kind of merged

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into something, something entirely new. It really

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has. Yeah. I was looking at the timeline while

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prepping for this, and it's actually baffling.

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You have a story that started with a fake heiress

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scamming banks in 2017. Right. Then it goes through

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this massive Netflix boom in 2022. And now here

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we are in 2026 and she's still culturally relevant.

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Still. I mean, she's modeling. She's modeling.

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She's a subject in The New Yorker as recently

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as May 2025. Yeah. It's not just a crime story

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anymore, is it? It's a survival story. Yeah.

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Or maybe a marketing story. Oh, it's. absolutely

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a marketing story. It's a masterclass in personal

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branding, albeit one built on a foundation of

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larceny. I think the reason we're doing this

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deep dive today and specifically why we aren't

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just doing a quick recap is because the whole

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Anna Delvey saga is actually a perfect lens for

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understanding the last 10 years of our culture.

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How so? Well, it sits right at the intersection

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of the girl boss era, the rise of the influencer,

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and the complete gamification of the financial

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system. It touches on everything. That is exactly

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the mission today. I don't want to just list

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the crimes. You can get that on Wikipedia. I

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want to understand the mechanics. The how. The

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how, exactly. Exactly. We have this massive stack

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of sources, biographies, the original New York

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Magazine expose, that Vanity Fair betrayal piece,

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court transcripts in the 2019 trial and all the

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updates through mid 2025. My goal is to figure

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out how a woman in her mid 20s with no college

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degree and no actual assets nearly convinced

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a hedge fund to give her 22 million dollars.

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Right. Like purely logistically, how does that

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happen? It happens because systems that we think

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are. Rigid banking, luxury hospitality, even

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the legal system are actually surprisingly porous

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if you know where to poke. And Anna, well, she's

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a genius at finding the soft spots. So let's

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peel this back then. Before she was a fake heiress

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or a house arrest celebrity, she was just a kid.

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And I think the contrast between the reality

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of her origin and the fantasy she sold is where

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we have to start. Yeah. Because the gap is...

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Well, it's continental. It is, literally and

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figuratively. She was born Anna Sorokin on January

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23rd, 1991 in Doma de Dovo. Doma de Dovo. Yeah.

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And for those who don't know Russian geography,

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this is a working class satellite town just south

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of Moscow. It's industrial. It is not the backdrop

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for a high society drama. Not at all. Her father,

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Fadim. He was a truck driver. A truck driver.

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And her mother ran a small convenience store.

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This is a very, very standard blue -collar existence.

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There's nothing wrong with it, obviously. But

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it's light years away from the trust fund baby

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narrative she later constructed. It's a whole

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different universe. Exactly. And the family migration

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pattern is interesting, too. In 2007, when Anna

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is 16, they move to Germany. They settle in North

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Rhine -Westphalia near Cologne. Her dad gets

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into the HVAC and transport business. Her mom

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becomes a housewife. But just... You know, try

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to picture Anna at that age. She's 16 years old,

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she's dropped into a German Catholic grammar

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school in a town called Eschweiler, and she barely

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speaks the language. That is a tough age to be

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an outsider. I mean, high school's brutal enough

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when you fit in. When you're the quiet foreign

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kid who can't speak the language, I mean, you

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retreat. You retreat, or you find an escape.

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And for Anna, that escape was the internet. And

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specifically the visual internet of the late

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2000s, early 2010s. Right, the blog era. era.

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She became obsessed with Vogue, with fashion

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blogs, with LiveJournal and Flickr. She was just

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consuming images of a world she had absolutely

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no access to. I think we've all been there to

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some degree, you know, doom scrolling through

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luxury lifestyles on Instagram or whatever. But

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most people look at those photos and think, I

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wish I had that. Anna seems to have looked at

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them and thought, I am that. I just need to get

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the logistics sorted. That's the key psychological

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shift, isn't it? She didn't want to earn her

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way into that world. She believed she was already

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of that world and reality just needed to catch

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up. Yeah. So after high school, she briefly moved

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to London in 2011 to attend Central Saint Martins,

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which is, you know, the art school. Huge deal.

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Yeah. But she dropped out almost immediately.

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She couldn't hack the structure or maybe the

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reality of it just didn't match the dream. So

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she went back to Germany for a bit, but then

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made the pivotal move to Paris for an internship

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at Purple Magazine. And purple is critical here

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because it's not just a fashion magazine. It's

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an edgy cultural touchstone. It's where the cool

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kids are. It gave her instant credibility. Precisely.

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And she was making peanuts about 400 euros a

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month, which her parents were subsidizing. But

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this is where Anna Delvey is born. The name changed.

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The name changed. She starts introducing herself

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as Anna Delvey. She claims it's her mother's

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maiden name. Which her parents later went on

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record saying is completely false. Totally false.

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Delvey doesn't exist anywhere in the family tree?

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Nope. It was a brand name she invented. And when

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she transfers to Purple's New York office in

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mid 2013, she brings that brand with her. OK,

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so she's in New York now. She's in New York.

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And this is where that outsider status becomes

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her greatest asset. In New York, being a German

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heiress is a very specific, very powerful currency.

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Because nobody can check. Nobody can check. And

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she had this European accent that Americans couldn't

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quite place. It was a mix of Russian, German,

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maybe some affected British vowels she picked

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up. She just sounded. exotic. She sounded like

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old world money. That is such a huge part of

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the con. If she had been a girl from Ohio trying

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to pull this off, nobody buys it for a second.

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Not a chance. But because she's European, Americans

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just assume there's a castle somewhere. We assume

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there's old money with complex structures we

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don't understand. Exactly. It's the unknown known.

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People filled in the blanks of her backstory

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with their own assumptions about European wealth.

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She didn't have to explicitly say, I have a trust

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fund every five minutes. She just had to act

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like someone who did. And she quit her job pretty

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quickly. Oh, yeah. She quit Purple pretty quickly

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once she got to New York. And that's when the

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real work began. She wasn't just trying to be

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a socialite. She wanted to build an empire. Okay,

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let's talk about the Anna Delvey Foundation,

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because this wasn't a lemonade stand. The scale

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of what she was pitching is actually kind of

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impressive, in a delusional way. It was incredibly

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detailed. She wanted to lease the Church Missions

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house. Which is a massive deal. It's a landmark

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building on Park Avenue South, owned by the real

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estate titan Abby Rosen. We were talking six

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floors, 45 ,000 square feet. It's an iconic space.

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And her vision was what exactly? A private members

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club mixed with a visual arts center. So think

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Soho House, but with a much heavier focus on

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high art. She wanted pop -up shops curated by

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the artist Daniel Arsham, exhibitions by Urs

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Fischer, Damien Hirst, Jeff Koons. So all the

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biggest names. All the blue chip artists. And

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she wasn't just daydreaming this in a notebook.

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She was taking meetings. She had a team. She

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enlisted the son of Santiago Calatrava, the famous

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architect. She was talking to Rue Rogers, the

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son of another famous architect, about beverage

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programs. She was putting together a legitimate

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looking business proposal. The vision was actually

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quite coherent then. That's the tragedy of it.

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If she had the money, it probably would have

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been a successful business. It was a good idea.

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But the problem always was the capital. She needed

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roughly $25 million to get this off the ground.

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And to get a loan of that size, you need collateral.

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A lot of it. And her collateral was a complete

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fiction. She claimed she had 60 million euros

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sitting in Swiss bank accounts. But. But, and

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here's the classic excuse, she couldn't access

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it because it was tied up in these complex trust

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structures. It was always just about to be released.

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The trust fund excuse is the grifter's best friend,

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isn't it? Yeah. It's just plausible enough. It

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is. It's plausible enough that wealthy families

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do have complicated trusts, but it's nearly impossible

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to verify without documentation. And this is

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where we get into the nuts and bolts, the mechanics

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of the fraud. How do you prove you have 60 million

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euros when you have zero? You use Microsoft Word.

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You use Microsoft Word. This part kills me. In

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an era of blockchain and encrypted banking and

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all this high tech security, she's sitting there

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with a laptop, literally editing numbers on a

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PDF of a bank statement. It's solo tech. It was,

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but it was effective enough to get her in the

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door. But she knew documents weren't enough.

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She needed a human element to vouch for her.

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So she invented a wealth manager. The legendary

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Peter. The one and only Peter Haneke. She gave

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him a fake email address and a phone number that,

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of course, she controlled. She would use a voice

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disguising app to pretend to be him on the phone.

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I mean, the sheer audacity of that. But here

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is the detail that I find fascinating, and it

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should have been a huge red flag. She used an

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AOL email address for him. An AOL address in

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2016 for a high -powered European wealth manager

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handling 60 million euros. Yes. And that should

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have been a screaming red flag to any banker.

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But again, she banked on the idea that These

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American bankers would just think, oh, maybe

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that's how eccentric old Europeans operate. They're

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old school. It's all social engineering. But

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the cracks did start to show, right? People started

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asking questions. Of course. People started asking

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why Peter was so hard to reach or why his email

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sounded exactly like Anna's speech patterns.

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They were getting suspicious. And her solution

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to this problem is one of my favorite details

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in the whole saga. She didn't just fire him.

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No, no. She killed him off. What? When the questions

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got too hot, she started telling people that

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Peter Heneke had died. It just passed away suddenly.

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You're kidding me. I'm not. And then she immediately

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invented a new persona, Bettina Wagner, to take

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over the account. It's like a soap opera. And

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prosecutors later found her Google search history.

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She was searching for things like, create fake

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untraceable email. That is just. It's improvisation

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at its finest. So, she has the fake documents,

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the dead fake manager, and the new fake manager.

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She takes this whole package to City National

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Bank and asks for a $22 million loan. A huge

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ask. And City National, to their credit, eventually

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balked because they just couldn't verify the

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Swiss assets. They did some digging and it wasn't

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adding up. But she didn't give up. No. She went

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to Fortress Investment Group. Now, Fortress is

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a serious, sharp -elbowed private equity firm.

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These guys are not known for getting played.

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They're the big leaguers. Yeah. But they were

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interested. They were interested enough to enter

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due diligence. The project itself sounded plausible,

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but due diligence costs money. Fortress told

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her, OK, we will. look into this we'll have our

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lawyers review everything but you need to send

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us a hundred thousand dollars to cover our fees

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and background checks a hundred grand yeah which

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she obviously didn't have so we enter this circular

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financial loop that makes my head spin she goes

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back to city national right correct she goes

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back to a contact she'd made at city national

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and somehow manages to charm them into giving

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her a one hundred thousand dollar temporary overdraft

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so basically a short -term loan a short -term

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loan based on the promise that her wire transfer

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from europe is coming any day now it was just

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a paperwork So she gets $100 of real money from

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City National based on a lie. And she immediately

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sends that money. Straight to Fortress. Exactly.

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She uses the proceeds of one attempted fraud

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to finance the application for a bigger fraud.

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It's just incredible. But Fortress actually did

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their job. They did. They started digging. They

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noticed discrepancies in her passport versus

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her stated birthplace. They were asking tough

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questions. And then the kill shot. Fortress said,

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OK, the next step is we need to send a team to

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Switzerland to physically meet your bankers and

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see the assets. And that is the moment the music

00:12:02.840 --> 00:12:05.960
stops because there is no vault. There are no

00:12:05.960 --> 00:12:08.639
bankers. There's no Peter, dead or alive. It's

00:12:08.639 --> 00:12:11.460
all smoke. Anna knew it was over. She panicked.

00:12:11.480 --> 00:12:13.440
She withdrew the loan application halfway through

00:12:13.440 --> 00:12:16.460
the process. Fortress had spent about $45 ,000

00:12:16.460 --> 00:12:18.740
of her deposit on their work, so they wired the

00:12:18.740 --> 00:12:22.279
remaining $55 ,000 back to her. So she is now

00:12:22.279 --> 00:12:25.480
walking around New York with $55 ,000 in cash.

00:12:26.000 --> 00:12:28.879
She still owes City National $100 ,000, so she's

00:12:28.879 --> 00:12:31.659
technically deep in the hole, but she has liquidity

00:12:31.659 --> 00:12:34.259
for the first time. Yep. And what does she do?

00:12:34.340 --> 00:12:36.340
Does she go pay down the debt? Of course not.

00:12:36.440 --> 00:12:38.759
She treats it as revenue. She goes on a spending

00:12:38.759 --> 00:12:41.120
spree. She hires a celebrity personal trainer,

00:12:41.320 --> 00:12:45.500
Casey Duke, who costs a fortune. She gets $800

00:12:45.500 --> 00:12:48.779
hair highlighting. She gets $400 eyelash extensions.

00:12:49.200 --> 00:12:51.519
She was investing in the image of Anna Delvey,

00:12:51.580 --> 00:12:53.600
hoping that if she just looked the part long

00:12:53.600 --> 00:12:55.740
enough, the money would eventually materialize.

00:12:55.799 --> 00:12:57.879
And this brings us to the lifestyle section.

00:12:58.279 --> 00:13:00.899
or what I call the tipping economy, because $55

00:13:00.899 --> 00:13:03.679
,000 burns fast in NYC when you're living at

00:13:03.679 --> 00:13:06.240
a luxury hotel. She checked in to Eleven Howard

00:13:06.240 --> 00:13:09.919
in Soho in February 2017. A very trendy, very

00:13:09.919 --> 00:13:11.840
expensive spot. She booked a room for roughly

00:13:11.840 --> 00:13:15.120
$400 a night, but, and this is a massive failure

00:13:15.120 --> 00:13:17.500
of hotel protocol, she didn't put a credit card

00:13:17.500 --> 00:13:19.860
on file for a long time. Wait, how is that even

00:13:19.860 --> 00:13:21.980
possible? I can't book a Motel 6 without a credit

00:13:21.980 --> 00:13:23.980
card. I know, but she managed to stay there for

00:13:23.980 --> 00:13:27.980
months. How? By weaponizing the $100 bill. This

00:13:27.980 --> 00:13:31.000
is such a specific and brilliant strategy. She

00:13:31.000 --> 00:13:33.100
would just walk around handing out hundreds.

00:13:33.379 --> 00:13:36.679
For everything. If she asked the concierge for

00:13:36.679 --> 00:13:39.360
a restaurant recommendation, here's $100. If

00:13:39.360 --> 00:13:43.580
a bellhop brought up a package, $100. She became

00:13:43.580 --> 00:13:45.460
known as the most generous guest in the hotel.

00:13:45.720 --> 00:13:47.710
So the staff loved her. They loved her money.

00:13:47.850 --> 00:13:49.490
And when you were tipping like that, the staff

00:13:49.490 --> 00:13:51.730
just assumes you're incredibly wealthy. They

00:13:51.730 --> 00:13:53.789
stop asking questions. They don't want to annoy

00:13:53.789 --> 00:13:56.330
the golden goose by asking for something as mundane

00:13:56.330 --> 00:13:59.570
as a credit card imprint. It's a bribe, essentially.

00:13:59.610 --> 00:14:01.750
It's a bribe for goodwill and for them to look

00:14:01.750 --> 00:14:04.190
the other way. But the reports say the staff

00:14:04.190 --> 00:14:06.769
didn't actually like her, did they? No, that's

00:14:06.769 --> 00:14:08.990
the irony. The reports say she was incredibly

00:14:08.990 --> 00:14:12.279
rude, classist, and demanding. She would walk

00:14:12.279 --> 00:14:15.340
around the lobby in just leggings and hotel robes,

00:14:15.340 --> 00:14:17.779
treating the staff like servants. But the money

00:14:17.779 --> 00:14:21.080
kept them quiet. She ate at Le Cucu, the high

00:14:21.080 --> 00:14:23.200
-end French restaurant attached to the hotel,

00:14:23.399 --> 00:14:26.399
constantly. She befriended the chef, Daniel Rose.

00:14:26.659 --> 00:14:29.100
She just billed it all to her room number. But

00:14:29.100 --> 00:14:32.059
eventually, even with all the tipping, the accounting

00:14:32.059 --> 00:14:34.539
department has to wake up. The bill hits $30

00:14:34.539 --> 00:14:38.669
,000. And they realize... There is no card. And

00:14:38.669 --> 00:14:41.009
this leads to one of the most pathetic and hilarious

00:14:41.009 --> 00:14:43.370
moments in the story. The hotel demands payment.

00:14:43.509 --> 00:14:46.590
They are locking her out of her room. Anna, stalling

00:14:46.590 --> 00:14:50.309
for time, sends a case of 1975 Dom Perignon to

00:14:50.309 --> 00:14:53.370
the front desk staff. No. Yes. Like, sorry I

00:14:53.370 --> 00:14:55.730
owe you 30 grand, but, you know, have some vintage

00:14:55.730 --> 00:14:58.090
champagne. It's so childish. It's like giving

00:14:58.090 --> 00:15:00.309
a shiny object to a baby. Here, look at this,

00:15:00.389 --> 00:15:02.600
please. Go away. And the staff couldn't even

00:15:02.600 --> 00:15:04.799
accept it because of hotel policy, so it just

00:15:04.799 --> 00:15:07.779
sat there, this monument to her delusion. Meanwhile,

00:15:07.960 --> 00:15:10.360
she is scrambling. She's scamming her friends

00:15:10.360 --> 00:15:13.220
to float her lifestyle. We have to talk about

00:15:13.220 --> 00:15:15.419
Michael Zufu Huang. Young art collector. Yes.

00:15:15.500 --> 00:15:17.519
He was a student at UPenn at the time, but very

00:15:17.519 --> 00:15:20.019
wealthy and connected in the art world. Anna

00:15:20.019 --> 00:15:22.379
latched onto him. They went to the Venice Biennale

00:15:22.379 --> 00:15:25.379
together in 2015. Anna asked if she could tag

00:15:25.379 --> 00:15:27.460
along, but then asked him to book the flights

00:15:27.460 --> 00:15:29.759
and hotel on his card, promising to pay him back.

00:15:29.960 --> 00:15:32.399
And the phrase pay you back is a concept Anna

00:15:32.399 --> 00:15:35.039
really struggles with. She never did. And this

00:15:35.039 --> 00:15:37.340
highlights a very specific social vulnerability

00:15:37.340 --> 00:15:40.399
of the elite. When you are genuinely rich, talking

00:15:40.399 --> 00:15:42.679
about money is considered tacky. It's gauche.

00:15:42.980 --> 00:15:44.539
Right. You don't want to seem petty. Exactly.

00:15:45.259 --> 00:15:47.639
Michael felt awkward asking her for the $2 ,000

00:15:47.639 --> 00:15:50.440
or $3 ,000 she owed him. He just assumed she

00:15:50.440 --> 00:15:53.039
was good for it and forgot. He didn't realize

00:15:53.039 --> 00:15:55.340
he was being scammed until much later when a

00:15:55.340 --> 00:15:57.700
restaurant called Siddell's contacted him. Oh,

00:15:57.799 --> 00:16:00.080
right, for the birthday party. Yes, she threw

00:16:00.080 --> 00:16:02.799
this lavish birthday party there, hired a PR

00:16:02.799 --> 00:16:06.059
firm, the whole nine yards, and then just didn't

00:16:06.059 --> 00:16:08.860
pay the bill. The restaurant saw Michael in the

00:16:08.860 --> 00:16:11.059
Instagram photos and tracked him down to ask,

00:16:11.220 --> 00:16:13.299
hey, do you know this woman? Do you know how

00:16:13.299 --> 00:16:15.799
we can get paid? That's when the penny dropped

00:16:15.799 --> 00:16:18.779
for him. But she just kept escalating. The Blade

00:16:18.779 --> 00:16:21.279
incident is another classic example of social

00:16:21.279 --> 00:16:24.080
proof overriding basic business sense. This one

00:16:24.080 --> 00:16:26.379
is amazing. She wanted to go to Omaha for the

00:16:26.379 --> 00:16:28.799
Berkshire Hathaway annual meeting to meet Warren

00:16:28.799 --> 00:16:31.639
Buffett. As one does. Just a casual trip to see

00:16:31.639 --> 00:16:33.919
the Oracle of Omaha. So she books a private jet

00:16:33.919 --> 00:16:36.419
through Blade, the helicopter and jet charter

00:16:36.419 --> 00:16:41.029
company. The cost is $35 ,390. And she does her

00:16:41.029 --> 00:16:43.149
usual move. She sends a forged Deutsche Bank

00:16:43.149 --> 00:16:45.490
wire confirmation. Now, Blade has a very clear

00:16:45.490 --> 00:16:49.210
policy. Payment must clear up front. But the

00:16:49.210 --> 00:16:52.190
CEO, Robert Weisenthal, had perhaps seen her

00:16:52.190 --> 00:16:54.029
around at parties or she name dropped enough

00:16:54.029 --> 00:16:56.990
of the right people. They overrode their own

00:16:56.990 --> 00:17:00.009
policy and let her fly before the money cleared.

00:17:00.450 --> 00:17:03.789
They let a $35 ,000 service happen on an IOU.

00:17:04.029 --> 00:17:07.430
That is wild to me. And she flew to Omaha. Claims

00:17:07.430 --> 00:17:09.549
she snuck into a party at the zoo and met Bill

00:17:09.549 --> 00:17:12.329
Gates, which is completely unverified, and then

00:17:12.329 --> 00:17:14.289
came back. Blade, of course, never got the money.

00:17:14.490 --> 00:17:16.990
They eventually had to involve the police. So

00:17:16.990 --> 00:17:19.369
the net is really tightening at this point. Eleven

00:17:19.369 --> 00:17:21.369
Howard has locked her out of her room for good.

00:17:21.470 --> 00:17:24.130
She's bouncing between hotels, the Mercer, the

00:17:24.130 --> 00:17:26.829
Beekman, the W New York, getting evicted from

00:17:26.829 --> 00:17:29.450
each one after a few days of nonpayment. She's

00:17:29.450 --> 00:17:31.670
literally homeless, but homeless in designer

00:17:31.670 --> 00:17:34.230
clothes. And this desperation, this is what leads

00:17:34.230 --> 00:17:37.019
to the climax of the story. The Morocco trip.

00:17:37.059 --> 00:17:39.099
This is where the genre shifts from quirky con

00:17:39.099 --> 00:17:41.720
artists to something much darker, almost a psychological

00:17:41.720 --> 00:17:45.160
thriller. This is May 2017. She needs a break.

00:17:45.480 --> 00:17:48.480
Or, more likely, she needs to flee her problems.

00:17:48.740 --> 00:17:51.720
So she invites Rachel Deloach -Williams, who

00:17:51.720 --> 00:17:54.339
is a photo editor at Vanity Fair. Right. And

00:17:54.339 --> 00:17:56.839
her trainer, Casey Duke, and a videographer to

00:17:56.839 --> 00:17:59.900
Marrakesh, she promises it's an all -expenses

00:17:59.900 --> 00:18:03.079
-paid trip. A creative retreat, she called it.

00:18:03.180 --> 00:18:05.720
And she books La Mamounia. Which is not just

00:18:05.720 --> 00:18:07.440
a nice hotel. It's one of the most expensive,

00:18:07.599 --> 00:18:09.759
opulent hotels on the planet. And they aren't

00:18:09.759 --> 00:18:12.460
just in a room. They are in a private riad, a

00:18:12.460 --> 00:18:15.099
whole villa with its own pool and a dedicated

00:18:15.099 --> 00:18:19.279
baller. The cost is $7 ,000 a night. I can feel

00:18:19.279 --> 00:18:21.680
the anxiety just thinking about this. They arrive.

00:18:21.960 --> 00:18:24.359
They are living the dream, eating amazing food,

00:18:24.440 --> 00:18:27.579
getting massages. And then the hotel manager

00:18:27.579 --> 00:18:29.640
knocks on the door. The credit card machine.

00:18:29.740 --> 00:18:32.299
The ultimate villain in Anna's life story. Her

00:18:32.299 --> 00:18:34.509
guards aren't working. Nope. She blames the bank.

00:18:34.690 --> 00:18:37.910
She blames the time zone. She blames typos. But

00:18:37.910 --> 00:18:40.769
days go by. The bill is ballooning. The hotel

00:18:40.769 --> 00:18:43.069
staff stops being polite. They start standing

00:18:43.069 --> 00:18:45.670
over them at dinner. They send two large men

00:18:45.670 --> 00:18:47.549
to their villa and they start threatening to

00:18:47.549 --> 00:18:50.170
call the police. And in Morocco, you can go to

00:18:50.170 --> 00:18:52.569
jail for unpaid debts. This isn't like the U

00:18:52.569 --> 00:18:54.869
.S. The threat of a Moroccan prison is very,

00:18:55.009 --> 00:18:57.930
very real. And Anna is just sitting there seemingly

00:18:57.930 --> 00:19:01.589
unbothered while Rachel is basically hyperventilating.

00:19:01.589 --> 00:19:03.549
That's the trap. That's how she gets her. That

00:19:03.549 --> 00:19:06.430
is the trap. Anna turns to Rachel and says, just

00:19:06.430 --> 00:19:08.490
put your card down for the hold. It's just a

00:19:08.490 --> 00:19:11.170
hold. I'll wire you the money as soon as we get

00:19:11.170 --> 00:19:14.289
back to New York. It's just a hold. The famous

00:19:14.289 --> 00:19:18.230
last words of so many scams. And Rachel, under

00:19:18.230 --> 00:19:20.509
extreme duress and wanting to avoid going to

00:19:20.509 --> 00:19:23.009
jail, hands over her personal American Express

00:19:23.009 --> 00:19:26.269
and her corporate vanity fare card. The hotel

00:19:26.269 --> 00:19:29.450
doesn't just put a hold. They charge it. All

00:19:29.450 --> 00:19:32.589
of it. How much was it? $62 ,000. Oh, my God.

00:19:32.710 --> 00:19:34.869
That is more than Rachel earned in a year. That

00:19:34.869 --> 00:19:36.970
is a life -ruining amount of debt for a normal

00:19:36.970 --> 00:19:39.750
person. It absolutely destroyed her financial

00:19:39.750 --> 00:19:41.950
stability. And the betrayal is the worst part.

00:19:42.210 --> 00:19:44.309
They get back to New York, and Anna gives her

00:19:44.309 --> 00:19:48.529
the runaround for weeks. She wires $5 ,000 here,

00:19:48.789 --> 00:19:51.670
promises a check is in the mail there. Rachel

00:19:51.670 --> 00:19:53.829
has to borrow money from her parents to pay her

00:19:53.829 --> 00:19:57.130
rent. She is having panic attacks. This is what

00:19:57.130 --> 00:19:59.430
finally pushed Rachel to go to the police and

00:19:59.430 --> 00:20:01.789
help set up the sting operation. We'll get to

00:20:01.789 --> 00:20:03.349
the sting in a second, but I want to pause on

00:20:03.349 --> 00:20:06.529
the check kiting aspect. Because while she was

00:20:06.529 --> 00:20:09.069
destroying Rachel's life, she was also committing

00:20:09.069 --> 00:20:12.750
serious federal bank fraud just to stay afloat

00:20:12.750 --> 00:20:15.740
back in NYC. Right. This was her last ditch effort

00:20:15.740 --> 00:20:18.779
for cash. She started depositing bad checks into

00:20:18.779 --> 00:20:21.819
a Citibank account. She would write a check for,

00:20:21.859 --> 00:20:24.420
say, $50 ,000 from an account that had zero money

00:20:24.420 --> 00:20:26.839
in it and deposit it. OK. Now, banks have this

00:20:26.839 --> 00:20:29.039
policy where they usually make a portion of those

00:20:29.039 --> 00:20:31.160
funds available immediately before the check

00:20:31.160 --> 00:20:33.619
actually clears. It's called the float. So she

00:20:33.619 --> 00:20:35.700
deposits the bad check. The bank says, here is

00:20:35.700 --> 00:20:38.000
$10 ,000 of it while we wait for the rest to

00:20:38.000 --> 00:20:40.380
clear. And she just withdraws that cash immediately.

00:20:40.779 --> 00:20:55.500
Exactly. And then she runs. So by October 2017,

00:20:55.740 --> 00:20:58.279
everyone is looking for her. The hotels, the

00:20:58.279 --> 00:21:02.680
banks, Blade, and now Rachel and the NYPD. And

00:21:02.680 --> 00:21:05.740
where is Anna? She is in California at Passages

00:21:05.740 --> 00:21:09.019
Malibu. A luxury rehab center. Of course she

00:21:09.019 --> 00:21:11.019
is. It's the perfect hiding spot. And that's

00:21:11.019 --> 00:21:13.099
where the trap is set. Rachel Williams, working

00:21:13.099 --> 00:21:15.299
with the NYPD and Officer Michael McCaffrey,

00:21:15.359 --> 00:21:17.740
arranges a lunch date. She tells Anna she's in

00:21:17.740 --> 00:21:19.779
the area for work and wants to catch up. A total

00:21:19.779 --> 00:21:22.599
sting. A total sting. Anna walks out of the facility

00:21:22.599 --> 00:21:24.700
to meet her for lunch at a restaurant, and the

00:21:24.700 --> 00:21:26.960
LAPD is waiting in the parking lot to arrest

00:21:26.960 --> 00:21:31.440
her. And so begins the legal saga. The trial.

00:21:32.009 --> 00:21:34.329
This was a circus. It was 201s. The media was

00:21:34.329 --> 00:21:36.690
obsessed. But Anna seemed to treat the courtroom

00:21:36.690 --> 00:21:39.630
less like a legal proceeding and more like a

00:21:39.630 --> 00:21:42.009
runway. It was the trial of the century for the

00:21:42.009 --> 00:21:44.609
Instagram generation. Her defense attorney, Todd

00:21:44.609 --> 00:21:46.710
Spodek, actually hired a professional stylist

00:21:46.710 --> 00:21:49.029
to dress her for court. Wait, I need to emphasize

00:21:49.029 --> 00:21:52.710
this. A stylist for a defendant facing up to

00:21:52.710 --> 00:21:56.230
15 years in prison. Yes. And the logic, Spodek

00:21:56.230 --> 00:21:59.309
argued, was if she looks like a criminal in a

00:21:59.309 --> 00:22:02.319
jail jumpsuit. the jury will convict her. But

00:22:02.319 --> 00:22:04.339
if she looks like a misunderstood businesswoman

00:22:04.339 --> 00:22:06.599
in Saint Laurent and Victoria Beckham, maybe

00:22:06.599 --> 00:22:08.880
they won't. So it was all about perception, even

00:22:08.880 --> 00:22:10.940
in court. It was all perception. She wore Michael

00:22:10.940 --> 00:22:13.859
Kors. She wore high -end designer clothes. There

00:22:13.859 --> 00:22:15.819
was one day where she refused to come into the

00:22:15.819 --> 00:22:17.259
courtroom because she didn't like her outfit.

00:22:17.460 --> 00:22:19.960
She threw a tantrum and delayed the proceedings

00:22:19.960 --> 00:22:23.779
for hours. The judge was furious. But the defense

00:22:23.779 --> 00:22:26.559
strategy wasn't just about clothes. It was about

00:22:26.559 --> 00:22:29.220
the narrative. Spodek argued that she wasn't

00:22:29.220 --> 00:22:32.480
a criminal. She was just ambitious. He literally

00:22:32.480 --> 00:22:34.980
called it the Sinatra defense. He quoted New

00:22:34.980 --> 00:22:37.259
York, New York to the jury. He said, if I can

00:22:37.259 --> 00:22:39.720
make it there, I'll make it anywhere. He argued

00:22:39.720 --> 00:22:41.559
that Anna was just digging a hole to build a

00:22:41.559 --> 00:22:44.079
foundation. He claimed she always intended to

00:22:44.079 --> 00:22:46.480
pay everyone back once her business launched.

00:22:46.720 --> 00:22:49.140
He tried to reframe the entire fraud as just

00:22:49.140 --> 00:22:51.640
fake it till you make it gone wrong. Exactly.

00:22:51.680 --> 00:22:54.140
And here is the nuance that I think gets lost

00:22:54.140 --> 00:22:56.890
in all the headlines. The jury. They actually

00:22:56.890 --> 00:22:59.170
bought some of it. They did, didn't they? They

00:22:59.170 --> 00:23:01.890
did. In April 2019, they convicted her on eight

00:23:01.890 --> 00:23:04.089
counts, including grand larceny and theft of

00:23:04.089 --> 00:23:07.289
services. But, and this is huge, they acquitted

00:23:07.289 --> 00:23:10.230
her on the attempted $22 million loan from City

00:23:10.230 --> 00:23:12.829
National. Why? Their reasoning was basically,

00:23:13.029 --> 00:23:15.250
well, the bank didn't actually give her the money,

00:23:15.309 --> 00:23:17.230
so no harm, no foul. And the Rachel Williams

00:23:17.230 --> 00:23:21.740
charge, the $62 ,000? Acquitted. not guilty that

00:23:21.740 --> 00:23:24.799
is shocking to me how did they justify that because

00:23:24.799 --> 00:23:27.880
the jury viewed it as a civil dispute not a criminal

00:23:27.880 --> 00:23:31.119
theft they reasoned that rachel willingly handed

00:23:31.119 --> 00:23:34.240
over her card she took a risk on a friend who

00:23:34.240 --> 00:23:36.609
turned out to be a liar It was a bad debt, yes,

00:23:36.750 --> 00:23:38.890
but not larceny in the eyes of the law. That

00:23:38.890 --> 00:23:40.670
must have been a bitter pill for Rachel to swallow.

00:23:40.849 --> 00:23:43.349
Oh, absolutely. So Anna is sentenced to four

00:23:43.349 --> 00:23:46.650
to 12 years. She owes $199 ,000 in restitution

00:23:46.650 --> 00:23:50.170
and a $24 ,000 fine. And before she heads to

00:23:50.170 --> 00:23:52.250
prison, she gives that infamous interview to

00:23:52.250 --> 00:23:54.269
the New York Times where she says, I'd be lying

00:23:54.269 --> 00:23:56.289
to you and to everyone else and to myself if

00:23:56.289 --> 00:23:58.569
I said I was sorry for anything. Zero remorse.

00:23:58.769 --> 00:24:01.349
None. She regretted the mistakes that got her

00:24:01.349 --> 00:24:05.029
caught, but she didn't regret the ambition. She

00:24:05.029 --> 00:24:06.930
saw herself as a businesswoman whose venture

00:24:06.930 --> 00:24:09.829
failed, not a criminal who stole. So she goes

00:24:09.829 --> 00:24:12.829
to prison. But in 2026, we know that prison was

00:24:12.829 --> 00:24:16.390
just a temporary setback. This brings us to monetizing

00:24:16.390 --> 00:24:18.569
the infamy, because while she was sitting in

00:24:18.569 --> 00:24:21.170
a cell at Albion Correctional Facility, Netflix

00:24:21.170 --> 00:24:24.329
was writing a check. A very big check. Netflix

00:24:24.329 --> 00:24:27.410
paid $320 ,000 for the rights to her life story,

00:24:27.650 --> 00:24:30.309
which became the Shonda Rhimes series Inventing

00:24:30.309 --> 00:24:32.869
Anna. Now, normally, criminals can't profit from

00:24:32.869 --> 00:24:35.549
their crimes. There's the Son of Sam law. So

00:24:35.549 --> 00:24:37.910
how did this transaction work? Well, the New

00:24:37.910 --> 00:24:39.990
York attorney general froze the funds immediately,

00:24:40.289 --> 00:24:42.710
exactly because of that law. However, the law

00:24:42.710 --> 00:24:44.869
allows the funds to be used to pay restitution

00:24:44.869 --> 00:24:48.339
to victims. Oh, OK. So most of that Netflix money

00:24:48.339 --> 00:24:50.200
went directly to the bank she stole from and

00:24:50.200 --> 00:24:52.819
to pay her court fines. Anna didn't get a briefcase

00:24:52.819 --> 00:24:55.099
of cash. She got her debts paid off by Shonda

00:24:55.099 --> 00:24:57.900
Rhimes. She ended up keeping only about $22 ,000

00:24:57.900 --> 00:25:00.700
of it for herself. Still, it cleared her ledger.

00:25:00.900 --> 00:25:03.319
And meanwhile, Rachel Williams wrote her own

00:25:03.319 --> 00:25:05.940
book, My Friend Anna. Which sold very well. Rachel

00:25:05.940 --> 00:25:09.559
made about $300 ,000 plus a TV option deal with

00:25:09.559 --> 00:25:12.579
Lena Dunham. And this sparked a massive public

00:25:12.579 --> 00:25:15.950
feud. Anna was furious that Rachel was profiting

00:25:15.950 --> 00:25:18.529
from the trauma while Anna felt she was the creator

00:25:18.529 --> 00:25:21.029
of the story. It's a total narrative war. But

00:25:21.029 --> 00:25:23.950
let's fast forward to her release. She gets paroled

00:25:23.950 --> 00:25:27.549
in February 2021 for good behavior. She's out.

00:25:27.609 --> 00:25:29.970
She immediately checks into the Nomad Hotel,

00:25:30.269 --> 00:25:33.390
again with the hotels. And she has a German camera

00:25:33.390 --> 00:25:35.789
crew following her for a reality show. She was

00:25:35.789 --> 00:25:38.069
ready for her close -up, but she forgot about

00:25:38.069 --> 00:25:40.380
the federal government. Six weeks later, ICE

00:25:40.380 --> 00:25:42.339
Immigration and Customs Enforcement arrested

00:25:42.339 --> 00:25:45.119
her. For the visa. For the visa overstay. She's

00:25:45.119 --> 00:25:47.539
a German citizen with a felony record. Technically,

00:25:47.539 --> 00:25:49.539
she should have been immediately deported. So

00:25:49.539 --> 00:25:51.480
she goes back into custody, this time in ICE

00:25:51.480 --> 00:25:54.160
detention. And she fights deportation for 19

00:25:54.160 --> 00:25:58.480
months. Finally, in October 2022, a judge grants

00:25:58.480 --> 00:26:00.700
a release on house arrest. But strict house arrest.

00:26:00.839 --> 00:26:05.000
A $10 ,000 bond. She's confined to a tiny 470

00:26:05.000 --> 00:26:07.559
square foot apartment in the East Village. She

00:26:07.559 --> 00:26:10.220
has to wear an ankle monitor 24 -7. And initially

00:26:10.220 --> 00:26:12.740
she was banned from all social media. Which for

00:26:12.740 --> 00:26:15.319
her is worse than prison. It is oxygen for her.

00:26:15.400 --> 00:26:17.039
But she eventually got those privileges back.

00:26:17.220 --> 00:26:19.519
And this brings us to the final chapter. The

00:26:19.519 --> 00:26:24.859
pivot. From 2022 to today, 2026, she has turned

00:26:24.859 --> 00:26:27.900
that East Village apartment into a content factory.

00:26:28.180 --> 00:26:30.400
Let's talk about the art, because I use heavy

00:26:30.400 --> 00:26:32.859
air quotes here. She started selling drawings

00:26:32.859 --> 00:26:36.400
she made in jail. Art is subjective, right? In

00:26:36.400 --> 00:26:39.680
March 2022, while still in detention, she had

00:26:39.680 --> 00:26:42.970
a pop -up show called Free Anna Delvey. It was

00:26:42.970 --> 00:26:45.250
co -curated by a man named Alfredo Martinez.

00:26:45.650 --> 00:26:47.309
Now, do you know who Alfredo Martinez is? The

00:26:47.309 --> 00:26:49.849
name sounds familiar. He is a convicted art forger.

00:26:49.990 --> 00:26:52.609
He went to prison for forging Jean -Michel Basquiat

00:26:52.609 --> 00:26:54.809
paintings. No way you can't make this up. You

00:26:54.809 --> 00:26:57.250
can't. It's scammers supporting scammers. Then

00:26:57.250 --> 00:27:00.509
she had a solo show called Allegedly in May 2022.

00:27:01.289 --> 00:27:03.470
Models walked around a nightclub with stockings

00:27:03.470 --> 00:27:05.150
over their heads, holding her pencil sketches.

00:27:05.509 --> 00:27:07.849
It's pure performance art. It's trolling. It

00:27:07.849 --> 00:27:11.240
is. But people bought it. By the end of 2022,

00:27:11.579 --> 00:27:15.279
she claimed to have sold $340 ,000 worth of sketches.

00:27:15.740 --> 00:27:17.700
Original drawings were going for $10 ,000 to

00:27:17.700 --> 00:27:20.940
$25 ,000. She used this money to pay her rent,

00:27:21.039 --> 00:27:23.359
which was over $4 ,000 a month, and her legal

00:27:23.359 --> 00:27:26.599
fees. She even launched an NFT collection because,

00:27:26.720 --> 00:27:30.519
well, it was 2022. But the peak of this absurdity

00:27:30.519 --> 00:27:33.480
has to be her mainstream media appearances. Dancing

00:27:33.480 --> 00:27:37.960
with the Stars. Season 33. September 2024. I

00:27:37.960 --> 00:27:39.839
still can't believe this happened. She was cast

00:27:39.839 --> 00:27:43.119
on a family dance competition show. And she danced

00:27:43.119 --> 00:27:46.460
wearing her icy ankle monitor. She had it bedaddled.

00:27:46.480 --> 00:27:49.119
It was part of the costume. That image. Seeing

00:27:49.119 --> 00:27:51.019
her do the cha -cha with a government tracking

00:27:51.019 --> 00:27:53.400
device on her leg. It feels like a Black Mirror

00:27:53.400 --> 00:27:55.579
episode. It's the ultimate symbol of her brand,

00:27:55.720 --> 00:27:57.759
isn't it? She isn't hiding the criminality. She

00:27:57.759 --> 00:27:59.980
is accessorizing it. She was eliminated first,

00:28:00.079 --> 00:28:01.799
by the way. Thank goodness. But she kept going.

00:28:01.900 --> 00:28:04.119
Fashion Week. She hosted a show on a roof because

00:28:04.119 --> 00:28:06.240
she couldn't leave the building. Yep. September

00:28:06.240 --> 00:28:09.680
2023, she teamed up with Kelly Catrone, the famous

00:28:09.680 --> 00:28:12.359
PR maven. Models were stomping around the roof

00:28:12.359 --> 00:28:14.920
of a walk -up in the East Village. Then, as her

00:28:14.920 --> 00:28:16.940
restrictions eased a bit, she started modeling

00:28:16.940 --> 00:28:19.859
herself. She walked for SHAO New York in 2024.

00:28:20.380 --> 00:28:23.480
In February 2025, she modeled for Elena Velez,

00:28:23.680 --> 00:28:26.240
again highlighting the ankle monitor. And now,

00:28:26.400 --> 00:28:29.660
in 2026, where is she? She moved out of the city

00:28:29.660 --> 00:28:32.440
in early 2024. She's living up in the Hudson

00:28:32.440 --> 00:28:34.920
Valley now, still fighting the deportation case,

00:28:35.059 --> 00:28:37.720
still creating content. She's seemingly pivoted

00:28:37.720 --> 00:28:40.980
from scammer to just fixture. She's just around.

00:28:41.240 --> 00:28:43.099
So let's wrap this up with a big question. We've

00:28:43.099 --> 00:28:45.480
looked at the scam, the trial, the prison time

00:28:45.480 --> 00:28:48.779
and the bizarre aftermath. Did she win? It's

00:28:48.779 --> 00:28:50.380
the uncomfortable question we have to answer,

00:28:50.440 --> 00:28:53.029
isn't it? If you define winning as getting the

00:28:53.029 --> 00:28:55.869
$60 million foundation, no. She failed miserably.

00:28:55.930 --> 00:28:58.029
She has a felony record. She faces deportation.

00:28:58.049 --> 00:28:59.809
She is under surveillance. But if you define

00:28:59.809 --> 00:29:02.569
winning as fame, as relevance, as staying in

00:29:02.569 --> 00:29:05.650
the conversation. Then she won, hands down. She

00:29:05.650 --> 00:29:08.349
hacked the attention economy. She proved that

00:29:08.349 --> 00:29:11.210
in modern America, infamy is just as spendable

00:29:11.210 --> 00:29:14.569
as currency. If you are famous enough, someone

00:29:14.569 --> 00:29:17.470
will always give you a platform, a check, a reality

00:29:17.470 --> 00:29:19.569
show. And I think there's a deeper point here

00:29:19.569 --> 00:29:22.410
about the people she scammed. Yeah. Why do we

00:29:22.410 --> 00:29:26.329
as a culture love this story so much? I think

00:29:26.329 --> 00:29:29.309
part of it is that she exposed the elite. That's

00:29:29.309 --> 00:29:31.940
the critical sociological take. She stress tested

00:29:31.940 --> 00:29:35.140
the system. She proved that high society isn't

00:29:35.140 --> 00:29:37.880
a meritocracy. It's a vibe. It's all transactional.

00:29:37.920 --> 00:29:40.099
Right. She proved that a hundred dollar tip matters

00:29:40.099 --> 00:29:42.180
more to a concierge than a background check.

00:29:42.480 --> 00:29:45.059
She proved that powerful bankers can be dazzled

00:29:45.059 --> 00:29:47.799
by a fake accent and a good suit. She embarrassed

00:29:47.799 --> 00:29:49.660
them because she showed everyone that the exclusive

00:29:49.660 --> 00:29:52.319
world is actually very cheap to buy into if you

00:29:52.319 --> 00:29:54.140
just have the confidence. She held up a mirror

00:29:54.140 --> 00:29:57.039
and they did not like what they saw. She was

00:29:57.039 --> 00:29:59.240
a fraud, yes. But she revealed that they were

00:29:59.240 --> 00:30:01.339
also faking it in their own way, playing by these

00:30:01.339 --> 00:30:03.400
unwritten rules that she just mastered. Exactly.

00:30:03.400 --> 00:30:05.420
And that's why we are still talking about her

00:30:05.420 --> 00:30:08.579
in 2026. She is the ultimate trickster figure

00:30:08.579 --> 00:30:11.819
for late stage capitalism. Well, on that cheery

00:30:11.819 --> 00:30:14.599
note, we will wrap up this Deep Dice. From the

00:30:14.599 --> 00:30:16.680
truck stops of Russia to the runways of New York,

00:30:16.819 --> 00:30:19.940
it has been a wild ride. It certainly has. To

00:30:19.940 --> 00:30:22.569
our listener, the learner. Thank you for sticking

00:30:22.569 --> 00:30:24.750
with us through the weeds of wire transfers and

00:30:24.750 --> 00:30:27.210
court filings. We hope this gave you a clearer

00:30:27.210 --> 00:30:30.309
picture of not just what happened, but how it

00:30:30.309 --> 00:30:32.410
all happened. Always a pleasure to connect the

00:30:32.410 --> 00:30:35.509
dots. I want to leave you with one final thought

00:30:35.509 --> 00:30:39.210
to chew on. We spend a lot of time judging Anna's

00:30:39.210 --> 00:30:42.569
victims, the bankers, the hotels, her friends.

00:30:42.970 --> 00:30:45.009
We think to ourselves, I would never fall for

00:30:45.009 --> 00:30:48.160
that. But ask yourself this. In your own life,

00:30:48.299 --> 00:30:50.859
how many times have you assumed someone was competent

00:30:50.859 --> 00:30:53.680
or wealthy or trustworthy just because they dressed

00:30:53.680 --> 00:30:56.559
the right way or knew the right people? What

00:30:56.559 --> 00:30:59.019
would it take for an Anna Delvey to slip past

00:30:59.019 --> 00:31:01.559
your defenses? That is a scary thought to end

00:31:01.559 --> 00:31:04.539
on. Stay skeptical, stay curious, and we will

00:31:04.539 --> 00:31:05.880
catch you on the next deep dive.
