This story was originally written in October 2022 as Anna Delvey born Anna Sorokin, otherwise known as the socialite swindler served an undetermined jail sentence in ICE (Immigration and Customs Enforcement). News has surfaced that a US immigration judge agreed to Anna's transfer from jail detention to home confinement while she fights deportation. In exchange for her ‘freedom’, Anna was required to post a $10,000 (£8,900) bail bond, provide a residential address where she will stay for the duration of her immigration case, and refrain from posting on social media. We look back at her time in jail and how she wanted to answer for her crimes in the depth of her legal troubles.
“Oh my God, I love your hair,” says Anna Delvey as she appears on the other end of my video call app, directly from Orange County Jail where she is currently serving an undetermined length sentence for overstaying her visa. Not the introduction I was expecting from one of the US’s most infamous ex-cons, but then, as I’m to discover in the next two hours, she is full of surprises. She speaks to me in her Valley Girl accent, with a smattering of German and Russian thrown in there, although not as jerky as Julia Garner’s interpretation on the hit Netflix series, Inventing Anna — Netflix’s second most watched show in 2022 (only toppled by Stranger Things). — Wearing a white-T and those infamous wide-framed glasses, she adjusts the iPad camera and tussles with her own long, wavy, middle-parted hair… “Is my hair okay?”
The world knows Anna Delvey (born Anna Sorokin), 31, as a con artist, fraudster, faux-billionairess, and perhaps even as the notorious socialite-swindler who climbed her way up the New York elite scene by lying about the size of her pockets. Does she think this assessment is a fair one and I wonder if she’s at all remorseful? The answer is a flat out: “No”. “I didn't scam any of my peers out of any money, “ she insists. “All my crimes were against financial institutions.’’
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Whichever way you look at it, Anna’s story has a chokehold on us all. New York Magazine journalist, Jessica Pressler’s famous profile of her for The Cut back in 2018 soon captured the attention of Grey’s Anatomy creator Shonda Rhymes, which – in turn – led to — Inventing Anna: the nine-part Netflix series that racked up 4.5 billion minutes of watch time within the first two weeks of its release in February.
Having been convicted for grand larceny in 2019 and serving four out of a potential 12 years in Rikers Island prison, Anna was released on parole early for good behaviour in February 2021. Before too long, she found herself back behind bars, which is where I find her now. After hours of battling my way through the temperamental county jail video call system (ironically named Getting Out App), I finally sit down with Anna.
Anna confesses that although she was consulted for the record-breaking Netflix series in return for $320,000 (mostly used on restitutions and legal fees) and an opportunity to tell her side of the story, she is yet to watch the series fully. “I don't really have Netflix [in jail],” she explains. “So these video calls would be the only way for me to watch and I watched maybe half an hour of it. I mean, I know the story, so…”
Did all of those shocking things actually happen?
Back to the big question: Who is Anna Delvey? She struggles to answer. “That’s a loaded question,” she replies. “I guess we’re still in the process of trying to figure it out.”
One thing I do quickly learn about her is that her work ethic is unmatched. Beyoncé and Kris Jenner must be shaking at the thought of someone matching their energy. Anna explains that working is one of her coping mechanisms for dealing with stress: “ I think the worst is, when I got arrested, you don't have a phone and you don't know anything, and you can't do anything about it, that was actually the worst for me. Just the inability to act. Mentally that's the hardest, but just being under stress or pressure, in a way it's motivational. I think I perform pretty well under stress. I guess, better than other people I'd say, from my experience.”
Considering how anxiety-inducing it was to watch Inventing Anna as a viewer, I ask how she coped during the height of her escapades. She doubles down on the work-over-stress mentality, explaining, “When all of those things were happening, I was always working towards fixing it. So I was never just sitting and waiting on what was going to happen next. I mean, it was stressful, but I kept busy trying to fix it.”
Her inspiration? Anna Wintour. Much like her namesake, Delvey has always desired to make it big in the fashion magazine world, and growing up, she admired Anna Wintour’s work ethic: “Just her sense of style and everything that she does. I really admired her aesthetic and her work ethic.” — Of which she attempts to channel while in prison: “I [still] work non-stop. [Here] I don't really have weekends or holidays. I have like a messaging app. I have a phone, so I'm always constantly working on something.”
Anna is reluctant to talk about life before New York, but she confirms that – contrary to some reports – her parents haven’t disowned her. “I still talk to my parents like every week, so I feel like whatever's been portrayed in the series, or wherever it’s been reported, it’s dramatised.”
Anna and ambition go hand in hand, so I had to ask her if there is a line she wouldn’t cross to get exactly what she wanted. “Well, murder...” she says in jest, as I sigh in relief. She then elaborates: “Well, there are a lot of lines I would not cross, but back then, I grew up with this ‘fake till you make it’, that the whole culture was really big on at the time, [this is] in the early tens, 2000s. So, it's way different now. There’s a big cultural shift around this whole kind of mentality. So for me, now, it’s too far when it's illegal.”
She candidly shares with me how she only learned about empathy later on in life. “I think I cared about people even along the way, even with everything that happened, five plus years ago, so I wouldn't say I was completely devoid of any empathy.” although she adds: “I think [people] are just born with certain traits of personality and I think some people are just different.”
Anna’s experiences in jail taught her a lot about caring for others. “I learned a lot about empathy and just being considerate of other people, (definitely more than, when I was younger anyway), from being in jail and just being around so many women who are in a way worse position than me.”
The scrutiny that Anna got by putting her desire for fame and fortune above others, led many to believe it could have only stemmed from pure narcissism. To that, she says: “I think a lot of entrepreneurs are just selfish by nature. It's like, you have to be selfish to a certain degree, and I won't deny that. You have to keep your eye on the prize. Just being able to do anything, whatever gets the job done. It’s certainly not the prettiest aspect of it, but it's just the reality.”
Where IS she?!
Anna’s ultimate goal was never to be a celebrity, but that doesn’t mean she hasn’t enjoyed her newfound fame. She shares with me how her celebrity status impacts her time in prison, saying, “Everybody here knows who I am. Definitely. Somebody sent me an Inventing Anna calendar to sign, which is a selection of photos from the show, and I was signing books for people’s mothers, for their kids… It's pretty cute. I mean, nobody's hating on me. Not to my face at least.” She laughs, and her laugh is contagious.
She reassures me that the intention behind her journey was never to acquire fame and she could never have predicted her story to get so much traction. However, the hype would simply be a gentle bonus.
“Power, money, fame, in that order,” she tells me without hesitation as I ask her to rank those three words in order of importance.
Although Anna appears to not care too much about people’s opinions of her, it’s clear that – deep down, perhaps – she does: “It's really hard to distinguish between my own perception of myself and what the public thinks of me, but I'm the one who has to live with myself. And I know what my intentions were, and none of them was to defraud anybody. So I did make some mistakes, but in the end, I'm trying to fix them. So I knew it was not completely and deliberately bad. I was not really trying to harm anybody.”
Anna strongly believes that scammers are only labeled scammers if they fail, but she was willing to succeed by any means necessary. Her egotism is apparent, and her desperation to be someone seeps through our poorly connected video call, but she’s likable and her palpable gumption can not be undermined. After all, she picked her victims well.
Determined to defend herself, she reminded me how her crimes were committed against institutions and not real people. To which I ask, “Are institutions not made up of real people?” Her response? “Well, it's totally different. Who suffered from my crimes really?” she then adds: “I mean, institutions are made of people, but it's not equal to defrauding a person.”
“Secondly, I was never trying to scam them. I always had a plan and my goal was never to permanently deprive anybody of their funds; I was going to return it. I just chose an unorthodox way to go about it.”
Anna explains that she was heavily influenced by the whole tech industry. In fact, her story is not unique, and many people around her were busy doing the same. Think Billy McFarland, the founder of the notorious Fyre Festival saga, whom she was well-acquainted with (pre-conviction). Or WeWork’s Adam and Rebekah Neumann, or even Elizabeth Holmes’ Theranos scandal in Silicon Valley — whose story led Amanda Seyfried to win an Emmy Award for Outstanding Lead Actress this year for her portrayal of Elizabeth in the limited series The Dropout streaming on Disney Plus. The business industry was rotten bottom-up with “bullshitters” who faked their way to the top without getting caught.
“All these famous venture capitalists and the CEOs, they all committed some kind of ‘little fraud’. If they were to get accused of any crimes down the line, that would be the same thing that would be used against them; used as proof of bad character. But if they succeed in the end, it doesn’t seem like something negative. It's actually being lauded and admired.”
Were there elements of naivety and delusion at play? “I knew it was ethically questionable, but I did not see myself as a criminal. It's definitely not the same as robbing a bank or just stealing from somebody.” When I ask her about male privilege, however, she responds without hesitation: “I feel that my being a woman played a big role in the outcome of my situation. I feel like women are not expected to be cunning or ambitious, and that is almost a dirty word when applied to a female. I mean, a lot has changed over past decades, but we are still dealing with this stigma.”
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I question whether her privilege as a white, cis-gendered woman would have played a role in how far it got her though, to which she candidly agrees. “Of course, yes. I mean, it definitely helped a lot that I'm white, and I definitely acknowledge the fact that had I been anything different, it probably would not have been as easy for me. I guess that everything we do in our life is built on our past experiences. From my experience, being in the world as a white woman definitely gave me the confidence to think I would be successful in [pushing boundaries].”
According to Anna, the trick was to not look overdressed. “If somebody just shows up and they're completely overdressed, it's like a sign that they're really invested in it,” she explains. “In clothing, it was a lot about the power dynamics. It was about showing up like you couldn't really care less about the meeting. Ultimately, none of these meetings were like my only chance to get the money anyway.”
Anna studied people to the nth degree. “I do research for everything,” she notes. “I always do my homework. I have internet now, so that hasn’t stopped.” What was impressive about her, I note, is that she always knew the endless possibilities of her power and used it to her advantage. As I ask her if she thinks she’s smarter than all the people she bamboozled from big corporations with degrees and big accolades, she snickers and tells me with a smirk, “I don’t know, maybe in some ways. I think there are different ways in which a person can be smart, so it's hard to compare myself to people.”
I couldn’t help but circle back to the fact that she chose this life in ICE detention over going off and seeking a peaceful life back home in Germany, to which she responds, “I don't think I'm interested in a peaceful life.”
Anna has cultivated strong relationships with her fellow inmates. They share beauty tips and she tells me very excitedly that the best beauty hack she learned from her prison-mates was doing her baby hairs. “We have those very small toothbrushes, so they do it with a toothbrush and with soap. I love it.” As for her other beauty must-haves, she tells me she’s more of a skincare babe and uses a lot of cocoa butter and hyaluronic acid for hydration. “I also stay out of the sun, it gives you wrinkles, and I don't drink or smoke, obviously. So that helps a lot.”
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As for friends outside of jail, Anna is not deprived of them either. In fact, Julia Fox — the 31-year-old actor who shot to fame for her brief romance with Kanye West earlier this year — was very outspoken about their friendship before Anna went to jail and they’ve remained friends since. “I text Julia. I have like this texting app which you know everything about. I have some other people on there.” She tells me she has a few other very-well-known celebrity friends who have reached out to her since her conviction via DMs, but then coyly shares with me that she wouldn’t want to put them on blast.
I ask Anna how she’d like to be remembered, and she shares with me candidly, “Hopefully, I will move on from the whole criminal story and will be able to show the world that there is more to me. I had an idea ,and I was working hard to try to make it happen. Unfortunately, I chose unconventional ways to go about it. Hopefully, I will correct the narrative and use my platform to do something good.”
I ask about her ambitions to have kids and build a family of her own, and she’s sheepish as if this is something that ever really occurred to her. “Um, maybe sometime in the future. I mean, it's really hard to think about that while being in jail. So I try to focus on things that I can control.”
From shows like Bad Vegan and the Tinder Swindler to podcasts like Sweet Bobby, we seem irresistibly drawn to tales of duplicity and deceit. But what’s the allure?
As Anna prepares for – what she believes is – an imminent release (she tells me her lawyers are positive and working hard to beat her immigration case), I can’t help but wonder where this path to redemption will take her. What I do know is that she’s a dreamer, and ultimately dreaming is not a crime.
“I feel like young people should be given a little bit more grace because I definitely would not have made the same choices I made when I was in my early to mid-twenties, you just learn so much. Seeing in jail how many young people come here and they literally just don't know any better and how easy it is to just ruin one's life. Society is so unforgiving that they label you as a felon and then you’re forever a felon. It pretty much makes it impossible for you to realign on a positive path of redemption. I don't know what it's like in Britain, but in America, it's kind of a pretense that people are given a second chance. I want a real second chance.”
For more from Glamour UK Beauty Writer Shei Mamona, follow her on Instagram @sheimamona
