The “Summer of Scam” may be over, but our public fascination with viral grifters is neverending: Anna Delvey, a Russian 20something pretending to be a German socialite born to a business-tycoon father, tricked New York City’s upper-crust elites for years before being caught and sentenced to between four and 12 years in prison. Then, we learned about Elizabeth Holmes, the unblinking, Steve-Jobs cosplaying founder of Theranos, who’s been charged by the Department of Justice for conspiracy to commit wire fraud. Without the armor of their grifts—their thinness, whiteness, and status as blond young women—they would’ve been immediately labeled con artists. Though Delvey wanted to seem like a well-connected party girl, there were clear inconsistencies between her self-constructed narrative, her behavior, and her appearance. Holmes, who dropped out of Stanford to start her company, was making bold claims that didn’t match the actual results. Yet, because of their whiteness, these women were able to earn the trust of their marks and scam them out of thousands—and sometimes millions—of dollars. Their stories were avidly consumed by the internet, sparking the curiosity of armchair psychologists in Holmes’s case while Delvey was turned into a tabloid-fixture anti-hero. Headlines reported Delvey’s courtroom attire, while an anonymous observer created an Instagram account (@AnnaDelveyCourtLooks) to specifically document Delvey’s outfits as though she were an influencer attending New York Fashion Week.
Social media allows us to become unapologetic voyeurs, consuming the personas of strangers as we passively scroll. You, too, can become a superstar without the calculated plotting of a dedicated PR team, generational wealth, or the serendipitous fortune of being in the right place at the right time. Instagram, in particular, has bred a new kind of notoriety—turning the mundane into aspirational status symbols. The photo-sharing platform has altered the path to celebrity, promoting an illusion of democracy through its ability to transform the average person into an influencer (especially when she has the privilege and wealth to purchase followers and fake sponsorships). Enter: Caroline Calloway, a University of Cambridge alumna whose longform Instagram captions netted her a $375,000 book deal (originally reported by Calloway as $500,000) for her memoir.
Calloway, who hails from Falls Church, Virginia, a county that is 80 percent white and had an annual median household income of $114,795 in 2017, crafted her persona around the novelty of being an American girl in England: Her followers watched her navigate undergraduate life and romantic entanglements against the backdrop of lush green fields and brick castles. As soon as Calloway rose to fame, however, she crashed back to Earth, abruptly cancelling her book deal because claiming the memoir publishers wanted her to write no longer aligned with her personal beliefs. After severing her book contact, Calloway decided to organize and host a creativity workshop wherein guests paid $165 for tips on harnessing their artistic vision. She regularly used her Instagram Story to complain about how much work the workshops were. Though she managed to pull off two seminars, Calloway canceled the rest of the dates.
Recently, Calloway’s former BFF Natalie Beach revealed in a story for The Cut that she wrote the captions for Calloway’s Instagram account and wrote a large portion of her book proposal. In Beach’s recounting of their friendship, they embodied the classic trope of the pretty friend and her almost invisible (in this case, literally invisible) sidekick. With her earnest naiveté and carefree attitude, Calloway flitted through life like Serena van der Woodsen while Beach played the role of the practical brunette. As Beach helped build the voice of Caroline Calloway, the Instagram Brand, she also became her friend’s emotional host, therapist, editor, rapt audience, and sometimes caretaker.
Despite the smattering of receipts tracking Calloway’s missteps, there’s still a refusal amongst some fans to hold the Instagram-darling-turned villain-in-a-flower-crown accountable. In true stan fashion, Calloway’s followers rushed to The Cut’s comment section to defend their visionary leader. pbuttercup333 wrote, “From what I can see Caroline had some mental health and addiction issues, but was never cruel or unkind. Natalie, on the other hand is a bitter, insecure ghoul, the kind of person who pretends to be your friend hoping to ride your coattails while secretly begrudging your success.” Another user responded, “I agree buttercup! Seems like Natalie is mostly the victim of her own character and her dreams of living the influencer life while having neither the assets, the grit, the character nor the fanbase to pull it off.”
For her part, Calloway viewed scamming as a rite of passage, akin to Taylor Swift being christened a “snake” by the Kardashians. “When people called me a scammer, I looked to Taylor for what to do,” Calloway wrote in an August 2019 essay for Refinery29. “I had created a pretty decent event for a community that I worked very hard to build. It was not a scam…But just like Taylor, my supposed ‘scam’ looked bad. There was evidence against me and it was enough to catch internet wildfire.” Calloway truly believes that she’s a blameless victim, so she’s either failing or refusing to acknowledge that she based her brand of emotional authenticity and vulnerability on a lie, and used those fictional ideas as a marketing ploy to attract the attention of major book publishers. (Beach alleges that Calloway bought ads that looked like genuine posts to promote her account and bought tens of thousands of followers.) In her eyes, the criticism lobbied at her is unjustified and unsubstantiated. After all, the workshop fiasco and inability to deliver a book to her publisher are the harmless errors of a young girl who didn’t know any better. But how many times can a person bend the truth before it qualifies as a clear character marker?
Chances are endless for white women who view scamming as a phase, a response to the patriarchal forces hell-bent on destroying female autonomy. “With the Manhattanite ‘It Girl’ glamour of Paloma Wool and Glossier intersected with irreverent praise for artists such as Hilma af Klint and Jules Bastien le Page, Calloway became an Instagram generated icon for a highly coded and classed brand of femininity,” Elise Bell wrote in a recent article for Dazed. The brand of femininity that Calloway capitalized on is not universal or relatable, two traits that she and her fans believe fostered her organic rise to internet fame. For girls and women of color, there’s no safety net or benefit of the doubt that chalks up mistakes as forgivable lapses in judgment.
Innocence is especially expendable for Black girls whose childhoods are cut short by societal biases. A 2017 study released by Georgetown Law’s Center on Poverty and Inequality found that adults believe Black girls between the ages of 5 and 19 “need less nurturing, protection, support and comfort than white girls of the same age.” The institution of whiteness renders Blackness criminal and inherently corrupt, an ideology that is rooted in a racist interpretation of the “Curse of Ham.” White girls are awarded a humanity that is ripped from Black girls before they are even born, so Black women are forced to constantly prove our worth and our right to exist time and again by meeting an ever-moving goal post. Black women can’t just “lean in” or take up the mantle of “girlboss” without facing harmful, even damaging consequences. Black women can’t make mistakes; it’s a luxury we can’t afford. On the other hand, Calloway was just perceived by Beach “as a person in need of help that I didn’t know how to give.” She seems to be following in the footsteps of confessional memoirists, like Lena Dunham, Cat Marnell, and Elizabeth Wurtzel, who share the messy details of their inner lives in order to be perceived as “raw” and “real.”
Being a walking trainwreck is more integral to their brand than the journey to recovery. In a recent Instagram post, Calloway hinted that she regrets momentarily losing control of the narrative more than her viral infamy: “Now I’m about to go meet a nice art history PhD boy I met last night for coffee and a museum date. The first thing I will say to him is, ‘Look at this piece the Washington Post published about me today? Isn’t this surreal?’ And maybe he won’t enjoy that, but this is my messy and meaningful life and some people have bad taste and they’re wrong.” In a 2018 interview with Man Repeller, Calloway frequently cited financial capital as her motivation for sustaining her Instagram career. She confesses, “However, as an artist and as a creative person, it’s both my responsibility and my right to support myself so that I can make the things I want to make. I acknowledge that in order to do that, it behooves me to understand and respond to the ways other people might see Caroline Calloway as a brand, and to act accordingly. Even though I don’t see it in my heart this way, I understand why I must in order to be the best businesswoman that I can be.”
We have reached a point in mainstream feminism where accepting and supporting all women, regardless of the impact of their actions, is the expectation, so it’s fitting that Calloway is modeling her tragic-heroine fable after Taylor Swift’s Reputation-era mythology. In Swift’s favored version of (white) feminism, women must stick together, pledging a loyalty that’s a cross between a sorority and an exclusive “squad.” And like Swift, Calloway is aware of the power of having a tried-and-true fanbase, a devout group of people ready to spring to retribution on your behalf. Being exposed hasn’t hurt Calloway’s status. At the beginning of September, Mic reporter Opheli Garcia Lawler noted that Calloway’s follower count was 782,000. After the publication of Beach’s essay, her count has increased to 798,000. She’s also acquired a manager. Reflecting on the 2018 year of scammers for the New Yorker, Jia Tolentino writes, “Scammers show us the glitzy bullshit intrinsic to stratospheric wealth in America; they show us that the best way to make money in this country is to treat everyone around you like a mark. But we prefer a clean arc in our morality play: in the end, we like scammers most when they fail.” Granted, it would be a gross generalization to say that Calloway is the sole representative of the white privilege associated with scammer culture. Rather, she is one microsomal example of the way in which some scammers are allowed to flourish. Her failure has only paved the way to the next stage of her act.
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