Why Are Women So Successful as Con Artists?

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In 1977, the New York Daily News published an article about a beautiful young con woman named Barbara St. James. (At least, that was one of her names.) “If you meet her, you will like her,” ran the article. “She will draw out your life story, your troubles and triumphs. She appears wealthy, a woman of substance and class. She drips with sincerity.”

Appears was the second-most important word in the paragraph, but the first was like. You will like her. Beautiful Barbara’s life story has long been forgotten, but that line could be used to describe almost every con woman before and after her. If you meet her, you will like her. The con woman’s likability is the single most important tool she has, sharp as a chef ’s knife and fake as a theater mask. Without her likability, she would be nothing. If you like her—and you will like her—then her work will be so much easier. It’ll all be over quickly. You’ll hardly feel a thing.

The fact that we like con artists so much is probably the greatest con of all time. How did they pull it off, these criminals, creating a world in which we call them “confidence artists” while other criminals get unembroidered titles like “thief” and “drug dealer”? Why do we call their crimes “playing confidence tricks,” like we’re talking about a mischievous toddler? When journalists, lawyers, and lovers spoke about the women in this book, it was as though they were remembering a brilliant performer who had sadly lost her way. “The woman would have been a great human creature had she been highly trained, highly educated,” wrote one journalist about a Canadian con woman. The brother of a British con artist insisted that if it weren’t for an “unfortunate quirk” in her character, “she would be a wonderful, wonderful person. In fact, she is anyway.” The lover of a French con artist said of her, “Without being aware of the danger, I admired this brave spirit that was checked by nothing.” The brother-in-law of an American con artist declared, “She’s one of the nicest persons I ever met.”

There’s no point in denying it: the women in this book are extremely charming. Most of them would be fantastic company on a bar crawl. Many had great taste in fashion. The designer handbags! The fur coats! Some could do fun accents, others could tell your future. One drove a pink car, while another had a license plate that read 1rsktkr—Number 1 Risk Taker. The most dangerous one had a habit of giving out $100 bills, just because. Delightful! Clearly these women would have been entertaining to know, assuming that you stayed on their good side. But why do we feel so comfortable admiring them? You can’t go around gushing about how your serialkilling sister-in-law is “a wonderful, wonderful person” and a “brave spirit that was checked by nothing,” but the internet is choked with articles like “Why We Are All So Obsessed With Scammers” and “How to Dress Up Like Your Favorite Con Artist for Halloween.”

A simple explanation for all this adulation is that con artists have a reputation for being nonviolent criminals. Rarely will you find a con artist stashing someone’s head in her freezer. Her victims almost never end up dead. Almost never! This makes it awfully convenient for us, because we can dismiss these victims as gullible-but-largely-unharmed idiots and focus all of our fawning attention on what makes the artists—er, criminals—so fabulous.

But perhaps there’s a darker reason we cheer on the con artist: secretly, we want to be her. Most people, especially women, live their lives rattling around inside a thousand and one social barriers. But, through some mysterious alchemy of talent and criminality, the con artist bursts through those barriers like Houdini escaping from one of his famous suspended straitjackets. The con artist doesn’t feel the need to use the correct Social Security number, or keep the name her parents gave her, or put her real eye color on her driver’s license. She doesn’t mind forgery. She’s not afraid of a little bigamy. She’ll drive a fancy car right off the parking lot or steal a necklace made of 647 diamonds, and she doesn’t care who pays the price for her crimes. And though people love to turn her into a metaphor—for entrepreneurship, for capitalist grift, for the American Dream, for America itself, for the Devil, or simply for the average woman’s life of mild duplicity—she doesn’t give a damn about your figures of speech. The only person she answers to is herself. Isn’t it shocking, that sort of naked selfishness? And doesn’t it sound sort of delicious?

It’s tempting to think that we could be her—if we were better at accents and owned a few more wigs and gave in, completely, to our basest social desires: for status, power, wealth, money, admiration, control. These desires may sound crass, but they’re inherent to our nature. A recent psychology study found that people crave high social rank not only because it satisfies our aching need to belong, but because it gives us a sense of control, better self-esteem, and even reproductive benefits. (Even animals want to be important. A 2016 study of female rhesus macaque monkeys showed that social climbing actually strengthened their immune systems.) Most of us indulge these desires in milquetoast ways; our tiny, depressing cons just never make the papers. We reinvent ourselves on New Year’s Day, we edit our life stories to sound more exciting, and we try our very, very best to be likable—when it benefits us. But we rarely let ourselves go all the way, whether through a sense of morality or social pressure or a good old-fashioned longing to stay out of jail. So when we read about the con woman’s hijinks, it’s tempting to put ourselves not in her victims’ shoes (we’re far too smart for that, we think), but in hers. What if we behaved like she does? What if we could charm like that? What if we shucked off morality, and society, and collective responsibility, and just let ourselves . . . indulge?

But we could never be her. There’s too much standing in our way. Too many rules to follow. Too many social contracts to uphold. This is a good thing, mostly, this following and upholding—a beautiful thing, even, though some of us will hopefully be forgiven for suppressing a small sigh of disappointment at the realization. And maybe that’s why the con artist finds it so easy to make us like her. She has to turn on the charm, sure, but we’re waiting to meet her with open mouths and shining eyes. As she performs for us, we think, “a great human creature” and “a wonderful, wonderful person” and “what if, what if, what if?” She has us right where she wants us. She’s about to make us an offer we can’t refuse.

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Excerpted from Confident Women: Swindlers, Grifters, and Shapeshifters of the Feminine Persuasion. Copyright (c) 2021 by Tori Telfer. Used with permission of the publisher, Harper Perennial, Inc. All rights reserved.

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