Celebrate Grifter Season With These 9 Literary Swindlers

The finest frauds, fakes, and con artists literature has to offer

Anna Delvey, the grifter who swindled loads of money out of New York’s elite by claiming she was a millionaire heiress, is our newest canonized saint of grifters. After New York magazine published a riveting longread on her implausible exploits, The New Yorker’s Jia Tolentino declared the opening of grifter season, which this year also includes venerable grifter Elizabeth Holmes of Theranos, a fake expert on the Royal Family, a spurious Saudi prince, and an ersatz Arctic explorer. “Grifter season comes irregularly, but it comes often in America, which is built around mythologies of profit and reinvention and spectacular ascent,” Tolentino writes. “The shady, audacious figures at its center exist on a spectrum, from folk hero to disgrace.”

For more concrete examples of the Great Grifter, we turned to books and found eight of literature’s finest swindlers and con-artists. The best grifters, it turns out, are those people who understand what we want more than we do. They take our money, sure. But what they actually swindle is our sense of self. They make a game of showing us exactly how much we’ll give up in order to believe we are who we say we are. And are we not entertained?

Mr. Wednesday in American Gods by Neil Gaiman

Shadow stoically and obediently endured a three-year prison sentence to return to his beloved wife. But days before his release, he learns that his wife has died in a car accident while engaging in a sexual act with Shadow’s best friend (awkward). On his way home for the funeral, he meets Mr. Wednesday, a con-man, who offers Shadow a shady job (Shadow/shady, I couldn’t help myself). Shadow, faced with limited employment prospects as an ex-con, reluctantly agrees to take the job. Slowly, strange details of Shadows own life surface in the reflections of people he meets on the job. A disturbed Shadow realizes too late that he’s stuck in an elaborate con of Mr. Wednesday’s design with no way out.

Manley Pointer in “Good Country People” by Flannery O’Connor

Manley Pointer is a Bible salesman with a gift for reading people. When he meets Helga, a well-read atheist and Mrs. Hopewell, her socially religious mother, he preys on both their sensibilities in succession — Mrs. Hopewell’s assumption that he is “good country people” and Helga’s desire to manipulate his desire. If you haven’t read this one, I don’t want to spoil the ending, but suffice it to say that Flannery O’Connor delivers her usual deflating crack that waits at the end of any hunt involving humans. While Manley Pointer may be the grifter in this short story, it’s the judgements that Helga and Mrs. Hopewell throw at each other that make this short story a devastating blast to read.

Louise, Social Creature by Tara Isabella Burton

29-year-old Louise is keeping the New York hustle alive — which is to say, she feels like she’s being slowly killed by working three jobs, living in a less-than-favorable part of Brooklyn, and trying to ignore the numbers (or lack of?) in her bank account. All this because she wants to be a writer. But when she meets Lavinia, the 23-year-old breezing through New York on a glittery sabbatical from her studies at Yale, Louise gets some of that sparkle stuck in her eye. Lavinia takes her to parties, introduces her to the people thriving in the city she’s barely surviving in. They even move in together, coming closer to collapsing the difference/distance between the two women. But when Lavinia starts to lose interest in their duo, Louise is determined to do whatever it takes to stay (near) Lavinia. In the words of the author, Social Creature is a story of how “the grifter represents a fundamental and universal truth. In a place like New York City, we are all faking it.

Kevin Kramer Starts on Monday by Debbie Graber

A college dropout, Kevin Kramer manages to con his way into becoming the senior vice president of a company that he destroys through nonsensical changes disguised as cost-cutting measures. Even as the company sinks into chaos (and bankruptcy), no one seems to challenge Kevin Kramer’s authority presumably because he’s straight white man who “always maintains eye contact” and speaks authoritatively “in a low baritone”. Ahh, white male privilege.

Kevin Kramer Starts on Monday

P.T. Barnum in The Colossal P.T. Barnum Reader, edited by James W. Cook

If you thought the circus was a great con — swindling your money for overpriced peanuts and pictures next to abused animals— step right up to glare at P.T. Barnum’s first attractions. We have P.T. Barnum to thank (or curse?) for the “art of humbug.” Humbug, according to P.T. Barnum, was a pretty trick with entertainment value. This book is a collection of P.T. Barnum’s slick, brash articles commissioned by newspapers in the 19th century to advertise his attractions like Joice Heth, the 161 year-old slave nanny of President George Washington (whom he would later claim was a robot), and the Feejee Mermaid (which was actually an orangutan’s head, sewed onto a baboon’s midsection, sewed onto a fish’s tale). P.T. Barnum presented a prescient challenge: if the most important thing is your entertainment, who cares if I swindle you to make it happen?

10 Books About Tricks, Pranks, Cons, and Scams

Tom Ripley in The Talented Mr. Ripley by Patricia Highsmith

The iconic grifter of the 20th century is one we end up problematically rooting for. Pitched on the publisher’s website as “the ultimate bad boy sociopath” (?) Tom Ripley is trying to slough off his early life as a “sissy” escaping a broken home when he arrives in New York and meets Dickie Greenleaf, who’s just come back from his sojourn in Italy with his girlfriend Marge. Tom Ripley is invited into their interior circle and quickly becomes obsessed with staying there. The desire to stay then spoils into rage at having to share the interiority of Greenleaf’s life with Greenleaf at all. If I’m being honest, after I saw the film adaption with Matt Damon starring as Tom Ripley, I could never look at Damon the same way again.

Beatriz Yagoda, Ways to Disappear by Idra Novey

Beatriz Yagoda is a sixty-something badass Brazilian novelist who smokes cigars and does want she wants — including disappear. Her adult children, Raquel and Marcus, and Beatriz’s ever faithful publisher can’t find her. Emma Neufeld, her devoted translator and fangirl decides to join the hunt, leaving her boring boyfriend in Pittsburgh. Though Raquel is reluctant to let Emma into their lives, Emma plods through the clues left behind by Beatriz Yagoda like the Portuguese texts she has translated for so many years. Emma encounters what gets lost in the translation, from words written down to the life being lived. Beatriz, meanwhile, remains a shadow over the text. Amid gossip columns in local papers, passages from Beatriz Yagoda’s previous works, and emails from Emma’s boring beau back in Pittsburgh, Emma and Beatriz’s children discover that the disappearance was a setup, and for reasons that only become apparent once everyone is in danger.

Gustavo (Highway) Sánchez Sánzhez in The Story of My Teeth by Valeria Luiselli

Gustavo (Highway) Sánchez Sánzhez sells off his old teeth as relics from well-known celebrities like Virginia Woolf, Borges, Montaigne, even Plato. What does he do with his earnings? Buys back his own grift by purchasing the teeth of Marilyn Monroe. Life is good until his own son knocks him out and steals his pearly Marilyns. Highway, deserted, eventually befriends Voraigne, who might be retelling the story we are reading. Where’s the truth? Somewhere between Highway’s stories, the photo series, the quoted passages from Voltaire and H.G. Wells, and Luiselli’s own afterword all wonderfully puzzled together in The Story of My Teeth.

Mr. Monck Mason and Mr. Harrison Ainsworth in “The Balloon Hoax” by Edgar Allan Poe

Mr. Monck Mason and Mr. Harrison Ainsworth are totally made up, but the Ballon Hoax was a real fake that actually happened. In 1844, The Sun newspaper in New York ran a series of articles penned by two scientists — Mr. Monck Mason and Mr. Harrison Ainsworth — who were making a three-day journey across the Atlantic Ocean in a gas balloon. The articles had diagrams and everything, so people believed the article was true. But two days after the articles ran, no balloon showed up on the East Coast, and the whole thing was revealed as a hoax perpetrated by Edgar Allan Poe. So I guess that makes Poe the grifter — famously swindling truth away from newspapers, creating fiction so good that it resembles like fact.

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