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Rags-to-Riches Stories Are Actually Kind of Disturbing

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Americans retain their faith in the American dream even as our prospects of upward mobility dim. The lives of the billionaires whose ranks continue to swell give us cause to hope, or envy. We avidly follow the doings of the ultrarich, both the real (Kim Kardashian, Elon Musk) and the unreal (Bobby Axelrod, Logan Roy). This isn’t new: Americans have always loved fiction that reaffirms our fantasies about wealth and social mobility. Perhaps no cultural figure helped to keep the American dream on life support longer than Horatio Alger, the 19th-century novelist who wrote adventure stories for boys.

Alger commanded enormous popularity in his time, and his novels became integral to the enduring fantasy of American egalitarianism. His name is synonymous with the “rags to riches” narrative we seem unable to relinquish. It is deployed so often in the context of economic journalism — often inaccurately — that it has become a capacious mythology with room for any number of misreadings. Malcolm Gladwell, for example, describes Alger’s books as works where “young boys born into poverty rise to riches through a combination of pluck and initiative.” Though Alger indeed extols the virtues of hard work, prayer, honesty and saving, his books also hinge upon chance encounters and the noblesse oblige of someone much higher on the class ladder. Hard work matters but not as much as a helping hand from a wealthy patron. In this sense, Alger’s novels are truer than many of the stories that real-life billionaires believe about themselves.

The 1868 bildungsroman “Ragged Dick,” the most popular of Alger’s books in his day, follows a 14-year-old bootblack as he makes his way in New York. Dick is industrious but profligate, working all day to polish shoes, treating his friends to “oyster-stew” with his pennies each night. He’s not a priggish bootstrapper but a plucky bon vivant who does his work with a smile, always “on the alert for business.” On the streets of New York, he meets the rich Mr. Whitney, who hires him as a guide for his nephew and gives him a new suit. “I may be rash in trusting a boy of whom I know nothing,” Whitney says, “but I like your looks.” Whitney gives Dick $5, and from that Dick pays for a week’s lodging, puts the rest in the bank and gets a lettered street-boy colleague to share his room in exchange for lessons in reading and writing. In the sequel, “Fame and Fortune,” another benefactor gives Dick $1,000, which he invests in real estate.

“Ragged Dick” is at its heart a well-worn fairy tale: Dick is pulled from penury to the middle class through the intercessions of several rich patrons. Dick notes the parallel himself. “It reminds me of Cinderella when she was changed into a fairy princess,” he says when he sees himself in a mirror, cleaned up and wearing new clothes. It’s a powerful fiction, one built on the easily abused power imbalance between a rich man and a poor teenager — and in free enterprise itself. We don’t think of the thousand other bootblacks who will not meet their benefactors, boys whom the text dismisses as ruffians or ne’er-do-wells or simply never acknowledges at all. Do Americans love and retell the story because we don’t really understand it or because something in its dark heart whispers those truths we pretend not to know?

The journalist who calls his or her subject a “real-life Alger story” is probably never thinking of Dick’s new clothes, but they are fundamental to his story. In his study “Erotic Innocence: The Culture of Child Molesting,” the literary scholar James R. Kincaid writes: “Alger may have felt he was inculcating a Protestant ethic, but he seems to have exploited instead a pedophilic fairy tale, a narrative that runs at least as deep in America as Puritanism. It’s not hard work that brings success but being cute, cute in the presence of susceptible adults.” This reading becomes more grim when we consider that before he was a novelist, Alger was a disgraced pastor, forced out of his church for molesting a 13- and a 15-year-old boy. Alger did not deny the charge when he left the post to begin a storied writing career and a lifelong patronage of down-on-their-luck boys. Seen thus, the Alger books are not merely encomia on hard work but disturbing texts about power, desire, eros and fantasy — elements that are also integral to American perceptions of wealth.

The embellishments that Alger made to the Cinderella story — the use of banking, the youthful initiative, the importance of education and prudent investment — carried much greater significance in the 19th century, when intergenerational mobility was in fact on the rise for a period. And while in recent decades mobility has languished and inequality has grown, we continue to be moved by Alger’s embellishments, by the idea that a little luck combined with hard work can lead to, if not great wealth, at least comfort and ease.

Today, whether or not they realize it, the wealthy tell the stories of their lives — and our class structure — within the framework that Alger articulated. They all cast themselves as scrappy entrepreneurs who start at the bottom, climb to the top and step into a benefactor role, transforming from Ragged Dicks into versions of Mr. Whitney. Rather than memoir, the autobiographies of billionaires are couched as business advice, self-help, policy prescriptions or even quasi-religious texts, all united by an Alger-inflected fantasy of class mobility that is increasingly imperiled, often by the political agendas of the very billionaires writing these books.

The collision of the bootstrapping fantasy with the reality of extractive wealth leads to some gnarled narrative efforts. This winter I read a large number of books by billionaires, who are united in our minds as a category even though they don’t have their own shelf in the library. One of these is Charles G. Koch’s 2015 book, “Good Profit,” an example of what happens when a billionaire adopts Alger’s preachy moralizing but forsakes the narrative of mobility that made him compelling. For Koch, that’s a matter of necessity: He is in no way a self-made man, having taken stewardship of Koch Industries from his father, an immigrant’s son who patented a new oil-refining process. But like many billionaire authors, Koch the younger stresses his own hard work, straining to place himself in that beguiling trajectory of ascent. In his telling, his father was a taskmaster, and Charles’s youth before following him to M.I.T., and eventually the family business, was spent “digging dandelions on our 160-acre property,” shoveling manure and other blue-collar pursuits. Because he can’t do rags-to-riches, Koch packages “Good Profit” like the business advice of a conservative grandfather who warns against “corporate welfare” and celebrates free markets.

But his grandfatherly mien becomes sinister when you locate it against a time and political context awash in money, where corporations are granted a person’s right to self-expression. In 2010, the journalist Jane Mayer published a long article titled “Covert Operations” on Charles and his brother David in The New Yorker. She documented the many extracorporate vehicles through which these Koch brothers were orchestrating a massive and opaque transfer of wealth into American politics, one meant to stymie environmental and business regulation and promote their ideals of libertarianism and untrammeled free markets.

When Mayer broke her story, which she turned into the best-selling 2016 book, “Dark Money,” published a year after Koch’s own book, she became the subject of a campaign to discredit her that she traced back to people affiliated with Koch business concerns. Seen in this context, “Good Profit” is almost comic in its hypocrisy, and the book takes on a defensive air. A chapter called “Learning From Adversity” includes a brief, apologetic mention of the death of two teenagers in a Koch pipeline accident but glides swiftly into a condemnation of individual actors within the company, disingenuous whistle-blowers and the overreach of the federal government.

There may be a business audience for Koch’s trademarked system of “Market-Based Management” or his enthusiastic quoting of Friedrich Hayek. But for the casual reader, it’s an airless enterprise that imparts none of the frisson of wealth. A book that elides the thrill of acquisition for the appearance of rectitude is not only a lie but also a boring one. “Ragged Dick” was good because it had jokes, villains, the eros of accumulation, the soft bed after the hard streets, the fairy godparent who arrives in the nick of time. Those of us who imbibed capitalism with our mother’s milk have a visceral, if latent, desire for accretion, growing fat, securing comfort. The author does well to remember this.

If any billionaire memoirist can be said to vibrate on the frequency that makes Alger’s stories beguiling, it’s a man whose name is often linked with Alger’s in the press: the oil tycoon T. Boone Pickens, a sometimes adversary of Koch’s who died in 2019. The two Great Plains oilmen tussled over the direction of America’s energy policy, in which each man had an enormous vested interest.

Pickens’s 2009 memoir, “The First Billion Is the Hardest,” is his third and last, revisiting and updating material introduced in “Boone” and “The Luckiest Guy in the World.” The voluble Pickens began his life in Oklahoma, the son of a landman who leased mineral rights from private landowners and sold them to oil companies. His family was not poor, he says, but they were thrifty and lean; his grandmother supped on “one cup of tea and a slice of dry whole-wheat toast,” and warned him that a fool and his money are soon parted. Pickens started his career mowing lawns and switched to a paper route at age 12. After college, he went to work for Phillips Petroleum, then formed his own oil company at 28; it eventually became Mesa Petroleum, which prospected for oil and gas and brought the art of the hostile takeover to the oil industry. When Mesa itself became the target of a takeover and defensively merged, Pickens, at 68, was out. He made his comeback by founding the BP Capital hedge fund in 1996 and becoming a billionaire. He was probably best known to the broader public for his Pickens Plan, a 2008 proposal to break what he called America’s “dependency on foreign oil” and convert its power generation to wind and its primary transportation to natural gas.

The relative pleasure in Boone’s writing comes from his performance as a folksy Oklahoman. While Koch litters “Good Profit” with anodyne corporatist rhetoric about how he aims to create “superior value for our customers,” Pickens constructs his narrative around what he calls Booneisms, aphorisms that summarize the lessons from the memoir’s many anecdotes. (No. 6: “In a deal between friends, there’s no place for a wolverine.”) Pickens describes one adversary as “so tight he wouldn’t have paid a dime to watch a pissant eat a bale of hay.” In this affable, aw-shucks register, he talks of being depressed and needing medicine to help him get better, about divorcing and fighting with his soon-to-be ex-wife over a papillon dog he loved. When he documents the early days of BP Capital, during which he lost millions of dollars of his rich friends’ money, he finds an earthy, populist expression for a deeply unrelatable predicament: “I was now scratching a poor man’s ass.”

Credit…Photo illustration by Ben Denzer

When Pickens introduces his BP Capital years, he says the story of its success is proof that “age is meaningless in some instances” and “opportunity in America is endless. We are allowed second, third, fourth and fifth acts.” We know this is untrue, but we read along with pleasure as he describes the bets that first had him scratching his rear, then had his fund soaring until it went up $252 million in the course of a year — a fantastical gain of 9,095 percent. We imagine, for a moment, what it would feel like to come into such a windfall, and it is exhilarating. When Pickens decides to use this success to start a second energy fund, haters and doubters tell him his track record isn’t good enough. But he forges ahead. As the weather gets cold, the price of natural gas rallies even higher and he’s up $300 million in a single month. We marvel, He’s done it again.

Most books by billionaires, particularly by people who came from corporate life, make Koch’s mistake of larding their pages with prose spreadsheets and five-point plans. To the novelist, it feels like a misguided instinct, because what most of us really want is the thrill of the Alger timeline, with all its ups and downs, the stumbles and resurrections. Pickens understands this and casts himself as an underdog and outsider. In the account of his early days at Phillips, he sets up the opposition beautifully: “At Phillips, I met the monster: Big Oil.” Big Oil is one of the easiest villains there is; for the rest of the book, Pickens is set in our minds as the scrappy upstart, a little guy who simply cares about shareholders and making America energy-independent. How dare these Big Oil men and mean ex-wives pick on little ol’ Boone?

Pickens’s narrative efforts are so disarming that you almost forget that his wealth came from a pioneering effort in corporate raiding that made his small oil company into a very large oil company, from the kind of trading that relied on the hoarding of commodities and the financialization of the oil-and-gas industry. When a cold snap and a natural-gas shortage coincide, you can make a fortune if you either have the gas yourself or simply had the foresight to bet against someone else who didn’t have it. At the end of the book, Pickens lays out the coming water crisis with a note of folksy concern, only to reveal that he has bought up huge chunks of land over the Texas portion of the Ogallala Aquifer, the largest reserve of groundwater in the United States. He positions himself to make a killing selling life itself, describing the resource wars he sees coming with concern that can’t be uncoupled from capitalist scheming.

In a survey of billionaire memoirs in Current Affairs, the journalist Nathan J. Robinson posited that “if there is a central recurring theme to billionaire literature, it is this: an insistence that what has made the billionaire rich is helping other people rather than helping themselves,” and it is true that most billionaire books spend a lot of time talking about how they give back. But the reality of our social inequality and their singular, often misguided, priorities intrudes. Pickens, for example, describes donating $165 million for a university stadium. The more he speaks, the more we realize the limits of his charm, just as the more we learn of Koch’s extra-corporate activities, the more odious his business advice becomes. The billionaire is perhaps most seductive when he’s not speaking.

Popular fiction can do the billionaire’s work for him, playing on our national fantasy in a way that a billionaire memoir — inevitably a work of singular solipsism — can never quite manage. Enter one of the 21st century’s most significant literary phenomena, which magnifies and refracts the unsettling power dynamics that lie at the heart of “Ragged Dick.” What does it mean if our pop culture all but affirms the futility of striving, even while it burnishes the myth of the deserving billionaire? I am speaking of what is perhaps our era’s most surprising Horatio Alger analogue, a work of fiction that has outsold any billionaire memoir by many millions of copies: E.L. James’s romance novel “Fifty Shades of Grey.”

The origins of “Fifty Shades of Grey” are perhaps more widely known than those of BP Capital or Koch Industries. “Fifty Shades” sprang from the mind of Erika Mitchell, an English television executive who in 2009 wrote a fan-fiction riff on Stephenie Meyer’s “Twilight” vampire-romance series under the name Snowqueens Icedragon. When the work picked up readers, Mitchell rewrote it, removing any references to Meyer’s material but keeping its spirit, and sold the resulting work to an Australian publisher as “Fifty Shades of Grey,” by E.L. James, in 2011. The small-press book became a sensation that resulted in a seven-figure deal, one that transferred the rights from the original press to Vintage Books, a division of Knopf Doubleday, a division of Penguin Random House. It’s the kind of deal that could form a chapter in one of the billionaire memoirs, a complex transfer of capital that spawned a billion-dollar book-and-movie franchise, even before estimating the cash value of the many books that have sprouted like mushrooms in its shadow.

“Poor [expletive]-up, kinky, philanthropic Christian,” the narrator of “Fifty Shades,” Anastasia Steele, muses about her billionaire, the eponymous Christian Grey. Steele is a graduating college senior and virgin who meets the 27-year-old “telecommunications” billionaire when she interviews him for the school paper. Grey has a large and mostly unexplained business empire that leaves him plenty of time to pursue his interest in sadomasochism, dominance and control — pursuits, we are told, that stem from a tortured childhood with a “crack-whore” mother and teenage sexual abuse by a much older woman. When he is not courting Steele or pressuring her to join him in his sex dungeon as a submissive, he is issuing gruff instructions about “Darfur” on the phone. In this setup, Grey is Ragged Dick reincarnated, the orphan made good, paying it forward to “Darfur” but also playing fairy goddaddy and letting Steele, another waif, step into her own power as the mistress of an astronomically rich man. The levels have levels.

If “Pretty Woman” was a Cinderella story for the “American Pyscho” era of corporate raiding, its hero wearing his aggression on his sleeve, “Fifty Shades” is one for the “Dark Money” era. James presents Grey’s frustrating silences and elliptical back story, his penchant for surveillance, as part of his allure. The fact that the effort is so wildly successful reveals the way that Alger’s DNA persists in chaotic bastardizations and reimaginings; “Fifty Shades” has all the potency of luxury and comfort but flirts also with the allure of submission, the dark side of the Alger oeuvre’s suppressed and troubled eroticism made palatable, mainstreamed.

Grey is controlling in and outside his dungeon. He finds out where Steele is by tracking her cellphone. He buys her a laptop that she uses only to email him. “I want you to behave in a particular way,” he tells her, “and if you don’t, I shall punish you, and you will learn to behave the way I desire.” Steele demurs. “I am not a merger. I am not an acquisition,” she thinks, before she is merged and acquired. And yet, while Grey does get Steele into his dungeon, ultimately the series is about his slow domestication — her ultimate rejection of his style of sexual dominance. Hailed as a filthy exploration of bondage, the S.&M. element is in fact subverted at every juncture for a marriage plot and what Grey calls “vanilla” sex.

“Fifty Shades” has played an outsize role in the destructive, hypercapitalist consolidation of Amazon’s algorithm-based book business. Digital and physical shelves teem with additions to the house that James and Meyer built. Many are in explicit conversation with “Fifty Shades.” In “Bared to You,” where the billionaire is again a bad boy with a traumatic past and a heart of gold, the author Sylvia Day thanks E.L. James in her acknowledgments. And there are thousands of these books. Searching “billionaire romance” on Amazon Books yields more than 50,000 results with series like “Billionaire Bad Boys,” “Blue-Collar Billionaire$,” “Billionaire’s Captive,” “Boston’s Billionaire Bachelors.” In fact, the only kind of book for which “billionaire” is an explicit category is the romance novel, where it has developed into its own distinct subgenre.

Ultimately, these books are rehabilitory projects for billionaires, laundering their exploitative politics and recasting them as mildly edgy sex — not to mention putting hot young faces on a class of men that is in reality mostly approaching or past retirement age, for an audience of women who often have far less economic power. In “Everything and Less: The Novel in the Age of Amazon,” the literary scholar Mark McGurl writes of Grey: “While it is tempting to read him as little more than a poster boy for neoliberal capitalism, for that set of brutalities, he is also the symbolic vehicle by which that system is ‘softened’ and made caring again in the little welfare state of a loving marriage.” Billionaires already lived rent-free in our heads; these books simply extend the lease, adding ever weirder terms, continuing to disappear everyone who falls outside the beautiful capitalist trajectory of up, up, upward to domestic comfort. After all, Grey’s “ultimate goal is to help eradicate hunger and poverty across the globe.”

“Ragged Dick” and its sequel end with Dick’s fortune secure enough that the third book in the series can turn to the betterment of another boy. The ladder of Alger’s mythology is narrow, a queue of boys up from the street, most of them only reaching as high as the middle, and always with help. Do our heroes become lazier as our realities become harder? At the beginning of “Fifty Shades Freed,” the last book in E.L. James’s primary trilogy, Steele struggles with changing her name and her new status as wife and mistress of a house. “Everything is being handed to me on a plate — the job, you, my beautiful husband,” she protests, feeling that it’s unearned, fearful of being “crushed” by her powerful man. But by the epilogue, Steele surveys her young family and the green lawn of the so-called Big House, savoring the ultimate pleasure: comfort without the taint of unease. All it took was a few light floggings along the way.

Alger put a line in Mr. Whitney’s mouth that resonates with any billionaire writing his or her story today: “In this free country there is every inducement for effort, however unpromising may be the early circumstances in which one is placed.” But Alger encoded something more truthful into the fantasy of “Ragged Dick,” one that James and her romance-novelist peers intuit to a better extent than the billionaires who set their recollections to paper today. We live under an economic system in which hard work by itself won’t get you to obscene wealth, not in a million years. So you better look cute, and hope someone comes along to give you what you need.


Lydia Kiesling is a frequent contributor to the magazine. She last wrote about onscreen portrayals of motherhood. She is the author of the novel “The Golden State,” which was a 2018 National Book Foundation “5 under 35” honoree and a finalist for the VCU Cabell First Novelist Award.

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