The Imperfect and Sublime ‘Gatsby’

F. Scott Fitzgerald, Zelda, and daughter Scottie in an automobile

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Zelda Fitzgerald, F. Scott, and their daughter Scottie out for a drive in Italy, circa 1924

I’m a late bloomer. So I can’t help but admire the blue flame of prodigy.

It took me eleven years to publish my first novel. A debut at age thirty-eight. A decade later, I published my second. I’m fifty-two years old and working on my third. I know.

Growing up, I never thought I’d be a writer. My family emigrated from South Korea when I was seven, and I grew up in Elmhurst, Queens. In our first year, my dad had a newspaper stand in a Manhattan office building. Then my folks ran a two-hundred-square-foot wholesale jewelry store in Koreatown until they retired. My sisters and I were latchkey kids. When we enrolled at P.S. 102, we received free lunch for a term, and then, at my mother’s insistence, we paid in full for all the years following. It was public school for me straight through until Yale, where I studied history, and then Georgetown for law school. I practiced law for two years. When I was twenty-six, I quit to write fiction.

When I started out, I knew nothing about being a professional writer. I learned how to write novels by reading and rereading great books and taking cheap classes at community centers. I wrote many terrible drafts, which I never published.

By your third novel, you know more about the craft and trade. You should know more about life and how to put it down on paper. You still have things to say, and that’s why you keep writing.

The Great Gatsby was F. Scott Fitzgerald’s third novel, and I’ve always loved it because it shows that Fitzgerald understood unfairness. Moreover, as a masterful novelist, Fitzgerald knew how to trick you into thinking about inequity by giving you that dreamy Jay Gatsby, “The poor son-of-a-bitch.”

Nearly a hundred years after its publication, Gatsby is considered “the Greatest American Novel.” I cannot imagine a more persuasive and readable book about lost illusions, class, White Americans in the 1920s, and the perils and vanity of assimilation. It remains a modern novel by exploring the intersection of social hierarchy, White femininity, White male love, and unfettered capitalism. I’ve read and loved Gatsby for a very long time, and with each new reading, my understanding of it has grown more layered and provocative. As a writer, I reckon with how a book like this was born, how its earnest author intended for us to read it, and how the novel has survived a century, defying obsolescence through its clear-eyed understanding of our wishful nature. I want you to know that the publication of Gatsby broke Fitzgerald’s heart, and he did not recover from it. That this book has endured so beautifully is a meaningful consolation for all of us who persist in making things of our private vision—paradoxically, beyond our reach, yet seemingly so close within our grasp.


“I want to be extravagantly admired again,” wrote Fitzgerald to a former college classmate, just days before Gatsby’s publication. He was twenty-seven years old, and already nostalgic for the early success of his debut novel, This Side of Paradise, published four years earlier, in 1920, when he was twenty-three. It was on the condition of his first novel’s being published that he was allowed to marry Zelda Sayre, a celebrated Southern debutante and daughter of a justice of the Alabama Supreme Court. Proving his worthiness as a breadwinner, Fitzgerald, the veritable prodigy, pulled off the hardest trick in literary publishing: both a critical and a commercial success.

In May 1924, Fitzgerald, Zelda, and their young daughter, Scottie, set sail for Europe. He felt “tired of being the author of This Side of Paradise” and wanted “to start over.” There, Fitzgerald continued to work on his new novel, which he felt was “wonderful.” He wrote to his college classmate that the manuscript—about four newcomers to New York during the Roaring Twenties: the bond salesman trainee Nick Carraway; his distant cousin Daisy Fay; her husband, Tom Buchanan; and the mythical Jay Gatsby—was “about ten years better than anything I’ve done.” Years later, Fitzgerald told his editor that Tom Buchanan was “the best character I’ve ever done,” and moreover that Tom may be among “the three best characters in American fiction in the last twenty years.”

That summer was a difficult one for the Fitzgeralds. While Scott was absorbed in revising his manuscript, Zelda met a French aviator, Édouard Jozan, and began spending time with him regularly. Their friends Sara and Gerald Murphy witnessed the growing flirtation and noticed how much it hurt Scott.

There are numerous accounts of this summer affair on the French Riviera; most agree on the following. In July, Zelda asked Scott for a divorce. Enraged, Scott sought to confront Jozan, and when he could not, he locked Zelda up in her room. In August, Zelda attempted suicide, by overdosing on sleeping pills. (In another version, it was a year later that Zelda attempted suicide.) In the fall of 1924, Jozan left the Riviera and never saw the Fitzgeralds again. Ernest Hemingway recalled Fitzgerald’s telling him of Zelda falling for Jozan, after the relationship had ended. Years later, in an interview, Jozan “emphatically denied having an affair with Zelda.” Affair or flirtation, divorce talk, house imprisonment, suicide attempt—regardless of the precision of the details, Scott recorded, “That September 1924 I knew something had happened that could never be repaired.”


There are parallel adulterous love affairs in Gatsby—one between the garage owner’s wife, Myrtle Wilson, and the polo-playing Tom Buchanan, the other between the former debutante Daisy Buchanan and the bootlegging Jay Gatsby. Through these class combinations—poor woman and rich man, and rich woman and poor boy turned rich man—Fitzgerald asks important questions about who gets to love, who gets to hurt, and who gets to walk away from the wreckage.

When George Wilson, the poor garage owner from the valley of ashes (what is now Flushing, Queens), discovers that Myrtle is having an affair, he locks her up in the house. When Myrtle rebels, she is imprisoned, and as she attempts to liberate herself, she is killed. In a letter to his editor, Fitzgerald insisted on her gruesome death: “I want Myrtle Wilson’s breast ripped off—its [sic] exactly the thing, I think.” He describes her lifeless body: “her left breast was swinging loose like a flap, and there was no need to listen for the heart beneath.” Fitzgerald, a former Catholic who had toyed with the idea of becoming a priest, and a lyrical writer who never misses an opportunity for symbolism, gives adulterous Myrtle a martyr’s punishment. Myrtle’s physical defilement is reminiscent of Saint Agatha, whose breasts were cut off as torture for refusing to marry a Roman ruler.

Is Myrtle’s death necessary?

Yes. It incites the murder-suicide of Gatsby and George, demonstrating that Daisy and Tom are “careless people…they smashed up things and creatures and then retreated back into their money” and would “let other people clean up the mess they had made.” The three tragic deaths prove Fitzgerald’s thesis on class and corruption in America. But is Fitzgerald—a fan of Karl Marx—also critiquing the institution of marriage and the idea of wives as commodities to be locked away? Knowing that Fitzgerald may have locked up his own wife could suggest otherwise.

In his writing, Fitzgerald took a great deal from his marriage. The parallels between Zelda’s alleged infidelity and Daisy’s and Myrtle’s affairs, and between Fitzgerald’s overweening ambition to marry Zelda and Gatsby’s grand campaign for Daisy, suggest that Fitzgerald’s feelings sprang from real life, and in creating characters of such authentic emotional resonance and vitality, he successfully pinned those feelings down. Mostly with her knowledge, Fitzgerald also lifted material from Zelda’s letters and diaries. Biographers agree that Zelda “was the dominant influence on Scott’s writing.” Fitzgerald himself admitted, “I don’t know whether Zelda and I are real or whether we are characters in one of my novels.” By the fall of 1924, the Jozan affair had ended, and Fitzgerald was ready to send out the manuscript. He wrote to his editor, “at last I’ve done something really my own.”       

In October 1924, Fitzgerald submitted The Great Gatsby to Maxwell Perkins, who thought it was “extraordinary.” A month later, Fitzgerald asked Perkins to change the title to Trimalchio in West Egg. In the ensuing months, he agonized over the title. Perkins preferred “The Great Gatsby,” as did Zelda.

Trimalchio, meaning “three times the master,” is a former slave turned wealthy freedman in The Satyricon, a first-century Roman picaresque fiction by Petronius, a courtier who served Emperor Nero. Like Trimalchio, Gatsby hosts lavish parties for freeloading guests who gossip about him. Fitzgerald’s allusion to Trimalchio reflects his preoccupation with class hierarchy, the meanness of the social elite, and our innate wish to be noticed by our betters. Economist E. Ray Canterbery argues that Fitzgerald saw himself “not only as a good historian, but a practicing socialist.” This makes sense to me. Gatsby, a great social novel, evinces the author’s keen interest in history and economics by serving as a critical portrait of an era characterized by the hedonism of barely taxed rich White plutocrats.

By invoking Trimalchio, Fitzgerald is choosing sides. Taking an anti-elitist stance, he indicts the American landed gentry of the Roaring Twenties for destroying the romantic Gatsby, the trusting George, and the discontented Myrtle, and draws a straight line from the mocking of outsiders by insiders in first-century Rome to the unchanged dynamic in 1920s America, when the mocking turns to murder. A hundred years hence, our nation struggles with profound income inequality, stagnant wages, and lost opportunities despite the diligent efforts of the diminishing middle class. Starkly different economic realities cannot help but create divergent class identities. Alas, Fitzgerald was prescient.



If Fitzgerald writes beautifully about White American men, he falls short in writing about White American women, and he knew it. He attributed the commercial failure of Gatsby not only to the title but also to the fact that it “contains no important woman character and women controll [sic] the fiction market at present.”

Four months prior to Gatsby’s publication, Fitzgerald had written to his editor about the weakness of his female characters: “I’m sorry Myrtle is better than Daisy. Jordan of course was a great idea (perhaps you know its [sic] Edith Cummings) but she fades out. Its [sic] Chap VII that’s the trouble with Daisy + it may hurt the book’s popularity that its [sic] a man’s book.”

Fitzgerald’s female characters are static. They are acted upon, unable to recognize or reverse how they are perceived or alter their behavior.

Myrtle Wilson is a castrating, betraying shrew who is killed graphically for seeking an escape from her marriage to a man she loathes. She is crass, vulgar, and deceitful.

Jordan Baker, the professional golfer, is “incurably dishonest” and a snob. She is unlovable, and Nick dumps her unceremoniously, lumping her with her corrupt social set even though he recognizes that it is not entirely fair.

Gatsby’s beloved Daisy embodies the worst possible qualities of White womanhood of that era, representing the Veblenesque lady of leisure—idle, status-conscious, and useless except as symbol. She is a trophy wife with a voice “full of money,” merely tolerated by her husband. Daisy marries Tom, her wealthiest prospect, whom she does not love, then remains with him despite his adultery, cruelty, elitism, and White supremacy. Tom chooses only to be himself; Daisy chooses him repeatedly. She commits vehicular manslaughter, flees responsibility, and rejects the man she loves because he is “Mr. Nobody from Nowhere.” She is a destructive siren whom Gatsby is powerless to resist. Literary critic Marius Bewley writes that Daisy expresses the “monstrous moral indifference” of the indolent rich. Thanks to bad film adaptations, there may be some temptation to fall under the spell of Daisy’s allure and, like Gatsby, become intoxicated by her appeal, but to do so would disregard Fitzgerald’s unhidden message: The “most popular of all” girl who grows up to be a rich wife is an unrepentant casual killer.

In short, Fitzgerald’s principal women characters are beyond redemption, and the married ones should come with warning labels.

The only females without a profound moral flaw are the very minor characters: Finn, Nick’s Finnish housekeeper; Stella, a “lovely Jewess,” who works for Wolfshiem, Gatsby’s cowardly mentor (who is drawn as a Jewish caricature); and Tom and Daisy’s baby, Pammy. Fitzgerald reserves his contempt for White native-born American women while being gracious to the help and the religious minority, who might as well have been added as scene props.

The novel’s rich people (Tom and Daisy) get away with murder, and the poor (Myrtle, George, and Gatsby) are sacrificed, so that the objective reader (“reserve all judgements” Nick) can learn the lessons of Fitzgerald’s allegory of class. This two-dimensionality of his female characters heightens the allegory, but I am unconvinced that Fitzgerald intended Gatsby to be pure allegory or satire—he was too ambitious for that.


The Great Gatsby was published on April 10, 1925, and it was not a commercial success. Fitzgerald’s legendary editor at Scribner’s, Maxwell Perkins, wrote to him that the reviews were “excellent” but the sales poor. For Fitzgerald, it was a grave disappointment—he needed money badly. He had a glamorous, artistic wife who liked fancy hotels and fur coats, and a baby daughter with a nanny. Traveling along the French Riviera in high style, Fitzgerald lived and spent like a CEO. He had hoped Gatsby would sell more copies than his first two books combined, but it ended up selling 20,870 copies, which, after he earned out his advance, left him with $261. The second printing of 3,000 copies never sold out in his lifetime.

The reviews were among the best Fitzgerald would receive in his career. T. S. Eliot read Gatsby three times and wrote that it “seems to me to be the first step that American fiction has taken since Henry James.” Edith Wharton said it was “a great leap” from his prior works. Gertrude Stein compared it to Thackeray’s Vanity Fair. In The Dial, critic Gilbert Seldes wrote that Fitzgerald “has mastered his talents and gone soaring in a beautiful flight…leaving even farther behind all the men of his own generation and most of his elders.” Nevertheless, proving that no author can make every critic happy, H. L. Mencken called Gatsby “a glorified anecdote.” Assuming you’re lucky just to get reviews, these were exceptional. Most authors could have died happy, but not our Scott. He had wanted so much more.

Instead, Fitzgerald died disappointed and broken. But that’s not how I see him. I agree with literary scholar and cultural historian Morris Dickstein’s assessment of him as a writer “who uses his frustrations and disappointments as new material, producing work that shows quantum leaps in human understanding.”

I think of Scott Fitzgerald fretting over bills, the girl who got away, his reputation, and the clubs that turned him down, and I know he wrote honestly about these things. He didn’t shirk from his own shame, self-loathing, or betrayals. He struggled through. He made sense of life’s confusions as best he could. That’s a lot more than most. His is a fine standard. For a time, his own generation of readers was lost to him; but the ones that came after could sense the truth of his questions and the fullness of his answers. It’s all there—both imperfect and sublime. I turn to Gatsby because it gives me the sober wisdom to imagine and revise my own American dream, and for that, it has a lasting hold.

This essay is adapted from the author’s introduction to a new edition of The Great Gatsby, published by Penguin Classics. 

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