“Let me tell you about the very rich. They are different from you and me. They possess and enjoy early, and it does something to them, makes them soft where we are hard, and cynical where we are trustful, in a way that, unless you were born rich, it is very difficult to understand.”

So said the most celebrated voice of the Jazz Age in his short story The Rich Boy (1926), which crystallized F. Scott Fitzgerald’s assessment of America’s old money elites. Some may question the current relevance of a discussion about family wealth when close to 70% of the richest Americans as measured by the The Forbes 400 list are self-made. Although the upper crust may represent a smaller piece of the pie than they did a century ago, their role in our society’s history is still germane to the present day. Michael Farris Smith’s scheduled January 2021 release of Nick, a much-anticipated prequel to Fitzgerald’s most famous novel The Great Gatsby (1925), evinces the public’s continuing fascination with the author’s tales about the rich.

While Fitzgerald’s body of work drew heavily from his personal life to romanticize the American aristocrats of his time, he also presciently saw the footsteps of the merit-based affluent coming across the horizon. And he memorialized their struggle for power and respectability against a multigenerational wealth machine. Over the course of his career, Fitzgerald experienced a metamorphosis in his perception of the economic leaders of America from unadulterated hero-worship for the old-money elites to a full embrace of merit-based wealth.

Fitzgerald’s first look at the elite was in This Side of Paradise (1920) a thinly veiled autobiographical roman à clef largely focused on his time as a student at Princeton University. The protagonist Amory Blaine is a self-described romantic who was attracted to Princeton’s “spires and gargoyles” because they enabled him to hobnob with the men of Andover, Exeter and The Hill School. When Amory’s family loses their money, he realizes he is no longer an acceptable marriage prospect for a debutante.

Fitzgerald, who left Princeton in 1917 to join the army, retained an idealistic memory of his time there, but he became increasingly frustrated with his reduced social and economic status. Amory as Fitzgerald’s mouthpiece flirted with socialism not because he truly espoused its tenets but rather because he resented not having the cushion of a family income to support his writing career. “This is the first time in my life I’ve argued Socialism,” he says. “It’s the only panacea that I know. I am restless. My whole generation is restless. I’m sick of a system where the richest man gets the most beautiful girl if he wants her, where the artist without an income has to sell his talents to a button manufacturer.”

Fitzgerald’s next book The Beautiful and the Damned (1922) puts the patrician class under a much harsher lens. The protagonist Anthony Patch, the grandson of a Wall Street multimillionaire, and his wife Gloria are depicted as vapid, self-involved, heavy drinkers who only care about money and status. Anthony, who believes he will ultimately inherit his grandfather’s millions, has no interest in paid employment and Gloria is equally lazy, vain and mean-spirted. While The Beautiful and the Damned is structurally more cohesive than This Side of Paradise, its cautionary tale fatalism is incredibly depressing. As Louise Maunsell Field wrote in The New York Times upon its release  “The novel is full of that kind of pseudo-realism which results from shutting one’s eyes to all that is good in human nature and looking only upon that which is small and mean … It is to be hoped that Mr. Fitzgerald, who possesses a genuine, undeniable talent, will someday acquire a less one-sided understanding.”

Fitzgerald would ultimately find the perfect shade of gray with his next and arguably most famous novel, The Great Gatsby (1925). Written with a precisely controlled narrative and well-defined characters, Gatsby oozes with rich, vibrant imagery. As Lillian C. Ford wrote in the The Los Angeles Times upon its publication, “The weight of the story as a revelation of life and as a work of art becomes apparent. And it is very great. Mr. Fitzgerald has certainly arrived.”

Gatsby’s titular character Jay Gatsby reinvented himself from his humble Minnesota roots as an east coast millionaire. While Fitzgerald does not stipulate the source of Gatsby’s wealth, a shadiness is implied. The novel is anchored around a reunion between Gatsby and Daisy Fay Buchanan, a wealthy debutante whom Gatsby romanced while stationed as a military officer in Louisville years ago. In allegiance to the adage that “rich girls do not marry poor boys,” Daisy ultimately ended her relationship with Gatsby to marry Tom Buchanan. The reunion is jointly brokered by Daisy’s childhood friend Jordan Baker and Nick Carraway, a cousin of Daisy’s who has recently moved to New York and is also Gatsby’s next-door neighbor. When the novel opens, Daisy and Tom are living in the old-money East Egg section of Long Island while Gatsby resides in a colossal mansion in the nouveau riche West Egg where he throws lavish parties. Fitzgerald uses the green light at the end of Daisy’s dock to represent Gatsby’s hope that his successful acquisition of wealth will enable him to someday win back Daisy’s heart.

The Great Gatsby demonstrates a shift in Fitzgerald’s perception of the elites. When Nick first meets Gatsby, he categorizes him as representing “everything for which I have a natural and sincere scorn.” Nick eventually recognizes the integrity of Gatsby’s ambitions and the purity of his affections for Daisy. Daisy and Tom’s accidental involvement in Gatsby’s and Myrtle’s senseless deaths are the catalyst for this epiphany. “They were careless people, Tom and Daisy—they smashed up things and creatures and then retreated back into their money or their vast carelessness or whatever it was that kept them together, and let other people clean up the mess they had made.”

Tender is the Night (1934), Fitzgerald’s most ambitious novel, addresses the complex relationship between Dick Diver, a Yale-educated psychiatrist, and Nicole Warren, his patient from an extremely wealthy Chicago family whom he marries. The novel which largely takes place on the Côte d’Azur provides a vivid portrait of the expatriate Americans of the 1920’s.

The novel juxtaposes the middle-class self-made Dick Diver against the aristocratic Warren family. While Dick truly loved Nicole, he allowed himself to be manipulated by Nicole’s sister Beth into accepting their money to underwrite his clinic.  The money coupled with Nicole’s psychological needs was so overpowering that he lost interest in his practice and dissipated into excessive drinking and inappropriate behavior. In his biography of Fitzgerald, Some Sort of Epic Grandeur, Matthew J. Bruccoli states that, “Fitzgerald believed that money corrupts the will to excellence and work is the only dignity.” Dick unwittingly surrendered that dignity by striking a Faustian deal with the Warrens.

Fitzgerald died in 1940 before completing his Hollywood novel The Last Tycoon, which was published posthumously in 1941 to wide acclaim. The Chicago Tribune wrote, “Even ‘out of focus’ this truncated novel is obviously not only the best thing Scott Fitzgerald ever did but it is the first major novel of Hollywood and the great director, Monroe Stahr, is the most completely realized of Hollywood characters.” Stahr, a self-made Brooklyn-born Jew, is Fitzgerald’s first flawless protagonist. The Last Tycoon also marks a pivotal shift in the author’s perception of the old-moneyed elites. Stahr’s rival Irish-American Pat Brady is also a self-made man. The outline for the unwritten chapters includes a face-off between Stahr and Brady for studio control with Stahr representing the capitalist perspective and Brady aligning with the unions. With The Last Tycoon, Fitzgerald has come full circle from This Side of Paradise in that the novel includes no old-money elites.

Fitzgerald has enjoyed tremendous posthumous popularity. The Great Gatsby has been adapted for film five times, most faithfully in 1974 and has been a staple of high school and college literature curricula for decades. Tender is the Night and The Last Tycoon have also been realized on screen. We continue to revisit Fitzgerald because he brings us back to what Zelda described as the “plush hush of the hotel lobby” and “pays tribute to the poetic tragic glamour of the gilded aspirations of a valiant and protesting age.”

A century after the publication of This Side of Paradise, Fitzgerald’s stories about Americans who used their ingenuity and creativity to rise above their social station still resonate and inspire us. The author’s body of work reminds us that we are forever linked to our history and that America’s promise of future greatness is rooted in our past successes, failures and lost opportunities. Fitzgerald’s stories evoke not only the great achievements of both the old and new moneyed but also the dark underbelly of both parties which is still evident today. Yet, despite his exposition of the ugliness of elitism, Fitzgerald continued to believe in Gatsby’s green light and America’s orgastic future. And that is why we continue to read him.