The Great Gatsby at 100: the Jazz Age novel that helps explain Trump’s America

F. Scott Fitzgerald’s The Great Gatsby, a top contender for the title of Great American Novel, turns 100 on April 10.

A century later, it is invoked to help make sense of a world that still confuses “material enterprise with moral achievement” – as critic Sarah Churchwell wrote in the foreword to Gatsby’s centennial edition.

A Meta insider’s memoir takes its title, Careless People, from Fitzgerald’s novel. The same phrase circulated on social media and in The New York Times during Donald Trump’s first presidency, referring to his administration’s downplaying of COVID-19.

In 2018, The Atlantic compared Trump to Tom Buchanan, one of Fitzgerald’s “careless people”, describing “an eerie symmetry […] as if the villain of F. Scott Fitzgerald’s 1925 novel had been brought to life in a louder, gaudier guise for the 21st century”. More recently, others have compared Trump to Gatsby himself.

The Great Gatsby tells the tale of a lovesick man striving for social acceptance, believing personal reinvention and riches can help to rewrite the past. It is a story of longing: not just for lost love, but for an unattainable ideal.

The centenary couldn’t be more timely for this literary masterpiece, preoccupied by the same things we are: immense affluence, privilege, the limits of social mobility and the hidden underbelly of the American Dream. The Great Gatsby, while a relative literary failure in Fitzgerald’s lifetime, is enduringly popular today, with at least 25 million copies sold to date, numerous film and stage adaptations (and literary riffs), and a staple position on school and university reading lists.

“What we think about Gatsby illuminates what we think about money, race, romance and history,” wrote The New York Times’ A.O. Scott recently. “How we imagine him has a lot to do with how we see ourselves.”

The Great Gatsby is set against the backdrop of Roaring Twenties America: an era Fitzgerald famously dubbed the Jazz Age.

Fuelled by the infectious rhythms of jazz, driven by the economic forces of market prosperity and mass consumerism, and heady on the alcoholic vapours and illicit thrills associated with Prohibition-era nightlife, the 1920s were a decade where American fortunes were made and lost.

It was also, as Fitzgerald’s novel outlines, a period where individual ambition burned as fiercely as desire.

The plot follows the enigmatic Jay Gatsby, a spotlight-eschewing, self-made millionaire whose seemingly breezy approach to life masks a singular obsession: the rekindling of a lost romance with a beautiful woman from his past.

Born James Gatz, Fitzgerald’s charismatic protagonist reinvents himself in the hope of winning back the love of his life, wealthy socialite Daisy Buchanan. Taken at face value, Gatsby’s world is one of incredible luxury and dazzling excess – lavish parties, fast cars and ostentatious attire – all designed to lure Daisy back into his arms.

But as we begin to scratch beneath the surface, the glittering facade Gatsby has constructed gives way to something far more fragile and tragic: an impossible fantasy driven by jealously, obsession and self-deception.

As the reader comes to appreciate, Gatsby’s accumulated gains may grant him partial access to the world of old money, but he will never truly be accepted by America’s elite. No matter how hard he might try, he cannot surmount the barriers of class and entitlement.

Ultimately, Gatsby’s misguided belief that he can somehow crowbar his way into the upper echelons of high society while simultaneously turning back the hands of time leads to his downfall. In Fitzgerald’s words, he ends up paying “a high price for living too long with a single dream”.

F. Scott Fitzgerald, literary celebrity

Francis Scott Key Fitzgerald was born in St. Paul, Minnesota, on September 24 1896. The son of middle-class Catholic parents, he spent much of his youth living in upstate New York. In 1913, he enrolled at Princeton University, where he formed a lasting friendship with future literary critic Edmund Wilson.

More absorbed in literary and dramatic endeavours than his studies, Fitzgerald’s grades suffered and he dropped out in 1917 – though not before falling deeply in love with Ginevra King, an heiress who would leave an indelible imprint on his writing. She would inspire many of his fictional female characters, including Daisy Buchanan.

Fitzgerald first encountered King during a winter vacation in St. Paul in January 1915. The debutante daughter of a wealthy Chicago stockbroker, she quickly became the object of Fitzgerald’s intense devotion (much to the disapproval of her family, who thought him beneath her).

In the wake of his heartbreak after the relationship broke down, Fitzgerald enlisted in the United States Army, earning a commission as a second lieutenant. During his military service, he met Zelda Sayre, the woman he would eventually marry. Meanwhile, he began work on his first novel, This Side of Paradise.

Released in 1920, Fitzgerald’s formally adventurous debut was a critical success and cultural sensation, capturing the restless energy and shifting moral landscape of a cohort coming of age in the wake of World War I.

The novel’s transparently autobiographical narrative centres on Amory Blaine, a young Midwesterner whose intellectual and romantic adventures at Princeton – especially a doomed affair with the beautiful, elusive Isabelle Borgé – struck a chord with readers. It turned Fitzgerald into a media celebrity and unofficial spokesman for his generation.

Two years later, Fitzgerald published The Beautiful and Damned. It details the disintegration of a wealthy, aimless couple – Anthony and Gloria Patch – whose hedonistic lifestyle and misplaced belief in their own brilliance leads to ruin.

Fitzgerald’s tonally pessimistic second novel was again shaped by his own experiences, drawing heavily on his tempestuous marriage to Zelda, who was exhibiting symptoms of profound mental instability.

However, in stark contrast to This Side of Paradise, The Beautiful and Damned sold well, but received a lukewarm reception from reviewers. Some found its characters unappealing and its plot depressing.

By then, the Fitzgeralds had grown accustomed to the finer things in life. Which meant they needed money. Lots of it. To keep up with their lavish spending, Fitzgerald started to churn out short stories for popular magazines at a rapid pace. While this move provided him with a degree of financial security, some critics and contemporaries questioned whether he was squandering his literary gifts. Ernest Hemingway, for one, was “shocked” by his friend’s willingness to pander to commercial tastes and imperatives.

‘I want to write something new’

That said, while he was generating copy for mass-market publication, Fitzgerald was also hard at work on The Great Gatsby. In July 1922, he declared:

I want to write something new – something extraordinary and beautiful and simple + intricately patterned.

Determined to prove his worth as an artist, Fitzgerald, who wanted “to write a novel better than any ever written in America”, began to play with “form and emotion”. As his ideas for the new novel – which at one point bore the working title Trimalchio – took shape, Fitzgerald set up shop in Great Neck, Long Island. This location became the inspiration for East and West Egg, the fictionalised island communities that are the novel’s primary setting.

Fitzgerald, clearly not lacking in confidence, set his sights high for his third novel, taking inspiration from James Joyce’s Ulysses and T.S. Eliot’s The Waste Land.

Departing from conventional realism, Fitzgerald experimented with modernist techniques, layering his narrative with symbolic depth, synesthetic imagery, fragmented storytelling and complex characterisation.

The result was a work both lyrical and impressionistic. Here’s a vivid, illustrative excerpt:

The lights grow brighter as the earth lurches away from the sun, and now the orchestra is playing yellow cocktail music, and the opera of voices pitches a key higher. […] The groups change more swiftly, swell with new arrivals, dissolve and form in the same breath; already there are wanderers, confident girls who weave here and there among the stouter and more stable, become for a sharp, joyous moment the center of a group, and then, excited with triumph, glide on through the sea-change of faces and voices and color under the constantly changing light.

Fitzgerald’s Midwestern narrator, Nick Carraway, is describing one of Gatsby’s legendary West Egg parties. He is renting the house next to Gatsby’s mansion, “a colossal affair by any standard”, with “a marble swimming pool, and more than forty acres of lawn and garden”.

At first, Nick is fascinated by his enigmatic neighbour, drawn in by the sheer force of Gatsby’s optimism and his unrelenting faith in the transformative power of love and the trappings of wealth. But as the novel progresses, events lead Nick to reevaluate. He describes his charming friend as possessing “one of those rare smiles with a quality of eternal reassurance in it, that you may come across four or five times in life”.

He continues, outlining attributes essential to a good confidence man:

It understood you just so far as you wanted to be understood, believed in you as you would like to believe in yourself, and assured you that it had precisely the impression of you that, at your best, you hoped to convey.

When he isn’t with Gatsby, Nick is often with his cousin Daisy and her husband, Tom, the embodiment of American aristocracy and snobbery. They are, in Nick’s damning estimation, “careless” and “rotten” people.

An unreconstructed white supremacist prone to casual displays of extreme prejudice and physical violence, the adulterous Tom – who wouldn’t be out of place in the more dismal real-world and online recesses of today – is, in particular, deeply suspicious of Gatsby, regarding him as an interloper with dubious intentions.

The Atlantic wrote that Tom, “the Yale man, the football star, the spender of old money, the scion of what he calls the Nordic race – embodies the peak of social status in his century”. And that “Trump – the former Playboy-cover subject, the billionaire celebrity, the most powerful man in America – does the same for his”.

And their shared personality traits are the product of their shared relationship to power – the casual unreflective certainty that comes from inheritance, and enables its holders to wield its blunt force as both a weapon and a shield.

Tom’s “little investigation” into Gatsby’s background and finances reveals they are not what they seem. This leads to unintended, disastrous consequences.

Nick, our disillusioned observer, doesn’t quite know what to make of it all. We take leave of him at the end of the novel, on “the beach and sprawled out on the sand”, reminiscing about “Gatsby’s wonder when he first picked out the green light at the end of Daisy’s dock”.

‘A flying leap into the future’

Fitzgerald knew he had achieved something special with The Great Gatsby. His peers did too. T.S. Eliot considered it “the first step” forward “American fiction has taken since Henry James”. Edith Wharton concurred, calling it “a flying leap into the future.”

Yet, for all this critical acclaim, The Great Gatsby failed to resonate with the reading public – much to Fitzgerald’s dismay. By October, the book had sold less than 20,000 copies. (By comparison, This Side of Paradise had sold nearly 50,000 copies, across multiple printings.) As his biographer Arthur Mizener observed, by February 1926, “a few thousand more copies had been sold and the book was dead”. It was a blow the writer never really recovered from.

Fitzgerald’s personal life was tumultuous, marred by alcoholism, Zelda’s mental health issues and financial debt. This had a negative effect on his work. While he completed one more novel in 1934 – the excellent, darkly romantic Tender is the Night, arguably his best book – Fitzgerald struggled to be productive.

Following several failed suicide attempts, in 1940 he died of a heart attack, believing himself an abject failure and his career a total write-off. His most recent royalty cheque had been for $13.13. He was 44.

In the immediate aftermath of his death, writers and critics began to reassess Fitzgerald’s accomplishments. This effort was initially spearheaded by his friends, notably Edmund Wilson, who, in 1941, organised a series of tributes to be published in The New Republic.

In 1945, Viking Press released The Portable F. Scott Fitzgerald, edited by Dorothy Parker, which brought Fitzgerald to the attention of a new generation of readers. At the same time, the US military distributed 150,000 copies of The Great Gatsby to American servicemen during World War II as part of their Armed Services Editions.

Before long, The Great Gatsby made its way into the classroom, where it remains a staple of countless high school and university syllabuses. It continues to inspire readers, many of whom encounter it at a formative stage in their lives.

It has been adapted for the screen on multiple occasions – with mixed results. Jack Clayton’s 1974 version, starring Robert Redford as the eponymous Gatsby, was faithful to Fitzgerald’s vision, but utterly lifeless, while Baz Luhrmann’s 2013 adaptation, a hollow exercise in audiovisual bluster, failed to do justice to the novel’s subtleties. For all their shortcomings, these films helped cement Gatsby’s place in the popular imagination.

An ‘uncannily prescient’ enduring classic

Novelist Jesmyn Ward suggests Fitzgerald’s novel is

a book that endures, generation after generation, because every time a reader returns to The Great Gatsby, we discover new revelations, new insights, new burning bits of language.

I agree – and I think Fitzgerald would have had rich material to work with, had he been alive today. Ours, lest we forget, is a world where ersatz robber barons hoard nearly all our shared available assets and resources, where racist discourse resounds, and where rampant consumerism remains unchecked.

Last year America magazine argued Gatsby himself “gives the greatest insight into why Mr. Trump is still popular”, comparing Trump’s “fraudulent real estate deals” to Gatsby’s nefarious way of making his money, and Gatsby’s huge parties to Trump’s rallies. Both, the writer argued, are nouveau riche outsiders, “hell-bent on being accepted by the Manhattan set”, and scorned by the elites. (Though Trump’s second presidency seems to be ushering in a new elite.)

Thinking aloud, perhaps it’s more accurate to say Trump is a weird combination of characters. On one hand, he resembles Gatsby: a self-mythologising social climber, nostalgic for a past that never really existed. On the other, he shares much with Tom Buchanan: unscrupulous, self-interested and protected by his wealth.

In a historical moment that mirrors his own in many ways, Fitzgerald’s essentially tragic masterwork, which ends suggesting we are all forever “borne back ceaselessly into the past”, strikes me as uncannily prescient and relevant today.

Alexander Howard does not work for, consult, own shares in or receive funding from any company or organisation that would benefit from this article, and has disclosed no relevant affiliations beyond their academic appointment.