Chicago's connection to ‘The Great Gatsby' as Fitzgerald's novel turns 100

Chicago Tribune

06-04-2025

This week marks the 100th anniversary of the publication of F. Scott Fitzgerald's 'The Great Gatsby.' It was destined to be the definitive literary monument of the Roaring '20s, a decade of fortunes made and lost on Wall Street. Prohibition gave booze the lure of the illicit.
But the novel's debut on April 10, 1925, was a dud.
It sold fewer than 20,000 copies. The reviews were generally favorable, if not enthusiastic. But it was trashed by H. L. Mencken, editor of the Baltimore Sun and dean of America's literary critics.
'The theme is the old one of a romantic and preposterous love,' he wrote, 'reduced to a macabre humor.'
That stung Fitzgerald, who had been developing the storyline through previous short stories and novels. Like many writers whose work is classified as fiction, that didn't mean that Scott, as he was known, made it up out of the whole cloth.
He distilled real-life experiences into characters moving through scenes he'd witnessed. Thanks to Fitzgerald's meticulous record-keeping, we know the route the novel's protagonists, under the aliases Jay Gatsby and Daisy Buchanan, took to the story's Long Island setting.
Fitzgerald kept a ledger book in which he listed his literary earnings and daily routine. At the top of page 169, he recorded Daisy Buchanan's conception, by noting: 'Met Ginevra.'
Ginevra King was a young socialite from Lake Forest, Illinois. 'Once I thought that Lake Forest was the most glamorous place in the world. Maybe it was,' Fitzgerald recalled to his daughter 25 years after his first visit. He was a houseguest there in 1915.
One of the homes he visited was on Kingdom Come Farm, a 50-acre estate designed for Ginevra King's father by the ultra-fashionable architect Howard Van Doren Shaw.
It and other mansions that line Lake Forest's ravines and shoreline are punctuated by so many windows they often look more like hotels than family residences.
They look like the world inhabited by Isabelle, the heroine of Fitzgerald's 1919 story, 'Babes in the Woods.'
'The vista of her life seemed an un-ended succession of scenes like this, under the moonlight and pale starlight, and in the backs of warm limousines and low cosy (sic) roadsters stopped under sheltering trees — only the boy might change.'
Time magazine pronounced Ginevra King and three friends the cream of the crop of Lake Forest debutantes in 1919. They wore gold pinkie rings engraved 'The Big Four.' One was Edith Cummings, a premier amateur golfer of the 1920s.
She appeared as Jordan Baker in 'Gatsby,' where Scottie wrote: 'there was a jauntiness about her movements as if she had first learned to walk upon golf courses on clean, crisp mornings.'
Years later, King described herself in a letter to Fitzgerald's daughter: 'Goodness, what a self-centered little ass I was!'
Fitzgerald and King met Jan. 4, 1915, at a sledding party in St. Paul, Minnesota, his hometown. She was 16 and visiting her roommate at the ultra-posh Westover School in Middlebury, Connecticut. He was 18 and a freshman at Princeton University.
'The couple next to them had their backs turned and he kissed her little neck and her ears and never her lips,'' he wrote in 'Winter Dreams,' a short story based on that sleigh ride.
From the moment they met, King and Fitzgerald were united in a peculiarly Jazz Age puppy-love affair. 'Her voice is full of money,' he wrote of Daisy Buchanan, King's alias in 'Gatsby.'
Fitzgerald and King remained emotionally linked through all the twists and turns of their lives.
When she returned to Westover, he deluged her with letters, which pleased her. Her self-esteem was based on how many letters she received from suitable suitors. But he was irked that she read his intimate letters to classmates and rival suitors for their amusement.
During one of the Lake Forest parties, Fitzgerald had heard something that should have alerted him to the peril posed by King's flirtatiousness.
She was his girlfriend. But another guest, Deering Davis, boastfully announced: 'I'm going to take Ginevra home in my electric.'
Was the dashing polo player and aviator emboldened because Fitzgerald didn't have a car? Let alone an electric one, then as now a prestigious automobile.
Fitzgerald's father lost his salesman's job in 1908. But his mother was heir to a highly successful grocery business. He was named after a distant relative of some note, Francis Scott Key, who wrote the lyrics for 'The Star-Spangled Banner.'
That gave the family status and an upper middle-class income, by St. Paul standards. His mother raised Fitzgerald to think that cachet and her money entitled him to membership in the upper class. Lake Forest's and Chicago's elite demurred.
'Poor boys shouldn't think of marrying rich girls,' Fitzgerald overheard a relative of King's pontificating.
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Ginevra King, center, with friends at the country wedding of Adele Blow and Lt. Wayne Chatfield-Taylor in La Salle, Illinois, on Aug. 22, 1917. The couple was married at Blow's parents estate, Deer Park, which is now Matthiessen State Park. Society members were brought to the wedding on a special train from Chicago. (Chicago Tribune historical photo)
In 1915, Fitzgerald asked King to be his date for Princeton's sophomore prom, but her mother forbade her to attend it with a middle-class young man. Two years later, King dumped Fitzgerald, telling him she'd found her true love, the fabulously wealthy William H. Mitchell.
'I wish you knew Bill so that you could know how very lucky I am,' she wrote to Fitzgerald.
Mitchell was the son of a business associate of her father's, who made an arranged marriage for them, a linking of two prominent families.
Years later, she moved on to the scion of another elite family.
Fitzgerald's exit from this emotional rollercoaster was the Army. He dropped out of Princeton and enlisted. Stationed in Montgomery, Alabama, he met and married Zelda Sayre, a southern socialite. She reminded him of King.
Upon being discharged from the Army, Fitzgerald wrote the emotional residue of his and King's affair into 'The Great Gatsby.' He conceived the book on Long Island and finished it while he and Zelda were living in a villa in Saint-Raphael, France.
The final line of the book observes, 'And so we beat on, boats against the current, borne back ceaselessly into the past.'
Its narrator works in a New York securities firm, lives in the West Egg section of Long Island, and has dinner with Tom Buchanan and his wife, Daisy.
'Daisy was my second cousin once removed, and I'd known Tom in college,' Nick Carraway explains.
His neighbor, Jay Gatsby, gives Saturday evening parties as fabulous as his origins and the source of his wealth are mysterious. 'The truth was that Jay Gatsby of West Egg, Long Island, sprang from his Platonic conception of himself,' Fitzgerald wrote.
Gatsby hoped the wild Bacchanalia would bring back Daisy, his former lover.
Because of his link to Daisy, Carraway is recruited into Gatsby's scheme to win her back. Gatsby dangles the prospect of giving Carraway business. The scheme is further complicated because Tom Buchanan is cheating on Daisy.
That soap-opera scenario is made palatable by the poetic beauty of Fitzgerald's imagery, such as: 'Her remark was addressed to the premature moon, produced like the supper, no doubt, out of a caterer's basket.'
But the novel didn't sell, and Fitzgerald sustained himself by churning out move scripts in Hollywood. Many weren't filmed. Others rewritten by teams of heavy-handed script doctors.
When King visited him there, Fitzgerald was drunk and incoherent. He died in 1940, broke and thinking he was a failure.
His death was followed by a real-life epilogue akin to a schmaltzy movie: 'The Great Gatsby' became a best seller and a perennial entry on the reading list of high school English courses. Over the 100 years until the Cambridge Centennial Edition was displayed in bookstore windows this year, approximately 30 million copies of 'The Great Gatsby' had been sold.
As Fitzgerald once noted: 'An author ought to write for the youth of his own generation, the critics of the next, and the school masters of ever afterward.'
Ron Grossman is a columnist emeritus for the Chicago Tribune. His columns vary from social and political commentary to chapters in Chicago history. Before turning to journalism, Grossman was a history professor. He is the author of 'Guide to Chicago Neighborhoods.'