Will the Real Great Gatsby Please Stand Up?

F. Scott Fitzgerald couldn’t resist putting his own life into his novels, but where’s the line between truth and fiction?

Leonardo DiCaprio plays Jay Gatsby in the latest adaptation of F. Scott Fitzgerald's novel (© Warner Bros / courtesy Everett Collection / Everett Collection)

Years after he wrote The Great Gatsby, in the back leaf of another book, F. Scott Fitzgerald scribbled a list of his most famous novel’s nine chapters. Next to each one, he wrote down his sources. There were the old-money, polo-playing Rumsies and Hitchcocks and the impressive parties thrown by movie director Allan Dwan and by Herbert Bayard Swope, the editor of the New York World. There were his own memories, of the ash heaps, of days spent in New York City, and, in particular, of one wedding—the wedding of Ginevra King, his first love. Out of the whole book, he marked only three chapters as “an invention,” “inv” or “all an invention.”

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Fitzgerald did not mean for The Great Gatsby to draw heavily from his own life. His first book, This Side of Paradise, had lifted from his days as a Princeton student, and his second, The Beautiful and the Damned, from his relationship with his wife, Zelda. As he was beginning to start work on the novel that would become The Great Gatsby, Fitzgerald wrote to his editor, Max Perkins, complaining that, at 27, he had dumped more of his personal experiences into his fiction than anyone else he knew. This next novel, his new novel, would be different. “In my new novel I'm thrown directly on purely creative work,“ he wrote, “not trashy imaginings as in my stories but the sustained imagination of a sincere and yet radiant world.” 

But as he wrote his book, he ended up drawing on the rowdy elegance of the Roaring Twenties milieu in which he lived to recreate that radiant world.

"He's borrowing from various kinds of sources to get his story across,“ says Scott Donaldson, the author of the Fitzgerald biography Fool for Love. "But he's really writing about himself in the book. And that's why it's so intimate and why it still resonates, I think."

To create Jay Gatsby, though, Fitzgerald also borrowed from the lives of other men, and devotees have been trying to pin down his real-life inspirations for decades. “The search for Gatsby has been one that preoccupied and eluded scholars and continues to,” says Bryant Mangum, a professor of English at Virginia Commonwealth University and the editor of F. Scott Fitzgerald in Context. “There are many, many models for Gatsby.” 

It’s pretty well agreed upon that Fitzgerald took Gatsby’s backstory from his friend Robert Kerr. In the novel, Gatsby’s rise to riches begins when, out rowing on Lake Superior, he meets a yacht owner and winds up working on the boat as a body man and confidante. As a young man, Kerr had rowed out to warn a “mysterious yachtsman” of a dangerous tide and had signed on to his service. Like Gatsby’s yacht owner, Dan Cody, Kerr's yachtsman had a saucy, famous journalist for a mistress—Nellie Bly.

But this is just the beginning of Gatsby’s career, a story he keeps secret. By the time the novel begins, the man who rowed out to the yacht, the young, striving James Gatz, has already transformed into Jay Gatsby—the mansion dweller who throws lavish parties, the businessman whose business dealings are not clearly honest, the bootlegger who’s obsessed with winning Daisy back.

The Great Gatsby is set in “West Egg” and “East Egg”—Long Island communities based, respectively, on Manhasset and Great Neck, where the Fitzgeralds had moved with their newborn daughter in 1922. As they got to know their fun-loving Great Neck neighbors, they met more than one man who might have served as the model for this Gatsby. "I have unearthed some of the choicest bootleggers," Zelda wrote to a friend not long after the move. One of Fitzgerald’s closest friends, Edmund “Bunny” Wilson, wrote a play in which a character who very much resembles Fitzgerald describes his new novel’s protagonist: "He's a gentleman bootlegger; his name is Max Fleischman. He lives like a millionaire." In the margins of his copy of the play, Fitzgerald wrote, “I had told Bunny my plan for Gatsby.”

Later in his life, Fitzgerald wrote to his friend John Peale Bishop that Gatsby "started out as one man I knew and then changed into myself." There are a couple of other clues, however, that a certain bootlegger, Max Gerlach, was the “one man” Gatsby began as. Arthur Mizener, a Fitzgerald biographer, wrote that Zelda, later in her life, said that a man named “von Gerlach” was the model for Gatsby. And in 1923 Gerlach wrote a note to the author, which Fitzgerald’s daughter, Scottie, kept. It ends with Gatsby’s signature phrase, which appears 45 times in the novel: “Enroute from the coast—Here for a few days on business—How are you and the family old sport?”

But playing this game gets frustrating. Matthew Bruccoli, the leading Fitzgerald scholar for decades, was convinced that there was more to find out about the connection between Gerlach and Gatsby. At one point, he hired a private investigator to track down more of Gerlach’s history. Around the same time, another Fitzgerald scholar, Horst Kruse, was digging into the connections between Gerlach and Fitzgerald as well.

About Sarah Laskow
Sarah Laskow

Sarah Laskow is a Brooklyn-based writer and editor of Smart News. Her work has appeared in print and online for Grist, GOODSalon, The American Prospect, Newsweek, New York among other publications.

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