But although these scholars (and the private detective) learned more about Gerlach’s life, the more details they turned up, the less likely it seemed that Fitzgerald modeled Gatsby directly on Gerlach, who was not just a bootlegger, but spent many less glamorous years as a car dealer.
This is where this game starts to lose its charm: the more you try to match Fitzgerald’s fiction up with his life, the more tenuous the connections become.
“When I began to study Fitzgerald, it looked very easy,“ says Fitzgerald scholar James L.W. West, III, who has written most extensively about Ginevra King, Fitzgerald's own first love. “You read about his life and you read his novels, and you said oh”—that person becomes that character. “The further you go with Fitzgerald, the more complicated it becomes.”
Some characters do seem to have straightforward inspirations. The golfer Jordan Baker, a close friend of Gatsby's long-lost love, Daisy Buchanan, is based on golfer Edith Cummings, the first female athlete to appear on the cover of Time magazine and a close friend of Ginevra. Meyer Wolfsheim, the underworld connection who, Fitzgerald intimates, is one source of Gatsby’s mysterious fortune, fixed the 1919 World Series—just like Chicago gambler Arnold Rothstein was rumored to have done.
But Daisy’s husband, Tom, could have been one or all of the pack of wealthy and imposing men that Fitzgerald knew: Tommy Hitchcock, who, like Tom Buchanan, owned polo ponies and a beautiful house on Long Island, or Ginevra’s father, Charles King (also the owner of a string of polo ponies), or her husband, who came from Chicago’s uppermost social stratum, like Tom.
Daisy herself takes bits from Zelda: she holds the same hope for her daughter that Zelda had for hers—that she’ll be “a beautiful little fool.” But Daisy also resembles Ginevra—she's willing to flirt with a suitor who's not born into money but decides to marry a man of her own class, just as Ginevra did. Ginevra certainly served as a beginning point for Daisy—and many other of the wealthy, unattainable women who Fitzgerald wrote about. In Ginevra's letters, though, West says, he found a kind-hearted, irreverent girl quite distinct from the cold-hearted little rich girl that Daisy can be. The woman who stole Gatsby's heart was, in the end, one that Fitzgerald dreamed up, a puzzle almost a complicated as Gatsby himself.
Not all novels are as playfully resistant to this type of autobiographical analysis. In Ernest Hemingway’s first novel, The Sun Also Rises, published in 1926, just a year after Gatsby, the characters closely resemble the people in his life, one to one. “Brett Ashley is Duff Twysden,” says Donaldson, who’s also extensively studied Hemingway. “There's a whole book about tracking the origins of the novelistic figures to actual people that's extremely persuasive. I don't think that you can do that to Gatsby. There's more distance and more invention going on than in Hemingway's novel.”
But that doesn’t mean that learning about the people in Fitzgerald’s life and the place where he lived won’t help Gatsby fans better understand the book. “He may not be writing directly about his own experiences,” says Donaldson, “but he's writing directly about his emotional connection to what's going on in the world and to the lost, unsuccessful love affair, which is always the one that's most poignant.”