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Water, Water, Everywhere

There were many low points in F. Scott Fitzgerald’s life, but 1936 has to have been his rock-bottom year. Fitzgerald was staying at the Grove Park Inn in Asheville, North Carolina, close to Highland Hospital, a sanitarium where Zelda was being treated for schizophrenia. Fitzgerald himself was recovering from one of his recurrent flare-ups of tuberculosis and valiantly trying to stay on the wagon. The previous year, in an effort to dry out, he had gone so far as to seclude himself in a “dollar hotel”¹ in Hendersonville, North Carolina, for a few weeks, where he lived on potted meat and crackers and washed his shirts out in the bathroom sink. Fitzgerald recalled that “it was funny coming into the hotel and the very deferential clerk not knowing that I was not only thousands, nay tens of thousands in debt, but had less than 40 cents cash in the world and probably a $13. deficit at my bank.”²

For almost all of Fitzgerald’s adult life, debt, like TB, had been a chronic condition. Ever since This Side of Paradise made him the sage of what he’d dubbed the Jazz Age in 1920, Fitzgerald had borrowed against his projected earnings as a writer to support the lavish style of living—servants, blowout parties, European travel, rented mansions—that he and Zelda had adopted. But by 1936, Fitzgerald was sunk in debt so deep that a veritable grand staircase built out of bestsellers would have been required to help him climb up onto firm ground again… and those bestsellers weren’t appearing. The only things that were appearing were bills. Fourteen-year-old Scottie was enrolled in a tony girls’ school in Connecticut; Zelda had been a resident for long stretches at private mental institutions in the United States and Europe ever since her first breakdown, in the fall of 1929 in France, when she was not yet thirty years old.

Fitzgerald’s confidence in his ability to write his way up and out of his financial messes had collapsed during the Great Depression, when literary tastes turned away from stories of giddy extravagance and toward socially conscious “proletarian fiction.” Tender Is the Night came out in 1934 to gentle applause and sold even fewer copies than The Great Gatsby, whose second printing had been gathering dust in the Scribner’s warehouse ever since it was published in 1925. His short stories, which had always been Fitzgerald’s bread and butter, were now being rejected by the very same magazines—the Saturday Evening Post, McCall’s, Collier’s—that had made him one of the highest paid American writers of the 1920s. Ill and deeply depressed, Fitzgerald diagnosed himself as being in a state of “emotional bankruptcy.”³

Those were just some of the by-now-familiar miseries of Fitzgerald’s life in 1936—a “nightmare” year that, as he would later tell his old Princeton friend John Biggs, had “a long build up to it.… After about six good punches you can be knocked down by carefully blown beans and that was what was happening.”⁴ Some of those punches were self-inflicted. While he’d been holed up in that crummy hotel in Hendersonville in 1935, Fitzgerald had written three essays that surgically probed his own despair. Esquire magazine bought the essays, later collected and released as The Crack-Up, at the bargain price of two hundred and fifty dollars apiece and began publishing them in February 1936. If Fitzgerald was generally dismissed as a Jazz Age literary relic in the Dirty Thirties, he was way too far ahead of his time with these confessional essays. Nowadays, the Crack-Up trilogy is venerated for its self-flagellating brilliance, but when the essays first appeared, they were greeted with regret by Fitzgerald’s great friend and editor Maxwell Perkins—he referred to them as the “cracked-plate” essays—and with scorn by chest-thumping peers like John Dos Passos and Ernest Hemingway.⁵

Hemingway in particular was appalled by such a public display of weakness from the writer who had once been his more famous contemporary. A great believer in toughing out depression with ridicule, Hemingway responded to a glum letter he’d received from Fitzgerald in 1935 by playfully suggesting that he, Hemingway, could arrange to have Fitzgerald murdered in Cuba so that Scottie and Zelda could collect the life insurance. On a roll, Hemingway further proposed scattering the dead Fitzgerald’s innards around significant landmarks of his life, donating “your liver… to the Princeton Museum, your heart to the Plaza Hotel… [and] if we can still find your balls I will take them via the Ile de France to Paris… and have them cast into the sea off Eden Roc.”⁶ Hemingway must have really gotten a kick out of that last image because he concluded this nasty letter with an even nastier poem he’d made up in the punning modernist style of T. S. Eliot and James Joyce. The poem is entitled “Lines to Be Read at the Casting of Scott Fitzgerald’s Balls into the Sea from Eden Roc (Antibes Alpes Maritimes).” Its last line imagines Fitzgerald’s manhood flung into the waves, “no ripple make as sinking sanking sonking sunk.”

As in so many of these exchanges after the first bloom of the friendship had faded, Hemingway comes off sounding like a bullying Tom Buchanan to Fitzgerald’s vulnerable Gatsby.

Then, as if the worst year of Fitzgerald’s life cried out for a symbolic moment to encapsulate his sense of being all washed up, summer came round and tempted Fitzgerald to go swimming. Every biography of Scott and Zelda presents a slightly different version of this story, but I prefer the one that Fitzgerald’s first biographer, Arthur Mizener, tells because it includes Zelda.⁷ One hot day in July, Scott drove over to Highland Hospital and checked Zelda out for a day trip to a local pool. The Fitzgeralds had always liked sloshing about. So many of the famous photographs of the couple and anecdotes about their lives involve water: pools and fountains; oceans and bathtubs. When Nancy Milford wrote her bestselling biography Zelda in 1970, she interviewed former classmates of Zelda’s who still remembered her as a beautiful teenager in Montgomery, Alabama, in 1916, scandalizing onlookers at a pool with her one-piece flesh-colored bathing suit that gave the illusion she was swimming in the buff.⁸ During their Roaring Twenties heyday in New York, Scott and Zelda were notorious for their impromptu leaps into fountains at Union Square and in front of the Plaza Hotel. There are even stories about Scott and Zelda, together and individually, making an “impression” at parties in the 1920s by taking off their clothes and disappearing into their host’s bathtub. These devil-may-care displays had grown more disturbing by 1926. That summer, Scott and Zelda were vacationing on the Riviera in the company of Gerald and Sara Murphy, the wealthy couple who served as hosts to so many artists and writers of the period (and who partly inspired the characters of Nicole and Dick Diver in Tender Is the Night). One evening, Zelda decided she wanted to climb diving rocks high above the sea. She stripped to her slip and turned to Scott, asking if he cared for a swim. He accepted her dare. The two dived from successively higher and higher rocks until they both finished the last dive at thirty feet. When Sara Murphy chided Zelda for her reckless behavior (the Fitzgeralds’ daughter, Scottie, would have been just four at the time), Zelda responded in her soft Southern accent: “But Sayra—didn’t you know, we don’t believe in conservation.”⁹

On that summer’s day in 1936 at the pool in Asheville, the now middle-aged and ailing Fitzgeralds must have been walking examples of the physical and mental consequences of not believing in “conservation.” Happily, though, Scott was feeling good that day. Maybe his unexpected sense of well-being made him flash back to that night on the Riviera a decade ago when he and Zelda had played Russian roulette with the rocks below and won. In any event, he got careless: Diving from a fifteen-foot board (“which would have seemed modest in the old days,” Fitzgerald lamented afterward to a friend¹⁰), he became overconfident and started “to show off for Zelda.”¹¹ He fractured his shoulder in midair, and his arm was so badly damaged it dangled a couple of inches out of the socket.

“No ripple make as sinking sanking sonking sunk.”

The great theme running throughout all of Fitzgerald’s writing—and his life—is the nobility of the effort to keep one’s head above water despite the almost inevitable certainty of drowning. While the name of the hero in Fitzgerald’s last completed novel has always struck me as comic-book silly, Dick Diver bluntly spells out what Fitzgerald’s work is all about. His best characters dive into life with abandon and then must fight to stay afloat. By the end of their stories, they’re almost always going under, if not altogether sunk, weighted down by money worries, overwhelming desire, the burden of their pasts.

A snapshot of an anonymous diver from Fitzgerald’s personal photo album of his first trip to the Riviera. (MATTHEW J. & ARLYN BRUCCOLI COLLECTION OF F. SCOTT FITZGERALD, UNIVERSITY OF SOUTH CAROLINA LIBRARIES)

The upward arc of the dive is all about aspiration, and it’s glorious: think of Gatsby flinging himself into a frenzy of parties and home redecoration in order to win back Daisy. Like the high-flying Gatsby, Fitzgerald himself started out by aiming for “the silver pepper of the stars.”¹² Indeed, Fitzgerald recorded in his notebooks that his very first word as a baby was up. But what goes up must come down. It’s a literal downer to read through any of the thirty-some-odd biographies of F. Scott Fitzgerald. There were so many evenings when I’d come home from my office at Georgetown or from the Library of Congress after finishing yet another account of Fitzgerald’s rise and fall and be good for nothing but walking the dog in the gloaming and then going to bed. Retracing Fitzgerald’s doomed life story over and over again reminded me of shuffling around the Stations of the Cross during Lent, back when I was a student in Catholic school—something Fitzgerald would have done, too, in his Catholic boyhood. Both pilgrimages end with a triumphant resurrection, but there’s a hell of a lot of misery to wade through first. Here are just a few selected stops on the Fitzgerald journey. Station 1: Disappointing sales and mixed reviews of Gatsby: “F. Scott Fitzgerald’s Latest a Dud” crows the headline in the New York World on April 12, 1925. Station 2: Following her initial hospitalization in Paris, Zelda enters Prangins, a Swiss mental clinic, in the summer of 1930, after bizarre behavior culminating in a suicide attempt becomes impossible to ignore. The Fitzgeralds’ marriage falls apart as Zelda spends the rest of her life in and out of mental institutions. In 1938, Fitzgerald writes to one of Zelda’s doctors: “I cannot live in the ghost town Zelda has become.”¹³ Skipping now to Station 4: Treasured friendship with Hemingway disintegrates. (One major irritant was the fact that Gertrude Stein had opined to both Hemingway and Fitzgerald that Fitzgerald was the better writer, the one with “the brightest flame.”) And now to Station 7: After nine years of work, in 1934, Fitzgerald finally finishes Tender Is the Night. Reception and sales in the depths of the Great Depression were respectable, but Fitzgerald regarded it as a “stillbirth.”¹⁴ Station 11: Weeks after the diving accident, at four o’clock in the morning, Fitzgerald, still in a plaster cast, trips on his way to the bathroom and makes an agonizing crawl to the hotel-room phone to call for rescue. A bad cold and arthritis set in. Mean-spirited “birthday interview” with Fitzgerald appears on front page of the New York Post on September 25, 1936. The headline of the article by Michel Mok reads: “The Other Side of Paradise: F. Scott Fitzgerald, 40, Engulfed in Despair.” Shortly thereafter, Fitzgerald attempts suicide. When he regains his spirits, Fitzgerald begins referring to Mok as “Michael Muck.” Station 13: Move to Hollywood, where Fitzgerald is treated dismissively by MGM as a Mr. Fix-It man on a number of scripts, including Gone with the Wind. Station 14: Fitzgerald dies on December 21, 1940. His promising Hollywood novel, which he planned to call The Love of the Last Tycoon, remains unfinished at his death. Fitzgerald’s funeral mirrors Gatsby’s: both services are held in the rain and are sparsely attended. In her unpublished memoir, Scottie Fitzgerald recalled that the Protestant minister who buried her father said, “The only reason I agreed to give the service, was to get the body in the ground. He was a no-good, drunken bum, and the world was well-rid of him.”¹⁵

Throughout the 1930s, Fitzgerald would be hospitalized several times for alcoholism. (During his worst binges, he would consume a quart of gin and twelve bottles of beer a day.)¹⁶ One can understand why he wanted to drown his sorrows in liquor. But even during his long, long free fall, Fitzgerald never stopped trying to reclaim the success that had been his as a young man of twenty-three, when This Side of Paradise came out. “Can’t repeat the past?” asks Gatsby in his signature line, “Why of course you can!” In the foolhardy attempt to once more strain upward, a prematurely aged Fitzgerald fractured his shoulder; a few short years later, he’d be dead. The official cause was a heart attack. Factors contributing to Fitzgerald’s frailty—he was a mere forty-four years old—were a lifetime awash in liquor and his recurrent TB, which had plagued Fitzgerald as early as his Princeton years. TB can fill a sufferer’s lungs with fluid, so maybe it’s not too morbidly fanciful to say that even when Fitzgerald was at the height of his Roaring Twenties success, he always carried the threat of drowning within his own body.

Sink or swim. It’s the founding dare of America, this meritocracy where everyone—theoretically, at least—is free to jump in and test the waters. The fear is, however, that if you don’t make it, you’ll vanish beneath the waves. So much of American literature is saturated with images of drowning, dissolving, being absorbed by the vastness of the landscape or crowds: it’s our national literary nightmare. Need I do more to start off the soggy Great Books parlor game than mention Moby-Dick? We spend so much time on our initial high-school forays into Gatsby focusing on those look-at-me! symbols of the green light and the eyes of Dr. T. J. Eckleburg (tailor-made for AP English exam questions) that we overlook the most pervasive symbol of all: water. Permit me, then, to begin this voyage out into Gatsby by retrieving some of the crucial messages about going under that inform Fitzgerald’s anxious masterpiece.

Almost every page of the novel references water; even the briefest summary of its plot is soaked to the bone: James Gatz is born again as Jay Gatsby through a watery rite of passage on Dan Cody’s yacht; he drowns (symbolically) in his pool when his dreams spring a leak and he can no longer float. Page for compact page, The Great Gatsby may be our dampest exemplar of the Great American Novel. Fitzgerald didn’t just stick his toes in the water here; in this, his most perfect meditation on the American Dream and its deadly undertow, he dives in and goes for broke.

People who don’t really know much about Fitzgerald’s work think, as so many of his proletarian critics in the 1930s did, that all he wrote about were the beautiful people buoyed up on bootlegged champagne bubbles. (When Tender Is the Night came out, Philip Rahv reviewed it for the Daily Worker and, invoking the novel’s Riviera setting, famously took Fitzgerald to task for his attraction to the rich: “Dear Mr. Fitzgerald, You can’t hide from a hurricane under a beach umbrella.”¹⁷) People think that Fitzgerald loves the rich, the good swimmers in this extended metaphor. How ironic that The Great Gatsby has been casually thought of by generations of readers (and moviegoers) as a celebration of Jazz Age wretched excess. Think, if you will, of the product tie-ins to the recent Baz Luhrmann film of Gatsby. Advertisements for the Tiffany and Brooks Brothers Gatsby collections touted a vintage pearl and diamond headpiece for $200, a straw boater for $198, and, of course, the famous pink suit—yours for a cool $1,000. Fitzgerald himself bears some blame for the cultural fascination with the bling in the novel. He and Zelda reveled in conspicuous consumption. When Fitzgerald describes Gatsby Land, he does so with an avid connoisseur’s eye, so its sumptuous details lodge in our brains: the chauffeur tricked out in a uniform of “robin’s egg blue,” the buffet tables groaning with “salads of harlequin designs and pastry pigs,” the bedrooms “swathed in rose and lavender silk,” and, most of all, the shirts—“shirts of sheer linen and thick silk and fine flannel… shirts with stripes and scrolls and plaids in coral and apple green and lavender and faint orange with monograms of Indian blue.”¹⁸

But don’t whip out the credit cards just yet. Simultaneous with all this delight in extravagance, there’s also a vigorous resentment of the upper class in Fitzgerald. Remember, this is the guy who famously said, “The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.”¹⁹ Fitzgerald may not have been overtly political in his life or writing the way that contemporaries like Hemingway and Dos Passos were (Fitzgerald quietly voted for Roosevelt), but his class politics were personal and intense. At key moments in his writing Fitzgerald betrays the scorn of the poor relation, the self-made man, railing against (and envying) those trust-fund babies who take their privilege for granted. In his 1931 essay “Echoes of the Jazz Age,” Fitzgerald anticipates the rhetoric of Occupy Wall Street when he talks about the “upper tenth”: “It [the Jazz Age] was borrowed time anyhow—the whole upper tenth of a nation living with the insouciance of grand dukes and the casualness of chorus girls.”²⁰

One place you can hear Fitzgerald’s ideas about class and America’s meritocratic promise expressed with uncharacteristic directness is in his letters to his daughter. Beginning in adolescence, Scottie was sent to exclusive East Coast boarding schools and eventually to Vassar. At times, Fitzgerald worried that she was in danger of turning into an entitled layabout. His “Tiger Dad” letters to Scottie, most of them written in the late thirties when Fitzgerald was working in Hollywood, constitute a series of epistolary kicks in the butt on the virtues of hard work and “keep[ing] your scholastic head above water.”²¹ In one letter, Fitzgerald worries that Scottie may be “accepting the standards of the cosmopolitan rich” and warns that “if I come up and find you gone Park Avenue, you will have to explain me away as a Georgia cracker or a Chicago killer.”²² Preparing Scottie for her first year at Vassar, Fitzgerald, surprisingly, writes: “You will notice that there is a strongly organized left-wing movement there.… I do not want you to set yourself against this movement. I am known as a left-wing sympathizer and would be proud if you were.”²³ In an undated fragment that comes from the same period, Fitzgerald recommends Marx: “Sometime when you feel very brave and defiant and haven’t been invited to one particular college function, read the terrible chapter in Das Kapital on ‘The Working Day,’ and see if you are ever quite the same.”²⁴ And then there’s this letter, written six months before he died, in which Fitzgerald puts himself forward as exhibit A of a great talent damaged by sloth and self-doubt. It’s addressed to Scottina, one of the many nicknames Fitzgerald gave to his daughter: “What little I’ve accomplished has been by the most laborious and uphill work, and I wish now I’d never relaxed or looked back—but said at the end of The Great Gatsby: ‘I’ve found my line—from now on this comes first. This is my immediate duty—without this I am nothing.’ ”²⁵

Even allowing for the fact that these letters are written by a middle-aged and often depressed Fitzgerald, they don’t sound like the thoughts of a man who uncritically worships wealth and luxury consumer goods. Yet the most famous anecdote about Fitzgerald—the one that even people who’ve never read him know—ridicules what’s alleged to be his wide-eyed reverence for the rich. The fact that, as so many scholars have pointed out, the anecdote is false doesn’t make a dent in its malicious authority. Hemingway and Fitzgerald are talking one day in Paris, and Fitzgerald breathlessly declares: “The rich are different than you and me.” Hemingway, comeback at the ready, growls, “Yeah, they have more money.” It might be pretty to think so, but that’s not the way that conversation actually happened. Hemingway and the critic Mary Colum had a conversation in the 1920s during which Hemingway uttered “the rich are different” line and Colum gave him the witty comeback. Later, Hemingway made Scott the butt of the joke in “The Snows of Kilimanjaro” and in his beautiful-but-corrupt memoir of Paris in the 1920s, A Moveable Feast. Here’s Fitzgerald, through the unnamed narrator of his 1926 story “The Rich Boy,” giving quite another spin to those lines that Hemingway later distorted:

“Let me tell you about the very rich. They are different from you and me.… They think, deep in their hearts, that they are better than we are… because we had to discover the compensations and refuges of life for ourselves. Even when they enter deep into our world or sink below us, they still think that they are better than we are. They are different.”²⁶

Sure, Fitzgerald writes about the rich and enjoyed living large, but he’s clear-eyed about the limits of money. He knows how near impossible it is to swim the marathon distance between West Egg and East Egg. “Americans should be born with fins,” he wrote in his bluntly titled story of 1929 “The Swimmers.” “Perhaps they were,” he continues, “perhaps money was a kind of fin.”²⁷ But Fitzgerald also knows that money isn’t enough to keep a striver afloat; breeding counts too. Even in one of the lushest, most romantic moments of the novel—the reunion of Daisy and Gatsby in chapter 5—Fitzgerald wedges in an ominous comment about class differences. Gatsby is showing Daisy around his mansion and calls in Klipspringer, the freeloading houseguest, to provide background music on the piano. What song does Klipspringer bang out after he finishes a rendition of “The Love Nest”? The 1920 foxtrot “Ain’t We Got Fun,” with its lines that declare “The rich get richer and the poor get—children.”

Look again at those words about the rich spoken by Fitzgerald’s narrator in “The Rich Boy”: Even when they enter deep into our world or sink below us, they still think that they are better than we are. They are different. That’s a statement about class, not money; it’s a statement about an internalized sense of privilege born out of wealth and out of what Fitzgerald called in a 1933 letter to his friend and fellow novelist John O’Hara “breeding.” Fitzgerald is one of our most sensitive literary chroniclers of class. He obsesses on the subject throughout most of his short stories and novels but nowhere more exquisitely and painfully than in Gatsby.

In focusing on class, Fitzgerald was following the old saw of “write what you know.” He came from people who were never quite certain where they stood, economically and socially. As a child, he saw firsthand what it was like for his family to almost go under. Of all our great writers, especially in the modern age, he has the most finely tuned antennae for the facial expressions, accents, manners, clothes, and posture that separate those to the manner born from those who desperately wanna be. Remember the comical way in which Nick, upon first seeing Jordan Baker, describes the way she holds her head? “She was… completely motionless and with her chin raised a little as if she were balancing something on it which was quite likely to fall.”²⁸ That’s the posture of a girl who’s so snootily self-assured, she doesn’t even bother to lower her head to nod at her hostess’s cousin. No wonder Nick falls (a little) for her.

That quick moment in Gatsby reveals one of Fitzgerald’s big insights about the rich: he knows that what makes them different is that they don’t need to try as hard as other people do. They float as if by birthright. Floating images cluster like jellyfish throughout Gatsby. They first surface in that aforementioned opening scene, where Nick enters the Buchanan mansion and glimpses Daisy and Jordan: “The only completely stationary object in the room was an enormous couch on which two young women were buoyed up as though upon an anchored balloon. They were both in white, and their dresses were rippling and fluttering as if they had just been blown back in after a short flight around the house.”²⁹ People generally remember that passage, even if it’s been many years since they read Gatsby in high school, because its language and images are so gorgeous. Daisy and Jordan loll about in such languid fashion, they’re virtually weightless. Tom, admittedly, is filled with passionate intensity about the invading hordes of darker-skinned immigrants pouring into America; otherwise, he’s idle. Early in the novel—before he rouses himself to obstruct Gatsby’s campaign for Daisy—Tom is little more than a wealthy former college football player gone to seed; he plays at life, the same way our entitled narrator, Nick, dabbles at learning the investment business.

It’s clear from that very first scene that Gatsby doesn’t belong with this crowd, that he’s never going to win Daisy precisely because he must try too hard to do so. That’s another reason why the novel begins with Nick presenting his class credentials for our inspection: we implicitly understand, as the story unfolds, that though Gatsby has plenty of money, he lacks breeding as well as cultural capital. The fact that he fills up a library with finely bound volumes (though, tellingly, their pages are uncut and, thus, unread) underscores that Gatsby feels his lack of education. Gatsby possesses merely what Meyer Wolfshiem calls “gonnegtions.” Briefly summarized, Fitzgerald’s waterlogged masterpiece about the realities of class in America is the story of a poor boy, “Mr. Nobody from Nowhere,” who, by his wits, contrives to get pulled up out of the waves of Lake Superior by a rich man, Dan Cody, who’s aimlessly sailing around the world on his yacht. Cody transforms young Gatz into a successful sailor (blue coat, six pairs of white duck trousers, and a yachting cap). But Gatz—by now metamorphosed into Gatsby—makes the fatal mistake of succumbing to a siren.

Though the film versions of The Great Gatsby would tell us otherwise, Daisy is never described in the novel as a total knockout. Instead, the thing that lures men close is her voice, a voice “full of money.”³⁰ Gatsby tries hard to win her and what she represents. The first time we see him in the novel, he’s standing in the dark, stretching out his arms to Daisy’s green light across Long Island Sound. She’s in East Egg, he’s in West Egg, and they’re separated by the Sound. That odd geographical formation of “the pair of enormous eggs”³¹ claims so much attention that, understandably, the fact that a body of water separates the eggs is barely noticed by most readers on their first forays into the novel. Fitzgerald, however, devotes more space in the novel to describing Manhasset Bay and Long Island Sound than he does the eggs.

In the pivotal reunion scene between Gatsby and Daisy, Gatsby’s death by drowning is already foretold. Recall that it rained almost all day. When the unsuspecting Daisy arrives for tea at Nick’s cottage, Gatsby, who’s been waiting anxiously for her, flees. Then there’s a knock at the door. Nick opens it to find that “Gatsby, pale as death, with his hands plunged like weights in his coat pockets, was standing in a puddle of water glaring tragically into my eyes.”³² In Gatz and in the 2013 Baz Luhrmann film of Gatsby, this scene gets a lot of laughs from the audience—particularly in the latter, given that screen idol Leonardo DiCaprio was the guy standing at that door, dripping wet. Fitzgerald, however, isn’t playing this moment strictly for comedy.

The last time we see Gatsby, he’s literally dead in the water. Gatsby may have been killed by George Wilson’s bullets, but he’s a dead man the minute he falls for Daisy the siren. Gatsby “run[s] faster, stretch[es] out [his] arms farther,” until, propelled by all that yearning, he leans too far out toward Daisy’s dock, falls into the Sound, and drowns. Gatsby’s pool, with its “little ripples that were hardly the shadows of waves,”³³ is the Long Island Sound in miniature.

Skeptics out there may think that the claim about Gatsby’s pool symbolically standing in for the Long Island Sound is, to use twenties slang, “all wet.” I’ll top it. This novel’s obsession with water and drowning imagery seeps into its very punctuation. I’ve already quoted part of the penultimate paragraph of Gatsby, but here’s the entire famous passage:

“Gatsby believed in the green light, the orgastic future that year by year recedes before us. It eluded us then, but that’s no matter—tomorrow we will run faster, stretch out our arms farther.… And one fine morning——”³⁴

Some critics have been struck by that extra-extra-long dash at the end of the final sentence fragment, “And one fine morning——” A few have even suggested that that supersize dash is a visual representation of the end of Gatsby’s own dock, near where we first see him at the close of chapter 1, stretching out his arms to Daisy’s dock across the Sound. If, to invoke Fitzgerald’s own language, we “run faster, stretch out our arms farther,” then, inevitably, there will come a day, like the day Gatsby died in his pool, when we reach the end of the dock, fall off, and drown. If you buy that reading, as I do, then that dash-as-dock punctuation that Fitzgerald implanted near the very end of Gatsby may just be one of the first graphic novel moments in American literature.

Whether all our frantic effort is noble or wasted—whether, in short, meritocracy really exists in America—is one of The Great Gatsby’s central questions. That’s the reason the novel so incessantly splashes about in water and drowning imagery: to consider the question of just how far a nobody in America can swim before he sinks. No wonder, then, that in the recent years of our own Great Recession, when mortgages are underwater and people are drowning in credit card debt, Gatsby has been cited frequently by cultural commentators. As Fitzgerald himself was thrashing about in the depths of his own personal depression in 1936 (when, as he chillingly put it in that interview with Michel Mok, “it’s always 3:00 in the morning, day after day”³⁵), he too must have wondered about whether, as a writer, he was still afloat above the masses or going, going, gone.

There’s one character in The Great Gatsby who bobs between the high-class world of the wealthy (the floaters) and the lower-class one of the strivers—including that “poor son-of-a-bitch” who drowns. I’m talking, of course, about our narrator, Nick Carraway. Nick is such a likable guy that it’s easy to forget that he’s one of Them. But Nick is, after all, Daisy’s cousin; he’s got breeding and bucks. Despite the fact that he’s crashing for the summer in a cottage in “less fashionable”³⁶ West Egg, virtually in the shadow of Gatsby’s garish mansion, Nick is an American aristocrat interning on Wall Street. In the light of the romance that dominates Gatsby’s plot and the enigma that is our title character, Nick’s opening riff on his pedigree (which reads as though he’s trying to impress the co-op board of an exclusive New York City apartment building) would mark him as a shallow snob, except for the fact that, as his last name signals to readers, he’s been carried away by Gatsby. Unlike Daisy and company, Nick possesses emotional depth and the secret soul of a poet. We need a character like Nick in The Great Gatsby, someone who’s an insider but who’s alienated and sensitive enough to appreciate—indeed, love—a noble striver like Gatsby. We also need Nick in this novel for practical reasons: he’s our survivor. The only reason we readers are treated to Gatsby’s story in the first place is that Nick dodges not only the wreck that kills poor Myrtle Wilson, but the two other violent deaths that follow, which effectively end the party that was the summer of 1922. I do mean wreck in the maritime sense too. Nick follows in the wet footsteps of Moby-Dick’s Ishmael as well as those of the unnamed narrator of The Rime of the Ancient Mariner, Samuel Taylor Coleridge’s poem about a shipwreck that Fitzgerald particularly liked. Nick, our Jazz Age Ishmael, survives to tell the tale—or, rather, write it, since he makes reference to “these pages” in the prologue to the novel. To do that, he’s got to make it back to dry land. Dry land is the solid ground of the Midwest, the place where F. Scott Fitzgerald was born and first began to absorb his ideas about class and the rise and fall in status that America might just make possible.

Francis Scott Key Fitzgerald: It’s quite a name. In fact, it’s a name that suggests the baby’s parents, Mollie McQuillan and Edward Fitzgerald, were not averse to “putting on airs.” Shortly after he was born in St. Paul, Minnesota, on September 24, 1896, Fitzgerald was christened with that triple-decker moniker that bespeaks Early American connections. Well, sort of. Fitzgerald was indeed related to Francis Scott Key of “Star-Spangled Banner” fame, but the link was distant: they were second cousins three times removed. Fitzgerald’s father, Edward, traced his family roots back to seventeenth-century Maryland. During the Civil War, the Fitzgeralds were sympathetic to the Confederacy. Another, even closer relative (who wasn’t claimed so ostentatiously) was Mary Surratt, who was hanged for conspiracy in the assassination of Abraham Lincoln. The Fitzgeralds, therefore, had “breeding,”³⁷ unlike the McQuillans (Fitzgerald’s mother’s family), who had merely lots of cash. Fitzgerald’s “black Irish” maternal grandfather was the quintessential self-made man, an immigrant who, by the mid-nineteenth century, had risen to become a grocery mogul in St. Paul. Mollie McQuillan, Fitzgerald’s mother, grew up in a Victorian mansion, was educated at a convent school, and traveled to Europe three times. At the near overripe age of twenty-nine, she met and married the charming thirty-seven-year-old Edward Fitzgerald. Soon after, the Irish Catholic princess, Mollie, would find that she had gotten herself hitched to more of a show horse than a sure thing.

Edward was president of a wicker furniture factory in St. Paul; in 1898 it went out of business and he took a job as a wholesale grocery salesman with Procter & Gamble in Buffalo, New York. Three years later, he was transferred to Syracuse, then again back to Buffalo. The family, which by 1901 included Scott’s sister Annabel, lived in apartment hotels and rented flats, anticipating a nomadic pattern that Fitzgerald would follow throughout his adult life.³⁸ Then, in 1908, his father lost his salesman’s job at Procter & Gamble. Edward Fitzgerald was fifty-five, and, as his son recalled in the depths of his own dark night of the soul almost thirty years later, his father “came home that evening, an old man, a completely broken man. He had lost his essential drive, his immaculateness of purpose. He was a failure the rest of his days.”³⁹ The day his father lost his job, eleven-year-old Scott overheard his mother talking about the frightening news on the telephone. When his mother hung up, Scott nobly gave her back the quarter she had just given him to go swimming, because he was sure the family was about to founder.

What happened next was a move into the sort of neighborhood and situation designed to produce—in the kind of sensitive boy Fitzgerald was—a permanent feeling of never quite measuring up. (In that 1933 letter to John O’Hara, where he reflected on his family background, Fitzgerald diagnosed his lifelong problem as “a two-cylinder inferiority complex.”) The Fitzgeralds moved back to St. Paul, to the Summit Avenue section of the city where Mollie’s family owned property. There, Edward was given a job by his brother-in-law, and for the next decade or so, the Fitzgerald family rented apartments and houses in what was then one of the swankiest residential sections of any city in the world. Summit Avenue, at the time Fitzgerald lived there, has been likened to the Fifth Avenue of the Gilded Age. Among the mansions were the University Club, designed by some of the same architects responsible for New York’s Grand Central Station, and the majestic residence of railroad tycoon James J. Hill, who would serve as an inspiration for Gatsby’s Dan Cody.

Thanks to Mollie’s inheritance from her tycoon father, the Fitzgeralds had the money to rent in the Summit section; thanks to their Catholicism and Edward Fitzgerald’s iffy income, they never belonged there in an assured way. When Fitzgerald pilgrims tour Summit Avenue, they can visit two sites associated with the author: his birthplace, at 481 Laurel Avenue, and the row house at 599 Summit Avenue where his parents were living in 1919, the year Fitzgerald moved back home after his engagement with Zelda was broken. The Summit Avenue house is the place where Fitzgerald sealed himself into the top floor throughout the summer of 1919 and doggedly rewrote his draft of This Side of Paradise into a publishable book. Mildly interesting as those sites may be, there is no Fitzgerald House in the way that there is an Emily Dickinson House and a Herman Melville House and a Mark Twain House. Fitzgerald, like his parents, never owned a home. He was a renter all his life.

The sense of being on the outside looking in, of wanting wealth and status and at the same time loathing the easeful rich who take their advantages for granted: these are bedrock elements in Fitzgerald’s fiction and their source can be traced to Summit Avenue. If childhood landscapes engrave themselves on our developing psyches, then Summit Avenue imprinted on Fitzgerald an inner geography of yearning, riven with contempt.

I love that odd moment early in Gatsby where Nick, stuck at that interminable, drunken party in the far Upper West Side love nest shared by Tom Buchanan and Myrtle Wilson, mentally splits into two people: the reluctant insider and the excluded observer:

“I wanted to get out and walk eastward toward the park through the soft twilight but each time I tried to go I became entangled in some wild strident argument which pulled me back.… Yet high over the city our line of yellow windows must have contributed their share of human secrecy to the casual watcher in the darkening streets, and I was him too, looking up and wondering. I was within and without, simultaneously enchanted and repelled by the inexhaustible variety of life.”⁴⁰

This is W.E.B. DuBois’s famous “double consciousness” dramatized through the scrim of class, not race. Alone among Fitzgerald’s novels, The Great Gatsby dramatizes that deeply felt social and psychic split in its very structure. Nick, our narrator, is a watcher, largely shut out of the main events of the story featuring his “high-bouncing” hero Gatsby. But the class situation is even more complicated because Fitzgerald’s “insider,” Gatsby, can’t comfortably settle into the world he’s attained. In terms of social class, Nick is much more of a natural-born insider than the man whose life he’s observing. The constant anxious calibration of insider-outsider status that runs throughout the conversations and descriptive passages in Gatsby constituted Fitzgerald’s everyday reality: he always felt one step down from his wealthier childhood playmates on Summit Avenue, his Princeton classmates, and, later, his fellow writers and artists, many of whom he idolized. He might well have appreciated the black humor surrounding his “first” funeral, where his body was denied interment in the Fitzgerald family plot by the Catholic Church. A final snub.

These rejections—subtle and overt; imagined and real—ate away at Fitzgerald’s self-confidence. It’s striking, too, how many times in his life Fitzgerald displayed over-the-top hero worship of his artistic idols. He flung himself at the feet of Edith Wharton, when he met her for the first time in Scribner’s New York offices, and Isadora Duncan, when he met her in a restaurant on the Riviera. (Wharton was taken aback; Duncan lapped the adulation up.) At a dinner in Paris, Sylvia Beach, the owner of the legendary bookstore Shakespeare & Company, introduced Fitzgerald to James Joyce, and Fitzgerald knelt in front of his idol and feverishly declared that he would show his admiration for Joyce’s genius by jumping out of a nearby window. Joyce stopped him and afterward commented, in puzzlement: “That young man must be mad—I’m afraid he’ll do himself some injury.”⁴¹ (The copy of The Great Gatsby that Fitzgerald presented to Beach as a token of his thanks for that evening is housed in Princeton’s Firestone Library; the inside cover is decorated with a charming drawing in ink by Fitzgerald of that odd dinner party, with Fitzgerald on his knees before Joyce.) The stories about Fitzgerald abasing himself before his disloyal friend Hemingway are especially cringe-making. Toward the end of his life, Fitzgerald definitively threw in the towel on the struggle with his rival when he wrote in his last notebook: “I talk with the authority of failure, Ernest with the authority of success. We could never sit across the same table again.”⁴²

When I think of these and a dozen more examples of Fitzgerald’s self-deprecating behavior, Frank O’Hara’s wonderful poem about his screen idol Lana Turner falling on a New York City sidewalk comes to mind. The last line of “Poem (Lana Turner Has Collapsed!)” reads: “oh Lana Turner we love you get up.” Fitzgerald always prostrated himself before those he revered or thought were his betters. The feeling of being at home in his own skin, of being enough—in terms of class or talent—was a utopian state that Fitzgerald never attained.

Bullies—from the ones in Fitzgerald’s childhood years to Hemingway—naturally took advantage of Scott’s tendency to defer. His angelic good looks couldn’t have helped. Judging by the many photographs that exist, Scott Fitzgerald was the kind of boy—more pretty than handsome—that mothers coo over and that other kids immediately label victim. His hair was golden, his eyes were light (different accounts describe them as green, blue, or gray), and his frame delicate. He liked clothes a lot and cared too much about his appearance; biographer Matthew J. Bruccoli says that “at seven he carried a cane when he went with his father to have their shoes shined on Sunday mornings.”⁴³ Fitzgerald also had a passion for football, but he lacked the build for it. Though he made some friends on Summit Avenue, Fitzgerald didn’t have an easy social passage through childhood and adolescence. For Fitzgerald’s sixth birthday, back in Buffalo, his mother threw him a birthday party and invited a crowd of children. Fitzgerald waited for his guests all afternoon. None of them showed up. At the St. Paul Academy, a private school that Fitzgerald entered at age twelve, he rubbed his classmates the wrong way by nervously bragging about himself. The school magazine, Now and Then, ran an article in which Fitzgerald was described as the know-it-all who freely dispensed wisdom about “How to Run the School”; the article snidely asked if there were not someone who would “poison Scotty or find some means to shut his mouth.”⁴⁴

You want to telepathically and retroactively tell young F. Scott Fitzgerald to calm down, act cooler. But that was never his style. Like the young James Gatz who made Benjamin Franklin–type self-improvement lists on the flyleaf of his copy of Hopalong Cassidy, Fitzgerald was a zealous list-maker from the time he was a boy until his death.⁴⁵ He made daunting self-improvement lists for himself and for his kid sister, Annabel. He wrote a stern letter to her in 1915 in which he enumerated her good and bad physical points: “A girl should always be careful about such things as… long drawers showing under stocking, bad breath, messy eyebrows (with such splendid eyebrows as yours you should brush them or wet them and train them every morning and night”⁴⁶). He put together exhaustive reading lists for Scottie, for Sheilah Graham (who wrote an entire book, College of One, about his Henry Higgins–like tutorials of her), and even for his private-duty nurse Dorothy Richardson, whom he hired after that diving accident in 1936 while he was once again trying to stop drinking. Such relentless striving would get Fitzgerald where he wanted to be, but it didn’t endear him to his schoolmates.

As he would later do at Princeton, Fitzgerald threw himself into the kinds of groups that have always been refuges for social outsiders (these days we might say nerds): the debate club and the drama club. So enthusiastic was Fitzgerald’s participation that his grades tanked. Fitzgerald’s wealthy aunt Annabel agreed to foot the bill for a more rigorous Catholic boarding school, and in 1911 Fitzgerald was packed off to the Newman Academy in Hackensack, New Jersey. Newman’s students were “drawn from the Roman Catholic families of wealth in all parts of the United States.”⁴⁷ There, too, Fitzgerald promptly alienated himself from the other boys by trying too hard, by being boastful, by his determined-but-poor athletic performances, and, worst of all, by not hiding his desire to be acknowledged as special. He was the most unpopular boy at the school, disliked by both students and faculty. In his ledger, Fitzgerald bitterly summarized the school year 1911–1912 as “a year of real unhappiness.”⁴⁸

Isolating as it sounds, Fitzgerald, as most of us do, muddled through. He was particularly helped by his burgeoning ability to achieve notice through his stories printed in the school newspaper and by the saving interventions of Father Sigourney Fay, a thirty-seven-year-old priest who would later serve as headmaster of Newman. These days, any mention of a priest taking special interest in a lonely young boy—especially a pretty one—sets off alarms, but nothing sinister has ever surfaced about their relationship. Portly Father Fay seems to have been one of those worldly priests that one finds in Evelyn Waugh novels: he was attracted to art, good conversation, and creature comforts. The two traveled together to Washington, DC, and the resort town of Deale, Maryland, where Fay’s family had a house. Father Fay fostered his young friend’s literary bent, introducing him to important writers like Henry Adams and the Irish novelist Shane Leslie. (Fitzgerald had a lifelong admiration for the Father Brown mysteries by G. K. Chesterton, perhaps another literary legacy of Father Fay.) Fitzgerald acknowledged the kindness of his priestly mentor when he dedicated This Side of Paradise to Fay (who died in 1919, a year before it was published). It’s likely that Fitzgerald was also thinking of his priestly mentor and friend when he gave Daisy Fay as her last name.

Fay also exerted a spiritual influence over Fitzgerald, stoking the adolescent’s flames of Catholic piety. By the time he entered Princeton, Fitzgerald was no longer a practicing Catholic, but, as many of us Catholic-school veterans are wont to say, “They get you early and they get you good.” Fitzgerald’s Catholicism seems to diffuse throughout his work like incense; occasionally, it coalesces into something more solid. In 1922, Fitzgerald wrote to his editor Max Perkins to say that he was working on a novel with Catholic themes. This is a fragment known to Fitzgerald scholars as the ur-Gatsby. All that remains of this ur-Gatsby is the moody short story “Absolution,” which describes an encounter between a young boy (possibly a childhood version of James Gatz) and a Catholic priest on the verge of a nervous breakdown. Since Gatsby is a novel about worship, it makes sense that its origins would lie in Fitzgerald’s own religious background. Or, to put it another way, Gatsby started life baptized Catholic.

While at Newman, Fitzgerald escaped to Broadway whenever he could, wrote plays during the summer for a local St. Paul amateur group, and published short stories in the school newspaper. Despite all this extracurricular literary activity, Fitzgerald’s graduation-year report card from Newman records that the man who would become one of America’s greatest writers received mediocre grades for his final two semesters of English: a C and a B. (A couple of decades later, Fitzgerald wrote an essay called “How I Would Grade My Knowledge at 40.” The highest mark he gave himself—a B+—was in “Literature and the attendant arts” and “History and biography.” Among the other subjects listed, “Military Tactics & Strategy” rated a D+ and “Marxian Economics” a D.)⁴⁹ Years later, when Scottie was in a slump in high school, Fitzgerald lectured her via letter: “I still believe you are swimming, protozoa-like in the submerged third of your class.”⁵⁰ At the end of his own high-school career, Fitzgerald himself was just another protozoa.

Entering Princeton in the fall of 1913 (tuition paid thanks to the timely death of Grandmother McQuillan that summer), Scott must have felt as though he were forever handcuffed to the same soul-deadening social treadmill at school. Football was the ticket to distinction at Princeton, so Fitzgerald gamely reported for freshman practice. At five foot seven and 138 pounds, he was a washout; some accounts say that he was cut from the squad on the first day. To add to his frosh humiliation, Scott went on to garner an alarming number of votes as “the prettiest” member of his class at Princeton.

But his social stock rose in other ways. Fitzgerald wrote musicals for the Triangle Club and stories for the Princeton Tiger (the humor magazine). As a sophomore, he became a member of the Cottage Club, one of the most prestigious eating clubs on campus. In 1938, looking back in a by-then-characteristic self-pitying mood, Fitzgerald recalled: “That was always my experience—a poor boy in a rich town; a poor boy in a rich boy’s school; a poor boy in a rich man’s club at Princeton… I have never been able to forgive the rich for being rich, and it has colored my entire life and works.”⁵¹ At the time, things didn’t seem altogether bleak: he made lasting friendships with the poet John Peale Bishop and with Edmund Wilson, both then upperclassmen, who would help form Fitzgerald’s reading tastes and, in Wilson’s case, proclaim Fitzgerald’s literary greatness during and after his lifetime. It was to Wilson that Fitzgerald wrote the vulnerable letter in college that included this question: “I want to be one of the greatest writers who ever lived, don’t you?”⁵²

By the time he returned home for the Christmas holidays in his sophomore year, Fitzgerald was every inch the Midwestern boy who’d conquered Princeton, and he was besieged with invitations to Christmas dances. It was at one of those dances that he met sixteen-year-old Ginevra King, who was visiting from Connecticut. Fitzgerald fell hard.

It’s always easy to diagnose (and feel superior to) other people’s neurotic patterns when it comes to relationships. In the three major romances of his life, Fitzgerald was drawn to the same type like a lemming to the sea. The girl—and she would always be “the girl” in his romantic imagination—was young, pretty, daring, very popular, and unavailable. Just as ordinary girls barely appear in his fiction, Fitzgerald himself never seemed to pay much attention to the waitresses and receptionists and secretaries by whom he was surrounded in the streets and offices of New York and Hollywood. Unlike his creator, Nick Carraway briefly goes slumming in The Great Gatsby: Nick tells us that while he was working on Wall Street during that fateful summer of 1922, he “even had a short affair with a girl who lived in Jersey City and worked in the accounting department.” So faintly does this affair register, however, that when the anonymous girl takes a vacation in July, Nick says, “I let it blow away.”⁵³ The kind of alpha girls Fitzgerald idolized were not likely to let themselves be blown off.

Sheilah Graham, Fitzgerald’s last love during his Hollywood years, was a Bright Young Thing engaged to the Marquess of Donegal when Fitzgerald first saw her at a party in the notorious Garden of Allah villas on Sunset Boulevard. Graham surely must have fascinated Fitzgerald because, like Gatsby, she had created a somebody out of a nobody: she had begun life in England as Lily Shiel, a poor Jewish girl who grew up largely in an orphanage in London’s East End. By the time Fitzgerald spotted her, she had been married once and was on her way to becoming a feared Hollywood gossip columnist. Zelda Sayre was the live-wire belle of Montgomery, Alabama, when she and Fitzgerald met, in 1918; Zelda kept many beaux on the string even after she and Fitzgerald became engaged, but the man who presented the greatest impediment to their union was Zelda’s father, the imperious Judge Sayre, who refused to give his daughter’s hand in marriage to Scott until he could prove himself capable of supporting her in the grand style to which she was accustomed. But before Zelda and Sheilah, there was Ginevra King. At that holiday party in 1914, the eighteen-year-old Scott Fitzgerald met his first out-of-reach, glittering girl to love, worship, and, in this case, lose. The Ernest F. Hollings Special Collections Library at the University of South Carolina has one of Ginevra’s dance cards. It’s tiny, meant to be worn around her wrist in a booklet or decorative case. Ginevra’s prospective dance partners wrote their names on the card, and one of them was a Princeton student who signed himself Scot Fitz on the fifth line with an X next to his name. An X is also written on line six; presumably, Scot Fitz booked a double whirl around the dance floor with Ginevra. So it began.

Because she’s the one who got away, Ginevra—even more than Zelda—is the love who lodged like an irritant in Fitzgerald’s imagination, producing the literary pearl that is Daisy Buchanan. Wistfully reflecting, decades later, on their romance, Fitzgerald referred to Ginevra as: “my first girl 18–20 whom I’ve used over and over and never forgotten.”⁵⁴

Ginevra was petite and dark. (Again, those distorting movie versions of The Great Gatsby have imposed Zelda’s blond radiance on Daisy, but in the novel, she, like Ginevra, is what the beauty magazines used to call a “brown-ette.”) All accounts describe her as beautiful and very rich; we’re talking serious “Diamond as Big as the Ritz”–type money. Ginevra’s father was a Chicago stockbroker, and the family owned a mansion in that city that appears, in photographs, to be the size of a department store. There was also a sprawling country retreat in Lake Forest. Ginevra was used to a life of tennis and polo ponies, private-school intrigues and country-club flirtations. She was one of a clique of Chicago debutantes who became famous in their day for (obnoxiously) referring to themselves as “the Big Four,” because of their uncontested beauty and social desirability. Fitzgerald may have internally identified with the wannabes, but he always dated the queen bees.

Given that Ginevra floated in another galaxy far removed from Fitzgerald’s own—geographically and economically—their two-year romance was mostly conducted via intense letters. Fitzgerald’s to Ginevra were destroyed, at his request, when the relationship ended, but Ginevra’s letters and a diary of hers written mostly during their time together came to light in 2003. In her early letters and diary entries, she sounds endearingly like a teenage girl in the throes of a huge crush: “Am absolutely gone on Scott!” Ginevra’s ardor, though, inevitably waned; after all, Scott was only one of her many beaux. “She ended by throwing me over with the most supreme boredom and indifference,”⁵⁵ he reminisced in a letter to Scottie. Decades after the two parted, Fitzgerald agreed to meet the visiting and now divorced Ginevra for an afternoon in Santa Barbara, California. On and off the wagon throughout his Hollywood years, Fitzgerald was memorably “off” that day and drank too much in order to fortify himself for their reunion. When Ginevra asked him if she had inspired any of the women in his fiction, Fitzgerald responded, “Which bitch do you think you are?”⁵⁶

Fitzgerald should have forthrightly told her, Many of them. Daisy is the most significant literary incarnation of Ginevra, but almost all of the elusive socialite teases in his other novels and short stories bear strong resemblances to her. There’s Isabelle Borge of This Side of Paradise and Judy Jones of the 1922 short story “Winter Dreams,” which Fitzgerald described to his editor Max Perkins in a letter of June 1924 as “a sort of first draft of the Gatsby idea.”⁵⁷ Also in the mix is Paula Legendre, the “dark serious beauty” of “The Rich Boy,” written in 1924 while Fitzgerald was working on Gatsby. Of course, even more than the resemblances to Ginevra, these works have in common their resemblances to Fitzgerald’s anguished feelings about her. In his wound-licking but lyrical 1936 essay “Afternoon of an Author,” Fitzgerald said that the distinctive emotional tone of his fiction was “taking things hard—from Genevra to Joe Mank—: That stamp that goes into my books so that people can read it blind like brail.… Whether it’s something that happened twenty years ago or only yesterday, I must start out with an emotion—one that’s close to me and that I can understand.”⁵⁸ Fitzgerald was a notoriously lousy speller, hence the misspelling of the name of the girl whose allure stayed with him all his life. In a letter of advice to a young family friend aspiring to be a writer, Fitzgerald recalled: “In This Side of Paradise I wrote about a love affair that was still bleeding as fresh as the skin wound on a haemophile.”⁵⁹ The date of that letter was 1938, yet the language in which Fitzgerald captures his heartbreak over Ginevra is raw.

In addition to serving as a model for Daisy, Ginevra provided Fitzgerald with three other crucial Gatsby ingredients: first, an introduction to her friend Edith Cummings, another one of the Big Four and a celebrated golfer known as “the Fairway Flapper.” Cummings, who in 1922 became the first female athlete to grace the cover of Time magazine, inspired the character of Gatsby’s androgynous sportswoman Jordan Baker. Ginevra also may have nudged Fitzgerald closer to his plot for Gatsby when she sent him an awkward short story that she had written at his urging about the reunion of two lovers (named Scott and Ginevra) whose relationship has been disrupted by the girl’s marriage.⁶⁰ Finally, Ginevra gave Scott the “gift” of class humiliation. The oft-repeated story goes that during an unhappy visit Scott paid to Ginevra’s Lake Forest vacation villa in the summer of 1916, her father pontificated, in a loud voice meant to be overheard: “Poor boys shouldn’t think of marrying rich girls.”⁶¹ Fitzgerald might have been happier, but literature would have suffered had he heeded this boor’s advice.

Princeton, also, was to become a prize that remained out of reach for Fitzgerald. Preoccupied with his social success and with writing and acting for the prestigious Triangle Club, he had racked up incompletes in Latin and chemistry; in the fall of 1915, he flunked his makeup exams in those subjects. At the end of the fall term, weakened from either an attack of malaria or an exacerbation of his tuberculosis, Fitzgerald voluntarily withdrew from Princeton. Ten months earlier, in February 1915, Fitzgerald had written in his ledger: “If I couldn’t be perfect I wouldn’t be anything.”⁶² That declaration—so earnest, so young—must have come back to haunt him many times in his life.

He gamely returned in the fall of 1916, but the chances of his making up all the missing course work were as good as, twenty years later, the chances of his quickly making good on all the debts he owed. To rub salt into his wounded ego, he was now ineligible for an honor he had assumed to be his: the presidency of the Triangle Club. Fitzgerald must have felt as though he were separated from the rest of his world-conquering classmates by a pane of glass.

Fitzgerald seems so lost at this point in his life. One gets the strong sense that, even though his parents were not without some capital, they couldn’t provide much guidance to Fitzgerald in his flailing efforts to make something of himself. Indeed, the older Fitzgeralds hardly make an appearance in his recorded life after he enters Princeton. Extraordinary for a writer who—like almost every other writer—mined his personal life for material to be transfigured into fiction, Fitzgerald wrote comparatively little about his parents. There was an essay on his mother after her death in 1936 and a moving piece called “The Death of My Father” that was posthumously published in 1951 in the Princeton University Library Chronicle. Some references to both parents pop up in letters and interviews, but in his published fiction, only the figure of Gatsby’s father seems to owe something to the real-life original—and even there, the debt is impressionistic rather than direct. Henry C. Gatz of Minnesota is described as “old” and “helpless” and “dismayed”⁶³ when he turns up at Gatsby’s mansion for the funeral, alerted, impersonally, by the coverage of his son’s death in the Chicago newspapers. After the initial shock passes, however, Gatsby’s father is mostly distinguished by his uncomprehending pride in his son “Jimmy’s” accomplishments. Waving the youthful self-improvement list under Nick’s nose, Mr. Gatz exclaims: “Jimmy was bound to get ahead.… Do you notice what he’s got about improving his mind? He was always great for that. He told me I et like a hog once and I beat him for it.”⁶⁴

By all accounts, Edward Fitzgerald was a reticent Southern gentleman whose table manners, we might assume, were beyond reproach, but the aching emotion that’s captured so vividly in those few pages where Mr. Gatz belatedly visits is one of parental bewilderment at a child who’s gone far beyond the known world of the parent. Surely, Edward and Mollie Fitzgerald must have felt left in the dust by their high-flying son, the Ivy League boy who became a famous author and was on easy terms with other writers and movie stars; the big spender who rented homes on the Riviera and estates in Delaware. The schism was between generations—the Victorian Age versus the Jazz Age—and between classes. Fitzgerald not only had more money than his parents (at times) but also acquired the intellectual chops and cosmopolitanism that even Summit Avenue couldn’t supply. With the exception of that one scene in The Great Gatsby, there were not many backward glances, not much avowed guilt. Like Gatsby, F. Scott Fitzgerald, to some extent, sprang from a “Platonic conception of himself,”⁶⁵ but the upward arc was bumpy.

By the time he withdrew from Princeton, Fitzgerald had been slapped down a number of times and in a number of ways. He acutely understood what it felt like to yearn for approval and be denied. The hunger and humiliation would be channeled into Gatsby. It’s not a big scene nor, apparently, a memorable one. (Most of my students and other folks whom I’ve lectured to about Gatsby over the years need to have their memories jogged about its existence.) But in terms of nailing the silent and brutal ways insiders communicate exclusion to outsiders, it’s a masterful passage. The scene takes place in chapter 6, right after Gatsby has finally achieved his reunion with Daisy at Nick’s cottage and right after we’ve heard, via flashback, about how Dan Cody fished the young James Gatz out of the waters of Lake Superior. Nick begins by telling us that he hasn’t seen Gatsby for several weeks; he (Nick) has occupied himself with brushing up on bonds and “trotting around with Jordan,” and Gatsby is presumably busy with Daisy. But one Sunday afternoon, Nick wanders over to Gatsby’s mansion, and a few minutes after he arrives, Tom Buchanan and two friends (a man named Sloane and an unnamed “pretty woman”) arrive on horseback. They seem to be propelled by Sunday boredom and the faint desire to sniff around a local curiosity; otherwise, there’s no reason given for their visit. Here’s Gatsby’s vigorous greeting followed by a strange aside by Nick:

“ ‘I’m delighted to see you,’ said Gatsby standing on his porch. ‘I’m delighted that you dropped in.’

“As though they cared!”⁶⁶

Nick hardly ever interrupts the flow of a remembered scene this way, but here he can’t restrain himself. It’s as though Nick, in replaying the scene, wants to do what he wishes he had done at the time: armor Gatsby against the cruelty to come by preemptively insulting these uninvited guests. Sadly, since Nick can only relay past events, not change them, the scene continues to unfold. Gatsby, always so eager to please his guests, scurries around offering refreshment (it’s turned down) and energetically asking questions (he receives curt replies). Finally, the “pretty woman” warms up after two highballs and invites Gatsby to her mansion for dinner. This invite—a signal, perhaps, that he’s being admitted into this haughty equestrians’ circle—sends Gatsby into a tizzy. As socially insecure people tend to do, he responds by apologizing.

“I haven’t got a horse,” Gatsby says. “I used to ride in the army but I’ve never bought a horse. I’ll have to follow you in my car. Excuse me for just a minute.”⁶⁷

And then, when Gatsby goes inside to gather his things (you can imagine him dashing into a nearby bathroom and running a wet comb through his hair; rifling through the closet to find something smart), the men mock Gatsby for not “getting it” that the woman’s invitation is insincere. Mr. Sloane and his lady friend and Tom mount their horses, and Sloane directs Nick, “Tell him we couldn’t wait, will you?” It’s evident that Nick and Sloane, as members of the same social club, understand the unspoken insult that’s being inflicted on Gatsby. Nick tells us that he shook hands with Tom (his cousin-in-law, after all), but that “the rest of us exchanged a cool nod.” Meanwhile, the one person who is most decidedly not “cool” in this scene arrives to find he’s been left flat. The trio disappeared down the drive “just as Gatsby with hat and light overcoat in hand came out the front door.”

Do you feel the rejection? That horrible sixth birthday party, the mean boys at the St. Paul Academy, the other mean boys at Newman (“the best Catholic families”), Ginevra King’s father, Princeton’s football team, Princeton’s dean’s office, and all the other slights of Fitzgerald’s young life are all swirled into that scene. It’s even, in a prescient way, the Baltimore Archdiocese deciding that Fitzgerald isn’t fit to nestle in the Catholic cemetery alongside his ancestors. Gatsby is trying so hard and he’s just brushed off by those “careless people” who don’t need to bother to try at all.

In danger of being kicked out of Princeton for good, in October 1917, Fitzgerald enlisted and received his commission as a second lieutenant. Always particular about his appearance, he took the train from Princeton to New York City to have his uniforms made at Brooks Brothers. A picture of Fitzgerald in that uniform is now posted on a creepy Tumblr site called My Daguerreotype Boyfriend whose motto is Where Early Photography Meets Extreme Hotness. Women (mostly, I assume) go on this site to post black-and-white photos of long-dead hunks. The woman (“Wendy”) who posted Fitzgerald’s photo in uniform wrote underneath it: “Anyhow, he’s adorable if you ask me.”

That “Anyhow” refers to a short summary of Fitzgerald’s military record, also posted by Wendy, which notes that Fitzgerald was never sent overseas during World War I. This lack of combat experience troubled Fitzgerald the rest of his life. On his first trip to France, Fitzgerald bought a collection of some one hundred glass slides of World War I battlefields. I gingerly looked at some of those very same slides—still in their varnished wooden box together with the viewer that Fitzgerald used—during a research trip to the Ernest F. Hollings Special Collections Library at the University of South Carolina in search of Fitzgeraldiana. The black-and-white scenes they depict are mostly of men posed formally on battlefields, a few in the company of a stray goat. No matter that the scenes are mundane; Fitzgerald felt the sting of missing out on his generation’s defining moment. I think it’s touching, then, that he endowed both Gatsby and Nick with the service record he lacked.

Overseas duty is the very first thing that Nick and Gatsby talk about when they meet at Gatsby’s house in chapter 3, in one of the oddest entrances, by the way, of any main character in a work of literature. Gatsby slips oh so quietly into the novel that bears his name. Remember? Nick has been invited, via chauffeur-delivered formal letter, to cross over his lawn on a Saturday night to attend one of Gatsby’s regular parties. Feeling socially awkward, Nick latches onto Jordan, the only person at the riotous gathering whom he knows. She tries to find Gatsby to introduce him to Nick, but our host is nowhere to be spotted in the crowd. Hours pass. Nick, now lubricated with champagne, is sitting at a small table with Jordan, “a man of about my own age and a rowdy little girl who gave way upon the slightest provocation to uncontrollable laughter.”

At a lull in the entertainment the man looked at me and smiled.

“Your face is familiar,” he said politely. “Weren’t you in the Third Division during the war?”

“Why, yes. I was in the Ninth Machine-Gun Battalion.”

“I was in the Seventh Infantry until June nineteen-eighteen. I knew I’d seen you somewhere before.”

We talked for a moment about some wet, gray little villages in France.

The very next moment, the daredevil Gatsby seals this World War I “band of brothers” relationship by inviting Nick to go out with him on Long Island Sound in the morning; always striving to ride high above the waves, Gatsby wants to try out his new hydroplane.

His lack of overseas military service put Fitzgerald at a disadvantage with contemporaries like Hemingway, John Dos Passos, and even Ring Lardner, who’d covered the war for Collier’s. Like so many “sad young men” of the time, Fitzgerald had images of chivalric sacrifice filling his head. But the trenches of World War I would be neither Fitzgerald’s fate nor his subject in fiction. Mizener writes in his biography of Fitzgerald that, in October 1918, Fitzgerald’s unit received its overseas order and was sent to Camp Mills, Long Island. From there, they were marched onto a transport, only to be marched off again. That’s as close as Fitzgerald came to seeing Europe while he was in uniform. Generously, though, Fitzgerald loads Gatsby’s pockets with physical evidence of glorious overseas service: that medal of valor from “little Montenegro,” that photograph of the recently demobbed Major Gatsby at Oxford. For the rest of his life, Fitzgerald craved similar souvenirs. (Edmund Wilson recalled that in the late 1920s, Fitzgerald “produced his old trench helmet which had never seen the shores of France and hung it up in his bedroom [in his house] at Wilmington.”)⁶⁸

Instead, Fate dispatched Second Lieutenant Fitzgerald off on a different sort of reckless adventure altogether. Before that Camp Mills farce, Fitzgerald had been sent to a series of army training camps in the South. In June of 1918, he wound up at Camp Sheridan near Montgomery, Alabama. There, as his ledger records, he “fell in love on the 7th of September.”⁶⁹ That was a prudent two months after Fitzgerald, who was serving as an aide to several senior officers in the camp, had accompanied the officers to a dance at the local country club. On the dance floor was a gaggle of noisy young people waiting for the next song to begin. Fitzgerald spotted Zelda Sayre in the group. She was a seventeen-year-old blond beauty wearing a fluttery dress. Fitzgerald promptly abandoned the officers upon whom he was supposed to be attending, walked up to the group, and introduced himself to Zelda.

In Delmore Schwartz’s classic 1937 short story “In Dreams Begin Responsibilities,” an unnamed narrator experiences a moment out of time in which he enters a movie theater and sits down to watch a movie. Surreally, the movie turns out to be a black-and-white film chronicling the courtship of his (now miserably married) parents. At one point, the narrator shouts at the screen: “Don’t do it. It’s not too late to change your minds, both of you.” Fitzgerald fans may feel that very same urge at this point in his life story.

Scott and Zelda partly created and all but destroyed each other. Along the way, they became the ultimate mascots of the Jazz Age. Scott called Zelda “the first American flapper,” which I guess would make him the top jelly bean or sheikh (the latter name for a flapper’s male counterpart derives from the 1921 Rudolph Valentino film). Together, they enjoyed ten pretty good to great years in their marriage. These were high-flying years, when money ran through their hands like water; years spent riding atop the roofs of taxicabs in New York and drinking “corn on the wings of an aeroplane in the moon-light”⁷⁰; nights exhausted in rushing from party to party, bar to bar, in Paris, in Rome, and on the Riviera. They called each other “Goofo” and reveled in the fact that their golden beauty made them look like twins. When daughter Frances Scott Fitzgerald—Scottie—came along in 1921 to complete their vagabond nuclear family, Scott and Zelda barely slowed their pace. During that first decade with Zelda, Scott wrote three of his five novels and the bulk of his 160 or so short stories. He became the highest-paid short-story writer of the time, earning up to four thousand dollars a story in the late 1920s from the Saturday Evening Post. Then, Zelda’s mental illness, their heavy drinking, the imagined and real infidelities, and all the other excesses that swirled into their folie à deux dragged them both down. The change in Zelda seen in her photographs over just sixteen months—from April 1930 (when she was admitted to her first sanitarium, the Malmaison Clinic outside Paris) to September 1931 (when she was discharged from Prangins Clinic in Switzerland)—is shocking. A plug has been pulled and all sparkle has drained out of her face; at only thirty-one, she’s doughy and flat. To paraphrase Gertrude Stein, there’s no longer a “there there.” A terrible recurring case of eczema, which would plague Zelda on and off for years, accounts for some of the outer ravages; inside, she heard voices urging her to suicide. Shortly before her first hospitalization, Zelda thought the flowers in an outdoor marketplace were talking to her; at one point, Scott came home early to their Paris apartment and discovered her on the floor playing with a pile of sand. She practiced ballet before a mirror for nine, ten hours at a time until she passed out. Scott began missing shirts and underwear; Zelda told him he was imagining things. Then, one day, he opened a closet to find it piled with weeks of soiled laundry that Zelda had tossed in and forgotten.⁷¹ The diagnosis covering these and so many other disturbing incidents was schizophrenia. In the 1931 photo taken at the time of her discharge from Prangins, either Scott or Zelda has written the word recovered, but Zelda never did recover. Schizophrenia is not curable, and in the 1930s it would have been near impossible to treat. By the time the Roaring Twenties were over, so too, effectively, was their marriage.

Fitzgerald always read his life as syncopated with the larger life of America: anyone familiar with his ethereal essay about New York, “My Lost City,” knows that he viewed his own depression as conjoined with the nation’s Great Depression. The onset of Zelda’s full-blown schizophrenia also eerily coincided with the Great Depression. One of the earliest signs that something was seriously wrong was an incident in France where Zelda tried to wrest the steering wheel of their car away from Scott and drive over a cliff. This near tragedy happened in October 1929, the very same month the Wall Street stock market crashed. Though there were periods when Zelda lived again with Scott and Scottie, the knowledge that another spectacular breakdown hovered on the horizon must have made for the quintessential walking-on-eggshells atmosphere in their various rented homes.

Zelda was a patient at the Highland Hospital in Asheville when a fire broke out in the kitchen there on the night of March 10, 1948. The fire spread through the dumbwaiter shafts and killed nine women. Zelda, locked in her room and scheduled to receive electroshock treatments the following day, was one of the victims.

There are lots of impassioned and knowledgeable Zelda partisans out there,⁷² some of whom blame Scott for Zelda’s mental agony. I’m not one of them. I don’t think anyone is to blame for Zelda’s terrible suffering. I think Zelda fell victim to a lot of things: her husband’s controlling tendencies, for sure, but also mental illness, which seems to have run in her family (her brother committed suicide), and way too much alcohol. In the 1920s, for the first time in American history, “nice girls” drank publicly, and Zelda was the head flapper, the girl who had to knock back the champagne and gin fizzes and try to keep up with the boys. There was no precedent for this behavior and, thus, no awareness of the toll it could take. Who knows how all that alcohol affected the trajectory of her schizophrenia, or bipolar disorder, which has also been suggested as the correct diagnosis for Zelda’s mental illness?

Zelda’s triple-threat career as a dancer, writer, and artist was stunted by her mental illness and, to a certain degree, by her own unfocused creative energies. She began studying ballet seriously very late: at twenty-seven. Nonetheless, in 1927, she was offered a spot as lead dancer in a ballet company in Naples, which she turned down. Her novel, Save Me the Waltz, barely sold any copies when it was published in 1932. Scott and Zelda became embroiled in a fierce argument about the novel before its publication: Scott insisted she revise or cut sections of it that he felt impinged too directly on his own novel in progress, Tender Is the Night. The published version of Save Me the Waltz (which Zelda wrote in three weeks) is sprinkled with occasional bright images and phrases, but it’s an ornate jumble of a book. Zelda’s paintings are charged and disturbing; unfortunately, her mother found them so disturbing that she destroyed most of them after Zelda’s death.

The gravest accusations against Scott are that he mined Zelda’s diaries and conversations for use in his own books, particularly The Beautiful and Damned and Tender Is the Night. Indeed he did. All writers are plagiarists, vampires, secret agents embedded within the family. At the end of that first dinner party at the Buchanans’ mansion, Daisy tells Nick that when she woke up out of the ether after giving birth and found out that the baby was a girl: “I turned my head away and wept. ‘All right,’ I said, ‘I’m glad it’s a girl. And I hope she’ll be a fool—that’s the best thing a girl can be in this world, a beautiful little fool.’ ”⁷³ Zelda had said the very same thing after Scottie was born. Fitzgerald’s grounding belief as a writer was that it was always necessary, always, to take notes. Apparently, even at the birth of his only child, he was mentally scribbling.

Though Fitzgerald was frequently a mean drunk and titanically self-absorbed (his constant complaints about money problems during the early years of the Great Depression—when he was still capable of earning three thousand dollars a short story—make you want to toss him over the Queensboro Bridge), he’s redeemed, for me, by his loyalty. Granted, Scott had affairs in the 1930s, but they seem more sad than riotous. (Maybe that early Catholic influence squashed whatever sexual hedonism lurked within.) When he began living with Sheilah Graham in Hollywood, he told her that he could never divorce Zelda while she was still ill and needed him. As novelist Jay McInerney points out, during those Hollywood years Scott oddly re-created his little golden nuclear family, the family that had, by then, been split apart by illness and distance. In Sheilah Graham, Scott found himself another dazzling blonde who resembled the young Zelda; in his shy young secretary Frances Kroll Ring, he acquired an admiring surrogate just a few years older than his own daughter, Scottie—and one who happened to share her actual given name, Frances.

Arguing with Zelda devotees about Scott’s responsibility for her ruin, however, is like arguing with Rush Limbaugh about Obamacare. That’s why I kept mum the day I went out to Old St. Mary’s Cemetery in Rockville, Maryland, to tape an interview with NPR senior editor Kitty Eisele about the strange story behind Fitzgerald’s two burials. (More about that later.) It was a hot August day and the churchyard was empty. Occasionally we would spot a few folks in the adjacent railroad parking lot, and Kitty, microphone in hand and ever hopeful, would hustle over and ask them if they were there to pay their respects to Fitzgerald. One woman Kitty approached told us in a thick accent that she didn’t know who F. Scott Fitzgerald was. Another woman certainly knew who Fitzgerald was and absolutely wanted no part of him. She said something dismissive like: “I like Zelda. I read her novel. Her husband stole from her and kept her down.” I kept a weak smile pasted on my face. The air was still and heavy with the threat of an afternoon thunderstorm. No spirit voices made themselves heard that day to set the record straight.

Let’s turn back to that first meeting between Scott and Zelda. (Don’t do it!) It’s one of the most famous meetings in all of literary romantic history. Shortly before that meeting, Scott had received word that Ginevra King was engaged to be married. That news may have intensified Zelda’s allure, but she was plenty magnetic on her own. Scott courted her, as did, it seems, half the platoon. Zelda later told Harold Ober, Scott’s literary agent, why she had married Scott: he made life “promisory” [sic].⁷⁴ Before they got to the altar (actually, the church office of St. Patrick’s Cathedral in New York; Zelda was not a Catholic so they couldn’t be married in the church proper), Scott had to prove to both Zelda and her stern father that he could support her by writing—a dubious proposition in any time.

Fitzgerald had been working on a novel about Princeton even before he’d enlisted; the long dull stretches in various army camps had been ideal for writing, and in May of 1918, he sent the manuscript of “The Romantic Egoist” to the publisher Charles Scribner’s Sons. In August, it was rejected. Fitzgerald quickly revised the manuscript and re-sent it to Scribner’s. In October 1918, it was again rejected. His best work makes writing seem effortless, but it hardly ever was for Fitzgerald. In February of 1919, Fitzgerald, newly discharged from the army, took a train to New York City, determined to find distinction and to win Zelda by getting published. This was a risky strategy, particularly because Zelda insisted on her right to date other men in Scott’s absence. We can only imagine his anxiety, masked by bravado, as he rode on that train alone up to New York City with only a belief in his own gifts to keep him steady.

Many years later, when Scottie declared her desire to be a writer, Fitzgerald would tell her that “all good writing is swimming under water and holding your breath.”⁷⁵ Note those italics, which are Fitzgerald’s. In the New York City of the dawning Jazz Age, the twenty-two-year-old Scott Fitzgerald dove in, swam under water, and held his breath. Then he broke to the surface with This Side of Paradise. Fitzgerald’s first novel was one of those books that define an era; like most such books, it’s now chiefly an interesting period piece. Five years after his much-heralded debut, Fitzgerald would write a masterpiece that, comparatively speaking, hardly made a ripple.