Greater Than Gatsby

September 2025

Scott Fitzgerald wrote his fantasies into existence, an unusual and in many ways unfortunate ability. In a telegram to Zelda during college he boasted that life was “something you dominate if you’re any good.” Having achieved, and then lost, the acclaim he craved, in his thirties he declared himself an “emotional bankrupt,” a loser in life’s great game.

From his debut This Side of Paradise which he wrote at age 23, Fitzgerald’s limitations were as remarked upon as his talent. Memorably, St. Vincent Millay compared him to a “stupid old woman with whom someone has left a diamond.” But any careful reader of stories like A Diamond as Big as the Ritz knows these limitations were the very contours of his talent. His best stories self-consciously work in the register of a fable. His least distinguished prose often came during tetchy attempts at social or historical realism. His best novels linger in the memory as pearl-strings of images, illuminated set pieces strung together along invisible threads. Fitzgerald’s verbal facility didn’t compete with his melodramatic and at times hysterical worldview. The former depended upon the latter. In leaping from scene to scene, image to image — in writing in sentence fragments appended with a dash — Fitzgerald was compulsively, continually recapitulating the mythic scope and allegro tempo he demanded from life. 

The defiant frivolity of Fitzgerald’s early work has led many, then and now, to ignore the notes of doom that sound beneath the glittering surface in all but the most minor of his stories. Gatsby’s tragic ending is the most distilled version of a thought that seems to have haunted the author as persistently as visions of personal glory: that fantasy always contains the seeds of its own destruction. James Gatz becomes a man, Jay Gatsby, who doesn’t exist, and he loves a woman, Daisy Buchanan, whom he doesn’t really know. The character is nothing but surface, the walls of his house and the gold of his suit. Like an optical illusion or a stage-set, he collapses upon contact with reality, his years of dreaming crushed by Tom Buchanan with ease. The inevitable — and in a sense superfluous — murder of Gatz marks the then-limit of Fitzgerald’s self-reflection at 29. The character has to die, because his fantasy has died. He’s not to be one of those men who “dominate” life, so he’s no one. But if the idea that one cannot survive a fantasy — is itself a fantasy?

By the time Fitzgerald adopted the moniker “emotionally bankrupt,” he had, in the public eye, frittered away his treasure trove of genius on misconceived novels, fatuous stories, an unstable wife, and, above all, drink. But alcohol alone does not account for the eight years between Gatsby and Fitzgerald’s next and last published novel, Tender is the Night. The collapse of his career and the onset of Zelda’s schizophrenia meant that Fitzgerald, who could only work from his “material,” meaning his life, was faced with a mismatch between how he wanted to write — the life he wanted to be living — and how he had to write — the life he was actually living. Eventually, and brilliantly, this mismatch became the very subject of his novel, which tracks the psychologist Dick Diver’s own collapse under the weight of curdled fantasy. 

Unlike Gatz, Dick doesn’t have the benefit of being put down by a gunshot. Like Fitzgerald, like most of us, he has to live in the wreckage of what he once wanted. This year marks the centennial of Gatsby’s publication. Accordingly, numerous essays have been piled onto the mountain of criticism — more often cultural than literary — and mythmaking that has accumulated atop this novella-length fairy tale and its author. But Fitzgerald’s development as a novelist didn’t end with Gatsby. The still unmatched achievement of its often overshadowed follow up is that through his belabored, tortuous composition process — and against all his own instincts — Fitzgerald forged a language and form that could depict what happens when life’s surplus bursts through fantasy’s dam, a process salutary as well as a destructive, a process sometimes also called aging. 

Tender is the Night begins twice and ends twice. Its novella length opening follows the 23 year old actress Rosemary Hoyt, her infatuation with Dick Diver and his rich, beautiful wife Nicole Warren. This section ends where nearly all previous Fitzgerald novels and stories do: at the moment of disillusionment. Rosemary finds Nicole raving on a bathroom floor, her latent madness activated by one of two, curiously incidental murders. But in a move that has often confused readers — and was hailed by Slavoj Zizek as the birth of postmodernism — the book abruptly jumps back to the beginning of Dick’s own love story, his fateful decision to marry the mental patient Nicole. Chronologically, Rosemary’s chapters occur in the middle of the events. It’s the story of Dick’s love and his eventual collapse that is the “real” story of the novel. A later, posthumous edition followed one of Fitzgerald’s schemes to rehabilitate his reputation by rechronologizing the chapters. As he intended, this arrangement does clarify that the novel is wholly “Dick’s novel.” But moving “Rosemary’s Angle” (as it’s pedantically labeled in this version) forward obscures Tender’s precise advance over Fitzgerald’s previous work.

“He seemed kind and charming,” he writes of Rosemary’s first impressions of Dick, and “his voice promised that he would take care of her, and that a little later he would open up whole new worlds for her, unroll an endless succession of magnificent possibilities.” There isn’t really proof of these characteristics. Instead, verbs assert direct impressions with all the confidence necessary for sleight-of-hand. The iconic imagery of Tender’s first chapters — the “bright tan prayer rug” of the Riviera beach, the Divers’ dinner table that seems “to have risen a little toward the sky like a mechanical dancing platform” — are a means of transposing Rosemary’s beguilement onto the reader, evoking a prelapsarian world that accords (all too neatly) with the dreams of a Romantic looking ahead to adulthood. First, we get Dick as Rosemary sees him — as he would very much like to be seen. In the rest of the book we get Dick as he sees himself.

Still, it’s not really accurate to say these early chapters track Rosemary’s “perspective.” The most singular (and thus most misunderstood) aspect of Fitzgerlad’s writing is that moods, impressions, images and pseudo-cinematic effects tend to float detached from any particular consciousness. In Tender, the authorial perspective hovers above the characters in a melancholy and often pointedly ironic retrospective. The empty beach that opens the novel may resemble an empty stage awaiting its actors; but equally a postapocalyptic waste, the villas rotting “like water lilies.” Rosemary may be taken in by Dick, but the writer knows appearances can be deceiving: 

[Dick] won everyone quickly with an exquisite consideration and a politeness that moved so fast and intuitively it could be examined only in its effect. Then, lest the first bloom of the relation wither, he opened the gates to his amusing world. So long as they ascribed to it completely, their happiness was his preoccupation, but at the first flicker of doubt…he evaporated before their eyes, leaving little communicable memory of what he had said or done.

In effect, Dick does “evaporate” for Rosemary once their brief affair ends. But he doesn’t for the reader. Rosemary’s chapters have the prototypical Fitzgeraldian arc of fantasy, disillusionment, and fade-to-black. As if in riposte, Dick’s chapters depict what it’s like to live with failed dreams when there’s no end to the story. The movement between the sections isn’t from fantasy to reality. It’s one from one kind disillusionment to another, more profound kind. 

Nicknamed “Lucky Dick” by his classmates at Yale, Dick avoids combat in World War One because he “was already too valuable…to be shot off in a gun.” He spends the war studying psychology in Vienna then Switzerland, burning textbooks for fuel and writing pamphlets that coalesce into his first (and as it turns out only) book: “A Psychology for Psychiatrists.”

 Dick has the makings of a fine practitioner. But he feels that “the price of his intactness” is “incompleteness,” that he needs to be “faintly destroyed” if he’s going to become the person he wants to be. He later remembers these student years as a “heroic period.” A hero requires a quest. Lacking in war stories, he settles for the battlefield of love. He meets Nicole Warren, a suffering patient at a mental clinic. As Fitzgerald writes, “Dick Diver’s moment now began.”

What Adorno said about poetry after Auschwitz might equally apply to duels after the Somme, the fourth-month stalemate between Allied and German forces in 1916 that generated over a million casualties to little discernible end. The meat-grinder of trench warfare (which Fitzgerald avoided by a few months despite his fatuous certainty of imminent death) provides the implicit backdrop upon which Dick’s heroic aspirations pale to insignificance, upon which the very idea of heroism or dignified violence seems facile. In Tender, the Romantic literary trope of the semi-farcical duel breathes its last when the grizzled mercenary Tommy Barban challenges the hack writer Albert McKisco. Here, and when Dick waxes sentimental on a visit to the Somme battlefield, Fitzgerald almost seems to be parodying his own compulsion toward yellow entertainment. But more often the intrusions of violence have a senseless, meaningless quality that marks out Tender as a work that, like its more recognized Modernist peers, grapples with the psychologically shattering effects of the war through literary form. In previous Fitzgerald works like Gatsby — and in several unfinished attempts at Tender that provided much of the imagery for Rosemary’s chapters — violence serves a dramatic purpose, putting into effect the “evaporation” that follows from fantasy’s puncture. Now it’s just atmosphere. The murders in Rosemary’s section announce shifts in tone without really impacting the plot. The brutal death of the Divers’ dear friend Abe North is discovered only in passing. On that visit to the Somme Dick isn’t mourning the dead. He’s envying them. The violence he has to face is of a self-inflicted nature: the wages of fantasy.

Nicole’s caregiver urges her to fixate on Dick to achieve “transference.” Medical malpractice, maybe. But core to Fitzgerald’s conception of the novel was another kind of transfer: Dick’s vitality is drained by what he gives to others. As with Fitzgerald’s oddly pecuniary notion of “emotional bankruptcy,” the idea is psychologically dubious but dramatically potent. Dick suspects Nicole’s older sister, the spinster Baby Warren, of pushing them together. But really “she only wanted to use him innocently as a convenience,” a temporary one. After his affair with Rosemary ends, he “saw that no provision had been made for him and Nicole” by her mother. The emotional economy of the book is zero-sum, and Dick is the only person who doesn’t realize this. Fantasy makes you a sucker, vulnerable to being used, especially by the rich and especially if your fantasy is of saving someone else. 

Upon publication, the chief criticism lobbed at Tender was the ambiguous nature of Dick’s collapse. Is he corrupted by wealth and excess, like Anthony Patch in The Beautiful and the Damned? Is he just a late-blooming alcoholic? By the time his affair with Rosemary ends Dick has just begun to tipple. He’s failing to write a book, and he’s increasingly resentful of the Warrens’ wealth. Fitzgerald thought Dick’s chief problem was his compulsive need to take care of those around him. To maintain Nicole’s salutary transference, for example, “[Dick] had for many years pretended to a rigid domesticity…and this pretense became more arduous in this effortless immobility… life was being refined to a point.” Yet Dick’s need to give is in the first instance self-imposed. Whether for his wife, for Rosemary, or for a party guest, he can’t bear to let lapse the image of the brilliant Mr. Fix-it he once very badly wanted to be. That is, he’s entrapped into others’ fantasies because trapped inside the ossified carapace of his own. Is Dick capable of leaving his burgeoning nightmare? Fitzgerald’s characterizations of Dick in his notes as a man wasted by what he gives away rhymes with his own frequent laments about himself: that he’d “wasted” his limited store of talent on short stories, and his energy on Zelda (a complaint that even at his most drunken and truculent he could never maintain for long). This self-conception as an emotional spendthrift, characteristically translated into his character as the more positive generosity of spirit, helped him ignore the self-inflicted nature of his wounds under the guise of self-blame. A ruined artist is a romantic figure, carried on by fate rather than choice. This was the fantasy — the myth — that allowed Fitzgerald to live with his failures and that, in this novel, resulted in a curious ambiguity about Dick’s motivations and possibilities that the book can never really resolve. Some readers may find this ambivalence a flaw; others, a virtue. 

Superficially, the Fitzgerald character Dick most closely resembles is James Gatz. But where Gatz’s dreams remain in the realm of fantasy, Dick has to live out his, and where Gatz is delusional, Dick is self-aware. He wanted to save Nicole because she was damaged, destroyed — after all, he literally married a mental patient — and because she might do the same to him. So he’s the dog who caught the bus. He’s the Gatsby who got the girl, who actually understood what he was getting: “He knew her problem was one they had together for good now.” His difficulty in breaking free from a life he no longer wants is that to do so he’d have to acknowledge that marrying Nicole was a mistake. He’d have to give up on the one genuinely heroic act of his life, a freely chosen trial of  his much-praised character that, in a bitter paradox, has resulted in a life that doesn’t feel heroic at all. If Gatsby did get Daisy, it’s hard not to think he’d be nostalgic for those long nights spent gazing at the Buchanan’s green dock light. What could beat that?   

Frustrated in his work, Dick agrees to use Nicole’s family money to open a clinic in Switzerland. The episode doesn’t mark the beginning of Dick’s ruin but of his post-Rosemary attempts to accommodate himself to an impossible situation. He begins to drink in earnest, to act out in ugly rebellions against his self-imposed prison, and finally escapes in ruinous fashion. 

In these chapters, the book’s retrospective tone moves from knowingness to confoundment. Frequently, it’s unclear how much time has passed, a confusion that partially obscures Dick and Nicole’s diverging trajectories as he declines (Dick Diver — Fitzgerald was never subtle with names) and she improves. The temporal confusions of these chapters owe less to Fitzgerald’s chronological errors, though there are several, than to his tendencies as a writer. Fitzgerald conceived of his works in isolated scenes that he freely rearranged and felt little need to connect through exposition. The mythic quality of his stories and novels comes from that very elision of cause-and-effect: fate fills in for the absent mechanisms of plot. Here though, the effect is closer to that of much later minimalist fiction where the lack of connective tissue gives the impression of cinematic drift without beginning or ending. The logic of fantasy, of a dramatic arc, has broken down. The character has lost the mental architecture that supported him. The author has repurposed his instincts for elision to render time as a tumbling in stages.

While seeing a patient, Dick almost seems to reflect on the necessity of the writer’s method of depiction: “Dick tried to dissect [the boy’s story] into pieces small enough to store away, realizing that the totality of life may be different in quality than its segments, and also that life during one’s late thirties seemed capable of being observed only in segments.” As Dick’s drinking worsens, segmentation descends from the level of chapter to that of sentence, image, clause. On a bender in Italy “the most remarkable thing happened…He was dancing with a girl — and she had disappeared… A row of Yenci dolls fell suddenly to the floor; there was subsequent confusion and he had the sense of having been the cause of it.” At the very level of syntax — that em-dash, the passive voice of “there was subsequent confusion” — we can see that Dick drinks because the dissolution of cause and effect makes his inability to influence, to dominate, his own life more bearable. It absolves him of will. Before he was “Lucky Dick,” a man who “had no idea his charm was anything unusual.” After a disappointing reunion with Rosemary, he announces, “I guess I’m the Black Death…I don’t seem to bring people happiness anymore.”

If Fitzgerald’s novel anticipates minimalism on a structural level, the sentences themselves never rely on the blunt declaratives so often used to convey passive disaffection in contemporary fiction. Instead he crafted a hypotactic idiom that seems to instantiate the conflict between aspiration, reality, and nostalgia, the characters’ victimization by external events. The passive voice is more often a vehicle for surprising juxtaposition than wry understatement; opening adverbs impose on factual statements with the ring of destiny (“[S]ymptomatically she had pulled two men from London…persistently she clung to the idea of Nicole’s tragic fate”); subjects and objects, causes and effects, tend to invert (“Into the dark, smoky restaurant, smelling of the rich raw foods of the buffet, slid Nicole’s sky-blue suit like a stray segment of the sky outside.”) Fitzgerald once wanted to dominate life, and for a time it appeared he had. But it was in portraying the experience of complete powerlessness that he reached his greatest heights as a writer. 

    

Dick’s impotence is first and foremost an inability to help others. In other words, a professional failure. None of his patients seem to improve. Those of his friends who do flourish, like the hack writer Albert McKisco (who has at least seen success through “pastiches of the work of the best people of his time, a feat,” Fitzgerald comments, “not to be disparaged”) do so because they don’t have any real problems, aren’t, like Dick or like the alcoholic Abe North, trapped in cycles of regret and self-laceration that appear to character and author alike as totally intractable. Dick can’t help other people because he can’t help himself, and vice versa. “It was as if for the remainder of his life he was condemned to carry with him the egos of certain people, early met and early loved, and to be only as complete as they were complete themselves.” 

While planning the novel Fitzgerald urged himself not to betray his ignorance of psychology. One can’t really say he succeeded. Given Zelda’s ongoing treatment, Fitzgerald probably had a great deal of skepticism about — alongside a great deal of nervous hope invested in — what psychiatry could accomplish. This ambivalence is likely reflected in the least well plotted part of the novel: Nicole’s improvement. In essence, she’s the one patient Dick actually cures, albeit at the cost of their marriage as she leaves him for Tommy Barban. 

It’s always tempting to equate Fitzgerald’s characters with their real-life bases, in particular author and wife. But Nicole’s mental illness doesn’t resemble Zelda’s in etiology. It’s brought on by a discrete problem: sexual abuse. And (in the dramatic rather than psychiatric logic of Fitzgerald’s text) because there’s a cause, there’s a potential cure. Really, the character closest to Zelda is a nameless patient at the clinic. A painter of thirty, she’s “coherent, even brilliant, within the limitations of her special hallucinations,” and she’s “especially Dick’s patient.” Like Zelda, she suffers from all-over sores “unsatisfactorily catalogued as nervous eczema” that cause untreatable agony. In Dick’s final act as a doctor he spends three nights awake with “the woman-artist he had come to love,” wanting “to throw as much light as he could onto the darkness ahead.” She dies from heart failure without ever getting a real diagnosis. It’s hard not to imagine Fitzgerald weeping as he wrote these sentences. 

 Much of Tender’s dramatic logic can be explained through Fitzgerald’s avowed ideas of emotional transfer and bankruptcy. But here, drawing on his despairing and unfortunately accurate presentiments about Zelda, the author has arrived at a senseless core that defies even these last comforting fantasies. No accounting system can explain why some thrive and others collapse. Taking his patient’s death as confirmation that he can’t help those he loves, at least not the way he wanted to — as a doctor, as a man — Dick agrees to give up the clinic. The only way he can help Nicole now is by inducing her to leave him, a savior-fantasy Fitzgerald sometimes entertained about Zelda and that gets enacted, if not totally convincingly, for Dick and Nicole. 

Essentially, Tender is a novel-length exercise in case-study. The patient is Dr. Diver, the disease is fantasy, and the prognosis is bleak. Falling beyond the reach of narration, Dick ends up “in one town or another” in New York. It’s clear that Fitzgerald didn’t imagine the rest of Dick’s life as happy. He’s still trying and failing to write a book, still having unwise affairs. But if this is an unhappy ending it is also an ambiguous one. The closing narration takes the form of rumors that reach Nicole, leaving the question of Dick Diver’s ultimate fate in doubt. Is there life after fantasy’s end? Or does fantasy never really die but, phoenix-like, continually birth itself anew from the ashes of failure — in new dreams and new hopes — in new disappointments and pains?     

  

 “For his external qualities,” Fitzgerald wrote of Dick while planning out his final and finally successful attempt at the novel, “use anything of Gerald, Ernest, Ben Finny, Archie McLiesh, Charly McArthur, and myself. He looks, though, like me.”

Dick Diver was first sketched as a portrait of Fitzgerald’s friend Gerald Murphy, one of those men who “dominate” life. Hemingway, another such man to Fitzgerald’s eyes, scolded Scott for imposing himself on his characters and their real-life counterparts, for distorting reality with personal fantasy. The objection is hard to take seriously when you recall the thees and thous peppering For Whom The Bell Tolls. More fundamentally, it betrays a misunderstanding (a willful one to my mind) of how fiction works. You don’t have to be a postmodernist to understand that no literary “realism” can ever be totally objective. The materials an author works from in describing any world, real or imagined, is the stuff of their own experience, concealed, amplified and channeled by the tools of the writer’s trade. Unfortunately, it’s hard to keep that in mind and maintain the confidence necessary to write a novel. Probably that’s one reason Fitzgerald struggled so much with this book. Working on Gatsby, he only belatedly realized he was “actually” writing about himself. Though Hemingway later came to admire Tender, what he instinctively disliked about it is also, I suspect, what he disdained in the Crack Up essays: the dramatization of self-doubt. 

There are those writers who, whether because of early success or sheer turpitude, cling to youthful fantasies for far too long. (Rather than writing pastiches of the “best people” of their time, these writers simply practice pastiche on their own corpus. As with McKisco’s efforts, the results are generally quite popular.) If Fitzgerald could not write another “short, dramatic” novel like Gatsby as he initially intended, it’s because he had changed as a person and a writer. These changes were brought on by unchosen pain. But also by the fortitude he displayed in refusing to write a novel that didn’t reflect his newfound knowledge, attained at such great cost. Tender is a unique book because, in reshuffling and reworking prose written over years of failed attempts, in searching for the causes of his misfortune, Fitzgerald wrote a novel that neither simply expressed nor deflated his fantasies, but captured the actual process of their collapse.

Is it possible then that F. Scott Fitzgerald, of all people, remains an underappreciated writer? That he has still not been sufficiently influential on American literature?

To me, Tender is the Night, a handful of later stories, and the unfinished Last Tycoon are sufficient grounds to make this speciously quixotic case. Gatsby will probably always be more popular, and not just for the oft-cited historical and cultural reasons. There’s a comfort to its Romantic and melodramatic logic. Its encoding of Fitzgerald’s then-worldview makes the book easy grounds for pat critical epiphany. No second acts in American life! Old money will never be new money! Dream big, young man, you’ll fail but oh how grandly you’ll fail! The dramatic logic is the same one adopted — still — by many more obviously autobiographical novels, the disaster that ends Gatsby inverted, according to the self-help ethos of our times, into personal epiphany, into an authorial claim of having broken free from delusion. Far less attractive, but also more true, is the realization Fitzgerald stumbled toward with Tender, a realization incomplete at the time of his death. Courage requires existing — requires acknowledging we always exist — at the collision point of fantasy and reality, each continually acting on the other. There is no end to fantasy; there is no dominating life. To think otherwise is to consign one’s self to a permanent adolescence. 

We don’t know what happens to Dick Diver. But we do know what happened to Fitzgerald. He moved to Los Angeles. He wrote letters to Zelda and to his daughter. He tried, and mostly failed, to become a successful screenwriter. He drank a lot. He dated Sheila Graham. He stopped drinking. He ate enormous amounts of chocolate. On December 20th 1940, less than a year before the Pearl Harbor attacks, he died sober, seemingly happy, and at work on a new novel. Literary characters die from a broken heart. Scott Fitzgerald died from a heart attack. 

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