Winter Dreams

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Winter Dreams

F. Scott Fitzgerald 1992

Author Biography

Plot Summary




Historical Context

Critical Overview



Further Reading

F. Scott Fitzgerald’s “Winter Dreams” was first published in Metropolitan Magazine in December 1922 and collected in All The Sad Young Men in 1926. The story has come to be regarded as one of Fitzgerald’s finest and most eloquent statements on the destructive nature of the American dream.

“Winter Dreams” chronicles the rise of Dexter Green, a hardworking, confident young man who becomes caught up in the pursuit of wealth and status. When he meets Judy Jones, a beautiful, vibrant young woman, he sees in her an embodiment of a glittering world of excitement and promise. Judy represents for him the epitome of what he considers to be the intense and passionate life of the American elite. Through her, Dexter hopes to experience all the benefits that he believes this lifestyle can afford him. At the beginning of their relationship, he feels ecstatic. His senses become fine-tuned to the rarefied world with which he has come in contact. As a result, he becomes filled with an overwhelming consciousness and appreciation of this new life, though at the same time he recognizes the ephemeral quality of this moment in time, admitting that he will probably never again experience such happiness. Yet he fails to see the hollowness beneath Judy’s surface, a hollowness that is also at the core of her world. By the end of the story, when Dexter watches his beautiful vision crumble, he is forced to admit the illusory nature of his winter dreams.

Author Biography

F. Scott Fitzgerald was born on September 24, 1896, in St. Paul, Minnesota, to Edward and Mary McQuillan Fitzgerald. From his father, a businessman, he inherited his predisposition for alcoholism and his romantic imagination; from his mother, an heiress, he developed an attraction to wealth, all of which would become major themes in his work. At a young age, Fitzgerald expressed an interest and a talent in writing as he began to write stories that echoed ones from popular magazines. The school magazines at St. Paul Academy and Newman School, where he attended school, published several of his short stories. Every summer from 1911 to 1914 he wrote plays that neighborhood children performed for charity groups.

He entered Princeton in 1913, where he wrote short stories, poetry, plays, and book reviews for the Nassau Literary Magazine and the Princeton Tiger, and wrote plays for the school’s shows. His concentration on writing took him away from his studies, and as a result, he left in January, 1916. He returned a year later but never finished his degree. When World War I broke out, he was appointed second lieutenant in the army, although he never served overseas. During his stint in the army, he completed a draft of a novel, The Romantic Egotist. Scribner’s publishers did not accept the manuscript, but they suggested that he continue working on it.

While stationed in Montgomery, Alabama, he met Zelda Sayre, daughter of an Alabama Supreme Court judge. He soon fell in love with the beautiful but troubled Zelda and married her. Their life together would come to epitomize the excitement and tragedy of the Jazz Age, as often fictionalized in his work.

After his discharge in 1919, he returned to St. Paul determined to be, as he told a friend, one of the greatest writers who has ever lived. He began his literary career with a rewrite of The Romantic Egotist, renaming it as This Side of Paradise, which was accepted by Scribner’s. The novel was well received by critics and the public, who applauded its accurate portrait of American society in the 1920s. In December 1922, Metropolitan Magazine published “Winter Dreams,” which was later included in his collection of short stories, All The Sad Young Men in 1926. The collection was a popular and critical success, cementing Fitzgerald’s reputation as a chronicler of the destructive nature of the American dream.

Fitzgerald’s subsequent novels and short stories were well received, but his and Zelda’s extravagant lifestyle kept him constantly in debt. Eventually, Zelda would be hospitalized for mental illness and Fitzgerald would suffer a breakdown. At the end of his career, with few copies of his works being sold, he turned to script writing in Hollywood, where he worked on, among others, the script for Gone with the Wind. He died there of a heart attack, probably brought on by his alcoholism, on December 21, 1940.

Plot Summary

Part I

At the beginning of the story, fourteen-year-old Dexter Green is a caddy at Sherry Island Golf Club. He works there only for pocket money, since his father owns “the second best grocery-store in Black Bear.” In the winter, Dexter frequently skis over the snow-covered fairways, a landscape that fills him with melancholy. During his days there, he frequently daydreams about becoming a golf champion and defeating the wealthy members of the club. One morning he abruptly quits when Judy Jones, a beautiful, eleven-year-old girl comes to play golf and treats him as an inferior.

Several years later he decides against attending the state university his father would have paid for and instead goes to a prestigious school in the East, although he has trouble affording it. The narrator makes it clear that he was more concerned with obtaining wealth than just associating with the wealthy.

After he graduates from college, he borrows a sum of money, and that and his confidence buy him a partnership in a laundry. He works hard at the business, catering to wealthy customers as he learns how to properly clean fine clothes. As a result, by the time he is twenty-seven, he is a successful businessman, who owns an entire chain of laundries.

Part II

One day, when he is twenty-three, one of the men he had caddied for invites him to play at the Sherry Island Golf Club. As he is playing, Judy Jones accidentally hits one of his foursome in the stomach with her ball. Later that afternoon, he goes swimming and runs into Judy, who asks him to go boating with her. When she invites him to dinner the next night, “his heart turned over like the fly-wheel of the boat, and, for the second time, her casual whim gave a new direction to his life.” After spending a romantic evening with her, Dexter decides “that he had wanted Judy Jones ever since he was a proud, desirous little boy.”

During the next few weeks, they see each other regularly, but Judy frequently flirts and goes off with other men, which, he discovers, is typical behavior for her. A year and a half later, Dexter grows tired of Judy’s inability to commit herself to him, and finally convinces himself that she will not marry him. He then becomes engaged to “sweet and honorable” Irene Scheerer. The following spring, just before his engagement to Irene is to be announced, he plans one night to take her to the University Club, but since she is ill, he goes by himself. There he sees Judy, and is “filled with a sudden excitement.” While he tries to be casual and composed, she tells him how much she has missed him and loves him and so insists that he should marry her. She soon persuades him to break off his engagement with Irene and restart his relationship with her.

Judy’s attentions toward him last for only one month. Yet, Dexter does not “bear any malice toward her.” Soon after they part, he moves East, intending to settle in New York. However, when World War II breaks out, he returns home and enlists, “welcoming the liberation from webs of tangled emotion.”

Part III

The story picks up in New York seven years later, where Dexter has relocated after the war. At thirty-two, he is more successful than he had been before the war. One day, a man named Devlin comes to see him about business and tells him that his best friend is married to Judy. Devlin admits that her husband “treats her like the devil” while she stays home and takes care of their children. He also reveals that “she was a pretty girl when she first came to Detroit,” but that “lots of women fade just like that.”

Dexter becomes extremely upset at the thought of Judy losing her beauty and allure, admitting that his “dream was gone.” He cries, not for her but for himself, knowing that his youthful illusions of perfection

have vanished. Despondent, he concludes that “now that thing is gone..., I cannot cry. I cannot care. That thing will come back no more.”



Devlin is a business associate of Dexter’s. He tells Dexter that Judy’s beauty has faded and she has become a passive housewife to an alcoholic and abusive husband.

Dexter Green

The story follows its main character, Dexter Green, over several years of his life. Fourteen at the beginning of the story, he is confident and full of “winter dreams” of a golden future. He feels superior to the other caddies, who are “poor as sin,” since he works only for pocket-money. He continually daydreams in “the fairways of his imagination” about gloriously besting the men for whom he caddies or dazzling them with fancy diving exhibitions.

The enterprising and resourceful young Dexter performs his duties expertly and so becomes the caddy most in demand at the club. As Mr. Jones notes, he never loses a ball, and he is a hard worker. Yet his desire to become a part of the glittering world of wealth he has only glimpsed compels him to abruptly quit his job when Judy Jones makes him feel that he is her inferior. The narrator explains, “as so frequently would be the case in the future, Dexter was unconsciously dictated to by his winter dreams.”

Dexter’s ambition prompts him to attend a prestigious university in the East, and then upon graduation, to work hard to master the cleaning trade and so become a successful businessman. He works diligently to improve his manners and dress so that he can become a part of the world he so admires. Besides adopting the mannerisms of those who attend a top university, he finds the best tailors to dress him.

Many who meet him, impressed with his success, like to say: “Now there’s a boy.” The narrator makes it clear, however, that Dexter is not a snob; he does not want “association with glittering things and glittering people, he wanted the glittering things themselves.” Yet Dexter does not appear to covet glittering things for their monetary value. He instead seems to need them to fulfill his vision of a perfect life, which includes gaining the love of Judy Jones.

He does not always, however, wear his success easily. When he returns to his hometown and is invited out by the men for whom he used to caddy, he tries to close the gap between the present and the past. He notes that he fluctuates from feeling as if he is an impostor to a sense that he is clearly superior to the men he used to work for.

He shows his emotional strength when he accepts Judy’s treatment of him, which causes him a great deal of pain, and does not feel any malice toward her. Yet when he learns that her beauty and vitality have faded, he breaks. Judy has been at the center of his vision of a golden world of wealth and opportunity. When she fades, so does his dream. As a result, he feels an overwhelming emptiness.

T. A. Hedrick

Dexter caddies for Hedrick, one of the wealthy patrons of the Sherry Island Golf Club. Judy Jones hits him accidentally in the stomach one day with her golf ball. Hedrick has definite ideas about a woman’s place, as he reveals in his criticism of Judy’s actions. He claims that “all she needs is to be turned up and spanked for six months and then to be married off to an old-fashioned cavalry captain.”

Judy Jones

Judy is Dexter’s ideal woman, beautiful, confident, and wealthy. When she is young, she is “inexpressibly lovely” and full of vitality, with a “continual impression of flux, of intense life.” She embodies everything that Dexter wants in life. However, she is shallow and coldhearted as she toys with the emotions of Dexter and other men who become enamored with her.

When Dexter sees her at the beginning of the story, she is imperious, barking orders at him and arguing with her nurse, whom she soon begins to attack with her golf club. Later, when she accidentally hits Mr. Hedrick in the stomach with her ball, she does not show much concern, telling her partner that she has been delayed because she has hit “something.” Dexter, however, appreciates her manner and becomes envious of it.

She becomes an extremely fickle young woman, favoring one man over another only for a brief time. When her suitors appear to lose interest, she reels them back to her. Yet, the narrator insists, her actions are considerably innocent; she treats men in such a manner not because she holds any malice toward them, but because she truly does not realize the consequences of her actions.

Her tenacity emerges as she goes after whatever she wanted “with the full pressure of her charm” and her beauty. As she turns her back on Dexter and the other men who pursue her, she is confident that she will be able to win them back if she so desires. She plays the mating game by her own rules, “entertained only by the gratification of her desires and by the direct exercise of her own charm.” Yet, at her core is a hollowness, which she notes when she declares, “I’m more beautiful than anybody else.... Why can’t I be happy?”

Irene Scheerer

Dexter becomes engaged to Irene after he decides that he will never be able to convince Judy to marry him. Irene is a “sweet and honorable,” popular young woman, who gives him a sense of “solidity.” She does not, however, have Judy’s vitality and beauty. Dexter “knew that Irene would be no more than a curtain spread behind him, a hand moving among gleaming tea-cups, a voice calling to children.” When Judy renews her interest in him, Dexter breaks his engagement with Irene.



Dexter’s vision of success involves a pursuit of the American dream of wealth and status. As Fitzgerald traces Dexter’s movement toward this goal, he becomes, in essence, a social historian of his generation, chronicling the dreams of the men and women of the 1920s who saw unlimited opportunities in the new century. Even as a teenager, Dexter dreams of success. While working at a local golf course, he fantasizes about becoming a golf champion and winning matches against the wealthy men for whom he caddies, or dazzling them with his expert diving exhibitions. Later, his dreams involve his movement up into the wealthy class where he would be rich enough to marry Judy Jones. She becomes the embodiment of his “winter dreams” of a glittering world with endless glamour and promise.

Dexter eventually gains wealth and status due to two qualities that are inherent in the American character: hard work and confidence. Even as a young man in his first job, Dexter strives to be the best. At the Sherry Island Golf Club, he is the favorite caddy, due to his devotion to learning and helping others excel at the game. He is such a success in his position that one of the men at the club, “with tears in his eyes,” begs him not to quit. But Dexter is too confident in his abilities to stay in a service position, especially when Judy treats him as her inferior.

Later, he turns his confidence and drive to his education, choosing a prestigious Eastern college over a state school that would have been easier to afford. After college, he dives into the business world, where he learns all he can about running a successful laundry. Soon Dexter achieves his goal: he becomes a wealthy businessman and as such, catches the eye of Judy Jones. Yet, eventually, he discovers the hollowness that exists at the core of his winter dreams.


Dexter soon confronts the reality of the glittering world of which he has become a part. That

Topics for Further Study

  • Read over the passage where Dexter skis on the snow-covered fairways and feels a sense of melancholy. Write a poem or a short sketch describing a scene in nature and your—or a character’s—emotional response to it.
  • Read one of the other stories in Fitzgerald’s collection All the Sad Young Men and compare its style and themes to that of “Winter Dreams.”
  • If you were going to make a film version of the story, how would you cinematically represent Dexter’s “winter dreams?”
  • Investigate the consequences the Depression had on the lives of Americans who had been wealthy during the 1920s. How many lost their fortunes? How did they survive?

reality is embodied in the character of Judy Jones, who has become the focus of his dreams of success and happiness. Underneath the beauty and vibrancy, however, Judy’s shallowness and destructive character emerge.

Judy’s ultimate goal is the gratification of her own desires, without any concern for those she destroys along the way. As she quickly becomes bored with one suitor, she replaces him with another, yet saves the first for future use. When she decides one of her admirers is beginning to lose interest, she pulls him back into her orbit with promises of fidelity, only to discard him again later. Dexter becomes caught up in this destructive game after he decides she has caused him to be “magnificently attune[d] to life,” to envision her world “radiating a brightness and a glamour he might never know again.” After he enters her world, he and the woman to whom he briefly becomes engaged suffer great pain and disillusionment.


At one point, Judy glimpses the hollowness of her existence when she admits, “I’m more beautiful than anybody else.... Why can’t I be happy?” Her and Dexter’s failure to achieve happiness illustrates Fitzgerald’s fundamental criticism of the American dream. At the heart of the dream is an illusory world of glitter and glamour that ultimately contains no substance. While Dexter could have found happiness through a satisfying relationship with Judy, she does not have the strength of character to commit herself to him.

By the end of “Winter Dreams,” Dexter has accepted the failure of his relationship with Judy because he still believes in the glittering dream of her and her world. However, when a business acquaintance tells him that she has lost her youthful beauty and has become a passive housewife to an alcoholic, abusive man, his illusions are shattered. As a result, he concludes, “the gates were closed, the sun was gone down, and there was no beauty but the gray beauty of steel that withstands all time.” Ultimately, he grieves not for Judy, but for his lost golden world, “the country of illusion, of youth, of the richness of life, where his winter dreams had flourished.”



Fitzgerald employs a third person omniscient narrator in “Winter Dreams,” but with an innovative twist. The narrator almost becomes a separate persona in the story, as he occasionally steps back from the plot and speaks directly to the reader, giving his critical perspective on the characters or on the action. Fitzgerald borrows this technique from Joseph Conrad, who, in works like Heart of Darkness and Lord Jim, creates the character Marlow, a seasoned sailor who narrates the story of the main characters through his sometimes subjective perspective. Fitzgerald perfected this technique in The Great Gatsby in the character of Nick Carraway, the naive Midwesterner whose task it is to pin down the enigmatic Gatsby for his audience.

In “Winter Dreams,” Fitzgerald does not name his character, but his presence is felt nevertheless. The first time his voice emerges is at the opening of Part II, where he tells readers, “of course the quality and the seasonability of [Dexter’s] winter dreams varied.” The inclusion of “of course” adds an almost conspiratorial note, as if the narrator is communicating a hidden detail of Dexter’s character, one of which Dexter is not aware.

Later, in Part IV, he speaks more directly to the reader just before he tells them about what happens after Dexter gets engaged to Irene Scheerer. Here he warns readers to remember Dexter’s illusion of Judy’s desirability, “for only in the light of it can what he did for her be understood.” Fitzgerald’s chatty and perceptive narrator becomes an appropriate vehicle for an analysis of a character who has trouble separating illusion from reality.


Fitzgerald uses setting as a symbol of Dexter’s changing state of mind during the course of his relationship with Judy. Initially, his restlessness in his position as caddy to the wealthy residents of his home town fills him with sadness, which Fitzgerald expresses through the landscape: as Dexter skis over the snow-covered fairways, he notes that “at these times the country gave him a feeling of profound melancholy” as he is “haunted by ragged sparrows” and “desolate sand-boxes knee-deep in crusted ice.” It is during these times that Dexter has his “winter dreams” of success, as represented by the “gorgeous” fall, which “filled him with hope.” After he returns from college and sees Judy again at the golf course, he takes a swim in the lake, which, due to his vision of his limitless future, becomes “a clear pool, pale and quiet,” turning “silver molasses under the harvest moon.”

Historical Context

The Jazz Age

In the aftermath of World War I, American society went through a period of dramatic change. Traditional beliefs in God, country, and humanity were shaken as Americans faced the devastation of a war of this magnitude. The feelings of confusion and dislocation that resulted led to a questioning and often a rejection of conventional morality and beliefs. In the 1920s, Americans recognized that an old order had been replaced by a new, freer society, one that adopted innovative fashions in clothing, behavior, and the arts. Fitzgerald called this decade the “Jazz Age,” which along with the “roaring twenties” came to express the cultural revolution that was then taking place.

Compare & Contrast

  • 1920s: The Flapper, who presents a new, freer female image, becomes the model for young American women.

    Today: Women model themselves after a wide-range of role models, from popular cultural icons to political, historical or international figures.
  • 1920s: As a result of the decade’s spirit of experimentation, sexual mores loosen and young men and women begin to engage in premarital sex.

    Today: The epidemics of AIDS and unwanted pregnancies prompt schools to augment sex education in the classroom, where one of the options stressed is abstinence.
  • 1920s: After the devastation of World War I, Americans turn to a pursuit of happiness through the acquisition of wealth. Their extravagant and unchecked spending habits contribute to the economic crisis America experiences at the end of the decade.

    Today: After a decade of unprecedented and unrealistic spikes in the stock market, the Dow has dropped considerably. As a result, many lose their jobs in corporate downsizing and restructuring.

During this era of Prohibition, Americans experimented with expressions of personal and social freedom in dress, sexuality, and lifestyle. Women cut their hair and wore shapeless “flapper” dresses that gave then an androgynous look. Premarital sex began to lose its stigma, and exciting developments in musical styles pulled whites into predominantly black neighborhoods. The pursuit of pleasure, especially as related to the accumulation of wealth, became a primary goal, overturning traditional notions of hard work, social conformity, and respectability. Literary historian Margot Norris in her essay “Modernist Eruptions” notes that during this age, “the aesthetics of glamour produced by material and social extravagance” were “simulated and stimulated by the celluloid images of the burgeoning movie industry.”

The Lost Generation

This term became associated with a group of American writers during this period that felt a growing sense of disillusionment after World War I. As a result, many left America for Europe. T. S. Eliot and Ezra Pound initially relocated to London, while Fitzgerald and Ernest Hemingway traveled to Paris, which appeared to offer them a much freer society than America or England did. During this period, Paris became a mecca for these expatriates, who congregated in literary salons, restaurants, and bars to discuss their work in the context of the new age. One such salon was dominated by Gertrude Stein, who at one gathering, insisted “you are all a lost generation.” Stein, an author herself, supported and publicized artists and writers in this movement. Ernest Hemingway immortalized her quote in For Whom the Bell Tolls, which like Fitzgerald’s The Great Gatsby, has become a penetrating portrait of this lost generation.

W. R. Anderson, in his article on Fitzgerald for Dictionary of Literary Biography, explains that the author never quite felt as comfortable in Paris as did his compatriots. Even though he lived there for over six years, during a most productive period in his literary career, “an air of transience” emerges in his writing. Yet, he notes, Paris, and his association with the other writers of the lost generation, had a major impact on his work.

The characters in works by these authors reflected their growing sense of disillusionment along with the new ideas in psychology, anthropology, and philosophy that had become popular in the early part of the century. Freudian psychology, for example, which had caused a loosening of sexual morality during the Jazz Age, began to be studied by these writers, as they explored the psyche of their characters, and recorded their often subjective points of view of themselves and their world. Hemingway’s men and women faced a meaningless world with courage and dignity, exhibiting “grace under pressure,” while Fitzgerald’s sought the redemptive power of love in a world driven by materialism.

This age of confusion, redefinition, and experimentation produced one of the most fruitful periods in American letters. These writers helped create a new form of literature, later called modernism, which repudiated traditional literary conventions. Prior to the twentieth century, writers structured their works to reflect their belief in the stability of character and the intelligibility of experience. Traditionally, novels and stories ended with a clear sense of closure as conflicts were resolved and characters gained knowledge about themselves and their world. The authors of the Lost Generation challenged these assumptions as they expanded the genre’s traditional form to accommodate their characters’ questions about the individual’s place in the world.

Critical Overview

“Winter Dreams,” first published in Metropolitan Magazine in 1922 and later collected in All The Sad Young Men in 1926, earned accolades for its thematic import and its style. Ruth Prigozy, in her article on Fitzgerald for the Dictionary of Literary Biography concludes, “The story is richly evocative, containing some of Fitzgerald’s best writing.” In an overview of “Winter Dreams,” Joseph Flibbert praises Fitzgerald’s skillful structuring of the story to highlight its themes.

All The Sad Young Men became Fitzgerald’s most popular collection of stories to date. In a review of the collection for Bookman, a reviewer concluded that the stories prove Fitzgerald to be “head and shoulders better than any writer of his generation.” Furthermore, the stories exhibit “compelling fineness, along with more conventional pieces of story telling that are sufficiently amusing with the old Fitzgerald talent.”

Ironically, today Fitzgerald’s works have become more popular than they were when they were published. None of his works became bestsellers in his lifetime and toward the end of his career, he was regarded as dated in his portraits of young men and women caught up in the Jazz Age. In the last few decades, however, he has come to be recognized as one of America’s most important writers. Few freshman survey courses do not include a reading of The Great Gatsby, and “Winter Dreams” is now considered to be one of his finest short stories.


Wendy Perkins

Perkins is an instructor of English and American literature and film. In this essay, Perkins considers Fitzgerald’s short story in relation to his novel The Great Gatsby.

Fitzgerald wrote his short story “Winter Dreams” while he was drafting The Great Gatsby, which became one of the most celebrated novels of all time. The two works share several thematic and stylistic elements as they each center on a young man from a modest background who strives to be a part of the exclusive world inhabited by the woman he loves. A close comparison of the two works will reveal that while The Great Gatsby becomes a more complex and penetrating critique of the pursuit of the wealth and status, the short story stands on its own as a compelling portrait of a man who is forced to face the illusory nature of his “winter dreams.”

There are strong similarities between Jay Gatsby and Dexter Green. Although Dexter, unlike Gatsby, came from a middle-class background, (his father owned the “second-best” grocery-store in his town), he subscribes to the same American dream as does Gatsby, who grew up in poverty. Both spent their childhood in the Midwest, and from an early age, were determined to gain entry into the glittering and glamorous world of the rich. Through a combination of ambition and hard work, they achieve their goal and become successful businessmen who are accepted into this exclusive world.

The process by which they rise to the top, however, is quite different. Fitzgerald clearly outlines the steps Dexter takes to become successful: he attends a prestigious Eastern university and upon graduation learns everything he can about the laundry business. The knowledge he gains, coupled with his confidence and a small financial investment, guarantees his prosperity. Fitzgerald is not as straightforward about Gatsby’s rise. There are suggestions that he may have been involved in a cheating

What Do I Read Next?

  • Fitzgerald’s highly celebrated novel, The Great Gatsby (1925), shares many of the same themes as “Winter Dreams.”
  • Fitzgerald’s “Rich Boy” presents a different view of a young man enamored with the world of the rich.
  • The Sun Also Rises (1926), by Ernest Hemingway, one of Fitzgerald’s “lost generation” compatriots, focuses on a group of disillusioned Americans living in Paris after World War I.
  • Discontented America: The United States in the 1920s (The American Moment) (1989), by David J. Goldberg, presents an overview of this fascinating decade and focuses specifically on how World War I affected American society.

scandal and a bootlegging operation with some shady New York entrepreneurs. Fitzgerald’s inclusion of the possibility that Gatsby may have prospered by his involvement in illegal activities highlights the sense of corruption he finds at the heart of American materialism, a theme he develops more completely in his searing portrait of Tom Buchanan, Daisy’s fabulously rich and morally corrupt husband.

While both of Fitzgerald’s protagonists start out wanting only the status and power that wealth will afford, they shift their focus to a beautiful woman who embodies their dream and with whom they fall in love. Eventually, each finds little satisfaction in purely materialistic gain. Initially Dexter, like Gatsby, is not a snob; he does not want “association with glittering things and glittering people,” but he does want “the glittering things themselves.” Both men amass fortunes, but their wealth ultimately does not fulfill their dream, which focuses on gaining the love of a beautiful woman who expresses the glamour and promise of that exclusive world. At Gatsby’s extravagant parties, for example, the host retreats to the study, waiting for Daisy to appear, refusing to participate in the hedonistic atmosphere of the gathering. Likewise, Dexter has no social aspirations and “rather despised the dancing men who were always on tap for the Thursday or Saturday parties and who filled in at dinners with the younger married set.” Neither man is affected by the attitudes of others in his pursuit of his dreams, nor does either bear any malice toward the women who repeatedly scorn them.

Daisy and Judy also are quite similar in character. Each is a shallow, ultimately cold-hearted woman who is entertained, as Fitzgerald describes Judy, “only by the gratification of her desires and by the direct exercise of her own charm.” Like Judy, Daisy enjoys “the mystery that wealth imprisons and preserves, of the freshness of many clothes ... gleaming like silver, safe and proud above the hot struggles of the poor.” The two male characters have their hearts broken by these lovely women who exhibit “a continual impression of flux, of intense life.” Daisy and Judy are “careless people” who “smashed up things and creatures and then retreated back into their money or their vast carelessness ... and let other people clean up the mess they had made.”

Daisy appears to be the crueler of the two, as she allows Gatsby to take the full responsibility for her accidentally running down Myrtle, Tom’s mistress, which results in Gatsby’s murder by Myrtle’s husband. Judy’s only crime is breaking hearts. Readers feel a bit sorry for her when she wonders to Dexter, in a broken voice, “I’m more beautiful than anybody else.... Why can’t I be happy?” But ultimately, Fitzgerald creates a fuller, more sympathetic character in Daisy.

Through his manipulation of the narrative’s chronology, readers are privy to a demonstration of the intense love Daisy had at one point for Gatsby, revealed when she breaks down in the shower, immediately before her marriage to Tom. Jordan notes how Daisy had to be forced into her wedding

“Through Dexter Green, Fitzgerald has chronicled the journey of a realist, who forces himself to shatter the illusions he has held for so long.”

dress by her parents, who were determined that their daughter marry so well. Readers also see how she suffers in her relationship with her brutish husband. Fitzgerald portrays Daisy as someone who had the potential for happiness, but was not strong enough to achieve that goal. By the end of the novel, she retreats with Tom into the only world she knows.

Fitzgerald does not develop Judy into a complete character. Readers never know how she became so callous and shallow, and as a result, they have little sympathy for her, even when they discover at the end of the story that her beauty has faded. Like Daisy, Judy has become a passive wife to an abusive husband, but because readers do not see how that process occurred, as they do with Daisy, her character remains undeveloped and not as interesting as her counterpart.

The settings of the two works reveal Fitzgerald’s rhetorical brilliance in his poetic descriptions of the landscape. He paints detailed portraits of the landscape that artfully reflect each work’s themes. Throughout much of The Great Gatsby, Fitzgerald concentrates on images that illustrate the corruption at the heart of the American dream. His landscapes become the wastelands of garbage heaps and burned out valleys of ashes. The eyes of Dr. T. J. Eckelberg, a symbol of crass materialism and loss of spirituality, peer down from billboards along the highway. At the end of the novel, however, Fitzgerald presents perhaps the most lyrical passage in literature when he describes Daisy’s green light, representing to Gatsby the possibility of an “orgastic future” with Daisy.

Fitzgerald’s descriptions in “Winter Dreams” are equally lyrical and resonant. They also reflect the dual nature of the main character’s experience. At the beginning of the story, when Dexter can only fantasize about a golden future, the landscape reflects his depression: the long winter “shut down like the white lid of a box” as he skis over the golf course’s snow-covered fairways. The narrator notes Dexter’s identification with his surroundings when he describes his melancholic response to the links’ “enforced fallowness, haunted by ragged sparrows for the long season” and “desolate sand-boxes knee-deep in crusted ice.” At that period of his life “the wind blew cold as misery” and the sun cast a “hard dimensionless glare.”

At the beginning of his relationship with Judy, however, when the world is filled with excitement and promise, the landscape dramatically changes. One afternoon, soon after he has run into Judy on the golf course, the sun sets “with a riotous swirl of gold and varying blues and scarlets” and the water turns “silver molasses under the harvest-moon.”

While Fitzgerald ends the two works with each main character losing the woman he loves, he leads the two in different directions, and as a result, creates two distinct and compelling commentaries on the pursuit of the American dream. As each story draws to a close, Fitzgerald delineates important differences between Dexter and Gatsby.

At the end of “Winter Dreams,” Dexter accepts the fact that he has lost Judy, and accepts also “the deep pain that is reserved only for the strong” since he had also, “tasted for a little while the deep happiness.” He does, however, receive a shock at the end that alters his vision of the golden world he experienced for a time. When a business associate tells him that Judy has lost her beauty and her vitality, his dream shatters and he breaks down, overcome by a profound sense of loss. Joseph Flibbert, in his critique of the story in the Reference Guide to Short Fiction, argues “As long as he could maintain a vision of Judy as the embodiment of genteel youth and beauty, he could continue to believe in an attainable ideal of power, freedom, and beauty.” The world now becomes cold and gray with no point to the accumulation of material objects.

Struggling desperately to regain that vision, Dexter tries to picture “the waters lapping on Sherry Island and the moonlit veranda, and gingham on the golf-links and the dry sun and the gold color of her neck’s soft down,” but cannot, insisting, “these things were no longer in the world! They had existed and they existed no longer.” He finally understands that he can never follow the same vision that had compelled him to travel in one direction all of his life. All he is left with now is a sense of emptiness, for “even the grief he could have borne was left behind in the country of illusion, of youth, of the richness of life, where his winter dreams had flourished.”

Gatsby, however, dies with his vision of Daisy and the promise of a life with her in tact. He never sees Daisy’s beauty fade, nor does he realize that she has returned to the safety of her relationship with Tom. His inability to give up his dream earns Nick’s respect and his conclusion that Gatsby was “worth the whole damn bunch put together.” Gatsby becomes a mythic figure in the novel, the tireless pursuer of the American dream—the “fresh green breast of the New World.” Fitzgerald’s closing lines reinforce this mythic dimension when Nick notes Gatsby’s inability to see through the illusion and so remain devoted to his vision of Daisy. Nick echoes this enduring sense of hope in the novel’s last lines as he insists that although happiness eludes people, “tomorrow we will run faster, stretch out our arms farther.... So we beat on, boats against the current, bourne back ceaselessly into the past.”

Fitzgerald’s exquisite crafting of these two works has created enduring portraits of characters whose fate expresses a deep resonance of the American experience. Through Dexter Green, Fitzgerald has chronicled the journey of a realist, who forces himself to shatter the illusions he has held for so long. In his creation of Gatsby, Fitzgerald presents the romantic, who refuses to give up his pursuit of the woman he loves, who represents to him, all that is possible in America.

Source: Wendy Perkins, Critical Essay on “Winter Dreams,” in Short Stories for Students, The Gale Group, 2002.

Clinton S. Burhans, Jr.

In the following essay excerpt, Burhans focuses on the character of Dexter and the loss of his idealized view of Judy.

Men like Dexter Green do not cry easily; his tears and the language explaining them therefore point either to melodrama or to a complex significance. The difficulty lies in understanding precisely what Dexter has lost and whether its loss justifies the prostration of so strong and hard-minded a man. It seems clear that he is not mourning a new loss of Judy herself, the final extinction of lingering hopes; he had long ago accepted as irrevocable the fact that he could never have her. Nor has he lost the ability to feel deeply, at least not in any general sense: Fitzgerald makes it clear that Dexter has lost only the single and specific ability to respond deeply to images of Judy and of their moments together; and he is certainly able to feel deeply the loss of this response. Similarly, he is not crying over the loss of any illusions of eternal youth or beauty. Given his character, the nature of his dreams, and the history of his striving to achieve them, Dexter is simply not the kind of man to have such illusions. And in the unlikely event that he could somehow entertain them, he is even less the kind of man to weep over the loss of abstractions. Hardly more plausible are the views that he is shocked by a sudden awareness of the destructiveness of time or of the impossibility of repeating the past. Again, it seems unlikely that this man, especially at thirty-two, could have missed the reality of time and the finality of the past.

What is it, then, that Devlin’s description of Mrs. Lud Simms has destroyed in Dexter Green? To begin with, Devlin has taken from Dexter’s image of Judy the same things he would have lost if he had married her and seen her suddenly “fade away before his eyes”: the specific features and qualities that comprised her unparalleled beauty and desirability, her appeal to him as one of the “glittering things,” one of the “best.” These had been the basis of his love for her—not her reflection of eternal youth or beauty but their physical and perishable realities. Once before, in turning from Judy to Irene Scheerer, he had found almost unendurable the loss of these tangible and emotional qualities: “fire and loveliness were gone, the magic of nights and the wonder of the varying hours and seasons... slender lips, down-turning, dropping to his lips and bearing him up into a heaven of eyes.... The thing was deep in him. He was too strong and alive for it to die lightly.” At first glance, thing may seem a strange and imprecise word for Dexter’s profound and encompassing love, but it is more consistent and apt than it might appear. His love for Judy is no more Platonic than his other winter dreams; it is sensuous and emotional, and “thing” suggests this tangible reality as well as the nature of what he has lost. Moreover, Fitzgerald’s conscious use of the term for these purposes is reflected in his repetition of it nine times in the final passage of the story.

Paradoxically, in finally giving up all hope of Judy and in going to New York, Dexter is able to have her in a way he never could had they married. With the real Judy out of his life, the girl he had dreamed of having can remain alive in his imagination, unchanging in the images of her youthful beauty and desirability. More importantly, these images keep alive in Dexter the “thing” they had

“When his images of Judy Jones no longer create an imaginative present, he loses not only his ability to go on loving her but also something else equally and perhaps even more shattering. Gone, too, is a part of himself,”

originally so deeply stirred in him—his love for Judy and his dream of having her. It is all this that Devlin kills in Dexter by forcing on him a new and intolerable image of Judy.

In Devlin’s description of her as Mrs. Lud Simms, Fitzgerald carefully strips away every feature and every quality of the Judy Jones Dexter had known and still loves in his images of her. His “‘great beauty’” becomes an ordinarily pretty woman; the unique and imperious paragon courted by worshippers becomes a conventional and submissively put-upon housewife; the queen of his love and dreams becomes a rather mousy commoner he could not conceivably love. No wonder Dexter is devastated. Having accepted the loss of the real Judy Jones, he had thought himself safe from further hurt; now, with every word of Devlin’s, he finds himself not only losing her again but what is worse losing the ability to go on loving her.

As long as Dexter knows little or nothing new about Judy, she can stay alive and immediate in his imagination; thus, the real past continues unchanged as the imaginative present. Responding to these images of Judy Jones, Dexter can continue to love her as he had in the beginning, when the dream of having this “glittering thing” and the striving for her could still be part of that love. But Devlin destroys the time-suspending equation. When he tells Dexter what has happened to Judy, when he forces him to imagine her as the older and fading Mrs. Lud Simms, then the young and vibrant girl Dexter had loved disappears into the wax museum of the irredeemable past. The real present supplants the imaginative present and forces the past to become only the past.

For Dexter, “the dream was gone”; when he tries to recall his images of the earlier Judy, they come to him not as a continuing present but as a completed past, as “things ... no longer in the world,” things that “had existed and... existed no longer.” Now they are only memories of a girl he had known and loved who has unaccountably become Mrs. Lud Simms, and they no longer have the power to stir his love or his dreams. “He did not care about mouth and eyes and moving hands. He wanted to care, and he could not care.” Dexter wants desperately to care because these images have been the source of his love for Judy Jones and the means of keeping it alive. The end of their power to stir him is therefore the end of that love, and his tears are a bitter mourning for a second and this time total loss of Judy Jones. ‘“Long ago,’ he said, ‘long ago, there was something in me, but now that thing is gone.... That thing will come back no more.’”

Dexter cries with good reason, then, but he has even more reason to cry. When his images of Judy Jones no longer create an imaginative present, he loses not only his ability to go on loving her but also something else equally and perhaps even more shattering. Gone, too, is a part of himself also deeply associated with and still alive in these images: the fragile moment in time when youth and his winter dreams were making his life richer and sweeter than it would ever be again.

Fitzgerald makes it clear that the story centers on this moment in time and its significance. The story is not Dexter’s “biography ... although things creep into it which have nothing to do with those dreams he had when he was young.” Specifically, Fitzgerald writes, “the part of his story that concerns us goes back to the days when he was making his first big success.” These are the years between twenty-three and twenty-five, the years just after college and just before New York. “When he was only twenty-three ... there were already people who liked to say: ‘Now there’s a boy—.’” Already Dexter is making a large amount of money and receiving guest cards to the Sherry Island Golf Club, where he had been a caddy and had indulged his winter dreams. At twenty-four he finds “himself increasingly in a position to do as he wished,” and at twenty-five he is “beginning to be master of his own time” as “the young and already fabulously successful Dexter Green....”

This progress towards making his winter dreams come true is not, however, unqualified. Almost from the beginning, disillusion casts strange shadows on Dexter’s bright successes. He had dreamed of being a golf champion and defeating Mr. T. A. Hedrick “in a marvellous match played a hundred times over the fairways of his imagination”; now, as a guest playing in a foursome on the real fairways of the Sherry Island Golf Club, Dexter is “impressed by the tremendous superiority he felt toward Mr. T. A. Hedrick, who was a bore and not even a good golfer any more.” A year later, “he joined two clubs in the city and lived at one of them.... He could have gone out socially as much as he liked—he was an eligible young man, now, and popular with the down-town fathers ... But he had no social aspirations and rather despised the dancing men who were always on tap for Thursday or Saturday parties and who filled in at dinners with the younger married set.” The farther he moves into the world of his winter dreams, the more he is disillusioned with it.

Significantly, and again reflecting Fitzgerald’s central concern with the relationship between reality and the imagination, the only one of Dexter’s winter dreams with which he is not ultimately disillusioned is the only one he cannot have in the real world and time—Judy Jones. After quitting his job rather than caddy for her, he doesn’t see her again until she plays through his foursome on the afternoon when he is a guest at the Sherry Island Golf Club. That evening they meet again and Fitzgerald carefully creates a scene in which Judy becomes identified with this particular moment in Dexter’s life. “There was a fish jumping and a star shining and the lights around the lake were gleaming.” Lying on a raft, Dexter is listening to a piano across the lake playing a popular song, a song he had heard “at a prom once when he could not afford the luxury of proms, and he had stood outside the gymnasium and listened. The sound of the tune precipitated in him a sort of ecstasy and it was with that ecstasy he viewed what happened to him now. It was a mood of intense appreciation, a sense that, for once, he was magnificently attune to life and that everything about him was radiating a brightness and a glamour he might never know again.”

For Dexter, the melody drifting over the water fuses the past and the present, the years of struggle just behind and the fulfillment just beginning. This is the magic moment when dreaming and striving reach out to grasp realization, the time of rapture before the fullness of achievement brings its seemingly inevitable disillusion. Suddenly, a motor-boat appears beside the raft, “drowning out the hot tinkle of the piano in the drone of its spray,” and Judy Jones becomes part of this moment in which Dexter is “magnificently attune to life” as he will never be again. She asks him to take her surf-boarding; and highlighting her association with Dexter’s “mood of intense appreciation,” Fitzgerald repeats the line with which he had begun the scene. As Dexter joins Judy in the boat, “there was a fish jumping and a star shining and the lights around the lake were gleaming.” When she invites him to dinner on the following night, “his heart turned over like the flywheel of the boat, and, for the second time, her casual whim gave a new direction to his life.”

This is the night Dexter realizes he is in love with Judy, and her identification with his sense of being “magnificently attune to life” deepens. ‘“Who are you, anyhow?’” she asks him. “I’m nobody,’ he announced. ‘My career is largely a matter of futures.’” He is ‘“probably making more money than any man my age in the Northwest”’; and with all the “glittering things” shining just ahead of him, Dexter realizes that he has wanted Judy since boyhood. She “communicated her excitement to him,” and her youthful beauty thus becomes both a part of his dreams as well as the embodiment of his “intense appreciation” of life at the beginning of their fulfillment.

As the next two years bring him increasing success and his first disillusion with its products, Dexter’s love for Judy remains constant. “No disillusion as to the world in which she had grown up could cure his illusion as to her desirability.” Not even her roller-coaster inconstancy can diminish his love for her or disillusion him with her. In Judy, he continues to find the excitement and anticipation that had made the striving for his winter dreams and the threshold of their fulfillment somehow better than their realization was proving to be. When he first loses her and becomes engaged to Irene, he wonders “that so soon, with so little done, so much of ecstasy had gone from him.” And when Judy returns to him, “all mysterious happenings, all fresh and quickening hopes, had gone away with her, come back with her now.” In finally giving up all hope of having her, Dexter is thereafter safe from being disillusioned with Judy and thus can keep imaginatively alive the excitement and anticipation she represents for him not only in herself but also in her identification with his youthful winter dreams.

Against this background, Dexter’s tears are even more comprehensible. At thirty-two, he finds that all his winter dreams, except for Judy Jones, have come true, and there are “no barriers too high for him.” But the world he has won has lost the brightness it had had in his dreams; realizing them has cost him the illusions that were their most precious dimension. Now, having long ago accepted the loss of Judy and with his illusions gone, he thinks he has “nothing else to lose” and is therefore “invulnerable at last.” Devlin’s detailed picture of Judy as Mrs. Simms strips away this last illusion.

Because Judy Jones and his love for her had become so closely associated with the untarnished richness of his youthful winter dreams, the imaginative present in which she remains alive for Dexter also preserves that youthful richness. When Devlin destroys this imaginative present, Dexter finally and forever loses not only Judy and his love for her but also his ability to keep alive in his imagination the best part of his youth and its winter dreams. He has “gone away and he could never go back any more.” Devlin has wrought a kind of death in Dexter’s imagination, and “even the grief he could have borne was left behind in the country of illusion, of youth, of the richness of life, where his winter dreams had flourished.” Dexter’s tears are justifiably for himself, then: he has lost even more than his love for Judy Jones. In realizing his winter dreams, he has discovered that their greatest value was in the dreaming; and now he has lost the only way left to preserve that priceless capacity.

In this complex and moving conclusion, “Winter Dreams” becomes a story with many values. In itself, it is an interesting and often profound treatment of the ironic winner-take-nothing theme, the story of a man who gets nearly everything he wants at the cost of nearly everything that made it worth wanting. In its relationship to Fitzgerald’s other writing, “Winter Dreams” makes a valuable prologue to The Great Gatsby and reflects several of the themes that characterize Fitzgerald’s view of the human condition.

Because of Fitzgerald’s explicit linking of the two works, it is common to parallel Dexter Green and Jay Gatsby, but the difference between them are even more instructive than the similarities. Both men have generally similar economic and social backgrounds: Dexter’s family is higher on the socioeconomic scale than Jimmy Gatz’s shiftless parents, but neither boy starts out anywhere near the wealthy upper class or social elite. Both boys are bright and ambitious, dream of wealth and position, and associate their dreams with a rich and beautiful young girl. Both achieve wealth at an early age, only to find its products strangely disillusioning; each loses the girl he loves and thereafter makes her the center of his imaginative life.

Nevertheless, the differences between Dexter Green and Jay Gatsby are essential and revealing: they not only point up the separate interest of the story but also illuminate by contrast many of the complexities of the novel. Dexter, for example, is from beginning to end Dexter Green; he wants not a different self but a richer life, and his dreams are mundane and specific. Jimmy Gatz, however, rejects Jimmy Gatz in favor of a “Platonic conception of himself”; he is “a son of God,” and he dreams of “a universe of ineffable gaudiness.” Similarly, Judy Jones is part of Dexter’s dreams, one of the “glittering things” he dreams of having who also embodies his reasons for wanting them. But Daisy is the incarnation of Gatsby’s dreams, the ineffable made flesh and therefore no longer ineffable.

Dexter gains his wealth by conventional and respectable means entirely consistent with his dreams and, indeed, largely indistinguishable from them. Gatsby’s means are apparently corrupt; but, even if they weren’t, no earthly means could be any more consistent with the nature of his dreams than is his incarnation of them in a mortal form. Dexter keeps alive his love for Judy Jones and the brightness of his youthful winter dreams in the only way the past can remain alive—by fixing its images out of time and the real world in an imaginative present. Gatsby tries to recapture the past by regaining the real Daisy and through her repeating in the real world the actual moment in time and the actual situation in which his dreams started to become “confused and disordered.”

In effect, then, Dexter Green succeeds in recapturing the past only to lose it when new images from the real world and the real present destroy his imaginative present. Gatsby fails to repeat the past and therefore never loses the illusion that he can; his failure is only a temporary setback making even more necessary and stronger his resolve to regain and thereby reshape the past. In his tears, Dexter realizes what Gatsby never learns—that his dreams are forever “behind him, somewhere back in that vast obscurity beyond the city, where the dark fields of the republic rolled on under the night,” back in “the country of illusion, of youth,” where dreaming was still untouched by the bruising fall of coming true. Dexter survives with most of his limited dreams realized but having lost twice and forever the richest dimension of those dreams; primarily, he symbolizes the power and also the tragic fragility of the imaginative present. Gatsby is killed, but he dies with his illimitable dreams apparently intact; ultimately, he symbolizes man’s unquenchable and tragic capacity for imagining a perfection he not only can never achieve but also inevitably destroys in pursuing.

Beyond its useful relationship to Fitzgerald’s masterpiece, “Winter Dreams” is also valuable in its early reflection of the themes that characterize most of his significant writing. The dream- and-disillusion motif in the story appears in varying forms and degrees from its intermittent emergence in This Side of Paradise to its central exploration in The Last Tycoon; it is Fitzgerald’s major theme. Dexter Green’s painful recognition that the richest part of dreams is not their fulfillment but the dreaming of and striving for them appears implicitly or explicitly in many other works; related to this theme and even more important in Fitzgerald’s thought and art is the central stress of the story on the power and value of imaginative life and time. Taken together, these themes reflect the essentially tragic vision of the human condition working at the core of Fitzgerald’s serious writing: his increasing concern with man as a creature whose imagination creates dreams and goals his nature and circumstances combine to doom. For any reader, then, “Winter Dreams” can be a fertile and challenging story; for a student of Fitzgerald, its careful analysis is a rewarding necessity.

Source: Clinton S. Burhans, Jr., ‘“Magnificently Attune to Life’: The Value of ‘Winter Dreams,’” in Studies in Short Fiction, Vol. 6, No. 4, Summer 2000, pp. 401-12.

Quentin E. Martin

In the following essay excerpt, Martin examines the contradictory, yet equally unrealistic, ways in which men react to Judy Jones in “Winter Dreams.”

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Source: Quentin E. Martin, “Tamed or Idealized: Judy Jones’s Dilemma in ‘Winter Dreams,’” in F. Scott Fitzgerald: New Perspectives, edited by Jackson R. Bryer, Alan Margolies, and Ruth Prigozy, University of Georgia Press, 2000, pp. 159–72.


Anderson, W. R., “F. Scott Fitzgerald,” in Dictionary of Literary Biography, Vol. 4: American Writers in Paris, 1920–1939, Gale Research, 1980, pp. 132–50.

Flibbert, Joseph, ‘“Winter Dreams’: Overview,” in Reference Guide to Short Fiction, 1st ed., St. James Press, 1994.

Norris, Margot, “Modernist Eruptions,” in The Columbia History of the American Novel, edited by Emory Elliot, Gale Research, 1989,311–30.

Prigozy, Ruth, “F. Scott Fitzgerald,” in Dictionary of Literary Biography, Vol. 86: American Short-Story Writers, 1910–1945, First Series, Gale Research, 1989, 99–123.

Review, in Bookman, May 1926.

Further Reading

Berman, Ronald, Fitzgerald, Hemingway, and the Twenties, University of Alabama Press, 2001.

Berman presents a penetrating analysis of the literary world in the 1920s.

Bruccoli, Matthew J., and Mary Jo Tate, F. Scott Fitzgerald A to Z: The Essential Reference to His Life and Work, Facts on File, 1998.

Bruccoli and Tate focus on the life and literary works of Fitzgerald and his wife.

Donaldson, Scott, Hemingway vs. Fitzgerald: The Rise and Fall of a Literary Friendship, Overlook Connection Press, 1999.

This work explores the friendship and rivalry between these two lost generation authors.

Fitzgerald, F. Scott, A Life in Letters, edited by Matthew J. Bruccoli and Judith S. Baughman, Scribner, 1994.

Bruccoli, a renowned Fitzgerald scholar, has amassed a fascinating collection of Fitzgerald’s letters that reveal his artistry and humanity.