Winter dreams summary

Winter Dreams Summary

Summary (Comprehensive Guide to Short Stories,
Critical Edition)
F. Scott Fitzgerald divides “Winter Dreams” into six episodes. In the first, fourteen-year-old
Dexter Green, whose father owns the “second best” grocery store in Black Bear Lake,
Minnesota, has been earning thirty dollars a month pocket money caddying at the Sherry Island
Golf Club. He is responsible and honest, touted by at least one wealthy patron as the “best caddy
in the club.” His decision to quit his job comes suddenly—proclaimed, to incredulous protests, to
be the result of his having got “too old.” Such public excuse masks the real and private reason:
Dexter has just been smitten head-over-heels by the willful, artificial, and radiant eleven-year-old
Judy Jones, who, with her nurse, shows up at the club carrying five new golf clubs in a white
canvas bag and demanding a caddy. Dexter watches her engage in a sudden and passionate
altercation with the nurse, which piques his interest and works to align him with Judy. He not
only sympathizes with her but also senses that an equally sudden and violent act on his part (his
resignation) can be the only possible response to the “strong emotional shock” of his infatuation.
In the second episode, which takes place nine years later, Dexter has become a successful
entrepreneur in the business world. His laundries cater to moneyed patrons by specializing in
fine woolen golf stockings and women’s lingerie. Playing golf one afternoon with men for whom
he once caddied, Dexter contemplates his humble past by studying the caddies serving his party,
but the reverie is broken when a golf ball hits one of the men in his party in the stomach. It was
driven by Judy Jones, now an “arrestingly beautiful” woman of twenty, who, with her partner,
nonchalantly plays through Dexter’s foursome.
After an early-evening swim, Dexter is resting on the raft farthest from the club and enjoying
strains of piano music from across the lake. Judy approaches by motorboat, introducing herself
and requesting that Dexter drive the boat so that she can ride behind on a surfboard, making clear
that she is dallying to delay returning home, where a young man is waiting for her. The encounter
ends with her offhand invitation to Dexter to join her for dinner the following night.
In the third episode, visions of Judy’s past beaux flit through Dexter’s mind as he waits
downstairs for Judy, dressed in his most elegant suit. When she does appear, though, Dexter is
disappointed that she is not dressed more elaborately. In addition, her depression disturbs him,

and when, after dinner, she confides that the cause of it lies in her discovery that a man she cared
for had no money, Dexter is able to reveal matter-of-factly that he is perhaps the richest man of
his age in the Northwest. Judy responds to this information with excited kisses.
The fourth episode forms the culmination of Judy’s tantalizing and irresistible charm. It shows a
dozen men, Dexter among them, circulating around her at any given moment, always entranced,
alternately in and out of her favor.
After experiencing three ecstatic days of heady mutual attraction following their first dinner,
Dexter is devastated to realize that Judy’s attentions and affections are being turned toward a
man from New York, of whom she tires after a month. Thereafter, she alternately encourages and


discourages Dexter, and when, eighteen months later, he realizes the futility of thinking that he
could ever completely possess Judy, he becomes engaged to a girl named Irene Scheerer, who
never appears as an actual character in the story. In contrast to the passion and brilliance that
Judy inspires in him, Dexter feels solid and content with the “sturdily popular” and “intensely
great” Irene.
One night when Irene has a headache, which precludes her going out with him, Dexter passes the
time by watching the dancers at the University Club and is startled by the sound of Judy’s voice
behind him. Back from Florida, Hot Springs, and a broken engagement, she seems eager to
tantalize Dexter again and asks if he has a car. As they drive around the city, Judy teases him
with “Oh, Dexter, have you forgotten last year?” and “I wish you’d marry me.” Dexter is
confused about whether the remarks are sincere or artificial, but when, for the first time, she
begins to cry in his presence, lamenting that she is beautiful but not happy, Dexter is passionately
drawn to her once again, despite his better judgment. When Judy invites him to come inside her
house, Dexter accepts.
The fifth episode takes place ten years later. Dexter reminisces about how the passion rekindled
from that one night lasted only a month, yet he feels that the deep happiness was worth the deep
pain. He knows now that he will never really own Judy, but that he will always love her. At the
outbreak of the war, having broken off his engagement with Irene and intending to settle in New
York, Dexter instead turns over the management of his laundries to his partner and enlists in an

officer’s training program.
The final episode occurs seven years after the war. Dexter is now a very successful
businessperson in New York City. Devlin, a business acquaintance from Detroit, makes small
talk by remarking that one of his best friends in Detroit, at whose wedding Devlin ushered, was
married to a woman from Dexter’s hometown. At the mention of Judy’s name, Dexter pumps
Devlin for more information and learns that Judy’s life has become an unfortunate one indeed—
her husband drinks and runs around with other women while she stays at home with the children.
Worst of all, though, is the fact that she has lost her beauty. When Devlin leaves, Dexter weeps,
not so much for the fact that Judy’s physical beauty has faded, but that something spiritual within
him has been lost: his illusion, his youth, his winter dream.

"Winter Dreams" and Gatsby
Writing “Winter Dreams” in 1922, Fitzgerald created characters and developed conflicts and
themes that made their way into The Great Gatsby where they are more fully realized and
artistically rendered. Dexter Green is not Jimmy Gatz or Jay Gatsby and Judy Jones is not Daisy
Fay Buchanan, but the parallels between the story’s characters and those of the novel are
numerous; moreover, it is in the similarities that the heart of The Great Gatsby is found. Dexter’s
pursuit of his dreams and his romantic idealizing of a shallow, selfish young woman clearly
foreshadow Gatsby’s. The destruction of Dexter’s romantic illusions and the death of his dream
are forerunners to the major themes in the novel.
The basic details of Jimmy Gatz’s personal history originate in Dexter Green’s. Dexter is born
into circumstances he longs to escape. As a boy, he is restless, ambitious, and subject to romantic


fantasies; he wants “glittering things” and “[reaches] out for the best ….” He creates a new life
and a new image for himself, builds a fortune, and lies about where he had grown up.
Much of Dexter’s relationship with Judy Jones and Judy herself are reflected in Jay Gatsby’s
love affair with Daisy Fay in Louisville before they are separated by World War I. The daughters
of wealthy men who own large, impressive homes, Judy and Daisy are both beautiful, charming,
and irresistible to the many young men who vie for their attention. Dexter’s obsessive love for

Judy prefigures Gatsby’s obsession with reliving the past with Daisy. Like Dexter, who idealizes
Judy and lives with the illusion that she is worth having, Gatsby idealizes Daisy and finds it
impossible to confront the reality of who and what she is. Years after falling in love, both Dexter
and Gatsby are nourished by their romantic memories and think of Judy and Daisy, respectively,
as they once had been.
In the conclusion of “Winter Dreams,” Dexter’s cherished perception of Judy is destroyed, and
he suffers the loss of an essential part of himself—the ability to live through his memories in “the
country of illusion, of youth, of the richness of life, where his winter dreams had flourished.”
Dexter’s pain as he realizes what “had been taken from him” is the pain Gatsby desperately
attempts to escape by denying reality and dedicating himself to his dream of Daisy and all that it
embodies. Whether Gatsby is still living in the “country of illusion” as he waits for Daisy’s
phone call in the novel's conclusion--or his dream dies before he does-- is subject to conjecture.
In this respect, the romanticism of Dexter Green is intensified in Gatsby, and Dexter’s sadness is
elevated to tragedy with Gatsby’s murder.
Winter Dreams Themes

Themes and Meanings (Comprehensive Guide to
Short Stories, Critical Edition)
In being heralded as the “laureate of the Jazz Age,” Fitzgerald struck in his very American
writing a balance between romance and disaster, glitter and delusion. His characters include the
petted and popular and rich, who both dream and live recklessly and who have as their biggest
enemy time, the time that ages and changes. The aging process is signified by the word “winter”
in the title, but “winter” also signifies a transition that is more tragic than physical deterioration;
by the end of the story, Dexter’s emotions have become frozen. He has lost the ability to care or
to feel. His “dream” of Judy had kept him energetic, passionate, and alive, and now the dream
has been taken from him.
The reader cares about Dexter at the beginning of the story and wants him to succeed in career
and in love. One myth associated with the American Dream is that even the poor, by spunk and
luck, have a chance of making it big, and Dexter, whose mother “talked broken English to the
end of her days,” has worked hard to raise himself out of the poor immigrant class to which he

was born. However, the dream of material success finally proves unsatisfying to Dexter, who
comes to know that money cannot buy his real dream. In contrast, Judy was born into wealth and
takes it as much for granted as she does her good looks. Judy, the spoiled little rich girl, gets
what she deserves. She has been a merciless flirt, using her attraction to break hearts for sport.
When the story reveals that she has become careworn and commonplace, married to a bully who


deceives her, it is obvious that the tragedy is not hers but Dexter’s, who most wanted not riches,
but a woman he could never have. What is the most tragic of all, the woman was not worth
having.

The Pain of Aging
The world shown in "Winter Dreams" places a primacy on being young. Dexter is at the pitch of
prosperity as a young man. Judy Jones controls the gaze of other people as a young woman.
Even when Dexter is poor, it is the firm determination of his youth that enables him to better
himself. The characters in Fitzgerald's creation place a great value on being young, and youth is
synonymous with opportunity, emotional commitment, and a sense of limitless boundaries.
Aging is shown to be something entirely different. Fitzgerald illuminates the social expectation
and attitude towards becoming old. As an older man, Dexter is accompanied only by the pain of
his "winter dreams." For Dexter, being old means "that thing is gone." Judy suffers the most as
she gets old. Judy is forced to marry Lud Simms and live a life of "quiet desperation" as a
housewife. It does not escape Fitzgerald's perception that women are shown to battle more
elements as they get older than men.
Dexter becomes older and must deal with emotional loss. Judy becomes old and finds that her
beauty and charms have evaporated with age, and accompanying her at this stage is desperation
and disrespect. The world in "Winter Dreams" is one in which the trappings of a world
predicated upon external success does not look kindly upon becoming old
Winter Dreams Analysis

Style and Technique (Comprehensive Guide to Short

Stories, Critical Edition)
Fitzgerald’s direct narrative style is as clear and straightforward as Dexter’s romantic purpose.
The flashbacks and gaps in the story mirror Dexter’s on-again, off-again affair with Judy, though
his unswerving obsession with her and the chronicle of it is emphasized here. Fitzgerald’s tale
uses poetic language and diction, yet it does not imply more than it states, and, in the story’s
episodic structure of fits and starts, it is loose enough to accommodate some things that are
almost irrelevant. Dexter’s business success, for example, is fortuitous; the real attraction and
attention of the protagonist and the reader is his private life.
The third-person limited omniscient point of view allows the reader to know Dexter’s story
exclusively through Dexter’s thoughts and reactions to what is happening. It is necessary to
remember that Dexter is a romantic idealist and that his temperament is responsible for both his
idealization of Judy and his subsequent disillusionment.
Dexter’s enchantment with Judy and the vitality he draws from her are symbolized by the color
and sparkle Fitzgerald uses to present her and to create a context in which Dexter can
contemplate her. When he first sees her as a young woman, Dexter notices the blue gingham
edged with white that shows off Judy’s tan; then, later in the afternoon, the sun is sinking “with a


riotous swirl of gold and varying blues and scarlets” and Dexter swims among waters of “silver
molasses.” The author establishes the painting motif when Dexter stretches out on the “wet
canvas” of the springboard, which suggests that Judy’s seeming art of beauty and charm is all
really superficial artifice. With Judy’s blue silk dress at their first dinner and her golden gown
and slippers at their last dance, Dexter swoons “under the magic of her physical splendor.”
During his engagement to Irene, Dexter wonders why the fire and loveliness and ecstasy have
disappeared. The very direction of his life, which he let Judy dictate by her casual whim, is gone
as well, until she appears to play his heartstrings once more. Irene quickly fades from Dexter’s
romantic imagination because there is nothing “sufficiently pictorial” about her or her grief to
endure after he breaks up with her. Judy is the picture of passion and beauty, energy and
loveliness, the true love and true dream that are with him until, learning of Judy’s decline, he
recognizes it as a signal of the demise of his own dreams.

Winter Dreams Characters

Characters
Devlin
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
Analyze the positive and negative sides of Dexter’s qualities in the story “winter
dreams” of F.Scott.Fitzgerald
Posted on 14.04.2014by xulingyi2012

In the early 20th century, American prosperous society created a genre of youth who were full of ambitions to search
for the glory and position, to rise above their poverty and to enter the wealthy upper- classes but had an erroneous
awareness of true love and happiness. That all made a big fancy dream of success in both love and wealth – so-called
American dreams of the youth. F.Scott. Fitzgerald, an American contemporary writer at that time declared his
attitude and his point of view of the social background in his story “Winter dreams”, especially through the story’s
main character, Dexter Green. The author characterized Dexter as a young guy who is ambitious in his career,
desirous but pragmatic and inconsistent in his love. By characterizing Dexter as a symbol of typical young successors
in America, the writer showed us the good sides and the bad sides of his qualities through his story of pursuing the
illusion of happiness in love and glory.
First of all, Dexter is an ambitious person. The good side of this quality is that it helped him reach a “golden future”
with extraordinary success, wealth, and stable social position in his “winter dreams”. To be detailed, at fourteen
Dexter was described as the best caddy worker in the club, making thirty dollars a month, which for the summer was
not able to be me made anywhere else on the lake. He was also a smart boy, who knew how to barter, asking Mr.
Jones for a raise making it “worth his while” since he was the best caddy. This shows that Dexter is not the type that
will just settle. He is really a very determined ambitious character. Moreover, he quit his job to attend a famous
university in the East although he didn’t have much money. After college, “Dexter borrowed a thousand dollars on his
college degree” and with his confident mouth, he bought a small laundry. In addition, the way he worked to reach his
“winter dreams” is: “He made a specialty of learning how the English washed fine golf-stocking without shrinking
them, and within a year he was catering to the trade that wore knickerbockers”. It leads to “Before he was twentyseven he owned the largest string of laundries in his section of the country”. Dexter became successful in the business
world. He moved his way up the economic ladder with all of his laundries being flourishing.
Next, Dexter is generally a desirous and pragmatic in love person, which leads him to a blind love. To be detailed, he
just cared about Judy Jones because of her appearance, her wealthy family background. He loved Judy Jones because
this girl was so beautiful. It can be seen clearly by the way author describes repeatedly the appearance of this girl. The

first time Dexter met her at the golf course, he looked at her carefully “her lips twisted down at the corners when she
smiled”, “the almost passionate quality of her eyes”. Then, when they met together second time “the color in her
cheeks was centered like the color in the picture”. And the way he looked at admire herself “she wore a blue gingham
dress, rimmed at throat and shoulders with a white edging that accentuated her tan”. Another aspect, he tried to
pursue Judy Jones because of her wealth “He confessed devotion to Judy Johns had rather solidified his position”. It
shows that he wanted Judy Johns because this woman was rich, full of energy and powerful. It causes that Dexter fell
in love with this woman as a blind person. He did not care the angry way she treated to her nurse although she was so
young – just a 11-year-old little girl. He also was not confused when she asked if him was rich enough for her to decide
to love him. Also, he did not consider the ways she denied to answer directly when he gave the proposal to her. As a
result, when loving this woman, he almost wasted his youth. Looking back his love at the age of 32, he found that he
had a life with no meaningful relationship and cried for himself.


Last but not least, another negative side of Dexter’s quality is that he himself created obstacles to his own happiness.
Another Dexter’s quality was inconsistent, so he did not stand his ground for his own love. First, he did not trust
Judy, but he still loved her. Many times, he knew that she insulted him and lied him.“She took him in her roadster to
a picnic supper, and after supper she disappeared, likewise in her roadster, with another man”. “When she assured
him that she had not kissed the other man, he knew she was lying”. However, after that nothing changed his love for
her and “for the first time, he had asked her to marry him”. Second, he recognized that he could not possess her, but
he still loved her above all, and canceled the engagement to Irene Scherer. He recognized that Judy could not be a
good wife. “He told himself the trouble and the pain she had caused him, he enumerated her glaring deficiencies as a
wife. Then he said to himself that he loved her”. Just one time, when returning to the University Club and meeting
Judy, Dexter could not prevent his emotion. “A million phrases of anger, pride, passion, hatred, tenderness fought on
his lips”. And then he broke up with Irene Scherer. Judy fascinated him by her looks, her words, and her charm. To
him “she had brought him ecstatic happiness and intolerable agony of spirit”. Once she lost her beauty and allure, he
lost his dreams and got full of emptiness. Dexter was not consistent with his love, so he could not be happy with
wealthy life.
To sum up, through the positive sides and the negative sides of Dexter’s qualities, we can find that his path of
conquering the perfectness of love and wealth have never led to a true happiness but ended by a symbolism of “winter
dreams” with hopelessness, loneliness, or even an emptiness in human soul. This story was valued not only in

American society in the early 20th century but also in the present time. It rises a much thoughtful question for the
young people nowadays: Are achievements of happiness through material means such as successful career, high social
position, richness of family background and beauty of appearance considered true endless dreams of happiness or
just “winter dreams of Dexter” which people always pursue to the end of their life?
Group members:
1. Châu Thị Ánh Hạnh
2. Võ Đông Hầu
3. Tôn Nữ Trúc Hương
4. Trần Quốc Lâm.

Themes
The Dark Side of the American Dream
The “winter dreams” of the story refer to the American Dream that Dexter comes to embody, but success brings a high cost, and
social mobility restricts Dexter’s capacity for happiness. Dexter is from humble origins: his mother was an immigrant who constantly
struggled with the language of her adopted homeland. The central irony of the story is that realizing the American Dream yields
bleak rewards. For example, when Dexter was a young caddy, he dreamed about success and wealth and the happiness they would
bring. When he finally beats T. A. Hedrick in a golf tournament, however, the triumph brings him little joy. Dexter is able to transcend
middle-class inertia but, despite his tireless efforts to advance his fortunes, forced to accept that money cannot buy happiness.
Dexter has an ambiguous relationship with the bluebloods and idle rich who populate his social world. On one hand, he is proud of
his self-made status and has no respect for the men for whom luxury and wealth were a given. Still, the men are emblems of a world
to which Dexter wants to belong. In pursuing Judy, he is attempting to validate his claim as a bonafide member of the upper class.
Dexter feels that he is a newer, stronger, and more praiseworthy version of the Mortimer Joneses of the world, but he still mimics the


rich in gesture and appearance. He pays meticulous attention to his appearance, concerned with small details that only an outsider
who was trying to disguise himself as a man of wealth would really notice. Dexter’s position in this world is precarious, and there is
no room for error in appearance or etiquette. Through Dexter and the world of earned distinctions that he comes to represent,
Fitzgerald exposes the hollowness that comes from the aggressive pursuit of the American Dream. Wealth and social status
substitute for strong connections to people, eclipsing the possibility of happiness of emotional fulfillment.

Reality versus Idealism
Reality and fantasy prove to be constantly at odds with each other as Dexter and Judy search for stability and meaning in “Winter
Dreams.” Dexter is the victim of his so-called winter dreams, adolescent fantasies that he is never able to fulfill. As he searches for
happiness and love, he unwisely focuses his quest exclusively on Judy Jones, making her the sole object of his romantic
projections. However, rather than provide fulfillment for Dexter, Judy and her displays of affection simply trigger more yearning.
Dexter never sees Judy for who she really is; rather, he sees her as an ideal of womanhood and the embodiment of perfect love.
Later, Judy reveals her self-serving nature when she confesses that she is breaking off relations with a man who has pursued her
simply because he is not of adequate financial means. Dexter, still blinded by his idealistic view of Judy, cannot digest this
information, because it suggests the reality of who Judy is.
Although Dexter recognizes the real threat of harm beneath Judy’s charm and beauty and tries to convince himself that he is no
longer in love with her, he cannot fully divorce himself from the romantic, uncontrollable attachment he has to her. Ultimately, Dexter
becomes the victim not of Judy’s fickle behavior but of his own stubborn ideals. Time and again, Dexter and Judy struggle with
contradictions between reality and fantasy. On their first date, Dexter is disappointed that Judy appears in an average dress and,
instead of the pomp and ritual he expected, blandly tells the maid that they are ready to eat. In their ambiguous and protracted
courtship, Judy treats him with “interest . . . encouragement . . . malice . . . indifference . . . [and] contempt.” The reality of this
relationship is bleak, but the idealistic vision of what it could be enables it to limp along.

Motifs
Similes
Fitzgerald uses similes throughout “Winter Dreams,” most notably at the beginning of the story, to make abstract notions, such as
the frustrations of love and drive to succeed, more concrete. The similes also suggest the gulf that separates reality from the
illusions the characters are subject to. In the first sentence of the story, we learn that, unlike Dexter, some of the caddies at the
country club are “poor as sin.” As winter settles on Minnesota, snow covers the golf course “like the white lid of a box,” and the wind
blows “cold as misery.” These similes, grimly preoccupied with gloomy notions of misery and poverty, set the tone for the unhappy
tale that Fitzgerald is about to convey.
Similes help clarify the abstract idea of Dexter’s winter dreams. His visions of grandeur involve vague, half-formed hopes for
success and wealth and the satisfaction he assumes will accompany them. Dexter is able to translate his dreams into reality. He
becomes the self-professed richest young man in his part of the country and gets to face off in a round of golf with Mr. Hedrick,
whom he easily beats. However, he is still dogged by the abstract—his struggle to find love and accept the responsibility of
belonging to someone else. During his first fateful meeting with the adult Judy, his heart “turned over like the fly-wheel on the boat.”

Fitzgerald’s use of simile helps provide a link between abstract and actual realms, reality and illusion, and love and its inevitable
disappointments.

Winter
The title, “Winter Dreams,” refers to the powerful desire for status and affluence and, with its suggestion of snowy barrenness, sets
the tone for the story that unfolds. Dexter forms his greatest aspirations for his life during a season of death and dormancy, an irony
that suggests that those aspirations will not be as life-affirming as Dexter imagines. Seasons in general highlight the unstoppable
passage of time in the story. As Dexter gets older but no wiser, each year finds him further from the happiness he seeks. He is in
many ways a misfit, his surroundings and ambitions out of synch with his humble origins. Fitzgerald highlights Dexter’s unresolved,
outsider status early in the story, when Dexter skis across the frozen, snowed-in golf course, using the space for something other


than what it was intended. These solitary, wintry outings signal the loneliness that he will never vanquish. The fact that his dreams
are born in a lifeless, stagnant season foreshadows the unhappiness and thwarted desires that await him in adulthood.

Symbols
The Boat
In the elite world of the Sherry Island Golf Club, the boat emerges not only as a symbol of luxury but also as a powerful reminder of
the emptiness a life of indulgence can lead to. The boat makes a memorable entrance, with Judy at the helm, as Dexter enjoys a
solitary moment on the raft anchored in the middle of the lake next to the country club. Lost in a reverie, Dexter is filled with the bliss
of arrival, having finally reached the success he had long anticipated. Entertaining only the most auspicious of prospects when he
looks to the future, Dexter feels at that moment a satisfaction that he may never again experience as intensely. Abruptly interrupting
Dexter’s musings, the whirr of the motor overpowers Dexter’s thoughts about the rosy life ahead. Judy speeds across the lake in the
boat, foreshadowing the profound ways that Dexter’s ensuing passion for Judy will impact his future happiness.
For Judy, flying behind the boat on a surfboard, the boat is an escape from reality. Her admirers learn quickly that she is too fast to
catch and lives solely for her own pleasure. Dexter obeys when she tells him to drive the boat for her, the first of an ensuing string of
commands he will obey. As an object of affluence, it shows how truly divorced from reality Judy is. She tells Dexter that she is
running from a man she had been dating who has begun to idealize her. The boat is her way of escaping the ways in which men try
to make her fit their own dreams and reflect their idealized visions of the perfect woman. Judy hides in the boat again later, when
she grows tired of the man from New York who is rumored to be her fiancé. The boat becomes Judy’s haven from the oppressive

affections of men who are captivated by her, an expensive toy that whisks her away from commitment or the need to accept
responsibility for her actions.

Golf Balls
Golf balls, part of the pristine world of the country club, suggest the harm that an idle life can lead to as well as the stringent
requirements one must meet to belong to the upper class. Dexter, with his self-made wealth, tries desperately to blend in with this
affluent world. The imagery of the golf balls emerges twice, both times reflecting the upper-class ease that the game itself embodies.
First, before the spring thaw in the north country, golfers use black and red balls, which stand out better in the patches of snow that
linger on the course. This reference comes early in the story, when Dexter is a young caddy, excluded from Judy Jones and her set
because he is a middle-class boy of limited means. When Dexter finally gets a toehold in her world, he sacrifices his individuality for
the identical white balls he uses at the club where he once caddied.
During Dexter’s once anticipated but ultimately disappointing golf outing with T. A. Hedrick, golf balls, in the hands of Judy Jones,
become an emblem of aggression. Judy’s ball hits Mr. Hedrick in the stomach, and her obliviousness, whether feigned or genuine,
serves only to further characterize her as a self-centered brat. Although there is little threat of real physical violence in this genteel,
upper-class world, the incident suggests that aggression lurks just beneath the surface. Although Judy embodies the light, almost
hedonist spirit that would eventually characterize the age, Fitzgerald reminds us in this episode that beneath the fun and leisure, real
harm can be done. Judy’s errant ball foreshadows the more potent emotional damage she imparts in trifling with Dexter’s and her
other admirers’ affections.

In A Nutshell
In an essay looking back on his literary career, author Francis Scott Fitzgerald reflected that he made $800 on his
writing in 1919 and $18,000 on his writing in 1920. (Source.) We have no idea what it would be like to see our salary
increase by two thousand percent in one year, but we imagine it would be pretty awesome. Fitzgerald enjoyed
amazing early success as a writer, and "Winter Dreams" is part of this burst of creative and economic achievement.
In fact, it helped launch his career as one of American literature's most well-known novelists.
After "Winter Dreams" first appeared in Metropolitan magazine in September of 1922, Fitzgerald reworked both the
overall plot of the story and some of its passages into his most famous novel, The Great Gatsby(1925). Yeah, that's
right: this little ol' story became one of the most important books in the history of American literature. Fitzgerald even
called "Winter Dreams" "[a] sort of 1st draft of the Gatsby idea." (Source, xxv.) He also went on to revise "Winter

Dreams" a second time for publication in his 1926 short story collection, All the Sad Young Men. Clearly, Fitzgerald
couldn't shake the themes and issues he was tackling in this story, and what he explores in "Winter Dreams" came to
define his writing in later years.
Like The Great Gatsby, "Winter Dreams" sketches a disillusioned view of the American search for wealth and its
horrible effect on relationships. But what exactly is that view, and what makes the American search for wealth so
terrible?
Fitzgerald often sets his stories among the glitz and glam of the American upper classes, and "Winter Dreams" is no
exception. We've got golfing, swanky dinner parties, boating expeditions, fancy cars, and even fancier clothes. It all
sounds good to us.
But Fitzgerald paints a bleaker picture. What's underneath all the glitter and gold? Not much, if you're asking our
friend F. Scott. "Winter Dreams," The Great Gatsby, and many of his other works aim to show us that material wealth,
at the end of the day, isn't all its cracked up to be.
Yeah yeah yeah, we know that money can't buy happiness. So what new idea does Fitzgerald have to add to that
age-old adage? Lots, as it turns out, but you'll have to read the story to find out for yourself. Trust us, Fitzgerald really
knows his stuff.
One last bit of coolness: at least some of the material for "Winter Dreams" comes from Fitzgerald's own experiences
living at the White Bear Yacht Club in St. Paul, Minnesota. Fitzgerald grew up in Minnesota, so when he talks about
the wind blowing "cold as misery" (1.2), he speaks from first-hand experience. Plus, as you'll read in our "Characters"
section, Fitzgerald had a lot in common with the story's protagonist, Dexter Green. So maybe there's an explanation
for Fitzgerald's obsession with the themes of "Winter Dreams." Could he have had some "Winter Dreams" of his
own?

WHY SHOULD I CARE?
Growing up is tough stuff, and F. Scott Fitzgerald doesn't try to sugarcoat that one bit. This isn't a fairy tale or an ifyou-dream-it-you-can-do-it kind of a story. The title is "Winter Dreams," but it might as well be "Where Winter Dreams
Go to Die."
There are plenty of coming-of-age stories out there, but "Winter Dreams" is unique because the ending is one of
(spoiler alert) total disappointment. As a kid, Dexter has big plans for himself. He wants to go somewhere in his life.
Nothing can stop him. But once he gets to where he's going, he's lost all over again. He no longer has the dreams of
his youth, and he's left with the painful reality that maybe all his hard work wasn't worth it. At the end of the story, the

world is no longer full of infinite possibility. Instead, it's full of cold hard truths.
Okay, wait a minute: "life stinks" is not the takeaway here. More like "life stinks if you live it this way." Dexter learned
the hard way that your grand plans aren't always what you think they'll be. We Shmoopers, on the other hand, get to
learn the easy way, by reading Dexter's story.
This doesn't mean we shouldn't dream big, it just means we have have to remember that nothing's perfect. And that's
what makes life so exciting.

How It All Goes Down
Dexter Green is a fourteen-year-old caddy at the Sherry Island Golf Club in Black Bear, Minnesota. His father owns
the second best grocery store in town, so Dexter is solidly middle-class—comfy, but by no means rich. One day, when
he is caddying at the golf course, he meets the lovely(ish) Judy Jones. At the sight of Judy, he decides to quit his
caddying job. He resolves to follow his "winter dreams" to become the kind of man who would fit into Judy Jones'
wealthy world.


Years later, after college, Dexter invests in a laundry business in the city nearest to Black Bear. It's not the sexiest job
in the world, but he makes a boatload of money and starts hanging out with the wealthy families of Sherry Island. He
meets Judy Jones a second time, when she accidentally hits one of Dexter's golf companions in the chest with a golf
ball (ouch). Later that evening, Dexter bumps into Judy on a raft in the middle of Black Bear Lake. She asks him to
join her for dinner, and Dexter eagerly accepts.
At dinner, Judy confesses that she is a bit blue because a man she really liked turns out to be poor. The horror! When
Dexter assures Judy that he is well-off, she leans over to kiss him. Dexter realizes that he has wanted Judy Jones
every since he was a teenager.
At this point, Dex is head-over-heels in love with Judy. Even though he knows that she has other lovers, he puts up
with it. But after a year and a half, Dexter finally gets it: Judy doesn't actually care about him. At all. She will never
return his feelings. So he gets engaged to Irene Scheerer, a nice (but slightly less attractive) girl with a friendly,
welcoming family. But not so fast: when Judy turns up again asking Dexter to marry her (not cool, Judy), Dexter
practically trips over Irene to begin, once again, his affair with Judy Jones.
Judy and Dexter's rekindled romance only lasts for a month. He moves east to New York the following year, and when
the Americans join World War I, Dexter signs up for the Army. He is glad to have a distraction from his pathetic

personal life. The poor guy actually prefers trench warfare to "webs of tangled emotion." (5.4)
Flash forward seven years from Dexter's failed engagement to Judy. Dexter is thirty-two. He hears from one of his
business associates that Judy Jones has become Judy Simms. Mr. Simms apparently drinks too much and cheats on
her. Oh, and one other thing: she's not the cutie patootie she once was. Dexter is horrified to hear that Judy's beauty
has faded. He understands that his "winter dream" has gone forever: he is no longer the idealistic young man who
loved Judy Jones.

WINTER DREAMS SECTION 1
SUMMARY
•

BACK

•

NEXT

•
•
•

Dexter Green is a fourteen-year-old caddy at the Sherry Island Golf Club in Black Bear, Minnesota.

•
•

One day, Dexter announces that he is going to quit working as a caddy at the Golf Club.

•
•

•

Dexter refuses: he has decided he is too old to caddy.

•

Judy calls out to Dexter and asks him where the golf teacher and the caddy-master are. It turns out they're
not around, and Dexter has been left to look after the caddy-house.

•

The nurse steps in to ask if they could have a caddy, since Judy's father wants Judy to learn golf. But Dexter
can't leave the caddy-house, since there's no one else in charge.

His father owns the second best grocery store in town, so Dexter is pretty well off.
But even though Dexter's family has some money, he still dreams of taking his place among the rich
members of the Golf Club.
One of the members, Mr. Mortimer Jones, begs him with tears in his eyes to stay on, since he is "best caddy
in the club" (1.5). Wow, these guys are really attached to their caddies.
In the end, Dexter quits because of eleven-year-old Judy Jones. She's that pretty.
He sees Judy standing at the caddy house with her nurse, Hilda, and can tell that she is going to be
beautiful in a few years. Sometimes you just know.


•

Judy and her nurse go off to talk and the little girl throws a fit and tries to hit her nurse with one of her golf
clubs. Note to self: don't get on her bad side.

•

•
•

Finally, the caddy-master arrives and tells Dexter to caddy for Judy.
No way. Instead, he quits his job on the spot. Bold move, Dex!
Dexter is not entirely sure why he has made this decision to quit his job., but it has something to do with his
"winter dreams" (1.46).

WINTER DREAMS SECTION 2
SUMMARY
•

BACK

•

NEXT

•
•

Following that whole fiasco, Dexter works to improve his social and economic standing.

•
•
•

Before he is even twenty-seven, he owns the largest string of laundries in the Midwest.

•

•

He plays golf with three wealthy guys, two of whom he used to caddy for. Ah, how the tables have turned.

•
•

The golf ball belongs to none other than Judy Jones. Golf paraphernalia is clearly her weapon of choice.

•

After sunset, Dexter goes swimming in Black Bear Lake. He reaches the furthest raft out on the lake, and as
he's lying there, a motorboat suddenly approaches him.

•
•
•

It's Judy Jones.

•

Dexter drives Judy's boat so that she can surf behind him, and on a whim, Judy invites Dexter to dinner the
next evening.

After college, he goes to the big city near Black Bear Lake and invests in a laundry business. He specializes
in high-quality laundry services for wealthy customers. (Good way to get in with them.)
Eventually, he'll sell the chain of stores and move to New York.
Before this move east, when Dexter is twenty-three, an older rich man named Mr. Hart gives Dexter a guest
pass to the Sherry Island Golf Club. Yep, same place he used to work.

As they are playing, one of them – Mr. T.A. Hedrick – takes a golf ball to the stomach. Ouch. (Although that
sounds better than a golf club to the chest, which is what Hilda almost got.)
She doesn't seem particularly sorry to have hit an old man in the stomach. She continues to play as the
other golfers – Mr. Hedrick, Mr. Sandwood, and Mr. Hart – all comment on her splendid physical
appearance.

She asks Dexter to drive the motorboat so that she can ride on a surfboard behind it.
Judy wants to avoid the man waiting for her in her house on Sherry Island, who has just told her she is his
ideal. She can't take a compliment, apparently. (Just kidding, that's actually kind of creepy.)

WINTER DREAMS SECTION 3
SUMMARY
•

•

BACK

•

NEXT

Dexter stands waiting for Judy to come downstairs to dinner. When she arrives, she behaves and is dressed
pretty informally, which disappoints Dexter, who had his hopes up for some glamor.


•
•
•
•

Her mother and father aren't home (scandalous!).

•
•
•
•

She wants to know all about Dexter right off the bat.

They chat about Dexter's college days and his business, but after dinner, Judy gets really moody.
She's bummed because a man that she really liked turns out to be poor.
It wouldn't be so bad if he had told her straight away, but she had an image in her head that he wasn't poor.
So it came as a shock, she says.
Dexter assures her, "I'm probably making more money than any man my age in the Northwest" (3.18).
She leans over to kiss him, smiling. (We ain't sayin' she's a gold digger...)
Dexter realizes that he has wanted Judy Jones since he was a boy.

WINTER DREAMS SECTION 4
SUMMARY
•

BACK

•

NEXT

•
•

•

Dexter falls for Judy, hard.

•
•
•
•
•

At the end of the summer, rumor has it that Judy has gotten engaged to a visiting New Yorker.

•

(It has taken Dexter six seasons [not like TV seasons, actual seasons] to realize that, at heart, Judy couldn't
care less about him.)

•

When he sees Judy at a dance, he doesn't pay any attention to her. Naturally, she doesn't notice; she's busy
with a new man.

•

Dexter sits with Irene Scheerer instead, and three months later, Dexter and Irene get engaged. (Things
happened quickly back then.)

•

After a long winter of making it clear to people that he is with Irene now, May finally arrives. Dexter is twentyfive.

•
•

One night, he arrives at Irene's house one day to pick her up for an evening out.

•
•
•
•
•
•

He hears a familiar voice: it is Judy Jones. She wants to talk to Dexter.

He knows that he's not her main squeeze, but he's game to put up with the other guys in her life.
Dexter feels ecstasy in Judy's presence, but he also feels restless and unhappy knowing that he can't satisfy
her.
Dexter is heart-broken, but after a month, Judy gets bored with her New York man and she returns to Dexter.
Our main man turns twenty-four (gettin' old) and starts thinking about moving east to New York.
He wants to take Judy with him.
Spoiler alert: it doesn't happen. Eighteen months after first meeting Judy, Dexter gets engaged to a woman
named Irene Scheerer.

Her mother, Mrs. Scheerer, tells him that Irene is in bed with a headache, so he goes back to the University
Club, where he's been living.
They go for a drive. This can't be good…
Judy seems melancholy. Uh-oh…
She asks Dexter to marry her. Oh geez.
She knows he's met Irene, but she can't believe that Dexter would leave Judy for another woman.

Judy begins to cry. She really knows how to work people!


•

The two of them arrive at the Jones family mansion, and Judy wants to know how she can be so unhappy
when she is "more beautiful than anybody else" (4.61). Ego much?

•

Dexter suddenly feels filled with tenderness and emotion, and when Judy asks him to come inside, he says
yes. Surprise surprise.

WINTER DREAMS SECTION 5
SUMMARY
•

BACK

•

NEXT

•
•

The romance with Judy fizzles after one month. What a shock.

•

Dexter realizes two things: he will always love Judy Jones, and he will never have her. Not a great situation
to be in.

•
•
•

Even though Dexter sees that Judy is a manipulative liar, he still doesn't blame her.

•
•

Dexter hands over his laundry management to his business partner and joins the Army.

It takes Dexter some time before he feels bad about the affair, even though he really hurt Irene and her
parents.

Our main man goes east in February of the next year after this disastrous month with Judy.
It must be 1917, because America joins the First World War (for more on the war, check out
Shmoop's learning guide).
Actually, he feels some relief to be escaping the emotion of his life.

WINTER DREAMS SECTION 6
SUMMARY
•

Fast forward seven years after Dexter's failed relationship with Judy. He is thirty-two years old, and he's
living the good (i.e. rich) life in New York.

•

A guy named Devlin comes to his office to talk business. This guy mentions that the wife of one of his best
friends in Detroit is also from Dexter's home town: maybe Dexter knows her?

•
•

Her name is Judy Simms; she was once Judy Jones. (!)

•
•

Actually, Devlin thinks Judy is a bit old for Lud Simms, but Dexter protests that she is only twenty-seven.

•
•
•

Devlin realizes that Dexter must know her rather well.

•
•
•

Devlin leaves and Dexter lies down in his office lounge.

Devlin says that he feels a bit sorry for her because her husband, Lud Simms, is a drinker who cheats on
her. She doesn't cheat on him, though; she stays at home with the kids.
(Hmm, that's weird. We think Dexter's math is off. When he first sees Judy, he is fourteen and she is eleven.
If he is now thirty-two, shouldn't she be twenty-nine?)

Even though Lud treats her badly, Judy is going to stay with him.
Dexter cannot understand what Devlin is telling him: that Judy's beauty has faded and that she has settled
down. It's all too much to process.
He feels that he has lost his winter dream, and he weeps for what he can never have.
But it's not just his dream he's lost: he has also lost that spark he once had. He doesn't even care too much
about Judy anymore.


•

That romantic boy he used to be is gone forever.

WINTER DREAMS THEME OF
SOCIETY AND CLASS
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BACK

•

NEXT

In our U.S. History Shmoop learning guide on the 1920s, we talk about the huge rise in consumer culture at this stage
of the twentieth century. Well, "Winter Dreams" was published in 1922, right at the start of the Roaring Twenties.
Fitzgerald is clearly responding to the sudden, visible signs that lots of Americans are getting very rich, very quickly.
Dexter Green's ease with making money demonstrates both the positives (yay! cash!) and the negatives (boo! bad
human relationships and loss of romance!) of this sudden rise in American wealth. The obvious and visible class
differences between the very rich and the middle class are what drive Dexter to succeed at any cost, even if it means
losing the romantic idealism of his boyhood.
Dexter strongly associates money with love in "Winter Dreams." He thinks that if he has money, he can win the love

of Judy Jones. One tiny problem: he doesn't get that having money might somehow replace love in his emotional life.
So when he dedicates himself to earning money, his ability to love dies away without him even knowing it. He is left
instead with "the gray beauty of steel that withstands all time" (6.35). Not even the loss of Judy can get to him. The
great irony of Dexter's life is that, as a boy, he links money and love together. But in Fitzgerald's world, money and
love are actually mutually exclusive. No one who has a real talent for making money can hang on to their romantic
ideals.

Questions About Love
1. How does Judy Jones think about her relationships with her lovers? How do her worries about love differ
from Dexter's?

2. What are the emotions that Dexter expresses toward Judy Jones? How does Dexter appear to define love?
3. How does Fitzgerald see the relationship between ambition and love? Can the two things coexist equally in
the same person?

Chew on This
Try on an opinion or two, start a debate, or play the devil’s advocate.
By making Judy Jones a two-dimensional character, Fitzgerald emphasizes that Dexter's attraction to her is not
personal, but just a symbol of his desire to achieve upper class status.
Dexter's character in "Winter Dreams" suggests that love and desire for money are incompatible. For Fitzgerald, it
appears that business success kills off human feeling.


WINTER DREAMS THEME OF
MEMORY AND THE PAST
•

BACK

•

NEXT

Memory and the past are everywhere in "Winter Dreams." Heck, the "Tone" of the story is wistful and nostalgic. On
the one hand, Dexter wants to forget his humble origins. He wants to leave behind the memories of his immigrant
mother and his grocer father, move to the East Coast, and make tons of money. Dexter's social success depends on
his willingness to ignore his lower class background so that he can attach himself completely to the upper class. On
the other hand, Dexter's eagerness to leave behind his social origins shows that he also has to sacrifice his own early
memories. To make lots of money, he also has to turn his back on the romantic idealism of his younger days. Dexter
appears perfectly fine with forgetting about his parents. (Nice, Dex.) But he weeps when he finally understands that
he has also cast aside "the country of illusion, of youth, of the richness of life" (6.36) that used to inspire him so much.
He has forgotten about the boy he used to be, which is the worst loss that Dexter can imagine.

Questions About Memory and the Past
1. What details does Fitzgerald give us of the Green family history? Why do these details matter to Dexter's
characterization?

2. There are points in "Winter Dreams" when Fitzgerald seems to be connecting Dexter's particular family
history with a larger narrative of the American class system. For example, Dexter (as an up-and-coming selfmade man) thinks of himself as "newer and stronger" (3.1) than the old money elites he meets at college.
How is Dexter's particular story also a more general tale of the American self-made man?

3. When does grown-up Dexter appear to feel the greatest distance from the boy he once was in Black Bear,
Minnesota? Are there other instances when he feels closer to his past? Why might Dexter's relationship to
his past matter in a story about ambition for a better future?

Chew on This
Try on an opinion or two, start a debate, or play the devil’s advocate.
"Winter Dreams" uses Dexter Green's sense of distance from his own past to show off the general flexibility of the
American class system. (I.e. Dexter can go from humble immigrant parents to a future in which his children can afford
"carelessness" [3.2] in just three generations.)

Dexter spends so much time in the past and the future that he forgets about the present moment. He would have had
a more fulfilling life if he'd remembered to live in the moment.

WINTER DREAMS THEME OF
GENDER
•

BACK

•

NEXT

Dexter is a man of action, a self-made man who can change his life by going to an elite college and investing cleverly
in business. But he can only do those things because he is, specifically, a man. Judy Jones has the same kind of


restless, melancholy spirit that Dexter does. But because she is a pretty lady, she becomes an object to be admired
(by men like Dexter). Her great talent is her physical beauty, and it is through her body that she tries to find emotional
fulfillment. What is this, the 1920s? Oh. Yeah, it is.
The other main female character in "Winter Dreams," Irene Scheerer, represents another possible, socially
acceptable role for upper class women in the 1920s: wife and mother. Irene is welcoming, friendly, and clearly
destined to be great with her kids. While in many ways, Judy and Irene seem like absolute opposites, they share the
same essential trait. Their characters are defined in relation to the story's central male figure, Dexter. We have no
sense of how Judy and Irene think as rounded characters. The fact that they are women limits their ability to move
through multiple social spaces the way that Dexter can.

Questions About Gender
1. Judy's beauty is what draws Dexter to her so strongly. Why is it impossible for Dexter to attach the same
romantic ideals to less-attractive Irene Scheerer? Why might it be important that the female characters are

represented in terms of physical beauty while the male characters are represented in terms of financial
ability and ambition?

2. How do Judy and Irene Scheerer contrast with one another? What do these contrasts suggest about the
social roles available to women in the early twentieth century United States?

3. How does Judy describe her own overall unhappiness? What kinds of assumptions does Judy make about
what should make her happy?

Chew on This
Try on an opinion or two, start a debate, or play the devil’s advocate.
Judy is a total diva. But her assumption that beauty means (or should mean) happiness is just the 1920s female
equivalent to Dexter's belief that money means happiness.
Judy is looking for the same kind of emotional fulfillment from her many partners that Dexter seeks in his business
investments. Their two separate responses to the same feeling of loneliness and isolation is the result of gender
difference.

WINTER DREAMS THEME OF
AMBITION
•

BACK

•

NEXT

Dexter is not ambitious just for the sake of making tons of money. The narrator of "Winter Dreams" is careful to
remind us that there is nothing "merely snobbish in the boy" (2.1). Dexter is an idealist: he associates cash with the
graceful, attractive lives of the members of the Sherry Island Golf Club. In fact, making money is almost secondary to

his main ambition of leaving behind his humble origins and joining the upper class. (Take, for example, his
embarrassment: "His mother's name had been Krimslich. She was a Bohemian of the peasant class and she had
talked broken English to the end of her days. Her son must keep to the set patterns" [3.2].) Dexter dreams of starting
a new family, in which his children won't have to worry about being of the right class or stock. Money is a way to make
that better life possible, but it's not a goal in itself.

Questions About Ambition


1. What distinguishes Dexter from the other men in "Winter Dreams" who are also seeking financial gain? How
does Dexter's success structure the plot of "Winter Dreams"?

2. Can we compare Dexter's desire for money to Judy's desire for sexual fulfillment? How are the two similar,
and how do they differ?

3. We mentioned in our character analysis of Judy Jones that Dexter strongly identifies Judy with his more
general financial ambitions. At what point in "Winter Dreams" does Dexter's desire for money separate from
his desire for Judy Jones? What is the cause of this eventual splitting of purpose?

Chew on This
Try on an opinion or two, start a debate, or play the devil’s advocate.
Dexter's effortless financial success allows Fitzgerald, as a writer, to downplay the difficulties of earning money. That
way, "Winter Dreams" can focus instead on the major emotional problems that accompany business ambition.
Dexter's ambition does him more harm than good. After all, he ends up miserable and alone.


"Winter Dreams" just like The Great Gatsby is one of Fitzgerald's diatribes against the Old
Money class in American society and its seeming false offer of equality to those who believe in
the American Dream. In the story, Dexter observes the wealthy golfers for whom he caddies and
believes that if he works hard enough, he can one day be just like them. He envisions scenes

where he drives up in luxurious cars and the wealthy surround him simply to listen to him speak.
Dexter does work hard and becomes wealthy, but once he makes it to the top, he realizes that the
dream has become corrupted (just like Daisy is the corrupted version of Gatsby's dream and can
never live up to his expectations).
Both of these works present Fitzgerald's frustration with his own life and attempts to achieve the
American Dream. He, like Dexter and Gatsby, became interested in a wealthy socialite (Zelda)
and was looked down upon by her social class and family. When he finally did win Zelda and
marry her, he endured a tumultuous relationship with her where their wealth was unstable and
their faithfulness to one another questionable. He believed (as he demonstrates in "Winter
Dream") that the Old Money portion of society corrupts the moral, decent Midwesterner.
Become a fan of scarletpimpernel. (What's this?)
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Ashley Kannan | Middle School Teacher | (Level 3) Distinguished Educator
Posted on April 19, 2010 at 9:21 AM (Answer #3)
The disillusionment featured in the short story revolves around Dexter's belief that happiness can
be attained through gain and want, without some type of moral foundation that serves as a
bedrock for all endeavor. In many ways, Dexter's belief in happiness is illusory. As a caddy, he
is entranced with the trappings of wealth, and the allure that high society features. When he
golfs at the same course for which he used to caddy, he realizes that he is playing in a foursome
with the same people for whom he used to be a caddy or a type of servant. His "love" for Judy is
one that is based on physicality and wealth. Dexter is entranced with what Judy represents and
the world of which she is a part. In the end, when he is told of her sad life and the beauty that is


now gone, Dexter weeps because it is the death of his illusions, with only reality left. The
disillusion present is one predicated upon firmament that lacks stability