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Corey M. Dunn

Professor Sung

English 113

3 February 2018

F. Scott Fitzgerald: Winter Dreams

F. Scott Fitzgerald’s short story, Winter Dreams, is full of vividly descriptive imagery

and melancholy writing that captivates the readers full attention to the subject matter. Reflective

of Fitzgerald’s own life, and pursuing his ambitions to become a writer, he gives us a six-part

story that follows the life of an ambitious young man named Dexter Green who believed that the

American dream was filled with images of glamour and fame. This dream was fueled by his love

for one Judy Jones whom does not regard the same sentiment towards him. Each story follows

Dexter and Judy through their disastrous on-again-off-again relationship. It is Fitzgerald’s

intention to express his view to the reader of the trials Dexter has that come with chasing

affluence and his delusional connection to love and why his materialistic American dream of

becoming rich is not everything that it is speculated to be.

Winter Dreams is a coming of age story that chronicles a period in the life of Dexter

Green over eighteen years, who has lofty ambitions for his future, but from the narrators’

perspective, for all the wrong reasons. It was during these winter months that bring us to Dexter

Green, who during the summer was a caddy for the wealthy members of the Sherry Island Golf

Club. While Dexter, [Who does not come from a poor background] only earned pocket money

during his employment at the club, his intentions were beyond his pay. Dexter enjoyed his job

because it embraced his fascination with the wealthy and how they lived. Being a member of a
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Golf club has always been a sign of wealth and affluence. Ideally, it became the symbol of what

Dexter spent his winter months dreaming of.

Unlike the other caddies, he stood out amongst them by carrying himself in a manner

that reflected such a stance. These actions did not go unnoticed. As stated by Mr. Mortimer

Jones, “Best caddy I ever saw! Never lost a ball! Willing! Intelligent! Quiet! Honest! Grateful!”

(Fitzgerald 1) Mr. Mortimer was a very wealthy man whom Dexter wanted to emulate. He was

also the father of the young Judy Jones who Dexter meets for the first time here in this point of

the story. He is awe struck from the moment he meets her while on the golf course with her

nanny attempting to play a round of golf. Judy was a beautiful girl who all her life got what she

wanted. Growing up knowing she could get her way with people made her a very spoiled and

demanding young lady, and she becomes a pivotal point [for the good and bad] in Dexter’s life.

It is here, Dexter correlates beauty to the same regard as wealth and fame. He feels that he would

have to become wealthy to win Judy’s affection. This led to a rash decision that the narrator

explicates “he had received a strong emotional shock, [From seeing Judy] and his perturbation

required a violent and immediate outlet” (Fitzgerald 2). It is this point that realizing that she

would never be attracted to a lowly caddy, he quits his job and begins a pursuit to become

wealthy.

The story returns seven years for Dexter who is now back in Minnesota and has created a

very lucrative laundry business which holds the same high regard for his professionalism as he

did as a caddy as the narrator points out, “Men insisting that their Shetland hose and sweaters go

to his laundry just as they had insisted on a caddy who could find golf balls”. Dexter finds

himself invited to the very golf club he had once caddied, and from his new perspective didn’t

seem to see the flare he had imagined as a teenager, as the narrator explains, “It was a curious
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day, slashed abruptly with fleeting, familiar impressions. One minute he had the sense of being a

trespasser--in the next he was impressed by the tremendous superiority he felt toward Mr. T. A.

Hedrick, who was a bore and not even a good golfer any more”. Fitzgerald gives the reader a

nostalgic moment for Dexter as he lays on a platform in the middle of the dark moon-lit lake. He

has a moment of clarity and reflection of what he has achieved. The excerpt gives a vivid

description of the music playing in the backdrop and the mood of the setting gives us a clear

understanding of the moments that Dexter accounts of his days from high school to his college

years. Fitzgerald engages the reader to see the memories in a way that show expressive

symbolisms in his writing describing the emotion Dexter feels when looking back at the

moments that would lead up to where he is in life,

The tune the piano was playing at that moment had been gay and new five years

before when Dexter was a sophomore at college. They had played it 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. (3)

It is at this point, Judy has returned to the story and Dexter finds his way back in her graces

after running into him while out on the lake. And through countless interactions, Dexter found

himself always being led on to believe he had a chance at love with Judy, only to be let down

again. Judy, who comes from wealth, always would get whatever he wanted she carried herself

with a confidence that teetered arrogance. Her spoiled and selfish attitude towards the men she
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dates appears to have an underlying meaning. One could imagine her loss of interest is because

she gets everything she wants, or possible rebellion to the notion of being associated with any

one man. One thing is a certainty, she is self-absorbed and perfectly okay with the idea of

keeping Dexter as a rebound relationship. After continuous affairs, Dexter decides to disbar their

relationship to pursue one more meaningful.

Now having found another relationship with Irene Sheerer whom Fitzgerald refers to as

“sturdily popular” (6). A woman who like Judy, comes from a wealthy family as well. However,

she did not have Judy’s vibrant looks and to Dexter she represented a mundane life that he had

no interest in as the narrator states “. He 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” (Fitzgerald 6).

The relationship becomes a short lived one because Judy returns yet once again, and whisks

Dexter away leaving Irene heartbroken. The disheartening evidence of it is that Dexter seems to

have no remorse for his actions because of his idealistic true love was in his mind, with Judy,

who even with her cheating habits, he feels she is his ideal sadly, because it is what his vision

has made her to be. Now having left Irene, he thinks that all his dreams are falling into place

only to be let down yet again by Judy who leaves him for good this final time throwing him into

a tail spin of emotion. His dream began to fade away of happily living in bliss to hopelessly in

love with an idea that never takes fruition.

Herein lies the end of the story, Dexter has succeeded in all his aspirations in life, he has

exceeded his own expectations in business, now being a successful businessman in New York on

Wall Street who had done so well that “there were no barriers too high for him” (Fitzgerald, 8)

except for the one true reason he sought the lifestyle of the wealthy, and that was the acceptance

of Judy Jones who was now a part of his past. Until the fateful day that his business associate
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Devlin begins discussing Dexter’s hometown. It is here Dexter hears of Judy’s current life and it

is not what he had expected it to be. With living with a cheating alcoholic husband and losing her

beauty that he had fallen in love with in the first place shook Dexter to his core. His

advancements and accomplishments in life reflected his connection to the idea of being a part of

her life. He feels that the “Thing” that carried him through life was indeed the dreams of a future

with Judy whom he was working so hard to succeed for. Now knowing the life, she is living, he

realizes that all his arduous work was a waste of time in his mind and his dream was destroyed.

Judy represented the “thing” that Dexter felt inside. She was from the beginning his inspiration

to seize his moment and strive for a better life. The problem is, Dexter only wanted this fabulous

life because he assumed it involved having Judy as a leading role in it. This was what his dreams

were about. This is what his ambition was based upon. All his memories of the once lavish

dreams as a young man were now fading away as Dexter states, “long ago, there was something

in me but now that thing is gone”. It is unknown exactly what the “thing” is that Dexter had

inside him, but we can speculate that it was directly related to his ambition of living out this

delusional romantic future he concocted back when he was a teenager. Knowing that Judy had

lost her looks and was in such a horrible marriage appeared to have been the last bit of hope and

connection to his dream and now this has caused his dream to vanish.

The conclusion to Fitzgerald’s story generalizes the pursuit of an illusion in the mind of

a man who had the drive to become whatever he wanted, he seized his moment in life but for all

the wrong reasons. In the end, Dexter’s pursuit felt to be a waste of effort. Though he fulfilled a

life of wealth, he realized it was not what he had expected, and all his arduous work still left him

empty and alone. He gives up the ideology that his youth was based upon and replaces it with his

strong-willed business sense. Even as he tried to feel some emotion from the news of Judy,” He
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wanted to care, and he could not care. For he had gone away, and he could never go back any

more” (Fitzgerald 9) his mind-set was changed and that part of him was now gone forever.

Dexter’s story is proof that the American dream does not always bring the happiness one would

hope for, coming to the realization that all along, his efforts were merely chasing an illusion.
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Works Cited

Fitzgerald, F. Scott. Winter Dreams. South Carolina: The Board of Trustees of the University of

South Carolina, 2008. Print