F. Scott Fitzgerald wrote short stories to earn a living during his career, with his story "Winter Dreams" examining the concept of achieving the American Dream. The story follows Dexter Green, who works hard and becomes very successful, but finds himself unfulfilled. Like the protagonist, Fitzgerald achieved wealth and fame through his early works but also struggled with the realities of the American Dream. Both Fitzgerald and Dexter came to realize that success did not guarantee happiness and had nothing left to strive for once all their dreams were achieved. Fitzgerald used his own experiences to illustrate how the American Dream could both provide hope but also leave one feeling empty once attained.

1. Megan Juarez
May 20, 2013
Fitzgerald’s Truths
As much as he is known today for his novel, The Great Gatsby, many do not realize
that F. Scott Fitzgerald’s main source of income during his years came from his short
stories. After his death in 1940, the New York Times stated, “Mr. Fitzgerald and his
writings epitomized ‘all the young sad men’... With the skill of a reporter and the ability
of an artist, he captured the essence of a period when flappers and gin and the ‘beautiful
and the damned’ were symbols of carefree madness of an age” (Collected Short Stories of
F. Scott Fitzgerald). Fitzgerald not only lived through the Jazz Age, but he gave it its
name; he illustrated it, defined it, and understood it. During a time when the American
Dream was at its highest, Fitzgerald conquered and dissected it. He understood the
concept of the American Dream so well that he felt he must share the truth’s of it with
society. It is in stories such as Winter Dreams, written in 1922, where Fitzgerald uses his
experience to honestly express the reality society lives in. Winter Dreams is about a
young man named Dexter who reaches high goals of being successful, ultimately
fulfilling the American Dream, however he unfortunately loses himself after
accomplishing so much. Through Winter Dreams, Fitzgerald proves how the American
Dream provides hope, yet it so easily overcomes one’s life that it steals their identity and
once succeeding their dreams, one has nothing left to hope for, leaving them empty.
F. Scott Fitzgerald lived during an age that was described as, “an age of miracles, it
was an age of art, it was an age of excess, and it was an age of satire” (Bruccoli). He was

2. born in St. Paul Minnesota in 1896 and grew up in a Catholic family. For his education,
he attended Catholic schools and eventually Princeton. While at Princeton, Fitzgerald
wrote for the school magazine and neglected his other studies because he enjoyed it
more. However, he quit Princeton to join the army in 1917. He was stationed at Camp
Sheridan where he decided he must publish a successful novel before dying in the war, as
he expected to. Camp Sheridan was also where he met his future wife, Zelda. Fitzgerald
and Zelda became engaged, but with no luck publishing his novel, and no other prospects
for his future, she broke it off. Finally, after a third attempt, This Side of Paradise was
published in 1920. Fitzgerald knew that to win Zelda’s heart he had to prove something
of himself. While trying to publish the novel, he claimed, “‘I have so many things
dependent on it- including, of course, a girl’” (This Side of Paradise). Fitzgerald acquired
enormous wealth and he and Zelda became quite the young celebrities. They lived a
flashy lifestyle by attending parties and wearing fancy clothes, ultimately becoming icons
of the Jazz Age. Along the way, Fitzgerald and Zelda had a daughter, Scottie, but they
still continued traveling. Their lifestyle eventually caught up to them and the Fitzgerald’s
fell into money issues. It is at this time that Fitzgerald’s marriage started to fall. Zelda
suffered from a mental breakdown in 1930 and from then on was in an out of the hospital.
Trying to support not only himself but his wife’s illness and Scottie’s schooling,
Fitzgerald’s only way to survive was by his short stories.
During his time, the novel that Fitzgerald made his largest profit from was This
Side of Paradise. While his other novels contributed to his earnings, his short stories were
his main source of income. Fitzgerald wrote for The Saturday Evening Post, The Smart
Set, and Collier’s (Bruccoli). Between the short time of November and April, 1923,

3. Fitzgerald wrote eleven short stories and managed to earn $17,000 (Quirk). Although
Fitzgerald was one of the highest paid writers of his time, he barely kept his head above
the water of his finances. His stories were and still are appreciated because of the truth he
incorporates into them. Fitzgerald understood how money was the main force of life.
Unfortunately, he learned the hard way that money does not necessarily make a man
successful and does not guarantee happiness. He himself accomplished the American
Dream when concerning wealth, fame, and success, but in the end, he lost control.
Fitzgerald dreamed of becoming somebody but he could not have expected where his
dreams would take him in the end. It is because Fitzgerald personally experienced
achieving the American Dream and the aftermath of it that he is able to write such
successful stories such as Winter Dreams.
Fitzgerald’s works have significant differences from one another but ultimately
support the same idea of the American Dream, especially in Winter Dreams. In his
stories, “Often, the central character is (like Fitzgerald himself) a young man from the
provinces who comes to conquer the big city” (Collected Stories of F. Scott Fitzgerald).
The protagonist in Winter Dreams is named Dexter Green. Although he came from a
family who lived a comfortable lifestyle, he still took it upon himself to earn money. As a
young boy, he caddied for pocket money. Dexter was not just an average caddie, he was
one of the best, even earning an “A Class” badge, meaning he was of the highest rank. He
always understood that if he wanted to achieve anything he would have to work for it.
Dexter’s “Winter Dreams” consisted of hope for the future and he strove toward that idea
with effortless determination. He not only caddied but he excelled at caddying. He not
only started a Laundry chain in his young twenties but he made it the best laundry chain

4. by perfecting how the English washed their fine woolen. Dexter is the kind of man who
never fails to exceed expectations, which is why other people would refer to him as,
“Now there’s a boy” (McMichael). As a young man, he daydreamed about one day
golfing with the members of the golf club he had caddied for. “He became a gold
champion and defeated Mr. T. A. Hendrick in a marvelous match...sometimes winning
with almost laughable ease, sometimes coming up magnificently from behind”
(McMichael). Dexter had determination ever since his caddying days and later becomes a
successful entrepreneur. It seemed as though Dexter had everything but someone to share
his life with.
These dreams were not just goals for Dexter, but hope. They persuaded him to keep
looking toward his future with a sense of wonder. After accomplishing his dreams of
becoming a successful man, Dexter found something else to hope for, and that was Judy
Jones. Judy Jones came into Dexter’s life at a perfect time for him. Just when Dexter had
nothing left to look forward to in his future, Judy casually intervenes. Judy has a
somewhat wild reputation. She is notorious for dating men simultaneously and breaking
engagements before the news could spread. There was something about her, though, that
Dexter found himself attracted to. Even when he was invited to her house for the first
time, and he found plenty of other eligible men there, his attraction toward her did not
change. If anything, it enhanced. “It excited him that many men had loved her. It
increased her value in his eyes” (McMichael). Judy was spontaneous and charming, yet
dangerous. She dropped men’s hearts like bombs, but that was no matter to Dexter.
Eventually, Judy did toss Dexter to the side, and he moved on.
Dexter meets a woman named Irene whom he gets engaged to. Irene was different

5. from Judy. Dexter felt “a sense of solidity to go with her-she was so sturdily popular, so
intensely a ‘good egg’” (McMichael). As perfect as she seemed for him, her solidity
made her predictable, leaving no room for any hope or mystery in their future. This might
have been why Dexter broke off their engagement so easily when Judy unexpectedly
comes back into his life. Once again, their endeavor did not last long, and Judy left
Dexter for good. Dexter accepted this though, “He loved her and he would love her until
the day he was too old for loving-but he could not have her. So he tasted the deep pain
that is reserved only for the strong, just as he had tasted for a little while the deep
sadness” (McMichael). Accepting the fact that he could never have Judy, Dexter decides
to move to New York where he accomplished even more and there “were no barriers too
high for him” (McMichael). It is in New York, about ten years after seeing Judy, that
Dexter hears about her one last time.
A business client brings up a mutual friend from Dexter’s hometown who
coincidentally happens to be Judy. Dexter is shocked when the man tells him how Judy
has settled down. Not only has she settled down with kids, but she is also married to a
drunk and has lost her “great beauty.” To Dexter, Judy had always remained the way she
had last left him- young, beautiful, and independent. Once losing Judy Jones, he assumed
there was nothing left to lose, making him invulnerable. After this surprising news, “he
knew that he had just lost something more, as surely as if he had married Judy Jones and
seen her fade away before his eyes” (McMichael). Judy had remained as a possible hope
for him until he learned this devastating news. Although he knew he would never be with
her, he now knew that he did not even have the slightest chance. There was nothing left
of the idea of having Judy Jones. His hopes for her were permanently gone.

6. One might question why this was so devastating to Dexter. He knew he would
never have her, and he seemed to accomplish everything else in life, but that was
precisely the problem. Dexter built up dreams and as he achieved one, another came
closely after that. His possibilities became infinite, almost as though anything was easily
attainable. Judy, however, was not attainable. These dreams of his provided hope. Dexter
had built his dreams of success and achieved them. The only dream he had left was his
dream to be with Judy Jones. He knew he would never have her, but the idea provided a
sense of hope that he had lost once he accomplished his ‘Winter Dreams.’ Being with
Judy Jones was his last dream that could be left as something to look forward to in the
future. His dream of being with Judy Jones is crushed, therefore he has nothing left.
Dexter says, “Long ago, there was something in me, but now that something is gone. I
cannot cry. I cannot care. That thing will come back no more” (McMichael). Dexter
becomes stoic about his life because there is nothing else to look forward to. As a young
man, he looked forward to his ‘Winter Dreams.’ Once older, he sought more success. In
New York, he still kept pushing for something more. After learning about Judy Jones, his
life was officially stagnant. He had achieved all that he could and had nothing else to
look forward to. It is as though he accomplished all the aspects of the American Dream,
concerning wealth and prominence, but purposefully left love out of the picture. What
else is there to hope for when all has been done? This is a concept Fitzgerald understood
well because he himself had achieved it all and the supposed American Dream had
backfired on him.
Fitzgerald, just like Dexter, had big dreams of his own. He wanted to be wealthy,
he wanted to be famous, and he wanted to have love; all of which he succeeded in. His

7. first novel, Tender is the Night, brought him wealth, fame and the love of his life, all over
night. He had high hopes in the very beginning of his career. He claimed, “I paid off my
terrible small debts, bought a suit and woke up every morning with a world of ineffable
toploftiness and promise’” (This Side of Paradise). His life moved to the top so fast, but
fell so rapidly. Before he knew it, he was making barely enough money to get by and his
wife was declared schizophrenic (Collected Stories of F. Scott Fitzgerald). Fitzgerald
realized that the American Dream cannot give anybody a perfect life because a perfect
life is unattainable. Dexter Green in Winter Dreams also expresses how the American
Dream does not automatically make one happy. Both he and Fitzgerald had worked so
hard to attain it that they somewhat lost themselves along the way. Fitzgerald resorted to
his writing, but Dexter resorted to stoicism. They succumbed to the ideals of society and
were left dumbfounded by what they gave up to gain what they did, which was the
unfortunate understanding of the American Dream.
Through Winters Dream, Fitzgerald proves how the American Dream provides
hope, yet it so easily overcomes one’s life that it steals their identity and once succeeding
their dreams, one has nothing left to hope for, leaving them empty. Dexter, just like
Fitzgerald, had chased the sun. In the end, unfortunately, they both found themselves
unhappy with the reality of what the American Dream really was. They each worked hard
to accomplish their goals and along the way they had lost themselves and their purpose.
Fitzgerald admits, however, that the dream did not take everything away from him. In his
journal he says, “There was one little drop of something not blood, not a tear, not my
seed, but me more intimately than these, in every story, it was the extra I had” (Collected
Stories of F. Scott Fitzgerald).

8. Works Cited
Bruccoli, Matthew J. "A Brief Life of Fitzgerald ." University of South Carolina . Board
of Trustees , 4 Dec. 2003. Web. 17 Jan. 2012.
<http://www.sc.edu/fitzgerald/biography.html>.
Fitzgerald, Francis S. This Side of Paradise. New York: Pocket Books, 1995. Print.
Quirk, William J. “Living On $500,000 A Year: What F. Scott Fitzgerald’s Tax Returns
Reveal About His Life And Times.” American Scholar 78.4 (2009): 96-101.
Academic Search Premier. Web. 10 May 2013.
Fitzgerald, Francis S. Collected Stories of F. Scott Fitzgerald. New York: Barnes &
Noble Inc., 2007. Print.
McMichael, George and James S. Leonard. Concise Anthology of American Literature.
Pearson Education Inc., 2011. Print.