Lamya Rhett

Dr. Tuttle
American Literature B
16 March 2024

Fitzgerald Essay Lesson

The story “Winter Dreams” by F. Scott Fitzgerald follows a Dexter Green, a caddy who’s
a young ambitious man, as he navigates the social hierarchy of Black Bear Village.
Dexter caddies for pocket money at a golf course frequented by wealthy patrons from
Sherry Island.
Despite his humble background, Dexter dreams of success and a high social status.
His encounters with the wealthy and alluring Judy Jones shape his aspirations and desire,
leading to a pivotal moment of realization about the superficiality of his ambitions.
Dexter Green is a young, ambitious boy from Black Beat Village, whose
aspirations are fueled by his exposure to the wealth and glamour of Sherry Island.
Hardworking and determined, Dexter is skilled at golf and dreams of climbing the social
ladder.
However, beneath his composed exterior lies a vulnerability stemming from his desire for
acceptance and validation in the affluent society he idolizes.
Dexter’s journey throughout the story reflects his pursuit of the American Dream and the
disillusionment that comes with it,
Judy Jones is the epitome of beauty of enchantment, captivating those around her
with her charm and confidence.
Despite her young age, Judy exudes an air of sophistication and worldliness, drawing
admirers wherever she goes.
Beneath her glamorous facade, Judy struggles with her own insecurities and the
expectations placed upon her by society.
Her complex character represents fleeting nature of youth and beauty, as well as the
emptiness that lies beneath the surface of superficial relationships.
The story “Winter Dreams” parallels the lives of its author, F. Scott Fitzgerald,
and his wife, Zelda Fitzgerald, offering a glimpse into the glamorous yet
tumultuous world of the Jazz Age.
Dexter Green’s infatuation with Judy Jones mirrors Scott Fitzgerald’s own
fascination with Zelda, whose beauty and charisma captivated him.
Like Dexter, Scot pursued the American Dream through his literary endeavors,
seeking success and recognition in elite social circles.
However, both Dexter and Scott come to realize the emptiness of their pursuits, as
they grapple with the fleeting nature of youth, beauty, and ambition.
Through Dexter’s journey, Fitzgerald critiques the superficiality of the American
Dream and the disillusionment that accompanies its pursuit, reflecting his own
experiences and observations of the Jazz Age society.