How is "Winter Dreams" a Modernist text?

"Winter Dreams" can be seen as a Modernist text in a couple of ways.  If we accept the premise of Modernism that the movement seeks to display a condition in which there is a "shift" between the relationships that people have towards one another, themselves, and their world, then the narrative shows this in a couple of ways.  Initially, I think that Fitzgerald displays Modernism in the entire premise of self- improvement.  The traditional notion is that an individual works hard, becomes successful, and in doing so represents a harmonious connection between themselves and the world around them.  Fitzgerald inverts this Horatio Alger "rags to riches" story in displaying that the more Dexter becomes successful, the more alienated and divided he becomes.  Dexter's unhappiness gains as he becomes more successful because his "Winter Dreams" are fundamentally corroded.  The vision that Fitzgerald offers of material success is a Modernist one, in which happiness is elusive no matter what.

The text is also Modernist in its ending.  In this, a "shift" is seen because of its dissonance.  Simply put, there is no resolution in this condition.  Dexter was unhappy when he didn't have Judy Jones.  Judy Jones was shown to be this ideal that motivated Dexter.  He was then unhappy when he had Judy Jones because of her infidelities and her unwillingness to emotionally commit to him.  Dexter is then finally shown to be unhappy when his life moves past Judy Jones and then hears about her loveless marriage and her faded beauty.  It is here in which Dexter cries about "That thing is gone."  This is a Modernist progression because it does not show anything in way of freedom or happiness.  There is only alienation and desolation waiting for the modern individual, a shift from the traditional construction of happiness and contentment that was previously understood.

How does "Winter Dreams" by F. Scott Fitzgerald reflect the modernism era?

According to Trent Lorcher in his article "Lesson Plans: Modernism in Literature:

Modernism is marked by a strong and intentional break with tradition. This break includes a strong reaction against established religious, political, and social views.

In Fitzgerald's "Winter Dreams," Dexter's behavior exemplifies the style of modernist authors, breaking with the realist style. (First printed in 1922, this is a time of economic growth and optimism, with many stories of success for all kinds of people.)

Dexter is a man of humble beginnings who defies the social rules of the time: he does not conform to the wishes of the upperclass. When offered a rare opportunity to caddy for a wealthy golfer, he refuses. Next, he quits rather than be forced to caddy for a tyrannical eleven-year old golfer.

The modernist view in this story focuses on the "strong reaction against...social views." Dexter does not conform to the whims of the rich as one might have expected him to.

He strategically chooses his own college, and creates a line of laundries catering to the wealthy. He becomes a young man of means, highly regarded by those in the elite class.

In this way, he is able to create a persona that easily mingles with the rich. When it seems that Dexter is in control of his life, he meets the eleven-year old child from his caddying days—Judy Jones. She is grown up, beautiful and desirable—to everyone.

While it seems that Dexter might be able to consciously protect himself from Judy's careless attentions, even seeming to understand what she is doing to him, he eventually falls for her. For a time, he loses his direction, though he understands his hopeless attraction to Judy.

Dexter continues to throw himself into his business, while dealing with Judy's casual regard of him. This goes on for months, and ultimately he removes himself from her circle. He concentrates even more on financial success, and starts seeing another young woman, Irene, to whom he eventually proposes.

It would appear to the reader, especially based on the norms of that time, that Dexter has finally found a way to leave Judy behind and move forward with his life. One would expect him to do the smart and predictable thing: he is bright and successful. It seems he will marry and settle down.

Based on one chance encounter with Judy, however, Dexter turns his back on Irene and becomes engaged to Judy; their engagement is short-lived. As painful as all this is, he continues to deal with disappointment while his pain seems to strengthen him. Dexter joins the war.

[Dexter] was one of those young thousands who greeted the war with a certain amount of relief, welcoming the liberation from webs of tangled emotion.

The war is over, years pass, and Dexter is firmly grounded again. By chance he meets a friend of Judy's. Judy has married, but her life is sadly changed—her husband fools around while she cares for her children; and, Dexter learns her beauty has faded.

This news, especially the last, causes him to mourn what is now gone forever. Where his winter dreams as a young man promised relief with the newness of spring, Dexter realizes that the chance of a life with Judy is gone forever.

The modernist style baldly shows Dexter's ongoing struggle, and the loss of his dream of Judy, as well as the loss of those years that brought him some kind of happiness. For all he could do, Dexter was never able to keep Judy from destroying the hope she created within him.

I hope this helps.

What quotes demonstrate modernism in "Winter Dreams"?

Quotes demonstrating modernism in "Winter Dreams" could include those that reflect a changing world or a refusal to follow the expectations of society.

Modernism often features characters who are struggling to adapt to a changing world. Often, these characters do not triumph over their challenges; instead, they barely emerge with modest success.

Dexter demonstrates this character arc through his pursuit of Judy Jones. Judy represents success, ambition, and societal influence. Though she has ambitions of her own, she enjoys keeping Dexter in the wings, and he is content to serve this role for her.

It was the exquisite excitability that for the moment he controlled and owned. But a week later he was compelled to view this same quality in a different light. She took him in her roadster to a picnic supper, and after supper she disappeared, likewise in her roadster, with another man.

Dexter allows himself to become "enormously upset" by Judy's inattentiveness, and he later discovers that he was one of a dozen men whom Judy spent time with that summer.

Eighteen months later, Dexter becomes engaged to a "sweet and honorable" girl. He finally begins to believe that he has gotten over Judy Jones:

When autumn had come and gone again it occurred to him that he could not have Judy Jones. He had to beat this into his mind but he convinced himself at last. He lay awake at night for a while and argued it over. 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, and after a while he fell asleep.

This is not a man who triumphs over the girl who has rejected him; instead, he continues to be burdened by the memories of her and by his own desire to prove that he can conquer the challenge of obtaining her favor. Sure enough, Judy eventually returns just in time to end his engagement and then leaves him again a month later.

When he later discovers that Judy Jones has gotten married, become a rather ordinary mother, and lost her beauty, he realizes that "the dream [is] gone." The resolution to his ongoing yet impossible pursuit lacks any sense of victory or peace. Instead, Dexter meets the news with grim acceptance:

For the first time in years the tears were streaming down his face. But they were for himself now ... The gates were closed, the sun was gone down, and there was no beauty but the gray beauty of steel that withstands all time. 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.

You could also look for quotes that reflect Dexter's unwillingness to follow the expectations of society, which is another characteristic of modernist literature. Dexter doesn't follow what might be the "predictable" path, and this break with tradition is often found in modernist texts.