In "Winter Dreams," how does Dexter Green realize the "American Dream" is an illusion?

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At the beginning of "Winter Dreams," we learn that Dexter Green is a teenager and a caddy at a golf club in Minnesota. He has vivid dreams of playing on the same golf course and beating the men he caddies for at golf. He aspires to success, wealth, and status. Eventually, he goes to college on the East Coast and becomes a successful businessman. In some ways, we might say Dexter achieves the "American dream" by advancing in socioeconomic class. He even plays golf on that course with at least one man for whom he used to caddy.

However, most of the story focuses on Dexter's relationship with Judy Jones, later Judy Simms. They first meet at the golf course when both are young. Judy wants Dexter to be her caddy, since he is at the course waiting for the caddy master to arrive. He decides to quit instead; for some reason, he does not want to serve as this girl's caddy. Later, when he returns to the course as a 23-year-old, he encounters Judy again during a golf game. The two begin a casual relationship, but Dexter knows she sees other men. Nonetheless, he imagines that Judy herself is what he wants, that she is basically his "American dream." The narrator remarks, "It did not take him many hours to decide that he had wanted Judy Jones ever since he was a proud, desirous little boy." Even though Judy expresses some interest in Dexter, she dates other men and even is rumored to be engaged to someone else. She says that she wants Dexter to marry her, but because of her erratic and flighty ways, Dexter does not seem to think that is really possible. Dexter becomes engaged to another woman, Irene, but he ends up breaking their engagement after Judy returns and their love is briefly reignited. It doesn't last long; Judy moves on, and Dexter does not have Judy, nor does he marry Irene. He continues to thrive in his business endeavors, but he never does achieve his dream of being with Judy.

At the end of the story, Dexter has a casual conversation with a man named Devlin, who reveals to Dexter that Judy is now married to a man who drinks and "runs around" and that Judy stays home with their children. He also notes that Judy is no longer exceptionally beautiful, and it seems that whatever made her special in Dexter's mind no longer exists. He feels betrayed by this information because his "dream" is now forever vanished; he even doubts whether the past or his memory of Judy is meaningful anymore in light of the way Judy has changed. The narrator ends the story by saying,

"Long ago," he said, "long ago, there was something in me, but now that thing is gone. Now that thing is gone, that thing is gone. I cannot cry. I cannot care. That thing will come back no more."

Dexter is completely disillusioned. His dream can never be achieved.

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Dexter struggles to define the American Dream when he is a young man; he knows it is more than acquiring wealth, success, and social position, (though those as elements of it) but he is unable to articulate it, even to himself. However, when he becomes involved with Judy Jones, he finds something to make it concrete: her. He makes the mistake of imagining a fallible human to be the incarnation of a lifelong dream. Even when Dexter's successes eclipse anything that Judy or her milieu have ever possessed, for a long time he stubbornly clings to the idea that she represents the kind of success, achievement, and love that would make his dream attainable.

When he ultimately realizes that his regard for Judy is a part of his lost youth, his lost hopes for the future, and his belief in the possible richness of life, he experiences the loss of all his youthful illusions.  

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From the time he is a poor boy caddying for rich people at the Sherry Island Country Club, Dexter's version of the American Dream is to live a life of  beauty and glamour that he believes he can achieve through money. He wants to be wealthy--to escape his ordinary life and the social class into which he was born. These are his romantic winter dreams.

Dexter works hard to achieve his dream. He scrimps to attend a college more expensive than he can really afford. He graduates, starts a business, expands it, and then sells out, making a lot of money. He is wealthy. Along the way, he has learned to speak and act and dress like members of the upper class. Dexter has money, but he does not have beauty and glamour in his life until he meets Judy Jones, whom he had known when she was a child.

After one gorgeous evening on the lake, Judy becomes Dexter's dream, all the beauty and glamour he has hungered for since he was a boy. His affair with Judy does not last long because her love was an illusion. Despite his pain, Dexter does not regret having loved her. He carries his memories of Judy with him always, still cherishing her beauty and reliving their affair. His memories are all that he has left of her. He lives for them.

The story ends when Dexter learns that Judy is no longer beautiful. She is unremarkably ordinary. His memories of her dissolve as he tries desperately to keep them. Her love had been an illusion. His memories have been lies. He is left with nothing.

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