Dexter's dreams include wanting to be, or feel, equal to the wealthy members of the Sherry Island Golf Club for whom he caddies, going to an exclusive university in the East, and achieving great wealth. To his credit, he realizes all of his "winter dreams." However, when he finally joins the men he once admired, particularly T.A. Hedrick, whom he had fantasized about defeating in a game of golf (he did not specifically want to become a golfer), he finds the experience underwhelming and does not think that Hedrick is such a great golfer but perceives him as a "boor."

He becomes rich, but still does not win Judy Jones, the girl from his town with whom he had fallen in love. He idealized Judy, which made it harder to accept his associate Devlin's news that she aged and had an unhappy marriage in Detroit. Dexter is also shocked by Devlin's assessment of Judy's looks—"pretty" when she was young, with "nice eyes"—because Dexter had always perceived her as "a great beauty."

Dexter's "winter dreams" are Fitzgerald's metaphor for the American Dream which relies on a never-ending pursuit for happiness. The pursuit is never-ending because someone like Dexter is never quite content with what he has accomplished and obtained, but always longs for the thing he could never have—in this case, Judy.

When he realizes that he "can never go back"—that is, never return to his hometown of Black Bear, Minnesota and resume his on-again, off-again relationship with Judy because she is not what she once was—he feels a sense of loss that makes everything in his life matter less.

Dexter dreams of becoming a famous golfer and playing golf against those for whom he caddies now.  By playing against them - and beating them - he sees the fulfillment of his deram.  He will be successful. 

His sense of deprivation does not subside when he becomes wealthy because there is always something more.  A wonderful young woman, for instance, becomes engaged to him, but he breaks it off to pursue Judy - a wealthy young woman who he had met in the past.  He is unable to enjoy his success because he always feels he has something else to prove and wants more. 

Even when Judy proves to be shallow and selfish, Dexter is unable to break with his imagined vision of her until the very end when he is told that Judy  has become a housewife married to an alcoholic husband and is no longer the beauty she once was.  This becomes a reality check for Dexter who realizes that there really is no stability in the dream he has chosen to pursue.

In "Winter Dreams," how do Dexter's "winter dreams" reflect discontent? Does this discontent subside when he becomes rich and respected?

Though Dexter hails from a quite respectable background, he's still profoundly dissatisfied with life. He doesn't just want to be filthy rich—though that would be a good start—he also craves the kind of social respectability denied him on account of his father's being a mere tradesman.

That's why he feels the need to caddy at an upscale country club. This gives him the opportunity to rub shoulders with the social elite, the kind of people he's previously only ever been able to admire from a distance. But even here Dexter remains frustrated with his lot. Although he may be closer than ever before to the upper crust, physical proximity only serves to highlight the vast social distance that separates him from them. Even though he's a valued caddy at the country club, he's still just a caddy; at no point have the rich patrons ever accepted him as one of their own. And for good measure, they never will.

That explains why Dexter develops such a powerful fixation on Judy Jones. On the face of it, this whiny, spoiled rich kid doesn't have much going for her. But for Dexter she becomes the symbol of the kind of life he so desperately wants to lead. As well as being filthy rich, Judy's also a free spirit, a young lady who does whatever she likes. It is this free-sprinted nature of hers, more than anything else, to which Dexter responds, and which causes him to quit his job as caddy at the country club and embark upon the journey of adulthood.

In "Winter Dreams," how do Dexter's "winter dreams" reflect discontent? Does this discontent subside when he becomes rich and respected?

The dominant fact of Dexter's character throughout the story is his obsession with Judy Jones. Though in the text the "winter dreams" are made to symbolize a kind of generalized, restless longing that's abstract in nature, we're made to understand that it's all about Judy. Or conversely, one could interpret Judy herself as a metaphor of the yearning that everybody has for perfection, for fulfillment in the abstract. It's human to be discontented—in a winter of our discontent—and Dexter seems to continue that way or becomes even more unfulfilled in a deeper sense, even after he is a "success" with money to burn.

The denouement does not come until it's revealed to Dexter, almost by chance, that Judy's marriage is an unhappy one, and that others no longer see her as a "great beauty," this icon of womanhood Dexter has created of her in his mind. One would almost think the revelation could bring an inner satisfaction to Dexter, a kind of relief that the woman he was obsessed with all those years wasn't so spectacular after all. But it has the opposite effect. It represents the end of Dexter's ability to maintain the Winter Dream that had given meaning to his life, even if it would be perpetually unfulfilled. Now he doesn't even have the ability to dream any longer. It's as if the longing for something is more satisfying that the possession of it. One wonders if he would have been just as unfulfilled even if the dream of finally marrying Judy Jones had become a reality for him.

The modern reader is probably struck by a rather juvenile quality in the behavior of Judy and in Dexter's response to her throughout the story, even though they are already adults during most of the narrative. Though this may have been typical of a time much more innocent than our own, it still imparts a kind of Never-Neverland feature to the world in which Dexter lives. His winter dreams are those of childhood, or of a lost Eden, that he can never regain as the story comes to an end.

In "Winter Dreams," how do Dexter's "winter dreams" reflect discontent? Does this discontent subside when he becomes rich and respected?

From the time he was a boy, Dexter was restless and discontented, reaching for a larger life than the working middle-class life into which he was born. He longed for a life of romance, beauty, and glamour; he wanted wealth and the "glittering" lifestyle money could buy. When he was young, Dexter escaped his limited personal circumstances through his dreams, imagining scenarios in which he was the star, the hero--one who was admired by the same wealthy people he encountered while working summers at the private and elite Sherry Island Golf Club. Dexter grew up as an outsider who longed to be an insider.

After scrimping to attend one of the "top" Eastern universities, Dexter built a fortune for himself through hard work and ingenuity. He returned to Sherry Island as a guest, not an employee. He had arrived, but in a substantial way, Dexter was still the outsider, and he was still enchanted by Judy Jones and the glamorous world she represented for him. He fell into a love affair with her, one that ended very painfully for him.

Going on with his life, Dexter became engaged to Irene, a fine young woman, but one who could not begin to compete with his memories of Judy. When Judy came into Dexter's life again, he dropped Irene instantly to pursue Judy anew, again with painful results.

Even as a wealthy, successful young man, Dexter continued to display--and to make life choices--as the result of his basic restlessness and discontent. It was his essential discontent, his need to reach for a romantic and more vibrant existence, that fed Dexter's obsession with Judy. She became the incarnation of all his fearly winter dreams, and he lived in them and for them for the remainder of his life, until the day in New York when Dexter's romantic dreams were destroyed by reality.