In "Winter Dreams," what makes Dexter "newer and stronger" than the "careless" wealthy people he meets?

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The classic short story "Winter Dreams" by F. Scott Fitzgerald tells of a golf caddy who overcomes his humble origins and becomes rich through a chain of laundries he owns. He meets a spoiled rich girl named Judy Jones and becomes infatuated with her. When she grows up...

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The classic short story "Winter Dreams" by F. Scott Fitzgerald tells of a golf caddy who overcomes his humble origins and becomes rich through a chain of laundries he owns. He meets a spoiled rich girl named Judy Jones and becomes infatuated with her. When she grows up to become a lovely woman, she has many suitors. Most of these are men who have been born into wealth, who have never known anything else and who take it for granted. Fitzgerald describes Dexter's impression of them:

He knew the sort of men they were—the men who when he first went to college had entered from the great prep schools with graceful clothes and the deep tan of healthy summers.

In other words, these men have the inherited wealth to go to expensive schools, buy nice clothes, and enjoy the leisure of lengthy vacations during the summer. Dexter considers himself to be better than them, to be "newer and stronger" because his wealth and status is not based upon the deeds of his parents. His origins are poor. His father was a grocer, and Dexter became a caddy to earn pocket change. From this low status he uses his inherent intelligence combined with hard work to achieve a position that the others suppose is theirs by right. That's why he considers himself to be superior.

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Dexter Green is "newer" than the "careless" wealthy people since wealth has been unfamiliar to him and not a matter of course. He also is "new" in the sense of being somewhat naive about what wealth can really bring him. 

Dexter is "stronger" because for him wealth is itself a means to a goal, but he is confident that he can attain it. On the other hand, the "careless" rich take their wealth and all that it affords them for granted. They feel no powerful need or deprivation. Once he attains his wealth through hard work and confidence, Dexter values this wealth as something that he must protect because he knows that without it, he cannot attain his goals. The "careless" wealthy often do not sense a real danger as Dexter does.

After Dexter has met the wealthy Judy Jones, who is "arrestingly beautiful," he sets his sights on becoming one of her social and economic class. Thus, he is driven to attain wealth: "...he wanted the glittering things themselves." Moreover, he is "unconsciously dictated by his winter dreams" of becoming rich. In his confidence Dexter chooses to attend a prestigious Eastern college over a state school. Eventually, he becomes a success in his own business.

But all that Dexter accomplishes is not done for the attainment of money per se. He desires wealth for a stronger purpose: the attainment of his dream of a perfect life that involves Judy Jones and her love.

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Dexter is "newer and stronger" in that he is the son of an immigrant mother and a member of the working class by birth. He is not a child of privilege; his family is not one that has built and inherited wealth for several American generations. Dexter worked from the time he was a boy because he needed the money, and he worked hard to attend a fine Eastern university, instead of settling for the less expensive state university. Going to a prestigious school was not a birthright for Dexter as it had been for the sons of the wealthy. After college, Dexter continues to work hard, building a business from very little except his own ingenuity. As a result, he becomes a quite wealthy young man. He is strong in that he knows how to work and plan for what he wants in life.

Dexter is superior in numerous ways to the idle rich he had grown up admiring; ironically, however, he wants his children to be children of social privilege. Dexter wants them to enjoy what he perceives to be the beauty, glamour, and romance of upper-class wealth.

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