Explain Dexter's rise to material success.

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Dexter Green, the main character in Fitzgerald's short story "Winter Dreams," does not come from a wealthy family, but isn't poor either. In the opening paragraph Fitzgerald tells us that Dexter's "father owned the second best grocery store in Black Bear." From the outset we also learn that the 14 year old Dexter is both industrious and well liked in his part time job as a caddy at the Sherry Island Golf Club. He is praised as the "best caddy I ever saw" who "never lost a ball."

By the time Dexter is twenty-seven he already owns "the largest string of laundries in his section of the country." He parlays his knowledge of golf into success by knowing exactly how the wealthy golfers like their stockings washed. Dexter eventually sells his laundries and moves to New York City where Fitzgerald suggests he increases his success. In section six we discover Dexter "had done well--so well that there were no barriers too high for him."

It's not surprising then that Fitzgerald gives his main character the sir name "Green" because Dexter is very good at making money. But, much like Jay Gatsby in Fitzgerald's famous novel, who is also capable of great earning power, Dexter is unable to secure the ideal love he seeks. 

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