Published in 1922, three years before his most famous novel, The Great Gatsby, the short story "Winter Dreams" evokes many of the same themes as that book, including the impetuous nature of the rich, the quest for wealth and social status and the preoccupation with ideal love.
Dexter Green is, in some ways, like Jay Gatsby. He comes from a modest, middle class background. Fitzgerald writes:
"...Dexter Green's father owned the second best grocery store in Black Bear--the best one was "The Hub" patronized by the wealthy people from Sherry Island..."
Also, like Gatsby, Dexter is a self made man. He is not nearly as rich as his college friends, who come from ultra rich families, but he does vey well for himself in the laundry business and by the time he is into his middle twenties Fitzgerald suggests that Dexter is making quite a bit of money. In section II, Fitzgerald writes:
"Before he was twenty-seven he owned the largest string of laundries in his section of the country. It was then that he sold out and went to New York."
We assume that Dexter does equally well in the big city because in the story's final section Fitzgerald writes:
"It took place in New York, where he had done well--so well that there were no barriers too high for him."
While the text never reveals just how rich Dexter has become the reader can assume he has risen to the top, much as Jay Gatsby had done.