Although it has been at least two years since I read The Great Gatsby, there are undoubtedly numerous similarities between that novel, and the short story "Winter Dreams." Jay Gatsby and Dexter Green are both men who come from humble beginnings, and who are utterly infatuated with two beautiful, upper-class women who they track around for years (Daisy and Judy Jones). Jay Gatsby knew that he wouldn't be enough for Daisy as he was, so he disappeared for a number of years, and then returned (after accumulating great wealth) to try to win her back... unfortunately, she had since married and Gatsby was forced to love her from afar. However, in The Great Gatsby, Gatsby's return seems to rekindle the fire between himself and Daisy... the only thing really stopping them is her marriage. The difference between the novel and the story is, that Gatsby has to leave again for Daisy to remain in good standing with her husband. In "Winter Dreams," Dexter Green started out poor as well, but his quick business sense, and smarts pulled him through, and he got to be very wealthy. His infatuation with Judy Jones lasted over the course of many years (beginning, he thinks, when she was only 11... until she reached 27 years of age). Judy was incapable of loving any one person, and instead merely used men and threw them out when she got bored. In the story, Judy is the one who leaves for a while, and on her return, her interest in Dexter flares up for merely one night... during which she ruins his future with his fiancée.
             The death of the American Dream is evidenced in this story, because the American Dreams is equivocal to success. No character in "Winter Dreams" really succeeds. Although Dexter Green makes a good deal of money out of running his small businesses, it never seems that riches is what he is after, and to him, money does not equal happiness. He doesn't get the girl in the end either... Judy...