The correct answer to this open question is the following.
Dexters views about the American dream change from the beginning to the end of the story "Winter Dreams, " in the following way.
Dexter starts his story in the novel, as a young man full of dreams and aspirations trying to fulfill the American Dream. He is convinced that the only way to the very top is through dedicated and committed hard work and perseverance. That is his approach to work as a caddy in a golf club, and later, in the laundry business. He indeed worked hard until he -in his later 20s- owns a large chain of laundries in Minnesota and decided to go to New York.
The big issue of his life. His love for Judy, a girl he had met when he was a kid and fell in love. Judy never took him seriously and Judy became his obsession all his life.
Years later, he still is in love with her when he knows that she is married, to the wrong guy, she is not happy, neither him. Then, Dexter realizes that he cannot fulfill his dream. He is rich and a successful businessman, but he is not happy, He feels he is missing something and that is Judy, the love of his life.
American author Scott Fitzgerald wrote the short story "Winter Dreams" in 1922.