In the short story "Winter Dreams" by F. Scott Fitzgerald, the protagonist Dexter Green comes from a middle-class background but aspires to rise in society. The story tells of Dexter's business success as well as his off-again on-again relationship with a wealthy socialite named Judy Jones.
Fitzgerald focuses on Dexter's relentless ambition just a few paragraphs into the story as he describes Dexter's "winter dreams." Although Dexter at the time is merely a caddy, he envisions himself as a brilliant golf champion who always wins matches, sometimes "with laughable ease" and sometimes coming up "magnificently from behind." He also imagines himself stepping out of an expensive automobile and meeting Mr. Mortimer Jones, Judy Jones's father, as an equal at the golf club. While there, he gives an imaginary "exhibition of fancy diving from the springboard of the club raft."
The next indication of Dexter's ambition in the story is when he quits caddying. Rather than behave as a servant and carry eleven-year-old Judy Jones's golf clubs, Dexter resigns from his position on the spot.
Fitzgerald continues to highlight examples of decisions Dexter makes with the goal of his "winter dreams" in mind. For instance, he passes up studying business at the local state university for an opportunity to study at an older, more prestigious eastern university. After college, he avoids the temptation to become involved in the buying and selling of bonds or other traditional business pursuits like his peers and instead buys a laundry business. He not only works hard, but also specializes in cleaning certain types of clothes to cater to the rich. As a result, while he is still very young he becomes rich and a member of the golf club at which he had once caddied.
The author also describes that while Dexter is still at university he affects the dress and mannerisms of young men he meets who are born into wealth. This makes it easier for him when he begins to pursue a relationship with Judy Jones. His ambition also extends to a marriage with Judy Jones, so much so that he is willing to drop his fiancé, Irene, when Judy accepts his proposal.