While “Winter Dreams” features many time jumps into the future, there is only one flashback in the story, which takes place on the day that Dexter decides to quit his job as a caddy at the golf course. The following passage captures how Fitzgerald shifts the narrative from the afternoon of that day back to the morning:
Dexter handed in his “A Class” badge, collected what money was due him from the caddy master, and walked home to Black Bear Village. “The best——caddy I ever saw,” shouted Mr. Mortimer Jones over a drink that afternoon. “Never lost a ball! Willing! Intelligent! Quiet! Honest! Grateful!”
The little girl who had done this was eleven […] She had come eagerly out on to the course at nine o’clock with a white linen nurse and five small new golf-clubs in a white canvas bag.
As this passage demonstrates, Fitzgerald builds suspense about why Dexter would quit a job at which he excelled (and was also lucrative) by having Dexter quit first and then flashing back to show the inciting event that took place at nine o’clock that morning. As the narrator goes on to explain in the rest of the flashback, Dexter decided to quit his caddy job after being treated cruelly by then-11-year-old Judy—he “received a strong emotional shock” about being unjustly treated by a child simply because he was an employee and “required a violent and immediate outlet” for his feelings. This moment ends up inspiring him to become wealthy in his own right and to become a player on the golf course rather than a lowly employee.
