The story starts as the protagonist, fourteen-year-old Dexter Fletcher, suddenly quits his very lucrative caddying job when he is told he has to caddy for a rich, spoilt girl called Judy Jones who exerts a powerful attraction on him. It is clear that Judy Jones becomes inextricably intertwined with his dreams of improving himself and becoming rich, and his decision to quit, we are told, is a result of the way that he "was unconsciously dictated to by his winter dreams."
After graduating from an older and more respectable college that he deliberately chose over a newer and cheaper college, Dexter returns to Minnesota and makes his fortune by starting up an incredibly successful laundry business. While playing golf again, he stumbles into Judy Jones, all grown up, and absolutely beautiful, and Dexter falls in love with Judy Jones. Judy however is a character who likes to play with men, and he soon realises that he is one of many "toys" that she likes to keep around her as a captive audience. Dexter eventually gives up and becomes engaged to another woman, only dropping it all when Judy proposes to Dexter. This engagement only lasts a month, and Dexter escapes America by fighing in World War I. the story ends a few years later when Dexter learns that Judy Jones is now just a shadow of her former self and is married to a man who abuses her. Dexter starts crying when he understands that his winter dreams are now lost forever.