At the start of "Winter Dreams," Dexter Green is a fourteen-year-old Minnesotan kid. He spends every winter waiting for the sun to melt the snow on the Sherry Island Golf Course so that he can caddy for the summer. Dexter has a natural attraction to the world of the wealthy. We know that he is better at mingling with the upper class than the other caddies because, when he quits his caddying job, Mr. Mortimer Jones says that Dexter is "The best — caddy I ever saw" (1.10).
The main conflict of "Winter Dreams" is that Dexter dreams of joining the ranks of the rich. But when he sees Judy Jones – the lovely daughter of one of Sherry Island Golf Club's members – on the golf course, he realizes that he has been going about it all wrong. He cannot become rich by earning extra pocket money here and there. He decides to remake himself entirely, so that he will be worthy of someone as lovely as Judy. Once Dexter sees Judy for the first time, his "winter dreams" of fame and fortune become definite ambitions that he will give anything to achieve.
Dexter Green has been busy remaking himself. It's been nine years since he quit his job at the golf course, he has gone to college on the East Coast, and he has come back to Minnesota to make some smart investments in the laundry business. Dexter is already an up-and-coming rich guy. He now plays golf with the men he used to caddy for back in the day. Just as it seems as though all of Dexter's dreams are coming true, Judy Jones comes back into his life. He meets Judy on a swimming platform in the middle of Black Bear Lake, near the Sherry Island Golf Club. Dexter realizes that he has always wanted Judy – but Judy doesn't want Dexter back in the same way. So even though Dexter's business life is running smoothly, his romantic dream of Judy Jones remains out of his reach.
We know that the introduction of Irene Scheerer into Dexter's life probably isn't going to alter Dexter's feelings for Judy. After all, the adjectives that Fitzgerald uses to describe Irene – "sturdily popular" (4.18) and "solid" (4.18) – are not the stuff of romance. We are just waiting for Judy to come back on the scene. And indeed, before we know it, Judy reappears and Dexter's on-again-off-again affair with her starts up once more.
We know that Dexter's relationship with Judy is doomed to failure (since she just is not that into him). How is this going to jive with the big dreams he has? What will happen next?
Failing in both his relationships with steady Irene and fickle Judy, Dexter gives up on women all together. He registers for the Army when the U.S. joins World War I in 1917. And then he moves to New York to make even more money. Dexter dedicates himself to becoming as rich as he possibly can – and he leaves behind his romantic illusions of Judy Jones for good.
By the end of the story, Dexter has apparently achieved all of his goals: he is rich and successful. In fact, he is so well off that "there were no barriers too high for him" (6.2) to overcome. At this point, Dexter has not been back to the Midwest for seven years. Those years pining after Judy Jones are long past. But it is not until his business associate, Devlin, mentions in passing that he knows an unhappily married woman named Judy Simms (maiden name Jones) that Dexter realizes how far he has come from the romantic boy he was in Black Bear, Minnesota. In his pursuit of money, Dexter has forgotten the ideals of romance and grace that led him to try to become wealthy in the first place. He has grown hard-minded and unemotional. Not even the news that Judy has ruined her life with a bad marriage can truly move him. Dexter weeps when he realizes there is nothing left of the boy he once was. Weirdly, Dexter's success has killed off his winter dreams.