Throughout "Winter Dreams," we are under the impression that this is the story of Dexter Green's love for Judy Jones. But at the end of the story, once Dexter finds out that Judy has lost her charms and settled into a bad marriage, we begin to wonder if this story is about something else entirely. Dexter does not weep for Judy. He weeps for himself, for the young man he once was and for the illusions he once held. Deep stuff.
Dexter thinks, "Long ago […] long ago, there was something in me, but now that thing is gone" (6.36). We can't be totally sure what Dexter means by "that thing," but we'll take a stab at it. Dexter falls in love with Judy the same day that he quits the Sherry Island Golf Club. It's at that moment that he decides he is going to be one of the rich and famous men who go to golf courses, and not the kid who helps them.
Our guy associates Judy with that dream of a rich and fabulous future. So once she loses her looks and falls into a marriage with a cheating alcoholic, Dexter loses the last of his illusions about the romantic life of the upper class.
And as for Dexter, he realizes that his pursuit of those dreams at all costs have left him with a big fat nothing. He has given up the idealistic feelings of his youth in favor of his hard-minded business sense. And now he can't recapture "the richness of life" (6.35) that he appreciated as a younger man. Not a very uplifting ending, to say the least.